NO314452B1 - Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater - Google Patents

Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater Download PDF

Info

Publication number: NO314452B1
Authority: NO; Norway
Prior art keywords: acid; hydroxyamide; alkyl; phenyl; phenylpentanoic
Prior art date: 1996-08-07

Application number

NO19990543A

Other languages

English (en)

Norwegian (no)

Other versions

NO990543D0 (no

NO990543L (no

Inventor

David Alan Owen

John Gary Montana

John Fraser Keily

Robert John Watson

Andrew Douglas Baxter

Original Assignee

Darwin Discovery Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-08-07

Filing date

1999-02-05

Publication date

2003-03-24

1996-08-07 Priority claimed from GBGB9616599.8A external-priority patent/GB9616599D0/en

1997-04-11 Priority claimed from GBGB9707427.2A external-priority patent/GB9707427D0/en

1999-02-05 Application filed by Darwin Discovery Ltd filed Critical Darwin Discovery Ltd

1999-02-05 Publication of NO990543D0 publication Critical patent/NO990543D0/no

1999-04-06 Publication of NO990543L publication Critical patent/NO990543L/no

2003-03-24 Publication of NO314452B1 publication Critical patent/NO314452B1/no

Links

NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title claims abstract description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 5
230000000694 effects Effects 0.000 title description 26
230000005764 inhibitory process Effects 0.000 title description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
201000010099 disease Diseases 0.000 claims abstract description 14
102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 12
108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 12
206010028980 Neoplasm Diseases 0.000 claims abstract description 9
230000001404 mediated effect Effects 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 144
-1 C1-6 alkyl-furyl Chemical group 0.000 claims description 43
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 30
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 18
102100040247 Tumor necrosis factor Human genes 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 17
125000005037 alkyl phenyl group Chemical group 0.000 claims description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
125000004076 pyridyl group Chemical group 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000006383 alkylpyridyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000005544 phthalimido group Chemical group 0.000 claims description 6
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims description 5
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
230000015556 catabolic process Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
LDHFAXJQJCDJMI-UHFFFAOYSA-N 2-(2-methylpropylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound CC(C)CS(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 LDHFAXJQJCDJMI-UHFFFAOYSA-N 0.000 claims description 2
XRDGJPMQIGBTKA-UHFFFAOYSA-N 2-(benzenesulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 XRDGJPMQIGBTKA-UHFFFAOYSA-N 0.000 claims description 2
QGTUQYNQWGAEBS-UHFFFAOYSA-N 2-(benzenesulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 QGTUQYNQWGAEBS-UHFFFAOYSA-N 0.000 claims description 2
WKJPRPPGHTXSOY-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 WKJPRPPGHTXSOY-UHFFFAOYSA-N 0.000 claims description 2
DGPNURFBITXCMQ-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 DGPNURFBITXCMQ-UHFFFAOYSA-N 0.000 claims description 2
TUWPGTXCEXYISO-UHFFFAOYSA-N 2-(cyclopentylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C1CCCC1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 TUWPGTXCEXYISO-UHFFFAOYSA-N 0.000 claims description 2
LEIHFCIHIPZCEU-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=COC=1CS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 LEIHFCIHIPZCEU-UHFFFAOYSA-N 0.000 claims description 2
DBSJXSQIQXSWQQ-UHFFFAOYSA-N 2-[(1-benzoylpiperidin-4-yl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 DBSJXSQIQXSWQQ-UHFFFAOYSA-N 0.000 claims description 2
LVDKTEQDJVFFDJ-UHFFFAOYSA-N 2-[(2-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound COC1=CC=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 LVDKTEQDJVFFDJ-UHFFFAOYSA-N 0.000 claims description 2
XGDKWIGZGLKQFC-UHFFFAOYSA-N 2-[(3-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound COC1=CC=CC(S(=O)(=O)CC(CCCC=2C=CC=CC=2)C(O)=O)=C1 XGDKWIGZGLKQFC-UHFFFAOYSA-N 0.000 claims description 2
VFHDJZZCEWOUOH-UHFFFAOYSA-N 2-[(4-acetylphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 VFHDJZZCEWOUOH-UHFFFAOYSA-N 0.000 claims description 2
ZIJFLRSKJUVAIL-UHFFFAOYSA-N 2-[(4-acetylphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 ZIJFLRSKJUVAIL-UHFFFAOYSA-N 0.000 claims description 2
CFIUSWWECGEZJW-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfinylmethyl]-5-phenylpentanoic acid Chemical group C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)CC(C(=O)O)CCCC1=CC=CC=C1 CFIUSWWECGEZJW-UHFFFAOYSA-N 0.000 claims description 2
BBRNTPFFJDHXMZ-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-3-phenylpropanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CC1=CC=CC=C1 BBRNTPFFJDHXMZ-UHFFFAOYSA-N 0.000 claims description 2
ZOZVXTYPDINXPB-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-(1,3-dioxoisoindol-2-yl)-n-hydroxypentanamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)NO)CS(=O)(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 ZOZVXTYPDINXPB-UHFFFAOYSA-N 0.000 claims description 2
OKNZAHMIAUSTEH-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-(1,3-dioxoisoindol-2-yl)pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)O)CS(=O)(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 OKNZAHMIAUSTEH-UHFFFAOYSA-N 0.000 claims description 2
CTGVDIGFCHCCJU-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 CTGVDIGFCHCCJU-UHFFFAOYSA-N 0.000 claims description 2
SYAAEFMNVNGONW-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 SYAAEFMNVNGONW-UHFFFAOYSA-N 0.000 claims description 2
RCFNAYUVPMRIJQ-UHFFFAOYSA-N 2-[(4-cyclopentyloxyphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(OC2CCCC2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RCFNAYUVPMRIJQ-UHFFFAOYSA-N 0.000 claims description 2
IZKHDGYESOPDLB-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]-3-methylbutanoic acid Chemical compound COC1=CC=C(S(=O)(=O)CC(C(C)C)C(O)=O)C=C1 IZKHDGYESOPDLB-UHFFFAOYSA-N 0.000 claims description 2
MXWKCWSXBXIQGR-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 MXWKCWSXBXIQGR-UHFFFAOYSA-N 0.000 claims description 2
ZVZUJPISSVKCNA-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC)C=C1 ZVZUJPISSVKCNA-UHFFFAOYSA-N 0.000 claims description 2
VNHDFBIMLUHZNY-UHFFFAOYSA-N 2-[2,6-dimethyl-4-(3-methyl-4-oxophthalazin-1-yl)phenoxy]-n-hydroxyacetamide Chemical compound CC1=C(OCC(=O)NO)C(C)=CC(C=2C3=CC=CC=C3C(=O)N(C)N=2)=C1 VNHDFBIMLUHZNY-UHFFFAOYSA-N 0.000 claims description 2
GLODGHWUWHRQAJ-UHFFFAOYSA-N 2-[[1-[(4-cyanophenyl)methyl]piperidin-4-yl]sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1CN(CC=2C=CC(=CC=2)C#N)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GLODGHWUWHRQAJ-UHFFFAOYSA-N 0.000 claims description 2
ZJICAGPAXQZDCW-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 ZJICAGPAXQZDCW-UHFFFAOYSA-N 0.000 claims description 2
PRVHDGXLSWBKHA-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]sulfonylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 PRVHDGXLSWBKHA-UHFFFAOYSA-N 0.000 claims description 2
XZMNZXGPDIGCKW-UHFFFAOYSA-N 2-[benzenesulfonyl(butoxy)methyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(OCCCC)C(C(=O)NO)CCCC1=CC=CC=C1 XZMNZXGPDIGCKW-UHFFFAOYSA-N 0.000 claims description 2
BQZHEGRXEZTRGH-UHFFFAOYSA-N 2-benzyl-3-(4-methoxyphenyl)sulfonylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CC1=CC=CC=C1 BQZHEGRXEZTRGH-UHFFFAOYSA-N 0.000 claims description 2
YEMUGQVDLSZREQ-UHFFFAOYSA-N 3-(4-benzoylphenyl)sulfonyl-n-hydroxypropanamide Chemical compound C1=CC(S(=O)(=O)CCC(=O)NO)=CC=C1C(=O)C1=CC=CC=C1 YEMUGQVDLSZREQ-UHFFFAOYSA-N 0.000 claims description 2
IJEXBTJECGSFQO-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-hydroxybutanamide Chemical compound ONC(=O)CC(C)S(=O)(=O)C1=CC=C(Cl)C=C1 IJEXBTJECGSFQO-UHFFFAOYSA-N 0.000 claims description 2
UFOFDNMTDJQVDY-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-4-phenylbutanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(O)=O)CC1=CC=CC=C1 UFOFDNMTDJQVDY-UHFFFAOYSA-N 0.000 claims description 2
NUSZCZOBSDRJEK-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-hydroxypropanamide Chemical compound ONC(=O)CCS(=O)(=O)C1=CC=CC=C1 NUSZCZOBSDRJEK-UHFFFAOYSA-N 0.000 claims description 2
ILICNRPUTUXICM-UHFFFAOYSA-N 3-[(4-methoxyphenyl)sulfonylmethyl]-6-phenylhexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(CC(O)=O)CCCC1=CC=CC=C1 ILICNRPUTUXICM-UHFFFAOYSA-N 0.000 claims description 2
CJVYAUOPKFJDEP-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)phenyl]sulfonyl-n-hydroxypropanamide Chemical compound C1=CC(S(=O)(=O)CCC(=O)NO)=CC=C1C1=CC=CC=C1Cl CJVYAUOPKFJDEP-UHFFFAOYSA-N 0.000 claims description 2
WASRPYPSPNBQPC-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)sulfonylmethyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCCN1C(=O)C2=CC=CC=C2C1=O WASRPYPSPNBQPC-UHFFFAOYSA-N 0.000 claims description 2
WMMSPEDOSMFAPB-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]pentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCN1C(=O)C2=CC=CC=C2C1=O WMMSPEDOSMFAPB-UHFFFAOYSA-N 0.000 claims description 2
OGKSJKFVMBKIMZ-UHFFFAOYSA-N 5-phenyl-2-(2-phenylethylsulfonylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 OGKSJKFVMBKIMZ-UHFFFAOYSA-N 0.000 claims description 2
MDMAPYXYBJUPHR-UHFFFAOYSA-N 5-phenyl-2-(3-phenylpropylsulfonylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCCS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 MDMAPYXYBJUPHR-UHFFFAOYSA-N 0.000 claims description 2
KNUFDULYTJPULS-UHFFFAOYSA-N 5-phenyl-2-(pyridin-4-ylsulfonylmethyl)pentanoic acid Chemical compound C=1C=NC=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 KNUFDULYTJPULS-UHFFFAOYSA-N 0.000 claims description 2
206010048998 Acute phase reaction Diseases 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
206010002198 Anaphylactic reaction Diseases 0.000 claims description 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
208000023275 Autoimmune disease Diseases 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
206010012438 Dermatitis atopic Diseases 0.000 claims description 2
201000009273 Endometriosis Diseases 0.000 claims description 2
206010014989 Epidermolysis bullosa Diseases 0.000 claims description 2
208000031886 HIV Infections Diseases 0.000 claims description 2
206010019280 Heart failures Diseases 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
102000010781 Interleukin-6 Receptors Human genes 0.000 claims description 2
108010038501 Interleukin-6 Receptors Proteins 0.000 claims description 2
201000009906 Meningitis Diseases 0.000 claims description 2
206010027476 Metastases Diseases 0.000 claims description 2
208000019695 Migraine disease Diseases 0.000 claims description 2
208000001132 Osteoporosis Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
206010037660 Pyrexia Diseases 0.000 claims description 2
206010063837 Reperfusion injury Diseases 0.000 claims description 2
208000017442 Retinal disease Diseases 0.000 claims description 2
206010038923 Retinopathy Diseases 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims description 2
208000002847 Surgical Wound Diseases 0.000 claims description 2
201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
206010047115 Vasculitis Diseases 0.000 claims description 2
229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
230000004658 acute-phase response Effects 0.000 claims description 2
208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
230000036783 anaphylactic response Effects 0.000 claims description 2
208000003455 anaphylaxis Diseases 0.000 claims description 2
208000022531 anorexia Diseases 0.000 claims description 2
208000006673 asthma Diseases 0.000 claims description 2
208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
201000008937 atopic dermatitis Diseases 0.000 claims description 2
230000000740 bleeding effect Effects 0.000 claims description 2
230000009400 cancer invasion Effects 0.000 claims description 2
230000015271 coagulation Effects 0.000 claims description 2
238000005345 coagulation Methods 0.000 claims description 2
206010061428 decreased appetite Diseases 0.000 claims description 2
208000007565 gingivitis Diseases 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
MQPLZZGXGXHGEL-UHFFFAOYSA-N methyl 6-(hydroxyamino)-5-[(4-methoxyphenyl)sulfonylmethyl]-6-oxohexanoate Chemical compound COC(=O)CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC)C=C1 MQPLZZGXGXHGEL-UHFFFAOYSA-N 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
KCFJQJBCBNSJPA-UHFFFAOYSA-N n-hydroxy-2-(2-methylpropylsulfonylmethyl)-5-phenylpentanamide Chemical compound CC(C)CS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 KCFJQJBCBNSJPA-UHFFFAOYSA-N 0.000 claims description 2
KNBDUWFRLKQEEC-UHFFFAOYSA-N n-hydroxy-2-[(2-methoxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound COC1=CC=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 KNBDUWFRLKQEEC-UHFFFAOYSA-N 0.000 claims description 2
XNRJUTGTRAWAEA-UHFFFAOYSA-N n-hydroxy-2-[(4-hydroxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound C=1C=C(O)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 XNRJUTGTRAWAEA-UHFFFAOYSA-N 0.000 claims description 2
RSOTXVOGGIMXHW-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RSOTXVOGGIMXHW-UHFFFAOYSA-N 0.000 claims description 2
URQUSFCKSGRQNP-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]pentanamide Chemical compound CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC)C=C1 URQUSFCKSGRQNP-UHFFFAOYSA-N 0.000 claims description 2
SCDTVKKBOXTTSJ-UHFFFAOYSA-N n-hydroxy-2-[[4-[hydroxy(phenyl)methyl]phenyl]sulfonylmethyl]-5-phenylpentanamide Chemical compound C=1C=C(C(O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 SCDTVKKBOXTTSJ-UHFFFAOYSA-N 0.000 claims description 2
JWOWZVHABOQFLT-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfinylpropanamide Chemical compound COC1=CC=C(S(=O)CCC(=O)NO)C=C1 JWOWZVHABOQFLT-UHFFFAOYSA-N 0.000 claims description 2
AFJPLWPNTPTDED-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfonyl-4-phenylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(=O)NO)CC1=CC=CC=C1 AFJPLWPNTPTDED-UHFFFAOYSA-N 0.000 claims description 2
QFCZCAQONLOMIR-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfonylpropanamide Chemical compound COC1=CC=C(S(=O)(=O)CCC(=O)NO)C=C1 QFCZCAQONLOMIR-UHFFFAOYSA-N 0.000 claims description 2
QIQIFNCOCJPZCE-UHFFFAOYSA-N n-hydroxy-3-[(4-methoxyphenyl)sulfonylmethyl]-6-phenylhexanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(CC(=O)NO)CCCC1=CC=CC=C1 QIQIFNCOCJPZCE-UHFFFAOYSA-N 0.000 claims description 2
WUHSUHMVCJFTLA-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonylbutanamide Chemical compound COC1=CC=C(S(=O)(=O)CCCC(=O)NO)C=C1 WUHSUHMVCJFTLA-UHFFFAOYSA-N 0.000 claims description 2
GIWDGXAGGVNBNU-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(1,3-thiazol-2-ylsulfonylmethyl)pentanamide Chemical compound N=1C=CSC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GIWDGXAGGVNBNU-UHFFFAOYSA-N 0.000 claims description 2
SEKBDJUABBQSMN-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(3-phenylpropylsulfonylmethyl)pentanamide Chemical compound C=1C=CC=CC=1CCCS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 SEKBDJUABBQSMN-UHFFFAOYSA-N 0.000 claims description 2
RBKNZUXIPZBSAN-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(piperidin-4-ylsulfonylmethyl)pentanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CNCCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RBKNZUXIPZBSAN-UHFFFAOYSA-N 0.000 claims description 2
FWHBWKUKOLGUQF-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(pyridin-4-ylsulfonylmethyl)pentanamide Chemical compound C=1C=NC=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 FWHBWKUKOLGUQF-UHFFFAOYSA-N 0.000 claims description 2
RFFOBOBJXKBARW-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(pyrrolidin-1-ylsulfonylmethyl)pentanamide Chemical compound C1CCCN1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RFFOBOBJXKBARW-UHFFFAOYSA-N 0.000 claims description 2
GMCIJHCORIMWCB-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-[[4-(pyridine-2-carbonyl)phenyl]sulfonylmethyl]pentanamide Chemical compound C=1C=C(C(=O)C=2N=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GMCIJHCORIMWCB-UHFFFAOYSA-N 0.000 claims description 2
IPFFYXSBDHVTMM-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-[[4-(thiophene-2-carbonyl)phenyl]sulfonylmethyl]pentanamide Chemical compound C=1C=C(C(=O)C=2SC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 IPFFYXSBDHVTMM-UHFFFAOYSA-N 0.000 claims description 2
230000004770 neurodegeneration Effects 0.000 claims description 2
201000001245 periodontitis Diseases 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
206010039083 rhinitis Diseases 0.000 claims description 2
230000035939 shock Effects 0.000 claims description 2
239000012453 solvate Substances 0.000 claims description 2
230000004614 tumor growth Effects 0.000 claims description 2
230000029663 wound healing Effects 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 4
208000025865 Ulcer Diseases 0.000 claims 2
KTXRFMIQNIJNBX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylsulfanylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C2OCOC2=CC=1SCC(C(=O)NO)CCCC1=CC=CC=C1 KTXRFMIQNIJNBX-UHFFFAOYSA-N 0.000 claims 1
IPICKZJENLRADB-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfinylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 IPICKZJENLRADB-UHFFFAOYSA-N 0.000 claims 1
XRNBYGJMXSBUCE-UHFFFAOYSA-N 2-[2,6-dimethyl-4-(3-methyl-4-oxophthalazin-1-yl)phenoxy]acetic acid Chemical compound CC1=C(OCC(O)=O)C(C)=CC(C=2C3=CC=CC=C3C(=O)N(C)N=2)=C1 XRNBYGJMXSBUCE-UHFFFAOYSA-N 0.000 claims 1
XCDKMSROUVZTFZ-UHFFFAOYSA-N 2-[[4-(2-amino-2-oxoethoxy)phenyl]sulfonylmethyl]-N-hydroxy-5-phenylpentanamide Chemical compound C1=CC(OCC(=O)N)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 XCDKMSROUVZTFZ-UHFFFAOYSA-N 0.000 claims 1
JGMMHYPSOVADIE-UHFFFAOYSA-N 2-[[4-[(4-cyanophenyl)methoxy]phenyl]sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C#N)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 JGMMHYPSOVADIE-UHFFFAOYSA-N 0.000 claims 1
ZBRBHYNTEYKKAE-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonyl-n-hydroxypropanamide Chemical compound ONC(=O)CCS(=O)(=O)C1=CC=C(Br)C=C1 ZBRBHYNTEYKKAE-UHFFFAOYSA-N 0.000 claims 1
OFEBCLDONYFCGJ-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)sulfonylmethyl]butanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCN1C(=O)C2=CC=CC=C2C1=O OFEBCLDONYFCGJ-UHFFFAOYSA-N 0.000 claims 1
201000006474 Brain Ischemia Diseases 0.000 claims 1
206010008120 Cerebral ischaemia Diseases 0.000 claims 1
206010012434 Dermatitis allergic Diseases 0.000 claims 1
101100134925 Gallus gallus COR6 gene Proteins 0.000 claims 1
208000037357 HIV infectious disease Diseases 0.000 claims 1
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 1
206010026673 Malignant Pleural Effusion Diseases 0.000 claims 1
206010025538 Malignant ascites Diseases 0.000 claims 1
241001307210 Pene Species 0.000 claims 1
206010064390 Tumour invasion Diseases 0.000 claims 1
230000033115 angiogenesis Effects 0.000 claims 1
230000002785 anti-thrombosis Effects 0.000 claims 1
206010008118 cerebral infarction Diseases 0.000 claims 1
230000001684 chronic effect Effects 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
208000024908 graft versus host disease Diseases 0.000 claims 1
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
208000031225 myocardial ischemia Diseases 0.000 claims 1
QRNBVNYYDYSPSN-UHFFFAOYSA-N n-hydroxy-2-(4-methoxyphenyl)sulfanyl-5-phenylpentanamide Chemical compound C1=CC(OC)=CC=C1SC(C(=O)NO)CCCC1=CC=CC=C1 QRNBVNYYDYSPSN-UHFFFAOYSA-N 0.000 claims 1
RMXTVEYOGWLQCF-UHFFFAOYSA-N n-hydroxy-2-[(3-methoxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound COC1=CC=CC(S(=O)(=O)CC(CCCC=2C=CC=CC=2)C(=O)NO)=C1 RMXTVEYOGWLQCF-UHFFFAOYSA-N 0.000 claims 1
DYQVGNGEEAJXDQ-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(quinolin-2-ylsulfonylmethyl)pentanamide Chemical compound C=1C=C2C=CC=CC2=NC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 DYQVGNGEEAJXDQ-UHFFFAOYSA-N 0.000 claims 1
208000028169 periodontal disease Diseases 0.000 claims 1
230000002265 prevention Effects 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
GBMIKQJFAKXAKB-UHFFFAOYSA-N tert-butyl 4-[2-(hydroxycarbamoyl)-5-phenylpentyl]sulfonylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GBMIKQJFAKXAKB-UHFFFAOYSA-N 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
231100000397 ulcer Toxicity 0.000 claims 1
230000036269 ulceration Effects 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 48
208000015122 neurodegenerative disease Diseases 0.000 abstract description 2
239000000543 intermediate Substances 0.000 description 351
238000004809 thin layer chromatography Methods 0.000 description 250
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 234
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 233
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 219
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 200
239000007787 solid Substances 0.000 description 172
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 118
239000000243 solution Substances 0.000 description 106
235000019439 ethyl acetate Nutrition 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
239000000203 mixture Substances 0.000 description 78
239000012230 colorless oil Substances 0.000 description 59
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000002904 solvent Substances 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
239000012267 brine Substances 0.000 description 26
238000000034 method Methods 0.000 description 26
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
239000000725 suspension Substances 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
210000004027 cell Anatomy 0.000 description 17
238000010790 dilution Methods 0.000 description 16
239000012895 dilution Substances 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000004440 column chromatography Methods 0.000 description 12
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000001914 filtration Methods 0.000 description 10
HUPQYPMULVBQDL-UHFFFAOYSA-N pentanoic acid Chemical compound CCCCC(O)=O.CCCCC(O)=O HUPQYPMULVBQDL-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
108060005980 Collagenase Proteins 0.000 description 9
102000029816 Collagenase Human genes 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
238000002474 experimental method Methods 0.000 description 9
125000001072 heteroaryl group Chemical group 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 9
230000035755 proliferation Effects 0.000 description 9
108091007196 stromelysin Proteins 0.000 description 9
108010026132 Gelatinases Proteins 0.000 description 8
102000013382 Gelatinases Human genes 0.000 description 8
102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
229960002424 collagenase Drugs 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
239000010410 layer Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 7
229920001436 collagen Polymers 0.000 description 7
RYFCSKVXWRJEOB-UHFFFAOYSA-N dibenzyl propanedioate Chemical compound C=1C=CC=CC=1COC(=O)CC(=O)OCC1=CC=CC=C1 RYFCSKVXWRJEOB-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
125000003710 aryl alkyl group Chemical group 0.000 description 6
239000000796 flavoring agent Substances 0.000 description 6
235000013355 food flavoring agent Nutrition 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000006228 supernatant Substances 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
102000008186 Collagen Human genes 0.000 description 5
108010035532 Collagen Proteins 0.000 description 5
238000008157 ELISA kit Methods 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
102000005741 Metalloproteases Human genes 0.000 description 5
108010006035 Metalloproteases Proteins 0.000 description 5
241000700159 Rattus Species 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000000654 additive Substances 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
150000004665 fatty acids Chemical class 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
229920000609 methyl cellulose Polymers 0.000 description 5
235000010981 methylcellulose Nutrition 0.000 description 5
239000001923 methylcellulose Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
230000028327 secretion Effects 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000375 suspending agent Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
101000611023 Homo sapiens Tumor necrosis factor receptor superfamily member 6 Proteins 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
102100040403 Tumor necrosis factor receptor superfamily member 6 Human genes 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000003086 colorant Substances 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000002158 endotoxin Substances 0.000 description 4
229940088598 enzyme Drugs 0.000 description 4
125000004475 heteroaralkyl group Chemical group 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
229920006008 lipopolysaccharide Polymers 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000036961 partial effect Effects 0.000 description 4
LFYXRHWUNNOEGI-UHFFFAOYSA-N phenyl-(4-sulfanylphenyl)methanone Chemical compound C1=CC(S)=CC=C1C(=O)C1=CC=CC=C1 LFYXRHWUNNOEGI-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
210000004881 tumor cell Anatomy 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
229920001917 Ficoll Polymers 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
108010092694 L-Selectin Proteins 0.000 description 3
102000016551 L-selectin Human genes 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
229920001213 Polysorbate 20 Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
230000009471 action Effects 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
ADPBTBPPIIKLEH-UHFFFAOYSA-N altenusin Chemical compound COC1=CC(O)=C(C(O)=O)C(C=2C(=CC(O)=C(O)C=2)C)=C1 ADPBTBPPIIKLEH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
235000011148 calcium chloride Nutrition 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
OBUNLFQVPAABFB-UHFFFAOYSA-N ethoxyethane;heptane Chemical compound CCOCC.CCCCCCC OBUNLFQVPAABFB-UHFFFAOYSA-N 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
229940057995 liquid paraffin Drugs 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
239000003475 metalloproteinase inhibitor Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000004006 olive oil Substances 0.000 description 3
235000008390 olive oil Nutrition 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 2
WFWGPHCUEMUEJE-UHFFFAOYSA-N 2-[[4-(2-amino-2-oxoethoxy)phenyl]sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(OCC(=O)N)=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 WFWGPHCUEMUEJE-UHFFFAOYSA-N 0.000 description 2
RVKKQSVRFNHZFQ-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]sulfonylmethyl]-5-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)pentanoic acid Chemical compound O=C1C(C)(C)N(C)C(=O)N1CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 RVKKQSVRFNHZFQ-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
JHVNSRJPBXPZJU-UHFFFAOYSA-N 4-(trifluoromethoxy)benzenethiol Chemical compound FC(F)(F)OC1=CC=C(S)C=C1 JHVNSRJPBXPZJU-UHFFFAOYSA-N 0.000 description 2
FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 2
LVTIZXGNLIKUQZ-UHFFFAOYSA-N 4-bromopiperidine;hydrobromide Chemical compound Br.BrC1CCNCC1 LVTIZXGNLIKUQZ-UHFFFAOYSA-N 0.000 description 2
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 2
WBDBVGKXLFOHAJ-UHFFFAOYSA-N 5-phenyl-2-(quinolin-2-ylsulfanylmethyl)pentanoic acid Chemical compound C=1C=C2C=CC=CC2=NC=1SCC(C(=O)O)CCCC1=CC=CC=C1 WBDBVGKXLFOHAJ-UHFFFAOYSA-N 0.000 description 2
102100026802 72 kDa type IV collagenase Human genes 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
235000006491 Acacia senegal Nutrition 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
108010002493 Arachin Proteins 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102100027995 Collagenase 3 Human genes 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
244000166102 Eucalyptus leucoxylon Species 0.000 description 2
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
208000001382 Experimental Melanoma Diseases 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229940124761 MMP inhibitor Drugs 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
102000003843 Metalloendopeptidases Human genes 0.000 description 2
108090000131 Metalloendopeptidases Proteins 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
206010033128 Ovarian cancer Diseases 0.000 description 2
102000035195 Peptidases Human genes 0.000 description 2
108091005804 Peptidases Proteins 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000004365 Protease Substances 0.000 description 2
101150085390 RPM1 gene Proteins 0.000 description 2
102100030416 Stromelysin-1 Human genes 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
102000004338 Transferrin Human genes 0.000 description 2
108090000901 Transferrin Proteins 0.000 description 2
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
201000008275 breast carcinoma Diseases 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
229910000389 calcium phosphate Inorganic materials 0.000 description 2
235000011010 calcium phosphates Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
WNPXRNJEBMRJGV-UHFFFAOYSA-N chembl1399590 Chemical compound COC1=CC=CC(C=2N=C3C=CC=CC3=C(N3C(CCCC3)C)N=2)=C1O WNPXRNJEBMRJGV-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000004404 heteroalkyl group Chemical group 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
210000000548 hind-foot Anatomy 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
239000003446 ligand Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
206010061289 metastatic neoplasm Diseases 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
210000001616 monocyte Anatomy 0.000 description 2
239000000346 nonvolatile oil Substances 0.000 description 2
230000002018 overexpression Effects 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000012545 processing Methods 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
230000007480 spreading Effects 0.000 description 2
238000003892 spreading Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
239000012581 transferrin Substances 0.000 description 2
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
230000006433 tumor necrosis factor production Effects 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
YMTFKKLFLLAFNI-UHFFFAOYSA-N (4-chlorophenyl)-pyridin-4-ylmethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=NC=C1 YMTFKKLFLLAFNI-UHFFFAOYSA-N 0.000 description 1
NLTRJPXIYKYMKT-UHFFFAOYSA-N (4-fluorophenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CS1 NLTRJPXIYKYMKT-UHFFFAOYSA-N 0.000 description 1
GARPGYHIBAKJBR-UHFFFAOYSA-N (4-sulfanylphenyl)-thiophen-2-ylmethanone Chemical compound C1=CC(S)=CC=C1C(=O)C1=CC=CS1 GARPGYHIBAKJBR-UHFFFAOYSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
FIUSOHUYWGYGPP-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfanyl-5-phenylpentan-2-one Chemical compound C1=CC(OC)=CC=C1SCC(=O)CCCC1=CC=CC=C1 FIUSOHUYWGYGPP-UHFFFAOYSA-N 0.000 description 1
QNGBRPMOFJSFMF-UHFFFAOYSA-N 1-(4-sulfanylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(S)C=C1 QNGBRPMOFJSFMF-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
DINSJTUYJLNARL-UHFFFAOYSA-N 1-methoxy-4-(2-phenylethylsulfanyl)benzene Chemical compound C1=CC(OC)=CC=C1SCCC1=CC=CC=C1 DINSJTUYJLNARL-UHFFFAOYSA-N 0.000 description 1
YFGFMGOJVTVNQB-UHFFFAOYSA-N 1-methoxy-4-(2-phenylethylsulfonyl)benzene Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CCC1=CC=CC=C1 YFGFMGOJVTVNQB-UHFFFAOYSA-N 0.000 description 1
FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
KXZSVYHFYHTNBI-UHFFFAOYSA-N 1h-quinoline-2-thione Chemical compound C1=CC=CC2=NC(S)=CC=C21 KXZSVYHFYHTNBI-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
FHIBZVMHVFTNPF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=C2OCOC2=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 FHIBZVMHVFTNPF-UHFFFAOYSA-N 0.000 description 1
JBIQVFROKJFTHY-UHFFFAOYSA-N 2-(2-methylpropylsulfanylmethyl)-5-phenylpentanoic acid Chemical compound CC(C)CSCC(C(O)=O)CCCC1=CC=CC=C1 JBIQVFROKJFTHY-UHFFFAOYSA-N 0.000 description 1
RNUWCQALPWWLTH-UHFFFAOYSA-N 2-(2-pyridin-2-ylethyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCC1=CC=CC=N1 RNUWCQALPWWLTH-UHFFFAOYSA-N 0.000 description 1
VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
ZCZCMCBHMZQTTD-UHFFFAOYSA-N 2-(4-hydroxy-3,5-dimethylbenzoyl)benzoic acid Chemical compound CC1=C(O)C(C)=CC(C(=O)C=2C(=CC=CC=2)C(O)=O)=C1 ZCZCMCBHMZQTTD-UHFFFAOYSA-N 0.000 description 1
BFDHEWHGNSIBIR-UHFFFAOYSA-N 2-(4-sulfanylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(S)C=C1 BFDHEWHGNSIBIR-UHFFFAOYSA-N 0.000 description 1
WEHIQENCAZPXLL-UHFFFAOYSA-N 2-(benzylsulfanylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=CC=CC=1CSCC(C(=O)O)CCCC1=CC=CC=C1 WEHIQENCAZPXLL-UHFFFAOYSA-N 0.000 description 1
HVZXUJMHBYZQHZ-UHFFFAOYSA-N 2-(bromomethyl)-3-methylbutanoic acid Chemical compound CC(C)C(CBr)C(O)=O HVZXUJMHBYZQHZ-UHFFFAOYSA-N 0.000 description 1
YZPRJOZOGMXKJJ-UHFFFAOYSA-N 2-(bromomethyl)-4-(1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound C1=CC=C2C(=O)N(CCC(CBr)C(=O)O)C(=O)C2=C1 YZPRJOZOGMXKJJ-UHFFFAOYSA-N 0.000 description 1
KWZTXIJMBRHNQG-UHFFFAOYSA-N 2-(bromomethyl)-4-pyridin-2-ylbutanoic acid hydrobromide Chemical compound Br.OC(=O)C(CBr)CCC1=CC=CC=N1 KWZTXIJMBRHNQG-UHFFFAOYSA-N 0.000 description 1
OPPRJXSIOPFPAD-UHFFFAOYSA-N 2-(bromomethyl)-5-(1,3-dioxoisoindol-2-yl)pentanoic acid Chemical compound C1=CC=C2C(=O)N(CCCC(CBr)C(=O)O)C(=O)C2=C1 OPPRJXSIOPFPAD-UHFFFAOYSA-N 0.000 description 1
XSYBHGKLJXXURX-UHFFFAOYSA-N 2-(bromomethyl)-5-(2,5-dioxopyrrolidin-1-yl)pentanoic acid Chemical compound OC(=O)C(CBr)CCCN1C(=O)CCC1=O XSYBHGKLJXXURX-UHFFFAOYSA-N 0.000 description 1
YSFDBCZCGQKQAZ-UHFFFAOYSA-N 2-(bromomethyl)-5-phenylpentanoic acid Chemical compound OC(=O)C(CBr)CCCC1=CC=CC=C1 YSFDBCZCGQKQAZ-UHFFFAOYSA-N 0.000 description 1
ZCAYXMOCHIDRBC-UHFFFAOYSA-N 2-(bromomethyl)hexanedioic acid Chemical compound OC(=O)CCCC(CBr)C(O)=O ZCAYXMOCHIDRBC-UHFFFAOYSA-N 0.000 description 1
XMGQOXFZOLHFQW-UHFFFAOYSA-N 2-(bromomethyl)pentanoic acid Chemical compound CCCC(CBr)C(O)=O XMGQOXFZOLHFQW-UHFFFAOYSA-N 0.000 description 1
XZHDHQLORNEKIT-UHFFFAOYSA-N 2-(cyclopentylsulfanylmethyl)-5-phenylpentanoic acid Chemical compound C1CCCC1SCC(C(=O)O)CCCC1=CC=CC=C1 XZHDHQLORNEKIT-UHFFFAOYSA-N 0.000 description 1
FWRFVHCCJRHRPW-UHFFFAOYSA-N 2-(cyclopentylsulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C1CCCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 FWRFVHCCJRHRPW-UHFFFAOYSA-N 0.000 description 1
GCEXRWFZJRJROZ-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfanylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=COC=1CSCC(C(=O)O)CCCC1=CC=CC=C1 GCEXRWFZJRJROZ-UHFFFAOYSA-N 0.000 description 1
FIYBVOKHZSBFAN-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=COC=1CS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 FIYBVOKHZSBFAN-UHFFFAOYSA-N 0.000 description 1
SOYGTWKKLYPHKJ-UHFFFAOYSA-N 2-(oxan-4-ylsulfanylmethyl)-5-phenylpentanoic acid Chemical compound C1COCCC1SCC(C(=O)O)CCCC1=CC=CC=C1 SOYGTWKKLYPHKJ-UHFFFAOYSA-N 0.000 description 1
CMZZDRGYBCAEFS-UHFFFAOYSA-N 2-(oxan-4-ylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C1COCCC1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 CMZZDRGYBCAEFS-UHFFFAOYSA-N 0.000 description 1
ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 1
DTZYBBWXZAYJAQ-UHFFFAOYSA-N 2-[(1-benzoylpiperidin-4-yl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 DTZYBBWXZAYJAQ-UHFFFAOYSA-N 0.000 description 1
JMYBQGJMVLYIGH-UHFFFAOYSA-N 2-[(1-benzylpiperidin-4-yl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1CN(CC=2C=CC=CC=2)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 JMYBQGJMVLYIGH-UHFFFAOYSA-N 0.000 description 1
CYYRZAFMILTSSS-UHFFFAOYSA-N 2-[(1-methylimidazol-2-yl)methylsulfanyl]-5-phenylpentanoic acid Chemical compound CN1C=CN=C1CSC(C(O)=O)CCCC1=CC=CC=C1 CYYRZAFMILTSSS-UHFFFAOYSA-N 0.000 description 1
LZJJAPKCYBSKLD-UHFFFAOYSA-N 2-[(1-methylimidazol-2-yl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound CN1C=CN=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 LZJJAPKCYBSKLD-UHFFFAOYSA-N 0.000 description 1
YGICLIWDBCXXPP-UHFFFAOYSA-N 2-[(3-methoxyphenyl)sulfanylmethyl]-5-phenylpentanoic acid Chemical compound COC1=CC=CC(SCC(CCCC=2C=CC=CC=2)C(O)=O)=C1 YGICLIWDBCXXPP-UHFFFAOYSA-N 0.000 description 1
LTMORSIOUZJCAG-UHFFFAOYSA-N 2-[(4-acetamidophenyl)sulfanylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1SCC(C(O)=O)CCCC1=CC=CC=C1 LTMORSIOUZJCAG-UHFFFAOYSA-N 0.000 description 1
PXNGUXFSTJOVJG-UHFFFAOYSA-N 2-[(4-acetamidophenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 PXNGUXFSTJOVJG-UHFFFAOYSA-N 0.000 description 1
UDUZLYJDDFXTHW-UHFFFAOYSA-N 2-[(4-acetylphenyl)sulfanylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1SCC(C(O)=O)CCCC1=CC=CC=C1 UDUZLYJDDFXTHW-UHFFFAOYSA-N 0.000 description 1
NRPPTNWDANVPIT-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfanylmethyl]-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1CC(C(=O)O)CSC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 NRPPTNWDANVPIT-UHFFFAOYSA-N 0.000 description 1
BYUIDTUPOLLPLU-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfanylmethyl]-5-(1,3-dioxoisoindol-2-yl)pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)O)CSC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 BYUIDTUPOLLPLU-UHFFFAOYSA-N 0.000 description 1
ITBWIDRGQLKOEG-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfanylmethyl]-5-(2,5-dioxopyrrolidin-1-yl)pentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1SCC(C(=O)O)CCCN1C(=O)CCC1=O ITBWIDRGQLKOEG-UHFFFAOYSA-N 0.000 description 1
QVFQOFPCCNBIQM-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfanylmethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 QVFQOFPCCNBIQM-UHFFFAOYSA-N 0.000 description 1
CLQGNALTAGFWOJ-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-(2,5-dioxopyrrolidin-1-yl)pentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CCCN1C(=O)CCC1=O CLQGNALTAGFWOJ-UHFFFAOYSA-N 0.000 description 1
SHNBNCILSFZVIR-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-n-hydroxy-3-phenylpropanamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CC1=CC=CC=C1 SHNBNCILSFZVIR-UHFFFAOYSA-N 0.000 description 1
LQNNJMYUCBDMHA-UHFFFAOYSA-N 2-[(4-benzylphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(CC=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 LQNNJMYUCBDMHA-UHFFFAOYSA-N 0.000 description 1
JYFUEWYSXGZTHE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)sulfanylmethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(O)C=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 JYFUEWYSXGZTHE-UHFFFAOYSA-N 0.000 description 1
SRPGKJKPROZLDP-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(O)C=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 SRPGKJKPROZLDP-UHFFFAOYSA-N 0.000 description 1
IEWZEBDYQFEHAZ-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)sulfonylmethyl]-n-[(2-methylpropan-2-yl)oxy]-5-phenylpentanamide Chemical compound C=1C=C(O)C=CC=1S(=O)(=O)CC(C(=O)NOC(C)(C)C)CCCC1=CC=CC=C1 IEWZEBDYQFEHAZ-UHFFFAOYSA-N 0.000 description 1
BAJQDTPRFAYZCG-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfanylmethyl]-3-methylbutanoic acid Chemical compound COC1=CC=C(SCC(C(C)C)C(O)=O)C=C1 BAJQDTPRFAYZCG-UHFFFAOYSA-N 0.000 description 1
OQWYJQJERWDFKY-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfanylmethyl]-4-pyridin-2-ylbutanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(C(O)=O)CCC1=CC=CC=N1 OQWYJQJERWDFKY-UHFFFAOYSA-N 0.000 description 1
QZISUAPCDONRAW-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfanylmethyl]hexanedioic acid Chemical compound COC1=CC=C(SCC(CCCC(O)=O)C(O)=O)C=C1 QZISUAPCDONRAW-UHFFFAOYSA-N 0.000 description 1
GJHYRSHNDZEPKW-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfanylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CSC1=CC=C(OC)C=C1 GJHYRSHNDZEPKW-UHFFFAOYSA-N 0.000 description 1
MYADBCXVWSFIAL-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]-4-pyridin-2-ylbutanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCC1=CC=CC=N1 MYADBCXVWSFIAL-UHFFFAOYSA-N 0.000 description 1
KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 1
GJBGGXFOJPFKGR-UHFFFAOYSA-N 2-[[4-(2-amino-2-oxoethoxy)phenyl]sulfanylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(OCC(=O)N)=CC=C1SCC(C(O)=O)CCCC1=CC=CC=C1 GJBGGXFOJPFKGR-UHFFFAOYSA-N 0.000 description 1
OLZVEFWMAQZIFX-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]sulfanylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CSC1=CC=C(OC(F)(F)F)C=C1 OLZVEFWMAQZIFX-UHFFFAOYSA-N 0.000 description 1
WZEDQUXJHXVVBX-UHFFFAOYSA-N 2-[[4-[(4-cyanophenyl)methoxy]phenyl]sulfonylmethyl]-n-[(2-methylpropan-2-yl)oxy]-5-phenylpentanamide Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C#N)C=CC=1S(=O)(=O)CC(C(=O)NOC(C)(C)C)CCCC1=CC=CC=C1 WZEDQUXJHXVVBX-UHFFFAOYSA-N 0.000 description 1
ULIBFHYRPZPXCT-UHFFFAOYSA-N 2-[benzenesulfonyl(butoxy)methyl]-n-[(2-methylpropan-2-yl)oxy]-5-phenylpentanamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(OCCCC)C(C(=O)NOC(C)(C)C)CCCC1=CC=CC=C1 ULIBFHYRPZPXCT-UHFFFAOYSA-N 0.000 description 1
VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 1
GPGSQGNEWQPPQR-UHFFFAOYSA-N 2-benzyl-3-(4-methoxyphenyl)sulfanylpropanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(C(O)=O)CC1=CC=CC=C1 GPGSQGNEWQPPQR-UHFFFAOYSA-N 0.000 description 1
VMKJARAVVAPSOR-UHFFFAOYSA-N 2-benzyl-3-bromopropanoic acid Chemical compound OC(=O)C(CBr)CC1=CC=CC=C1 VMKJARAVVAPSOR-UHFFFAOYSA-N 0.000 description 1
BSKDSCGZWSBLGT-UHFFFAOYSA-N 2-benzyl-n-hydroxy-3-(4-methoxyphenyl)sulfonylpropanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(=O)NO)CC1=CC=CC=C1 BSKDSCGZWSBLGT-UHFFFAOYSA-N 0.000 description 1
RYNDYESLUKWOEE-UHFFFAOYSA-N 2-benzylprop-2-enoic acid Chemical compound OC(=O)C(=C)CC1=CC=CC=C1 RYNDYESLUKWOEE-UHFFFAOYSA-N 0.000 description 1
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
GGSTYRUVNWSFHO-UHFFFAOYSA-N 2-methylidene-4-pyridin-2-ylbutanoic acid Chemical compound OC(=O)C(=C)CCC1=CC=CC=N1 GGSTYRUVNWSFHO-UHFFFAOYSA-N 0.000 description 1
BLXPDRMJKIQIKT-UHFFFAOYSA-N 2-methylidene-5-phenylpentanoic acid Chemical compound OC(=O)C(=C)CCCC1=CC=CC=C1 BLXPDRMJKIQIKT-UHFFFAOYSA-N 0.000 description 1
GQXRTXAQSDUAEY-UHFFFAOYSA-N 2-methylidenehexanedioic acid Chemical compound OC(=O)CCCC(=C)C(O)=O GQXRTXAQSDUAEY-UHFFFAOYSA-N 0.000 description 1
HEBDGRTWECSNNT-UHFFFAOYSA-N 2-methylidenepentanoic acid Chemical compound CCCC(=C)C(O)=O HEBDGRTWECSNNT-UHFFFAOYSA-N 0.000 description 1
ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
DQEUFPARIOFOAI-UHFFFAOYSA-N 2-propan-2-ylpropanedioic acid Chemical compound CC(C)C(C(O)=O)C(O)=O DQEUFPARIOFOAI-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
AQJADTWQVKINNH-UHFFFAOYSA-N 3-(4-benzoylphenyl)sulfanylpropanoic acid Chemical compound C1=CC(SCCC(=O)O)=CC=C1C(=O)C1=CC=CC=C1 AQJADTWQVKINNH-UHFFFAOYSA-N 0.000 description 1
WABPBVKTVGVJGY-UHFFFAOYSA-N 3-(4-benzoylphenyl)sulfonylpropanoic acid Chemical compound C1=CC(S(=O)(=O)CCC(=O)O)=CC=C1C(=O)C1=CC=CC=C1 WABPBVKTVGVJGY-UHFFFAOYSA-N 0.000 description 1
CGKAMPCZJIBUGT-UHFFFAOYSA-N 3-(4-bromophenyl)sulfanylpropanoic acid Chemical compound OC(=O)CCSC1=CC=C(Br)C=C1 CGKAMPCZJIBUGT-UHFFFAOYSA-N 0.000 description 1
VIZYBBUNMITQFV-UHFFFAOYSA-N 3-(4-bromophenyl)sulfonylpropanoic acid Chemical compound OC(=O)CCS(=O)(=O)C1=CC=C(Br)C=C1 VIZYBBUNMITQFV-UHFFFAOYSA-N 0.000 description 1
NPUIQANQRDIHLU-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonylbutanoic acid Chemical compound OC(=O)CC(C)S(=O)(=O)C1=CC=C(Cl)C=C1 NPUIQANQRDIHLU-UHFFFAOYSA-N 0.000 description 1
YGLGCLKWXCJXRC-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanylpropanoic acid Chemical compound COC1=CC=C(SCCC(O)=O)C=C1 YGLGCLKWXCJXRC-UHFFFAOYSA-N 0.000 description 1
HUAPPNLSFUBEIF-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfinylpropanoic acid Chemical compound COC1=CC=C(S(=O)CCC(O)=O)C=C1 HUAPPNLSFUBEIF-UHFFFAOYSA-N 0.000 description 1
JRUQWLFYNOXBSV-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonylpropanoic acid Chemical compound COC1=CC=C(S(=O)(=O)CCC(O)=O)C=C1 JRUQWLFYNOXBSV-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
ZXDFVBJYBXOOJK-UHFFFAOYSA-N 3-(iminomethylideneamino)-n,n-dimethylpentan-2-amine Chemical compound N=C=NC(CC)C(C)N(C)C ZXDFVBJYBXOOJK-UHFFFAOYSA-N 0.000 description 1
DFUHRZSNUZPBAJ-UHFFFAOYSA-N 3-[(4-methoxyphenyl)sulfanylmethyl]-6-phenylhexanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(CC(O)=O)CCCC1=CC=CC=C1 DFUHRZSNUZPBAJ-UHFFFAOYSA-N 0.000 description 1
RQDFDSGDMOXPIB-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)phenyl]sulfanylpropanoic acid Chemical compound C1=CC(SCCC(=O)O)=CC=C1C1=CC=CC=C1Cl RQDFDSGDMOXPIB-UHFFFAOYSA-N 0.000 description 1
UWSGEAGYZDJGBW-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)phenyl]sulfonylpropanoic acid Chemical compound C1=CC(S(=O)(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1Cl UWSGEAGYZDJGBW-UHFFFAOYSA-N 0.000 description 1
DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 1
MBRVKEJIEFZNST-UHFFFAOYSA-N 3-methyl-2-methylidenebutanoic acid Chemical compound CC(C)C(=C)C(O)=O MBRVKEJIEFZNST-UHFFFAOYSA-N 0.000 description 1
OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 1
XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
JLMICRZDTPIVIW-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)sulfanylmethyl]butanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(C(O)=O)CCN1C(=O)C2=CC=CC=C2C1=O JLMICRZDTPIVIW-UHFFFAOYSA-N 0.000 description 1
MUURBKHGHHGJBV-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-2-methylidenebutanoic acid Chemical compound C1=CC=C2C(=O)N(CCC(=C)C(=O)O)C(=O)C2=C1 MUURBKHGHHGJBV-UHFFFAOYSA-N 0.000 description 1
OMEZZCIYLLHOEH-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfanylbutanoic acid Chemical compound COC1=CC=C(SCCCC(O)=O)C=C1 OMEZZCIYLLHOEH-UHFFFAOYSA-N 0.000 description 1
BLSXZZMPDARMGD-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonylbutanoic acid Chemical compound COC1=CC=C(S(=O)(=O)CCCC(O)=O)C=C1 BLSXZZMPDARMGD-UHFFFAOYSA-N 0.000 description 1
STABAPSYCQFWOK-UHFFFAOYSA-N 4-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C(Cl)C=C1 STABAPSYCQFWOK-UHFFFAOYSA-N 0.000 description 1
UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
FPXMAHGIKRNYAB-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)sulfanylmethyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(C(O)=O)CCCN1C(=O)C2=CC=CC=C2C1=O FPXMAHGIKRNYAB-UHFFFAOYSA-N 0.000 description 1
IZKKJNOOMWATBZ-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-2-methylidenepentanoic acid Chemical compound C1=CC=C2C(=O)N(CCCC(=C)C(=O)O)C(=O)C2=C1 IZKKJNOOMWATBZ-UHFFFAOYSA-N 0.000 description 1
FRWLIFNQOZCZGS-UHFFFAOYSA-N 5-(2,5-dioxopyrrolidin-1-yl)-2-[(4-methoxyphenyl)sulfanylmethyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1SCC(C(O)=O)CCCN1C(=O)CCC1=O FRWLIFNQOZCZGS-UHFFFAOYSA-N 0.000 description 1
ZHSSJOVNJDGCQA-UHFFFAOYSA-N 5-(2,5-dioxopyrrolidin-1-yl)-2-[(4-methoxyphenyl)sulfonylmethyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCCN1C(=O)CCC1=O ZHSSJOVNJDGCQA-UHFFFAOYSA-N 0.000 description 1
NLBYSUQOVNXUCX-UHFFFAOYSA-N 5-(2,5-dioxopyrrolidin-1-yl)-2-methylidenepentanoic acid Chemical compound OC(=O)C(=C)CCCN1C(=O)CCC1=O NLBYSUQOVNXUCX-UHFFFAOYSA-N 0.000 description 1
HQWVXDINKBWCBH-UHFFFAOYSA-N 5-phenyl-2-(1,3-thiazol-2-ylsulfanylmethyl)pentanoic acid Chemical compound N=1C=CSC=1SCC(C(=O)O)CCCC1=CC=CC=C1 HQWVXDINKBWCBH-UHFFFAOYSA-N 0.000 description 1
MXGLYDSDDKMTSC-UHFFFAOYSA-N 5-phenyl-2-(1,3-thiazol-2-ylsulfonylmethyl)pentanoic acid Chemical compound N=1C=CSC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 MXGLYDSDDKMTSC-UHFFFAOYSA-N 0.000 description 1
WLNKDIGNAIRLGT-UHFFFAOYSA-N 5-phenyl-2-(2-phenylethylsulfanylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCSCC(C(=O)O)CCCC1=CC=CC=C1 WLNKDIGNAIRLGT-UHFFFAOYSA-N 0.000 description 1
YMGACEDKYGYOOT-UHFFFAOYSA-N 5-phenyl-2-(3-phenylpropylsulfanylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCCSCC(C(=O)O)CCCC1=CC=CC=C1 YMGACEDKYGYOOT-UHFFFAOYSA-N 0.000 description 1
MVJGMKIOOYXCES-UHFFFAOYSA-N 5-phenyl-2-(phenylsulfanylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 MVJGMKIOOYXCES-UHFFFAOYSA-N 0.000 description 1
BYCVDDJICANCER-UHFFFAOYSA-N 5-phenyl-2-(pyridin-4-ylsulfanylmethyl)pentanoic acid Chemical compound C=1C=NC=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 BYCVDDJICANCER-UHFFFAOYSA-N 0.000 description 1
MPANSNMWQPWRIZ-UHFFFAOYSA-N 5-phenyl-2-(pyrrolidin-1-ylsulfonylmethyl)pentanoic acid Chemical compound C1CCCN1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 MPANSNMWQPWRIZ-UHFFFAOYSA-N 0.000 description 1
WYLCWUHKXDQONI-UHFFFAOYSA-N 5-phenyl-2-(quinolin-8-ylsulfanylmethyl)pentanoic acid Chemical compound C=1C=CC2=CC=CN=C2C=1SCC(C(=O)O)CCCC1=CC=CC=C1 WYLCWUHKXDQONI-UHFFFAOYSA-N 0.000 description 1
NKMDZHNRIDKAMW-UHFFFAOYSA-N 5-phenyl-2-(quinolin-8-ylsulfonylmethyl)pentanoic acid Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 NKMDZHNRIDKAMW-UHFFFAOYSA-N 0.000 description 1
AONCXXXLKNHUNE-UHFFFAOYSA-N 5-phenyl-2-[[4-(pyridine-4-carbonyl)phenyl]sulfanylmethyl]pentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CN=CC=2)C=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 AONCXXXLKNHUNE-UHFFFAOYSA-N 0.000 description 1
PMBOYJYVFVWNAT-UHFFFAOYSA-N 5-phenyl-2-[[4-(thiophene-2-carbonyl)phenyl]sulfanylmethyl]pentanoic acid Chemical compound C=1C=C(C(=O)C=2SC=CC=2)C=CC=1SCC(C(=O)O)CCCC1=CC=CC=C1 PMBOYJYVFVWNAT-UHFFFAOYSA-N 0.000 description 1
RFUPWGSRRNAYAV-UHFFFAOYSA-N 5-phenyl-2-[[4-(thiophene-2-carbonyl)phenyl]sulfonylmethyl]pentanoic acid Chemical compound C=1C=C(C(=O)C=2SC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 RFUPWGSRRNAYAV-UHFFFAOYSA-N 0.000 description 1
RQYLTZYPLSGJQX-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxyphenyl)sulfanylmethyl]-6-oxohexanoic acid Chemical compound COC(=O)CCCC(C(O)=O)CSC1=CC=C(OC)C=C1 RQYLTZYPLSGJQX-UHFFFAOYSA-N 0.000 description 1
LAIPGYPKPAGVKP-UHFFFAOYSA-N 6-methoxy-2-[(4-methoxyphenyl)sulfonylmethyl]-6-oxohexanoic acid Chemical compound COC(=O)CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC)C=C1 LAIPGYPKPAGVKP-UHFFFAOYSA-N 0.000 description 1
101710151806 72 kDa type IV collagenase Proteins 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
108091022885 ADAM Proteins 0.000 description 1
102000029791 ADAM Human genes 0.000 description 1
102000036664 ADAM10 Human genes 0.000 description 1
108091007504 ADAM10 Proteins 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
102000034473 Adamalysin Human genes 0.000 description 1
108030001653 Adamalysin Proteins 0.000 description 1
ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
LIWMQSWFLXEGMA-WDSKDSINSA-N Ala-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@H](C)N LIWMQSWFLXEGMA-WDSKDSINSA-N 0.000 description 1
241001263092 Alchornea latifolia Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
208000006386 Bone Resorption Diseases 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
239000011547 Bouin solution Substances 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
238000011740 C57BL/6 mouse Methods 0.000 description 1
QCEIKCDKANUOCZ-UHFFFAOYSA-N C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCN1C(=O)CCC1=O Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCN1C(=O)CCC1=O QCEIKCDKANUOCZ-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PWCHHYODGIKDTE-UHFFFAOYSA-N Cl.C=1C=NC=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 Chemical compound Cl.C=1C=NC=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 PWCHHYODGIKDTE-UHFFFAOYSA-N 0.000 description 1
108050005238 Collagenase 3 Proteins 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
WVDYBOADDMMFIY-UHFFFAOYSA-N Cyclopentanethiol Chemical compound SC1CCCC1 WVDYBOADDMMFIY-UHFFFAOYSA-N 0.000 description 1
102000005927 Cysteine Proteases Human genes 0.000 description 1
108010005843 Cysteine Proteases Proteins 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
241000283086 Equidae Species 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
101000801232 Homo sapiens Tumor necrosis factor receptor superfamily member 1B Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
101150014058 MMP1 gene Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 1
108010076503 Matrix Metalloproteinase 13 Proteins 0.000 description 1
108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 1
108010016160 Matrix Metalloproteinase 3 Proteins 0.000 description 1
102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 1
102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
241001529936 Murinae Species 0.000 description 1
102000047918 Myelin Basic Human genes 0.000 description 1
101710107068 Myelin basic protein Proteins 0.000 description 1
FFKZOUIEAHOBHW-UHFFFAOYSA-N N,4-dimethyl-N-nitrosobenzenesulfonamide Chemical compound O=NN(C)S(=O)(=O)C1=CC=C(C)C=C1 FFKZOUIEAHOBHW-UHFFFAOYSA-N 0.000 description 1
YGPMQMOOKATMHE-UHFFFAOYSA-N N-hydroxy-2-[(1-methylimidazol-2-yl)sulfonylmethyl]-5-phenylpentanamide Chemical compound ONC(C(CCCC1=CC=CC=C1)CS(=O)(=O)C=1N(C=CN=1)C)=O YGPMQMOOKATMHE-UHFFFAOYSA-N 0.000 description 1
108010032605 Nerve Growth Factor Receptors Proteins 0.000 description 1
102100030411 Neutrophil collagenase Human genes 0.000 description 1
101710118230 Neutrophil collagenase Proteins 0.000 description 1
108030001564 Neutrophil collagenases Proteins 0.000 description 1
102000056189 Neutrophil collagenases Human genes 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
241000219061 Rheum Species 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
102000012479 Serine Proteases Human genes 0.000 description 1
108010022999 Serine Proteases Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
101710108790 Stromelysin-1 Proteins 0.000 description 1
230000006044 T cell activation Effects 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
108700012920 TNF Proteins 0.000 description 1
102100023935 Transmembrane glycoprotein NMB Human genes 0.000 description 1
102100033725 Tumor necrosis factor receptor superfamily member 16 Human genes 0.000 description 1
102100033733 Tumor necrosis factor receptor superfamily member 1B Human genes 0.000 description 1
206010064996 Ulcerative keratitis Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
UOIFTOBIGNZZSO-UHFFFAOYSA-N acetic acid;ethyl acetate;hexane Chemical compound CC(O)=O.CCCCCC.CCOC(C)=O UOIFTOBIGNZZSO-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000011149 active material Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002001 anti-metastasis Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
210000001188 articular cartilage Anatomy 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
210000003719 b-lymphocyte Anatomy 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000024279 bone resorption Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000007012 clinical effect Effects 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
108700004333 collagenase 1 Proteins 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
VSIDXRKMJGUEFU-UHFFFAOYSA-N dibenzyl 2-(3-phenylpropyl)propanedioate Chemical compound C=1C=CC=CC=1CCCC(C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 VSIDXRKMJGUEFU-UHFFFAOYSA-N 0.000 description 1
NPKCXZXTBRSLST-UHFFFAOYSA-N dibenzyl 2-[2-(1,3-dioxoisoindol-2-yl)ethyl]propanedioate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 NPKCXZXTBRSLST-UHFFFAOYSA-N 0.000 description 1
MCEIBRVLVAPEGM-UHFFFAOYSA-N dibenzyl 2-[3-(1,3-dioxoisoindol-2-yl)propyl]propanedioate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 MCEIBRVLVAPEGM-UHFFFAOYSA-N 0.000 description 1
XYERVJMMPNUEFU-UHFFFAOYSA-N dibenzyl 2-[3-(2,5-dioxopyrrolidin-1-yl)propyl]propanedioate Chemical compound O=C1CCC(=O)N1CCCC(C(=O)OCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 XYERVJMMPNUEFU-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
YECKMMDDSDRKPI-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfanylbutanoate Chemical compound CCOC(=O)CCCSC1=CC=C(OC)C=C1 YECKMMDDSDRKPI-UHFFFAOYSA-N 0.000 description 1
DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
230000029142 excretion Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000006260 foam Substances 0.000 description 1
210000002683 foot Anatomy 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
WLKKJDMRRBROBV-UHFFFAOYSA-M lithium;2-bromoacetate Chemical compound [Li+].[O-]C(=O)CBr WLKKJDMRRBROBV-UHFFFAOYSA-M 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
239000003771 matrix metalloproteinase inhibitor Substances 0.000 description 1
229940121386 matrix metalloproteinase inhibitor Drugs 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
SQBDDCLTIMQETN-UHFFFAOYSA-N methyl 2-(acetylsulfanylmethyl)-5-phenylpentanoate Chemical compound CC(=O)SCC(C(=O)OC)CCCC1=CC=CC=C1 SQBDDCLTIMQETN-UHFFFAOYSA-N 0.000 description 1
METCVQAYKKZJLQ-UHFFFAOYSA-N methyl 2-(bromomethyl)-5-phenylpentanoate Chemical compound COC(=O)C(CBr)CCCC1=CC=CC=C1 METCVQAYKKZJLQ-UHFFFAOYSA-N 0.000 description 1
QDBLPEJNKICFEF-UHFFFAOYSA-N methyl 2-(chlorosulfonylmethyl)-5-phenylpentanoate Chemical compound COC(=O)C(CS(Cl)(=O)=O)CCCC1=CC=CC=C1 QDBLPEJNKICFEF-UHFFFAOYSA-N 0.000 description 1
LFPHSFCDHACAEG-UHFFFAOYSA-N methyl 2-[(4-bromophenyl)sulfanylmethyl]-5-phenylpentanoate Chemical compound C=1C=C(Br)C=CC=1SCC(C(=O)OC)CCCC1=CC=CC=C1 LFPHSFCDHACAEG-UHFFFAOYSA-N 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
CTSAXXHOGZNKJR-UHFFFAOYSA-N methyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC CTSAXXHOGZNKJR-UHFFFAOYSA-N 0.000 description 1
NDYZSNJRULAEIO-UHFFFAOYSA-N methyl 3-(4-bromophenyl)sulfanylpropanoate Chemical compound COC(=O)CCSC1=CC=C(Br)C=C1 NDYZSNJRULAEIO-UHFFFAOYSA-N 0.000 description 1
NGNWWQQPVCJDRB-UHFFFAOYSA-N methyl 3-(4-methoxyphenyl)sulfanylpropanoate Chemical compound COC(=O)CCSC1=CC=C(OC)C=C1 NGNWWQQPVCJDRB-UHFFFAOYSA-N 0.000 description 1
JEVHXKOCFCYMPG-UHFFFAOYSA-N methyl 3-[(4-methoxyphenyl)sulfanylmethyl]-6-phenylhex-2-enoate Chemical compound C=1C=C(OC)C=CC=1SCC(=CC(=O)OC)CCCC1=CC=CC=C1 JEVHXKOCFCYMPG-UHFFFAOYSA-N 0.000 description 1
JGKZWSCEVCSIDQ-UHFFFAOYSA-N methyl 4-[4-(2-chlorophenyl)phenyl]sulfanylbutanoate Chemical compound C1=CC(SCCCC(=O)OC)=CC=C1C1=CC=CC=C1Cl JGKZWSCEVCSIDQ-UHFFFAOYSA-N 0.000 description 1
XHUSHCLFYZFIHO-UHFFFAOYSA-N methyl 5-phenyl-2-(pyrrolidin-1-ylsulfonylmethyl)pentanoate Chemical compound C1CCCN1S(=O)(=O)CC(C(=O)OC)CCCC1=CC=CC=C1 XHUSHCLFYZFIHO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
KTDNLFILVOTVAX-UHFFFAOYSA-N n-[(2-methylpropan-2-yl)oxy]-5-phenyl-2-[(4-phenylmethoxyphenyl)sulfonylmethyl]pentanamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NOC(C)(C)C)CCCC1=CC=CC=C1 KTDNLFILVOTVAX-UHFFFAOYSA-N 0.000 description 1
JVLQTFWIBKTBDE-UHFFFAOYSA-N n-hydroxy-2-(oxan-4-ylsulfonylmethyl)-5-phenylpentanamide Chemical compound C1COCCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 JVLQTFWIBKTBDE-UHFFFAOYSA-N 0.000 description 1
SPCFBCARJYFPAZ-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]-3-methylbutanamide Chemical compound COC1=CC=C(S(=O)(=O)CC(C(C)C)C(=O)NO)C=C1 SPCFBCARJYFPAZ-UHFFFAOYSA-N 0.000 description 1
QXBZUANJYGJRHA-UHFFFAOYSA-N n-hydroxy-2-[[4-(trifluoromethoxy)phenyl]sulfonylmethyl]-5-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)pentanamide Chemical compound O=C1C(C)(C)N(C)C(=O)N1CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 QXBZUANJYGJRHA-UHFFFAOYSA-N 0.000 description 1
GVIQBUBYLQMLPA-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-(quinolin-8-ylsulfonylmethyl)pentanamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GVIQBUBYLQMLPA-UHFFFAOYSA-N 0.000 description 1
GBQQZCLSBRDVFT-UHFFFAOYSA-N n-hydroxy-5-phenyl-2-[(4-phenylmethoxyphenyl)sulfonylmethyl]pentanamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GBQQZCLSBRDVFT-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940053128 nerve growth factor Drugs 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
HDEOKHIQTDMWTQ-UHFFFAOYSA-N oxane-4-thiol Chemical compound SC1CCOCC1 HDEOKHIQTDMWTQ-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
NNLJLPZWDPOEAW-UHFFFAOYSA-N potassium;pyrrolidine-2,5-dione Chemical compound [K].O=C1CCC(=O)N1 NNLJLPZWDPOEAW-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
AMMGCGVWJMRTQI-UHFFFAOYSA-N prop-1-en-2-yl carbonochloridate Chemical compound CC(=C)OC(Cl)=O AMMGCGVWJMRTQI-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000012264 purified product Substances 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
CFIKPWOOXQYEJO-UHFFFAOYSA-N pyridin-4-yl-(4-sulfanylphenyl)methanone Chemical compound C1=CC(S)=CC=C1C(=O)C1=CC=NC=C1 CFIKPWOOXQYEJO-UHFFFAOYSA-N 0.000 description 1
MHTSJSRDFXZFHQ-UHFFFAOYSA-N quinoline-8-thiol Chemical compound C1=CN=C2C(S)=CC=CC2=C1 MHTSJSRDFXZFHQ-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000000163 radioactive labelling Methods 0.000 description 1
238000011552 rat model Methods 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
SDWFMPSNHFWVOV-UHFFFAOYSA-N s-(1-benzoylpiperidin-4-yl) ethanethioate Chemical compound C1CC(SC(=O)C)CCN1C(=O)C1=CC=CC=C1 SDWFMPSNHFWVOV-UHFFFAOYSA-N 0.000 description 1
BYUNVFSCFPTRBA-UHFFFAOYSA-N s-(oxan-4-yl) ethanethioate Chemical compound CC(=O)SC1CCOCC1 BYUNVFSCFPTRBA-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000012622 synthetic inhibitor Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
230000008354 tissue degradation Effects 0.000 description 1
108091007466 transmembrane glycoproteins Proteins 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
WNBQNJANYUENGZ-UHFFFAOYSA-N triethyl butane-1,1,4-tricarboxylate Chemical compound CCOC(=O)CCCC(C(=O)OCC)C(=O)OCC WNBQNJANYUENGZ-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
230000005748 tumor development Effects 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
230000004572 zinc-binding Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Ophthalmology & Optometry (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Biomedical Technology (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Pyrane Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Furan Compounds (AREA)
Pyridine Compounds (AREA)
Quinoline Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO19990543A 1996-08-07 1999-02-05 Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater NO314452B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9616599.8A GB9616599D0 (en)	1996-08-07	1996-08-07	Compounds
GBGB9707427.2A GB9707427D0 (en)	1997-04-11	1997-04-11	Compounds having mmp and tnf inhibitory activity
PCT/GB1997/002129 WO1998005635A1 (fr)	1996-08-07	1997-08-07	Derives de l'acide hydroxamique et de l'acide carboxylique dotes d'une activite inhibitrice vis a vis des mmp et du tnf

Publications (3)

Publication Number	Publication Date
NO990543D0 NO990543D0 (no)	1999-02-05
NO990543L NO990543L (no)	1999-04-06
NO314452B1 true NO314452B1 (no)	2003-03-24

Family

ID=26309836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19990543A NO314452B1 (no)	1996-08-07	1999-02-05	Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater

Country Status (17)

Country	Link
US (1)	US6118001A (fr)
EP (1)	EP0968182B1 (fr)
JP (1)	JP2000517297A (fr)
KR (1)	KR20000029858A (fr)
CN (1)	CN1227540A (fr)
AT (1)	ATE266000T1 (fr)
AU (1)	AU730464B2 (fr)
BR (1)	BR9711027A (fr)
CA (1)	CA2263154A1 (fr)
CZ (1)	CZ297278B6 (fr)
DE (1)	DE69729007T2 (fr)
DK (1)	DK0968182T3 (fr)
ES (1)	ES2217425T3 (fr)
NO (1)	NO314452B1 (fr)
PL (1)	PL193829B1 (fr)
PT (1)	PT968182E (fr)
WO (1)	WO1998005635A1 (fr)

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4456183B2 (ja)	1997-01-22	2010-04-28	アベンテイス・フアーマシユーチカルズ・インコーポレーテツド	置換β−チオカルボン酸類
US7115632B1 (en)	1999-05-12	2006-10-03	G. D. Searle & Co.	Sulfonyl aryl or heteroaryl hydroxamic acid compounds
IL131494A (en) *	1997-03-04	2005-06-19	Monsanto Co	N-hydroxy 4-sulfonyl butanamide compounds and their use to prepare medicaments for treating conditions associated with matrix metalloproteinase activity
WO1998039316A1 (fr)	1997-03-04	1998-09-11	Monsanto Company	Composes n-hydroxy-4-sulfonyl-butanamide
US6794511B2 (en) *	1997-03-04	2004-09-21	G. D. Searle	Sulfonyl aryl or heteroaryl hydroxamic acid compounds
US6696449B2 (en)	1997-03-04	2004-02-24	Pharmacia Corporation	Sulfonyl aryl hydroxamates and their use as matrix metalloprotease inhibitors
AUPO721997A0 (en) *	1997-06-06	1997-07-03	Queensland Institute Of Medical Research, The	Anticancer compounds
BR9814699A (pt)	1997-11-21	2000-10-03	Pharmacia & Up John Company	Derivados alfa-hidróxi, amino e halo de ácidos beta-sulfonil hidroxâmico como inibidores de metaloproteinases matrizes
DK1357109T3 (da)	1998-06-18	2008-09-08	Hoffmann La Roche	Fremgangsmåde til arylalkylsulfid
FR2780402B1 (fr) *	1998-06-30	2001-04-27	Adir	Nouveaux composes acides carboxyliques et hydroxamiques inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JP2002523492A (ja) *	1998-08-29	2002-07-30	ブリティッシュバイオテックファーマシューティカルズリミテッド	タンパク質分解酵素阻害剤としてのヒドロキサム酸誘導体
GB9919776D0 (en) *	1998-08-31	1999-10-27	Zeneca Ltd	Compoujnds
US6858598B1 (en)	1998-12-23	2005-02-22	G. D. Searle & Co.	Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
GB9911075D0 (en)	1999-05-12	1999-07-14	Darwin Discovery Ltd	HYdroxamic and carboxylic acid derivatives
GB9911073D0 (en) *	1999-05-12	1999-07-14	Darwin Discovery Ltd	Hydroxamic and carboxylic acid derivatives
GB9916562D0 (en)	1999-07-14	1999-09-15	Pharmacia & Upjohn Spa	3-Arylsulfonyl-2-(substituted-methyl) propanoic acid derivatives as matrix metalloproteinase inhibitora
GB9922825D0 (en) *	1999-09-25	1999-11-24	Smithkline Beecham Biolog	Medical use
US6667316B1 (en) *	1999-11-12	2003-12-23	Celgene Corporation	Pharmaceutically active isoindoline derivatives
US20030139419A1 (en) *	2000-02-21	2003-07-24	Bernard Barlaam	Arylpiperazines and arylpiperidines and their use as metalloproteinase inhibiting agents
GB0009760D0 (en)	2000-04-19	2000-06-07	Oxford Biomedica Ltd	Method
US6506773B2 (en)	2000-05-15	2003-01-14	Darwin Discovery Ltd.	Hydroxamic and carboxylic acid derivatives
EP1282614B1 (fr)	2000-05-15	2003-11-12	Darwin Discovery Limited	Derives d'acide hydroxamique
EP1286994A1 (fr)	2000-05-15	2003-03-05	Darwin Discovery Limited	Derives d'acides hydroxamique et carboxylique possedant une activite inhibitrice des metalloproteinases et du facteur de necrose tumorale
GB0020498D0 (en)	2000-08-18	2000-10-11	Sterix Ltd	Compound
US7842727B2 (en)	2001-03-27	2010-11-30	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors
CA2344208A1 (fr)	2001-04-30	2002-10-30	Oxford Biomedica (Uk) Limited	Methode
GB0119474D0 (en)	2001-08-09	2001-10-03	Astrazeneca Ab	Compounds
WO2003099272A1 (fr)	2002-05-22	2003-12-04	Errant Gene Therapeutics, Llc	Inhibiteurs d'histone desacetylase bases sur des composes alpha-ceto-epoxydes
AU2003247390A1 (en) *	2002-05-22	2003-12-12	Errant Gene Therapeutics, Llc.	Histone deacetylase inhibitors based on alphachalcogenmethylcarbonyl compounds
DE10226370B4 (de)	2002-06-13	2008-12-11	Polyic Gmbh & Co. Kg	Substrat für ein elektronisches Bauteil, Verwendung des Substrates, Verfahren zur Erhöhung der Ladungsträgermobilität und Organischer Feld-Effekt Transistor (OFET)
DE10233085B4 (de)	2002-07-19	2014-02-20	Dendron Gmbh	Stent mit Führungsdraht
US8425549B2 (en)	2002-07-23	2013-04-23	Reverse Medical Corporation	Systems and methods for removing obstructive matter from body lumens and treating vascular defects
WO2004012663A2 (fr)	2002-08-01	2004-02-12	Bristol-Myers Squibb Company	Derives d'yhydantoine utilises comme inhibiteurs de metalloproteases maticielles et/ou d'enzyme de conversion de tnf-alpha
AU2003300076C1 (en)	2002-12-30	2010-03-04	Angiotech International Ag	Drug delivery from rapid gelling polymer composition
GB0411562D0 (en)	2004-05-24	2004-06-23	Sterix Ltd	Compound
GB0412492D0 (en)	2004-06-04	2004-07-07	Sterix Ltd	Compound
US20050277897A1 (en) *	2004-06-14	2005-12-15	Ghannoum Ziad R	Handpiece tip
DE102005019181A1 (de) *	2005-04-25	2006-10-26	Novartis Ag	Peptid-Deformylase (PDF) Inhibitoren 1
KR20080002866A (ko) *	2005-04-25	2008-01-04	노파르티스 아게	펩티드 데포르밀라제 (ｐｄｆ) 억제제로서 유용한이미다조(1,2-ａ)피리딘 유도체
SI2002003T1 (sl)	2005-05-27	2016-05-31	Ospedale San Raffaele S.R.L.	Genski vektor, ki vsebuje mi-RNA
GB0513702D0 (en)	2005-07-04	2005-08-10	Sterix Ltd	Compound
GB0526210D0 (en)	2005-12-22	2006-02-01	Oxford Biomedica Ltd	Vectors
GB0604142D0 (en)	2006-03-01	2006-04-12	Sterix Ltd	Compound
EP2041181B1 (fr) *	2006-06-08	2011-05-18	Helmholtz Zentrum München Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH)	Inhibiteurs spécifiques de protéase et leur utilisation pour le traitement du cancer
CA2672267C (fr)	2006-07-27	2016-05-31	Emisphere Technologies, Inc.	Composes arylsulfanyles et compositions pour administrer des agents actifs
GB0706072D0 (en)	2007-03-28	2007-05-09	Sterix Ltd	Compound
US8088140B2 (en)	2008-05-19	2012-01-03	Mindframe, Inc.	Blood flow restorative and embolus removal methods
US11337714B2 (en)	2007-10-17	2022-05-24	Covidien Lp	Restoring blood flow and clot removal during acute ischemic stroke
GB0722779D0 (en)	2007-11-20	2008-01-02	Sterix Ltd	Compound
KR101819554B1 (ko)	2008-02-22	2018-01-17	마이크로 테라퓨틱스 인코포레이티드	혈류를 회복하는 방법 및 기구
EP2307551B1 (fr)	2008-06-18	2016-12-14	Oxford BioMedica (UK) Limited	Purification de virus
US9938540B2 (en)	2008-11-12	2018-04-10	Ospedale San Raffaele S.R.L.	Gene vector for inducing transgene-specific immune tolerance
SG175839A1 (en)	2009-04-30	2011-12-29	San Raffaele Centro Fond	Gene vector
GB0914767D0 (en)	2009-08-24	2009-09-30	Sterix Ltd	Compound
US9039749B2 (en)	2010-10-01	2015-05-26	Covidien Lp	Methods and apparatuses for flow restoration and implanting members in the human body
WO2012156839A2 (fr)	2011-05-19	2012-11-22	Ospedale San Raffaele S.R.L.	Nouvelle génération de vecteurs lentiviraux sans épissures pour des applications de thérapie génique plus sûres
JP6360500B2 (ja)	2013-02-06	2018-07-18	メルクパテントゲゼルシャフトミットベシュレンクテルハフツングＭｅｒｃｋＰａｔｅｎｔＧｅｓｅｌｌｓｃｈａｆｔｍｉｔｂｅｓｃｈｒａｅｎｋｔｅｒＨａｆｔｕｎｇ	骨関節炎の処置のためのアグリカナーゼ阻害剤としての置換カルボン酸誘導体
US20160024125A1 (en)	2013-03-11	2016-01-28	Life Science Nutrition As	Natural lipids containing non-oxidizable fatty acids
US10076399B2 (en)	2013-09-13	2018-09-18	Covidien Lp	Endovascular device engagement
EP3060670B1 (fr)	2013-10-24	2019-07-10	Ospedale San Raffaele S.r.l.	Méthode
GB201322798D0 (en)	2013-12-20	2014-02-05	Oxford Biomedica Ltd	Production system
GB201407322D0 (en)	2014-04-25	2014-06-11	Ospedale San Raffaele	Gene therapy
GB201412494D0 (en)	2014-07-14	2014-08-27	Ospedale San Raffaele And Fond Telethon	Vector production
GB201418965D0 (fr)	2014-10-24	2014-12-10	Ospedale San Raffaele And Fond Telethon
GB201608944D0 (en)	2016-05-20	2016-07-06	Ospedale San Raffaele And Fond Telethon	Gene Tharapy
GB201706394D0 (en)	2017-04-21	2017-06-07	Ospedale San Raffaele Srl	Gene Therapy
DE102017211110A1 (de)	2017-06-30	2019-01-03	Continental Reifen Deutschland Gmbh	Verfahren zur Herstellung eines Silans, Verfahren zur Modifizierung einer Kieselsäure mit dem Silan und modifizierte Kieselsäure
GB201807945D0 (en)	2018-05-16	2018-06-27	Ospedale San Raffaele Srl	Vector production
GB201807944D0 (en)	2018-05-16	2018-06-27	Ospedale San Raffaele Srl	Compositions and methods for haematopoietic stem cell transplantation
KR20210030941A (ko)	2018-06-25	2021-03-18	오스페달레 산 라파엘 에스.알.엘.	유전자 요법
AU2019358519A1 (en)	2018-10-11	2021-05-27	Fondazione Telethon Ets	Selection by means of artificial transactivators
WO2020148445A1 (fr)	2019-01-18	2020-07-23	Société des Produits Nestlé S.A.	Agents et procédés pour augmenter la fonction de cellules souches
EP4058067A1 (fr)	2019-11-12	2022-09-21	Oxford BioMedica (UK) Limited	Système de production
US20240052366A1 (en)	2020-02-13	2024-02-15	Oxford Biomedica (Uk) Limited	Production of Lentiviral Vectors
WO2021181108A1 (fr)	2020-03-13	2021-09-16	Oxford Biomedica (Uk) Limited	Vecteurs lentiviraux
GB202007106D0 (en)	2020-05-14	2020-07-01	Ucl Business Plc	Cyclosporine analogues
GB202007199D0 (en)	2020-05-15	2020-07-01	Oxford Biomedica Ltd	Viral vector production
EP4217470A1 (fr)	2020-09-28	2023-08-02	Société des Produits Nestlé S.A.	Compositions et procédés pour augmenter la fonction de cellules souches
CA3188629A1 (fr)	2020-09-28	2022-03-31	Nicola Vannini	Compositions et procedes pour augmenter la fonction de cellules souches
GB202017725D0 (en)	2020-11-10	2020-12-23	Oxford Biomedica Ltd	Method
JP2024506751A (ja)	2021-02-01	2024-02-14	イプシレンバイオエス．アール．エル．	遺伝子サイレンシング
AU2021202658A1 (en)	2021-04-28	2022-11-17	Fondazione Telethon	Gene therapy
CA3213384A1 (fr)	2021-05-05	2022-11-10	Mukul Girotra	Urolithine pour augmenter la fonction de cellules souches
GB202114530D0 (en)	2021-10-12	2021-11-24	Oxford Biomedica Ltd	Retroviral vectors
GB202114534D0 (en)	2021-10-12	2021-11-24	Oxford Biomedica Ltd	Novel viral regulatory elements
GB202114528D0 (en)	2021-10-12	2021-11-24	Oxford Biomedica Ltd	Lentiviral vectors
GB202114532D0 (en)	2021-10-12	2021-11-24	Oxford Biomedica Ltd	Lentiviral Vectors
GB202114529D0 (en)	2021-10-12	2021-11-24	Oxford Biomedica Ltd	Lentiviral vectors
GB202114972D0 (en)	2021-10-19	2021-12-01	Ospedale San Raffaele Srl	Gene therapy
GB202117844D0 (en)	2021-12-09	2022-01-26	Oxford Biomedica Ltd	Purification method
EP4514364A1 (fr)	2022-04-28	2025-03-05	Ospedale San Raffaele S.r.l.	Procédés de transplantation de cellules souches hématopoïétiques
GB202206346D0 (en)	2022-04-29	2022-06-15	Ospedale San Raffaele Srl	Gene therapy
GB202209098D0 (en)	2022-06-21	2022-08-10	Ucl Business Ltd	Cyclosporine analogues
GB202211935D0 (en)	2022-08-16	2022-09-28	Oxford Biomedica Ltd	envelope proteins
WO2024079644A1 (fr)	2022-10-11	2024-04-18	Fondazione Telethon Ets	Procédés de culture cellulaire 3d
IT202300011790A1 (it)	2023-06-08	2024-12-08	Fond Telethon Ets	Protocolli di manipolazione genica in cellule immunitarie

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4127722A (en) *	1975-10-02	1978-11-28	Laboratoire L. Lafon	Benzhydrylsulphinyl derivatives
CH630606A5 (en) *	1977-02-15	1982-06-30	Lafon Labor	Phenylamidine derivatives useful especially in therapeutics
JP3348725B2 (ja) *	1992-04-07	2002-11-20	ブリティッシュバイオテックファーマシューティカルズリミテッド	ヒドロキサム酸ベースのコラゲナーゼとサイトカイン阻害剤
GB9404046D0 (en) *	1994-03-03	1994-04-20	Smithkline Beecham Corp	Novel compounds
AU692102B2 (en) *	1995-05-10	1998-05-28	Darwin Discovery Limited	Peptidyl compounds and their therapeutic use
US5665777A (en) *	1995-11-14	1997-09-09	Abbott Laboratories	Biphenyl hydroxamate inhibitors of matrix metalloproteinases
EP0780386B1 (fr) *	1995-12-20	2002-10-02	F. Hoffmann-La Roche Ag	Inhibiteurs de métalloprotéases matricielles
DE69728375T2 (de) *	1996-01-02	2005-02-10	Aventis Pharmaceuticals Inc.	Substituierte (aryl, heteroaryl, arylmethyl oder heteroarylmethyl) hydroxamisaeureverbindungen
PL332509A1 (en) *	1996-09-27	1999-09-13	Upjohn Co	Beta-sulphonyl-hydroxamic acids as inhibitors of intercellular substance metaloproteinases
WO1998039316A1 (fr) *	1997-03-04	1998-09-11	Monsanto Company	Composes n-hydroxy-4-sulfonyl-butanamide

1997
- 1997-08-07 DK DK97935666T patent/DK0968182T3/da active
- 1997-08-07 PL PL97331598A patent/PL193829B1/pl not_active IP Right Cessation
- 1997-08-07 EP EP97935666A patent/EP0968182B1/fr not_active Expired - Lifetime
- 1997-08-07 CN CN97197048A patent/CN1227540A/zh active Pending
- 1997-08-07 KR KR1019997001020A patent/KR20000029858A/ko not_active Ceased
- 1997-08-07 BR BR9711027A patent/BR9711027A/pt unknown
- 1997-08-07 DE DE69729007T patent/DE69729007T2/de not_active Expired - Fee Related
- 1997-08-07 AU AU38564/97A patent/AU730464B2/en not_active Ceased
- 1997-08-07 JP JP10507741A patent/JP2000517297A/ja not_active Ceased
- 1997-08-07 US US08/908,397 patent/US6118001A/en not_active Expired - Fee Related
- 1997-08-07 AT AT97935666T patent/ATE266000T1/de not_active IP Right Cessation
- 1997-08-07 PT PT97935666T patent/PT968182E/pt unknown
- 1997-08-07 CZ CZ0036899A patent/CZ297278B6/cs not_active IP Right Cessation
- 1997-08-07 CA CA002263154A patent/CA2263154A1/fr not_active Abandoned
- 1997-08-07 WO PCT/GB1997/002129 patent/WO1998005635A1/fr active IP Right Grant
- 1997-08-07 ES ES97935666T patent/ES2217425T3/es not_active Expired - Lifetime
1999
- 1999-02-05 NO NO19990543A patent/NO314452B1/no unknown

Also Published As

Publication number	Publication date
DE69729007T2 (de)	2005-04-07
PL331598A1 (en)	1999-08-02
NO990543D0 (no)	1999-02-05
KR20000029858A (ko)	2000-05-25
ATE266000T1 (de)	2004-05-15
EP0968182B1 (fr)	2004-05-06
BR9711027A (pt)	1999-08-17
NO990543L (no)	1999-04-06
EP0968182A1 (fr)	2000-01-05
DK0968182T3 (da)	2004-08-16
WO1998005635A1 (fr)	1998-02-12
CA2263154A1 (fr)	1998-02-12
CN1227540A (zh)	1999-09-01
US6118001A (en)	2000-09-12
CZ297278B6 (cs)	2006-10-11
AU3856497A (en)	1998-02-25
DE69729007D1 (de)	2004-06-09
JP2000517297A (ja)	2000-12-26
PT968182E (pt)	2004-08-31
CZ36899A3 (cs)	1999-07-14
PL193829B1 (pl)	2007-03-30
AU730464B2 (en)	2001-03-08
ES2217425T3 (es)	2004-11-01

Publication	Publication Date	Title
NO314452B1 (no)	2003-03-24	Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater
US6566384B1 (en)	2003-05-20	Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity
EP0960108B1 (fr)	2004-10-27	Inhibiteurs de metalloproteinases matricielles
US5120718A (en)	1992-06-09	Candida acid protease inhibiting compounds
US5554767A (en)	1996-09-10	Alpha-mercaptoacrylic acid derivatives having calpain inhibitory activity
US6329418B1 (en)	2001-12-11	Substituted pyrrolidine hydroxamate metalloprotease inhibitors
US6465468B1 (en)	2002-10-15	Hydroxamic and carboxylic acid derivatives
WO2002085899A1 (fr)	2002-10-31	Heterocyclyl-dicarbamides en tant qu'inhibiteurs de caspase
EA002810B1 (ru)	2002-10-31	Сульфамидные ингибиторы металлопротеаз
HUP0100152A2 (hu)	2002-02-28	MMP és TNF inhibitor aktivitású hidroxámsav- és karbonsavszármazékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk
HU217344B1 (hu)	2002-02-28	Merkapto-acil-dipeptid-származékok és alkalmazásuk metalloproteináz inhibitor hatású gyógyszerkészítmények előállítására
DE69620639T2 (de)	2002-10-17	Mercaptoalkylpeptidylverbindungen mit einem imidazolsubstituenten und ihre verwendung als inhibitoren der matrix metalloproteinasen (mmp) und/oder des tumor necrosis faktors (tnf)
JP2002535392A (ja)	2002-10-22	マトリックスメタロプロテイナーゼ阻害剤としての２，３，４，５−テトラヒドロ−１ｈ−〔１，４〕ベンゾジアゼピン−３−ヒドロキサム酸
NO326266B1 (no)	2008-10-27	Hydroksam- og karboksylsyrederivater, farmasoytiske preparater inneholdende slike for anvendelse i terapi samt anvendelse av slike forbindelser for fremstilling av medikamenter for behandling eller forebygging av sykdommer
US6455531B1 (en)	2002-09-24	Hydroxamic acid derivatives
EP1053233B1 (fr)	2003-08-20	Derives d'acide hydroxamique et carboxylique
WO1997012861A1 (fr)	1997-04-10	Derives mercaptoamide et leur utilisation therapeutique
US6680338B2 (en)	2004-01-20	Hydroxamic and carboxylic acid derivatives
MXPA99001298A (es)	1999-06-01	Derivados de acido hidroxamico y carboxilico que tienen actividad inhibitoria de mpm y fnt
JP2001522843A (ja)	2001-11-20	Ｍｍｐおよびｔｎｆ抑制作用を有するヒドロキサム酸およびカルボン酸誘導体
US7015234B2 (en)	2006-03-21	Hydroxamic acid derivatives
MXPA00007570A (en)	2002-02-26	Hydroxamic and carboxylic acid derivatives
MXPA00004747A (en)	2001-09-07	Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity
HK1016996A (en)	1999-11-12	Thio-substituted peptides as inhibitors for metalloproteinases and thf liberation