WO1996039391B1 - Derives de styryl benzimidazole inhibiteurs de la proliferation des cellules musculaires lisses - Google Patents
Derives de styryl benzimidazole inhibiteurs de la proliferation des cellules musculaires lissesInfo
- Publication number
- WO1996039391B1 WO1996039391B1 PCT/US1996/008375 US9608375W WO9639391B1 WO 1996039391 B1 WO1996039391 B1 WO 1996039391B1 US 9608375 W US9608375 W US 9608375W WO 9639391 B1 WO9639391 B1 WO 9639391B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- compound
- hydrogen
- alkyl
- pharmaceutically acceptable
- Prior art date
Links
- 230000004663 cell proliferation Effects 0.000 title claims abstract 8
- 210000000329 smooth muscle myocyte Anatomy 0.000 title claims abstract 8
- 239000003112 inhibitor Substances 0.000 title abstract 2
- QQLPPRIZUPEKMV-UHFFFAOYSA-N 2-(2-phenylethenyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1C=CC1=CC=CC=C1 QQLPPRIZUPEKMV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 27
- 239000001257 hydrogen Substances 0.000 claims abstract 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- 150000002431 hydrogen Chemical class 0.000 claims abstract 20
- 150000003839 salts Chemical class 0.000 claims abstract 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 10
- 150000002367 halogens Chemical class 0.000 claims abstract 10
- -1 nitro, carboxyl Chemical group 0.000 claims abstract 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims abstract 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000002541 furyl group Chemical group 0.000 claims abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 53
- 241000124008 Mammalia Species 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 238000002399 angioplasty Methods 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- GQIFVGIZDNGSCZ-CSKARUKUSA-N 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C1=NC2=CC=CC=C2N1 GQIFVGIZDNGSCZ-CSKARUKUSA-N 0.000 claims 1
- RBGOSUBTEIUSSA-XBXARRHUSA-N 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C1=NC2=CC(C(O)=O)=CC=C2N1 RBGOSUBTEIUSSA-XBXARRHUSA-N 0.000 claims 1
- VEIKFDKHUBMRBI-XBXARRHUSA-N 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-6-nitro-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C1=NC2=CC=C([N+]([O-])=O)C=C2N1 VEIKFDKHUBMRBI-XBXARRHUSA-N 0.000 claims 1
- ZUMIBXPTGMOQDK-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)ethenyl]-1h-benzimidazole Chemical group ClC1=CC(Cl)=CC=C1C=CC1=NC2=CC=CC=C2N1 ZUMIBXPTGMOQDK-UHFFFAOYSA-N 0.000 claims 1
- GQIFVGIZDNGSCZ-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC2=CC=CC=C2N1 GQIFVGIZDNGSCZ-UHFFFAOYSA-N 0.000 claims 1
- LCBMHTYNXWUSPE-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,7-dimethoxy-5,6-dimethyl-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC2=C(OC)C(C)=C(C)C(OC)=C2N1 LCBMHTYNXWUSPE-UHFFFAOYSA-N 0.000 claims 1
- FMNIIPCIVIAMRR-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-5,6-dimethyl-1h-benzimidazole-4,7-dione Chemical compound C1=C(OC)C(OC)=CC=C1C=CC1=NC(C(C(C)=C(C)C2=O)=O)=C2N1 FMNIIPCIVIAMRR-UHFFFAOYSA-N 0.000 claims 1
- DWRQQZSAQGSHFJ-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxy-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1C=CC1=CC=C(OC)C(OC)=C1 DWRQQZSAQGSHFJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- XTAPZTRJPVKGEV-DAFODLJHSA-N 6-nitro-2-[(e)-2-pyridin-4-ylethenyl]-1h-benzimidazole Chemical compound N=1C2=CC([N+](=O)[O-])=CC=C2NC=1\C=C\C1=CC=NC=C1 XTAPZTRJPVKGEV-DAFODLJHSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- VZFYIURHZDVBMS-WEVVVXLNSA-N methyl 2-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-3h-benzimidazole-5-carboxylate Chemical compound N=1C2=CC(C(=O)OC)=CC=C2NC=1\C=C\C1=CC=C(OC)C(OC)=C1 VZFYIURHZDVBMS-WEVVVXLNSA-N 0.000 claims 1
- GDBDEXWEXJJQCV-UHFFFAOYSA-N methyl 4-[[2-[2-(3,4-dimethoxyphenyl)ethenyl]-4,7-dimethoxy-5,6-dimethylbenzimidazol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C2=C(OC)C(C)=C(C)C(OC)=C2N=C1C=CC1=CC=C(OC)C(OC)=C1 GDBDEXWEXJJQCV-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Abstract
Composés de formule (I) ou (II), dans lesquelles R est phényle ou phényle substitué; ou R est furyle, pyridyle ou quinolinyle; R1 et R2 sont hydrogène, halogène, alkyle, alcoxy, nitro, carboxyle, alcoxy-carbonyle ou aryloxycarbonyle; R3 est hydrogène, alkyle, aryle ou arylalkyle; R4 et R5 sont hydrogène ou alkyle; ou leur sel pharmaceutiquement acceptable, servant d'inhibiteurs de la prolifération des cellules musculaires lisses.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT96916978T ATE205196T1 (de) | 1995-06-06 | 1996-06-03 | Styrylbenzimidazolderivate als inhibitoren der glatten muskelzellenproliferation |
| BR9609153A BR9609153A (pt) | 1995-06-06 | 1996-06-03 | Derivados de estiril-benzimidazol como inibidores da proliferação de celula de musculo liso |
| NZ309499A NZ309499A (en) | 1995-06-06 | 1996-06-03 | Styryl benzimidazole derivatives useful as inhibitors of smooth muscle cell proliferation |
| DE69615023T DE69615023T2 (de) | 1995-06-06 | 1996-06-03 | Styrylbenzimidazolderivate als inhibitoren der glatten muskelzellenproliferation |
| EP96916978A EP0830345B1 (fr) | 1995-06-06 | 1996-06-03 | Derives de styryl benzimidazole inhibiteurs de la proliferation des cellules musculaires lisses |
| JP9500994A JPH11506753A (ja) | 1995-06-06 | 1996-06-03 | 平滑筋細胞増殖の阻害薬としてのスチリルベンゾイミダゾール誘導体 |
| DK96916978T DK0830345T3 (da) | 1995-06-06 | 1996-06-03 | Styryl-benzimidazol-derivater som inhibitorer af glatmuskel-celleproliferation |
| AU59684/96A AU711965B2 (en) | 1995-06-06 | 1996-06-03 | Styryl benzimidazole derivatives as inhibitors of smooth muscle cell proliferation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/468,271 US6444694B1 (en) | 1995-06-06 | 1995-06-06 | Styryl benzimidazole derivatives |
| US08/468,271 | 1995-06-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996039391A1 WO1996039391A1 (fr) | 1996-12-12 |
| WO1996039391B1 true WO1996039391B1 (fr) | 1997-01-09 |
Family
ID=23859136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/008375 WO1996039391A1 (fr) | 1995-06-06 | 1996-06-03 | Derives de styryl benzimidazole inhibiteurs de la proliferation des cellules musculaires lisses |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6444694B1 (fr) |
| EP (1) | EP0830345B1 (fr) |
| JP (1) | JPH11506753A (fr) |
| KR (1) | KR19990022266A (fr) |
| CN (1) | CN1192206A (fr) |
| AR (1) | AR002749A1 (fr) |
| AT (1) | ATE205196T1 (fr) |
| AU (1) | AU711965B2 (fr) |
| BR (1) | BR9609153A (fr) |
| CA (1) | CA2223585A1 (fr) |
| DE (1) | DE69615023T2 (fr) |
| DK (1) | DK0830345T3 (fr) |
| ES (1) | ES2162063T3 (fr) |
| HU (2) | HUP9900914A2 (fr) |
| IL (1) | IL118385A0 (fr) |
| NZ (1) | NZ309499A (fr) |
| PT (1) | PT830345E (fr) |
| WO (1) | WO1996039391A1 (fr) |
| ZA (1) | ZA964693B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| EP2335700A1 (fr) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Inhibiteurs de la polymerase du virus hepatitis C avec une structure heterobicylic |
| US7098231B2 (en) | 2003-01-22 | 2006-08-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7223785B2 (en) | 2003-01-22 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| KR20120091276A (ko) | 2004-02-20 | 2012-08-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 바이러스 폴리머라제 억제제 |
| EP1915378A4 (fr) | 2005-08-12 | 2009-07-22 | Boehringer Ingelheim Int | Inhibiteurs de polymerase virale |
| CA2656851C (fr) | 2006-07-05 | 2013-12-10 | Fibrotech Therapeutics Pty Ltd | Composes d'anthranilate de cinnamoyle substitues presentant une activite anti-fibreuse |
| US9062076B2 (en) | 2009-10-22 | 2015-06-23 | Fibrotech Therapeutics Pty Ltd | Fused ring analogues of anti-fibrotic agents |
| EP3577103A1 (fr) | 2017-02-03 | 2019-12-11 | Certa Therapeutics Pty Ltd. | Composés anti-fibrotiques |
| KR102853258B1 (ko) * | 2023-06-20 | 2025-09-01 | 이원다이애그노믹스(주) | 암의 예방, 치료 또는 개선에 유효한 효과를 나타내는 신규한 화합물, 이의 제조방법 및 이를 유효 성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3575956A (en) * | 1967-07-24 | 1971-04-20 | Sterling Drug Inc | 2-substituted-benz-x-azol-6-ylazo-aminonaphthalene compounds |
| DE1670908A1 (de) * | 1967-08-16 | 1971-04-29 | Hoechst Ag | Neue Benzimidazolverbindungen,Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufhellungsmittel |
| FR2104717A1 (en) * | 1970-09-28 | 1972-04-21 | Dynachim Sarl | Organophosphorus pesticides stabilised with benzimidazole derivs - - for controlling insects and internal parasites of animals |
| DE3505609A1 (de) | 1985-02-19 | 1986-08-21 | Merck Patent Gmbh, 6100 Darmstadt | Benzimidazolyl-pyridazinone |
| US5196446A (en) | 1990-04-16 | 1993-03-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Certain indole compounds which inhibit EGF receptor tyrosine kinase |
| WO1991016305A1 (fr) | 1990-04-16 | 1991-10-31 | Rhone-Poulenc Rorer International (Holdings), Inc. | Composes d'ethenediyle heterocyclique qui inhibent la kinase de tyrosine de recepteur egf |
| DE4212748A1 (de) | 1992-04-16 | 1993-10-21 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5387600A (en) | 1992-07-30 | 1995-02-07 | Fuji Photo Film Co., Ltd. | Treating arteriosclerosis using benzimidazole compositions |
-
1995
- 1995-06-06 US US08/468,271 patent/US6444694B1/en not_active Expired - Fee Related
-
1996
- 1996-05-22 IL IL11838596A patent/IL118385A0/xx unknown
- 1996-05-30 AR ARP960102799A patent/AR002749A1/es unknown
- 1996-06-03 PT PT96916978T patent/PT830345E/pt unknown
- 1996-06-03 CN CN96195860A patent/CN1192206A/zh active Pending
- 1996-06-03 KR KR1019970708745A patent/KR19990022266A/ko not_active Withdrawn
- 1996-06-03 HU HU9900914A patent/HUP9900914A2/hu unknown
- 1996-06-03 DE DE69615023T patent/DE69615023T2/de not_active Expired - Fee Related
- 1996-06-03 AT AT96916978T patent/ATE205196T1/de not_active IP Right Cessation
- 1996-06-03 AU AU59684/96A patent/AU711965B2/en not_active Ceased
- 1996-06-03 HU HU9900679A patent/HUP9900679A3/hu unknown
- 1996-06-03 BR BR9609153A patent/BR9609153A/pt unknown
- 1996-06-03 JP JP9500994A patent/JPH11506753A/ja active Pending
- 1996-06-03 NZ NZ309499A patent/NZ309499A/xx unknown
- 1996-06-03 ES ES96916978T patent/ES2162063T3/es not_active Expired - Lifetime
- 1996-06-03 CA CA002223585A patent/CA2223585A1/fr not_active Abandoned
- 1996-06-03 DK DK96916978T patent/DK0830345T3/da active
- 1996-06-03 WO PCT/US1996/008375 patent/WO1996039391A1/fr not_active Application Discontinuation
- 1996-06-03 EP EP96916978A patent/EP0830345B1/fr not_active Expired - Lifetime
- 1996-06-05 ZA ZA9604693A patent/ZA964693B/xx unknown
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