NO315273B1 - Trisykliske vasopressinagonister, farmasöytiske sammensetninger omfattendedisse, deres anvendelse samt en fremgangsmåte for fremstillingderav - Google Patents

Trisykliske vasopressinagonister, farmasöytiske sammensetninger omfattendedisse, deres anvendelse samt en fremgangsmåte for fremstillingderav Download PDF

Info

Publication number: NO315273B1
Authority: NO; Norway
Prior art keywords: benzodiazepine; pyrrolo; methanone; phenyl; pyrazol
Prior art date: 1997-07-30

Application number

NO20000242A

Other languages

English (en)

Norwegian (no)

Other versions

NO20000242D0 (no

NO20000242L (no

Inventor

John Paul Dusza

Peter Sinchun Chan

Jay Donald Albright

Jehan Framroz Bagli

Amedeo Arturo Failli

Mark Anthony Ashwell

Albert John Molinari

Thomas Joseph Caggiano

Eugene John Trybulski

Original Assignee

Wyeth Corp

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.)

1997-07-30

Filing date

2000-01-18

Publication date

2003-08-11

2000-01-18 Application filed by Wyeth Corp filed Critical Wyeth Corp

2000-01-18 Publication of NO20000242D0 publication Critical patent/NO20000242D0/no

2000-03-06 Publication of NO20000242L publication Critical patent/NO20000242L/no

2003-08-11 Publication of NO315273B1 publication Critical patent/NO315273B1/no

Links

238000000034 method Methods 0.000 title claims description 63
238000002360 preparation method Methods 0.000 title claims description 20
229940083335 Vasopressin agonist Drugs 0.000 title claims description 11
239000008194 pharmaceutical composition Substances 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 279
125000004432 carbon atom Chemical group C* 0.000 claims description 74
-1 [4-(4-Methyl-pyrazol-1-yl)-2-trifluoromethyl-phenyl]-(5H,1H-pyrrolo[2,1-c][1,4]benzodiazepine-10-yl)-methanone Chemical compound 0.000 claims description 73
229910052739 hydrogen Inorganic materials 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 46
125000000623 heterocyclic group Chemical group 0.000 claims description 46
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
238000011282 treatment Methods 0.000 claims description 32
150000002431 hydrogen Chemical class 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 26
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical group 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 17
FBLUCKXWFZKVCT-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound C1C2=CC=CN2CC2=CC=CC=C2N1C(=O)C(C=C1)=CC=C1C1=CC=NN1 FBLUCKXWFZKVCT-UHFFFAOYSA-N 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 14
239000003795 chemical substances by application Substances 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 8
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
229910052721 tungsten Inorganic materials 0.000 claims description 8
229910052727 yttrium Inorganic materials 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
208000008967 Enuresis Diseases 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
201000010064 diabetes insipidus Diseases 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
230000027939 micturition Effects 0.000 claims description 7
208000005346 nocturnal enuresis Diseases 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 6
229910052796 boron Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000011630 iodine Substances 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
206010046543 Urinary incontinence Diseases 0.000 claims description 5
230000000740 bleeding effect Effects 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
206010029446 nocturia Diseases 0.000 claims description 5
UAKRIFYMKVWWSB-UHFFFAOYSA-N 1-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 UAKRIFYMKVWWSB-UHFFFAOYSA-N 0.000 claims description 4
IAUVQLCYHAXTKP-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[2-methoxy-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(OC)=CC=1N1C=CC(C)=N1 IAUVQLCYHAXTKP-UHFFFAOYSA-N 0.000 claims description 4
UQMZWIPRZOTGON-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbaldehyde Chemical compound O=CN1CC2=CC=CN2CC2=CC=CC=C12 UQMZWIPRZOTGON-UHFFFAOYSA-N 0.000 claims description 4
206010053567 Coagulopathies Diseases 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
208000031169 hemorrhagic disease Diseases 0.000 claims description 4
150000002429 hydrazines Chemical class 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
208000015294 blood coagulation disease Diseases 0.000 claims description 3
230000009852 coagulant defect Effects 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
URZRRURVKJYAAW-UHFFFAOYSA-N (2,4-difluorophenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 URZRRURVKJYAAW-UHFFFAOYSA-N 0.000 claims description 2
PFIHUWCMYUUTJM-UHFFFAOYSA-N (2-chloro-4-pyrrol-1-ylphenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1N1C=CC=C1 PFIHUWCMYUUTJM-UHFFFAOYSA-N 0.000 claims description 2
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 claims description 2
FLICMWMJGBRJBU-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzamide Chemical compound ClC1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 FLICMWMJGBRJBU-UHFFFAOYSA-N 0.000 claims description 2
KUIQZKCWIAZFLF-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 KUIQZKCWIAZFLF-UHFFFAOYSA-N 0.000 claims description 2
DSDRQBPGBZCVCN-UHFFFAOYSA-N 3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)benzonitrile Chemical compound ClC1=CC(C#N)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 DSDRQBPGBZCVCN-UHFFFAOYSA-N 0.000 claims description 2
BPJFXRBPXNGTAI-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-(4-pyrazol-1-ylphenyl)methanone Chemical compound C1C2=CC=CN2CC2=CC=CC=C2N1C(=O)C(C=C1)=CC=C1N1C=CC=N1 BPJFXRBPXNGTAI-UHFFFAOYSA-N 0.000 claims description 2
MHPFBCSULPHXGZ-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-methylpyrazol-4-yl)phenyl]methanone Chemical compound C1=NN(C)C=C1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 MHPFBCSULPHXGZ-UHFFFAOYSA-N 0.000 claims description 2
APJKVNDKNAGLPV-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-propylpyrazol-3-yl)phenyl]methanone Chemical compound CCCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 APJKVNDKNAGLPV-UHFFFAOYSA-N 0.000 claims description 2
FMOQJUMNVLFHBN-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 FMOQJUMNVLFHBN-UHFFFAOYSA-N 0.000 claims description 2
ZMDLMIADSBRABU-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=CN1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 ZMDLMIADSBRABU-UHFFFAOYSA-N 0.000 claims description 2
AVPKUAHXGQKTRJ-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(4-methylpyrazol-1-yl)phenyl]methanone Chemical compound C1=C(C)C=NN1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 AVPKUAHXGQKTRJ-UHFFFAOYSA-N 0.000 claims description 2
QOVQKXLSPAUMBR-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(5-methyl-1h-pyrazol-3-yl)phenyl]methanone Chemical compound N1C(C)=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 QOVQKXLSPAUMBR-UHFFFAOYSA-N 0.000 claims description 2
FLXNQADSXVDDED-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(2-methylbenzoyl)pyrazol-3-yl]phenyl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 FLXNQADSXVDDED-UHFFFAOYSA-N 0.000 claims description 2
IRJHPKKQWIRRDH-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(5-fluoro-2-methylbenzoyl)pyrazol-3-yl]phenyl]methanone Chemical compound CC1=CC=C(F)C=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 IRJHPKKQWIRRDH-UHFFFAOYSA-N 0.000 claims description 2
ZOPZYYBHDGGLSD-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[6-(1-methylpyrazol-4-yl)pyridin-3-yl]methanone Chemical compound C1=NN(C)C=C1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=N1 ZOPZYYBHDGGLSD-UHFFFAOYSA-N 0.000 claims description 2
KPZHSXCQKPNVKU-UHFFFAOYSA-N [2-chloro-4-(1-methylpyrazol-4-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C1=NN(C)C=C1C(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 KPZHSXCQKPNVKU-UHFFFAOYSA-N 0.000 claims description 2
SRPPGGPQIGOELK-UHFFFAOYSA-N [2-chloro-4-(2h-tetrazol-5-yl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1C=1N=NNN=1 SRPPGGPQIGOELK-UHFFFAOYSA-N 0.000 claims description 2
RTRBDFZJXIBNFC-UHFFFAOYSA-N [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-(9-methyl-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound N1=C(C)C=CN1C(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C(C)=CC=C2C1 RTRBDFZJXIBNFC-UHFFFAOYSA-N 0.000 claims description 2
JHPDHIYVIDFZBV-UHFFFAOYSA-N [2-chloro-6-(3-methylpyrazol-1-yl)pyridin-3-yl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound N1=C(C)C=CN1C(N=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 JHPDHIYVIDFZBV-UHFFFAOYSA-N 0.000 claims description 2
VTTSWHYXLTVYDF-UHFFFAOYSA-N [2-chloro-6-(4-methylpyrazol-1-yl)pyridin-3-yl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C1=C(C)C=NN1C(N=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 VTTSWHYXLTVYDF-UHFFFAOYSA-N 0.000 claims description 2
ABIVFJRWLYBHFL-UHFFFAOYSA-N [4-(3-cyclopropylpyrazol-1-yl)-2-(trifluoromethyl)phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(C(F)(F)F)=CC=1N(N=1)C=CC=1C1CC1 ABIVFJRWLYBHFL-UHFFFAOYSA-N 0.000 claims description 2
QOKBTDWACCQPEV-UHFFFAOYSA-N [9-[(dimethylamino)methyl]-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl]-[2-methoxy-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C(CN(C)C)=CC=C3C2)C(OC)=CC=1N1C=CC(C)=N1 QOKBTDWACCQPEV-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
238000012546 transfer Methods 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims 4
WSWLBSBMRCHUEH-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3-methylpyrazol-1-yl)-2-(trifluoromethyl)phenyl]methanone Chemical compound N1=C(C)C=CN1C(C=C1C(F)(F)F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 WSWLBSBMRCHUEH-UHFFFAOYSA-N 0.000 claims 2
FBENLRZSVRQZHY-UHFFFAOYSA-N (2-chloro-4-pyrazol-1-ylphenyl)-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound C=1C=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C(Cl)=CC=1N1C=CC=N1 FBENLRZSVRQZHY-UHFFFAOYSA-N 0.000 claims 1
QVSKPOGUURMZEN-UHFFFAOYSA-N 1-[2-chloro-4-(2-methyl-1,2,4-triazol-3-yl)phenyl]-2-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)ethane-1,2-dione Chemical compound CN1N=CN=C1C(C=C1Cl)=CC=C1C(=O)C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 QVSKPOGUURMZEN-UHFFFAOYSA-N 0.000 claims 1
JDQPHLSKTFNWKS-UHFFFAOYSA-N 1-[3-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]pyrazol-1-yl]butan-1-one Chemical compound CCCC(=O)N1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 JDQPHLSKTFNWKS-UHFFFAOYSA-N 0.000 claims 1
XPSWCLNIVATKRD-UHFFFAOYSA-N 1-[3-[4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]pyrazol-1-yl]propan-1-one Chemical compound CCC(=O)N1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 XPSWCLNIVATKRD-UHFFFAOYSA-N 0.000 claims 1
GATZRWSXCKUPBW-UHFFFAOYSA-N 1-[3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 GATZRWSXCKUPBW-UHFFFAOYSA-N 0.000 claims 1
ZACOHTBOHFCQIE-UHFFFAOYSA-N 1-[4-(4,10-dihydropyrazolo[5,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1C2=CC=CC=C2CN2N=CC=C2C1 ZACOHTBOHFCQIE-UHFFFAOYSA-N 0.000 claims 1
HZKMKSBSEYMPCW-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[2-fluoro-4-(3-methylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=CN1C(C=C1F)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 HZKMKSBSEYMPCW-UHFFFAOYSA-N 0.000 claims 1
ULGQCNKQHORZJF-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(1-ethylpyrazol-3-yl)phenyl]methanone Chemical compound CCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 ULGQCNKQHORZJF-UHFFFAOYSA-N 0.000 claims 1
VKBOUDPLTDGHDT-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-(3,5-dimethylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=C(C)N1C1=CC=C(C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 VKBOUDPLTDGHDT-UHFFFAOYSA-N 0.000 claims 1
QBUWLGWIBRDKEN-UHFFFAOYSA-N 6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl-[4-[1-(methoxymethyl)pyrazol-3-yl]phenyl]methanone Chemical compound COCN1C=CC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)=N1 QBUWLGWIBRDKEN-UHFFFAOYSA-N 0.000 claims 1
CNTDFFHQKBTDDT-UHFFFAOYSA-N [2-chloro-4-(3-methylpyrazol-1-yl)phenyl]-[9-[(dimethylamino)methyl]-6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl]methanone Chemical compound C12=CC=CC=C2CN2C(CN(C)C)=CC=C2CN1C(=O)C(C(=C1)Cl)=CC=C1N1C=CC(C)=N1 CNTDFFHQKBTDDT-UHFFFAOYSA-N 0.000 claims 1
HXBSWLVZOHGNHL-UHFFFAOYSA-N [4-[1-(2,4-dichlorobenzoyl)pyrazol-3-yl]phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 HXBSWLVZOHGNHL-UHFFFAOYSA-N 0.000 claims 1
PSWYTXVNFQEIDD-UHFFFAOYSA-N [4-[1-(2-chloro-4-fluorobenzoyl)pyrazol-3-yl]phenyl]-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepin-5-yl)methanone Chemical compound ClC1=CC(F)=CC=C1C(=O)N1N=C(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3CN3C=CC=C3C2)C=C1 PSWYTXVNFQEIDD-UHFFFAOYSA-N 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
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239000006071 cream Substances 0.000 description 1
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150000001931 cyclobutenes Chemical class 0.000 description 1
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239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
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235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
230000009424 thromboembolic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
WARKYKQCOXTIAO-UHFFFAOYSA-N tributyl(2-ethoxyethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C/OCC WARKYKQCOXTIAO-UHFFFAOYSA-N 0.000 description 1
LNECVNPGDBLIEM-UHFFFAOYSA-N tributyl-(1-methylpyrazol-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=1C=NN(C)C=1 LNECVNPGDBLIEM-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
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 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO20000242A 1997-07-30 2000-01-18 Trisykliske vasopressinagonister, farmasöytiske sammensetninger omfattendedisse, deres anvendelse samt en fremgangsmåte for fremstillingderav NO315273B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US90336997A	1997-07-30	1997-07-30
PCT/US1998/015495 WO1999006409A1 (fr)	1997-07-30	1998-07-24	Agonistes tricycliques de la vasopressine

Publications (3)

Publication Number	Publication Date
NO20000242D0 NO20000242D0 (no)	2000-01-18
NO20000242L NO20000242L (no)	2000-03-06
NO315273B1 true NO315273B1 (no)	2003-08-11

Family

ID=25417392

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20000242A NO315273B1 (no)	1997-07-30	2000-01-18	Trisykliske vasopressinagonister, farmasöytiske sammensetninger omfattendedisse, deres anvendelse samt en fremgangsmåte for fremstillingderav

Country Status (22)

Country	Link
EP (1)	EP1000062B1 (fr)
JP (1)	JP4338305B2 (fr)
KR (1)	KR100580805B1 (fr)
CN (1)	CN1183134C (fr)
AR (1)	AR016557A1 (fr)
AT (1)	ATE277050T1 (fr)
AU (1)	AU756959B2 (fr)
BR (1)	BR9811585A (fr)
CA (1)	CA2297406C (fr)
DE (1)	DE69826487T2 (fr)
DK (1)	DK1000062T3 (fr)
ES (1)	ES2229525T3 (fr)
HU (1)	HUP0002480A3 (fr)
IL (1)	IL133788A0 (fr)
NO (1)	NO315273B1 (fr)
NZ (1)	NZ502449A (fr)
PT (1)	PT1000062E (fr)
RU (1)	RU2213094C2 (fr)
SI (1)	SI1000062T1 (fr)
TW (1)	TW502035B (fr)
WO (1)	WO1999006409A1 (fr)
ZA (1)	ZA986784B (fr)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7138393B2 (en) *	1998-07-24	2006-11-21	Wyeth	Biologically active vasopressin agonist metabolites
PL205704B1 (pl) *	1999-01-19	2010-05-31	Ortho Mcneil Pharm Inc	Związki tricyklicznej benzodiazepiny, kompozycja farmaceutyczna zawierająca te związki oraz ich zastosowanie
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1998
- 1998-07-24 RU RU2000104865/04A patent/RU2213094C2/ru not_active IP Right Cessation
- 1998-07-24 EP EP98938017A patent/EP1000062B1/fr not_active Expired - Lifetime
- 1998-07-24 AT AT98938017T patent/ATE277050T1/de not_active IP Right Cessation
- 1998-07-24 SI SI9830693T patent/SI1000062T1/xx unknown
- 1998-07-24 CA CA002297406A patent/CA2297406C/fr not_active Expired - Fee Related
- 1998-07-24 ES ES98938017T patent/ES2229525T3/es not_active Expired - Lifetime
- 1998-07-24 JP JP2000505167A patent/JP4338305B2/ja not_active Expired - Fee Related
- 1998-07-24 DK DK98938017T patent/DK1000062T3/da active
- 1998-07-24 KR KR1020007000977A patent/KR100580805B1/ko not_active Expired - Fee Related
- 1998-07-24 IL IL13378898A patent/IL133788A0/xx unknown
- 1998-07-24 HU HU0002480A patent/HUP0002480A3/hu unknown
- 1998-07-24 BR BR9811585-5A patent/BR9811585A/pt not_active IP Right Cessation
- 1998-07-24 NZ NZ502449A patent/NZ502449A/xx unknown
- 1998-07-24 AU AU86633/98A patent/AU756959B2/en not_active Ceased
- 1998-07-24 WO PCT/US1998/015495 patent/WO1999006409A1/fr active IP Right Grant
- 1998-07-24 DE DE69826487T patent/DE69826487T2/de not_active Expired - Fee Related
- 1998-07-24 CN CNB988096412A patent/CN1183134C/zh not_active Expired - Fee Related
- 1998-07-24 PT PT98938017T patent/PT1000062E/pt unknown
- 1998-07-28 TW TW087112353A patent/TW502035B/zh not_active IP Right Cessation
- 1998-07-29 AR ARP980103736A patent/AR016557A1/es unknown
- 1998-07-29 ZA ZA9806784A patent/ZA986784B/xx unknown
2000
- 2000-01-18 NO NO20000242A patent/NO315273B1/no unknown

Also Published As

Publication number	Publication date
HUP0002480A2 (hu)	2000-11-28
NO20000242D0 (no)	2000-01-18
CA2297406C (fr)	2009-02-24
PT1000062E (pt)	2004-12-31
KR20010022398A (ko)	2001-03-15
NZ502449A (en)	2002-08-28
EP1000062A1 (fr)	2000-05-17
JP4338305B2 (ja)	2009-10-07
EP1000062B1 (fr)	2004-09-22
ES2229525T3 (es)	2005-04-16
SI1000062T1 (en)	2004-12-31
NO20000242L (no)	2000-03-06
CA2297406A1 (fr)	1999-02-11
DE69826487T2 (de)	2005-12-01
HUP0002480A3 (en)	2002-09-30
ATE277050T1 (de)	2004-10-15
IL133788A0 (en)	2001-04-30
BR9811585A (pt)	2000-09-26
TW502035B (en)	2002-09-11
CN1183134C (zh)	2005-01-05
CN1272111A (zh)	2000-11-01
DK1000062T3 (da)	2004-11-22
JP2001512125A (ja)	2001-08-21
WO1999006409A1 (fr)	1999-02-11
ZA986784B (en)	2000-06-22
AR016557A1 (es)	2001-07-25
AU8663398A (en)	1999-02-22
AU756959B2 (en)	2003-01-30
KR100580805B1 (ko)	2006-05-17
DE69826487D1 (de)	2004-10-28
RU2213094C2 (ru)	2003-09-27

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