SK8812000A3 - Substituted amidino compounds in the treatment of chronic obstructive pulmonary disease - Google Patents

Substituted amidino compounds in the treatment of chronic obstructive pulmonary disease Download PDF

Info

Publication number: SK8812000A3
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; alkyl; substituted; aliphatic
Prior art date: 1997-12-12

Application number

SK881-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Paul James Marshall

Roger Aki Fujimoto

Original Assignee

Novartis Ag

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.)

1997-12-12

Filing date

1998-12-10

Publication date

2000-12-11

1998-12-10 Application filed by Novartis Ag filed Critical Novartis Ag

2000-12-11 Publication of SK8812000A3 publication Critical patent/SK8812000A3/sk

Links

208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 title claims abstract description 13
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 title 1
-1 aliphatic hydrocarbon radical Chemical class 0.000 claims abstract description 116
150000001875 compounds Chemical class 0.000 claims abstract description 61
150000003839 salts Chemical class 0.000 claims abstract description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 27
125000001931 aliphatic group Chemical group 0.000 claims abstract description 26
229910052736 halogen Inorganic materials 0.000 claims abstract description 25
125000001424 substituent group Chemical group 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 14
150000002367 halogens Chemical group 0.000 claims abstract description 14
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
239000001301 oxygen Substances 0.000 claims abstract description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 4
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 134
125000000217 alkyl group Chemical group 0.000 claims description 94
125000003545 alkoxy group Chemical group 0.000 claims description 41
125000002947 alkylene group Chemical group 0.000 claims description 37
125000002252 acyl group Chemical group 0.000 claims description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 18
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 17
125000003884 phenylalkyl group Chemical group 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 9
125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
125000002071 phenylalkoxy group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 5
230000002685 pulmonary effect Effects 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 4
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
206010006458 Bronchitis chronic Diseases 0.000 claims description 3
206010006451 bronchitis Diseases 0.000 claims description 3
208000007451 chronic bronchitis Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims 2
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract description 3
239000004215 Carbon black (E152) Substances 0.000 abstract 3
229930195733 hydrocarbon Natural products 0.000 abstract 3
239000005864 Sulphur Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 14
150000002431 hydrogen Chemical class 0.000 description 13
239000002253 acid Substances 0.000 description 11
125000000304 alkynyl group Chemical group 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
125000004423 acyloxy group Chemical group 0.000 description 8
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
125000003302 alkenyloxy group Chemical group 0.000 description 7
239000002158 endotoxin Substances 0.000 description 7
229920006008 lipopolysaccharide Polymers 0.000 description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 5
125000000392 cycloalkenyl group Chemical group 0.000 description 5
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
239000002245 particle Substances 0.000 description 5
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
239000000725 suspension Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
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 4
230000000694 effects Effects 0.000 description 4
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 3
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 3
102000003896 Myeloperoxidases Human genes 0.000 description 3
108090000235 Myeloperoxidases Proteins 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
206010035664 Pneumonia Diseases 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003435 aroyl group Chemical group 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
238000002156 mixing Methods 0.000 description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000003380 propellant Substances 0.000 description 3
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 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
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 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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 2
239000005977 Ethylene Substances 0.000 description 2
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PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
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229930006000 Sucrose Natural products 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
230000004913 activation Effects 0.000 description 2
125000005042 acyloxymethyl group Chemical group 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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238000009505 enteric coating Methods 0.000 description 2
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229940098779 methanesulfonic acid Drugs 0.000 description 2
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XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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229920001817 Agar Polymers 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system

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Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Pulmonology (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)
Medicinal Preparation (AREA)

SK881-2000A 1997-12-12 1998-12-10 Substituted amidino compounds in the treatment of chronic obstructive pulmonary disease SK8812000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11200297P	1997-12-12	1997-12-12
PCT/EP1998/008066 WO1999030695A1 (fr)	1997-12-12	1998-12-10	Utilisation de composes amidino substitues dans le traitement des maladies respiratoires chroniques obstructives

Publications (1)

Publication Number	Publication Date
SK8812000A3 true SK8812000A3 (en)	2000-12-11

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ID=22341609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK881-2000A SK8812000A3 (en)	1997-12-12	1998-12-10	Substituted amidino compounds in the treatment of chronic obstructive pulmonary disease

Country Status (15)

Country	Link
US (1)	US6380259B2 (fr)
EP (1)	EP1037617A1 (fr)
JP (1)	JP2002508313A (fr)
KR (1)	KR20010033018A (fr)
CN (1)	CN1281360A (fr)
AU (1)	AU2270399A (fr)
BR (1)	BR9813538A (fr)
CA (1)	CA2314395A1 (fr)
HU (1)	HUP0100733A3 (fr)
ID (1)	ID24720A (fr)
IL (1)	IL136663A0 (fr)
NO (1)	NO20002943D0 (fr)
PL (1)	PL340910A1 (fr)
SK (1)	SK8812000A3 (fr)
WO (1)	WO1999030695A1 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
EP1450787A4 (fr)	2001-11-15	2006-01-25	Galileo Pharmaceuticals Inc	Formulations et procedes destines au traitement ou l'amelioration des etats inflammatoires
GB2445920A (en) *	2007-01-25	2008-07-30	Mucokinetica Ltd	Amidino compounds for treatment of respiratory disease
US10328045B2 (en)	2014-09-12	2019-06-25	Children's Medical Center Corporation, Inc.	Dietary emulsion formulations and methods for using the same

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Publication number	Priority date	Publication date	Assignee	Title
US5451700A (en) *	1991-06-11	1995-09-19	Ciba-Geigy Corporation	Amidino compounds, their manufacture and methods of treatment
US5246965A (en)	1991-06-11	1993-09-21	Ciba-Geigy	Arylethers, their manufacture and methods of treatment
US5488160A (en) *	1991-06-11	1996-01-30	Ciba-Geigy Corporation	Amidino compounds, their manufacture and method of treatment
DK0625138T3 (da)	1992-02-05	1999-11-15	Boehringer Ingelheim Int	Nye amidinderivater, deres fremstilling og anvendelse som medikament med LTB-4 antagonistvirkning
US5455274A (en) *	1992-12-09	1995-10-03	Ciba-Geigy Corporation	Hydroxyamidine derivatives
US5846963A (en) *	1995-06-07	1998-12-08	University Of Utah Research Foundation	Methods for preventing progressive tissue necrosis, reperfusion injury, bacterial translocation and adult respiratory distress syndrome
DE4309285A1 (de)	1993-03-23	1994-09-29	Boehringer Ingelheim Kg	Heterocyclen enthaltende Amidinderivate, ihre Herstellung und Verwendung
DE4424713A1 (de)	1994-07-13	1996-01-18	Boehringer Ingelheim Kg	Substituierte Benzamidine, ihre Herstellung und Verwendung als Arnzneistoffe
DE4424714A1 (de)	1994-07-13	1996-01-18	Boehringer Ingelheim Kg	Neue chemische Verbindung, ihre Herstellung und ihre Verwendung als Arnzneistoff
DE19546452A1 (de)	1995-12-13	1997-06-19	Boehringer Ingelheim Kg	Neue Phenylamidinderivate, Verfahren zu ihrer Herstelung und ihre Verwendung als Arzneimittel

1997
- 1997-12-10 ID IDW20001093A patent/ID24720A/id unknown
1998
- 1998-12-10 KR KR1020007006371A patent/KR20010033018A/ko not_active Withdrawn
- 1998-12-10 HU HU0100733A patent/HUP0100733A3/hu unknown
- 1998-12-10 EP EP98966292A patent/EP1037617A1/fr not_active Withdrawn
- 1998-12-10 SK SK881-2000A patent/SK8812000A3/sk unknown
- 1998-12-10 AU AU22703/99A patent/AU2270399A/en not_active Abandoned
- 1998-12-10 CN CN98812122A patent/CN1281360A/zh active Pending
- 1998-12-10 WO PCT/EP1998/008066 patent/WO1999030695A1/fr not_active Application Discontinuation
- 1998-12-10 JP JP2000538678A patent/JP2002508313A/ja active Pending
- 1998-12-10 BR BR9813538-4A patent/BR9813538A/pt not_active Application Discontinuation
- 1998-12-10 PL PL98340910A patent/PL340910A1/xx unknown
- 1998-12-10 IL IL13666398A patent/IL136663A0/xx unknown
- 1998-12-10 CA CA002314395A patent/CA2314395A1/fr not_active Abandoned
2000
- 2000-06-08 NO NO20002943A patent/NO20002943D0/no not_active Application Discontinuation
- 2000-12-07 US US09/732,453 patent/US6380259B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUP0100733A3 (en)	2003-07-28
JP2002508313A (ja)	2002-03-19
US6380259B2 (en)	2002-04-30
WO1999030695A1 (fr)	1999-06-24
NO20002943L (no)	2000-06-08
AU2270399A (en)	1999-07-05
US20010000341A1 (en)	2001-04-19
NO20002943D0 (no)	2000-06-08
CA2314395A1 (fr)	1999-06-24
ID24720A (id)	2000-08-03
PL340910A1 (en)	2001-03-12
KR20010033018A (ko)	2001-04-25
IL136663A0 (en)	2001-06-14
EP1037617A1 (fr)	2000-09-27
HUP0100733A2 (hu)	2001-08-28
WO1999030695A8 (fr)	1999-07-29
BR9813538A (pt)	2000-10-10
CN1281360A (zh)	2001-01-24

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