Benzimidazoles useful as angiotensin-11 antagonists
AssigneeDr. Karl Thomae GmbH
InventorsNorbert Hauel, Berthold Narr, deceased, Uwe Ries, Jacobus C. A. van Meel, Wolfgang Wienen, Michael Entzeroth
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Abstract
Disclosed herein are angiotensin-II antagonists of the formula ##STR1## wherein R.sub.1 is, other than hydrogen and, inter alia, halogen, lower alkyl or cycloalkyl; R.sub.2 is, inter alia, optionally substituted benzimidazol-2-yl, 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-2-yl, butanesultam-1-yl, imidazol-4-yl, and tetrahydobenzimidazol-2-yl; R.sub.3 is, inter alia, lower alkyl; and, R.sub.4 is an acidic group, such as carboxyl or tetrazolyl. An exemplary compound is: (a) 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazole-2-yl)-benzimidazol-1-yl] methyl]-biphenyl-2-carboxylic acid.
Claims8
A compound of the formula I ##STR30## wherein R.sub.1 is in the 4-position and represents a C1-4-alkyl, C.sub.3-7 -cycloalkyl or trifluoromethyl group,
- R.sub.2 represents a benzimidazol-2-yl group optionally substituted in the 1-position by C.sub.1-6 -alkyl or C.sub.3-7 -cycloalkyl group, whilst the phenyl nucleus of the above-mentioned benzimidazole groups may additionally be substituted by a fluorine atom or by a methyl or trifluoromethyl group,
- R.sub.3 represents a C.sub.1-5 -alkyl group or cyclopropyl, and
- R.sub.4 denotes a 1H-tetrazolyl group or an R.sub.a O--CO-- group, wherein
- R.sub.a denotes a hydrogen atom or a straight-chained or branched C.sub.1-4 -alkyl group,
- or a pharmaceutically acceptable salt thereof.
A compound selected from the group consisting of:
- (a) 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]- methyl]-biphenyl-2-carboxylic acid,
- (b) 4'-[[2-n-propyl-4-methyl-6-(1 -methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-2-(1H-tetrazol-5-yl)- biphenyl,
- (c) 4'-[(2-n-propyl-4-methyl-6-(1-methyl-5-fluoro-benzimidazol-2-yl)-benzimida zol-1-yl)-methyl]-biphenyl-2-carboxylic acid,
- (d) 4'-[[2-n-butyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-m ethyl]-2-(1H-tetrazol-5-yl)-biphenyl,
- (e) 4'-[[2-n-propyl-4-methyl-6-(1-methyl-6-fluoro-benzimidazol-2-yl)-benzimida zol-1-yl]-methyl]-biphenyl-2-carboxylic acid,
- (f) 4'-[(2-ethyl-4-methyl-6-(1-methyl-5-fluoro-benzimidazol-2-yl)-benzimidazol -1-yl)-methyl]-biphenyl-2-carboxylic acid,
- and pharmaceutically acceptable salts thereof.
4'-[[2-n-Propyl-4-methyl-6-(1-methylbenzimi dazole-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylic acid or a pharmaceutically acceptable salt thereof.
4'-[[2-n-Propyl-4-methyl-6-(1-methylben zimidazol-2-yl)-benzimidazol-1-yl]-methyl]-2-(1H-tetrazol-5-yl)-biphenyl or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.