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US 5,401,736 AGranted
4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid amide
AssigneeKureha Kagaku Kogyo Kabushiki Kaisha
InventorsHiroyuki Enari, Mikiro Yanaka
Life of this patent
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Abstract
Disclosed herein are 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid amide derivatives having a high antagonistic activity against angiotensin II and a high specificity to angiotensin II receptors, intermediates for preparing the derivatives, and antagonists against angiotensin II comprising the derivatives.
Claims7
A compound of the formula (I):
- ##STR50## or a pharmaceutically acceptable salt thereof;
- wherein R.sup.1 represents
- hydrogen atom,
- halogen atom,
- C.sub.1 -C.sub.6 alkyl,
- C.sub.3 -C.sub.6 alkenyl,
- C.sub.3 -C.sub.6 alkynyl,
- R.sup.20 (CH.sub.2).sub.n -- wherein R.sup.20 represents C.sub.3 -C.sub.8 cycloalkyl, naphthyl, phenyl, or phenyl substituted with one to five of C.sub.1 -C.sub.4 alkyl, halogen atom, trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.3 acyloxy, amino, N-mono-C.sub.1 -C.sub.4 alkylamino, N-di-C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 thioalkyl, C.sub.1 -C.sub.3 alkylsulfonyl, nitro, and --NHCOR.sup.21 wherein R.sup.21 represents C.sub.1 -C.sub.3 alkyl, phenyl, C.sub.1 -C.sub.3 alkylphenyl, aminophenyl, or C.sub.1 -C.sub.4 alkylaminophenyl, and n is an integer of 1 to 6,
- R.sup.20 --C(O)-- wherein R.sup.20 is as defined above, or
- R.sup.20 --CH(OH)-- wherein R.sup.20 is as defined above;
- R.sup.2 represents carbamoyl, mono- or di-C.sub.1 -C.sub.6 alkylcarbamoyl, or 4- to 6-membered saturated N, S or O-containing heterocyclic carbamoyl;
- R represents amino, carboxy, (1H-tetrazol-5-yl)phenyl, carboxyphenyl, carboxybenzamido, (1H-tetrazol-5-yl)benzamido, carboxyphenylcarbamoyl, or (1H-tetrazol-5-yl)-phenylcarbamoyl;
- represents --CH.sub.2 (phenyl), --CH(phenyl).sub.2, --CH(phenyl)CH.sub.3, --CH(phenyl)(cyclohexyl), --CH.sub.2 CH.sub.2 (phenyl), --CH.sub.2 (C.sub.1 -C.sub.6 alkoxyphenyl), or --CH.sub.2 (hydroxyphenyl);
- and
- R.sup.4, R.sup.7, and R.sup.8 each represent independently hydrogen atom or C.sub.1 -C.sub.6 alkyl.
12 more elements
A compound of the formula (XIII):
- ##STR52## or a salt thereof;
- wherein R.sup.1 represents
- hydrogen atom,
- halogen atom,
- C.sub.1 -C.sub.6 alkyl,
- C.sub.3 -C.sub.6 alkenyl,
- C.sub.3 -C.sub.6 alkynyl,
- R.sup.20 (CH.sub.2).sub.n -- wherein R.sup.20 represents C.sub.3 -C.sub.8 cycloalkyl, naphthyl, phenyl, or phenyl substituted with one to five of C.sub.1 -C.sub.4 alkyl, halogen atom, trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.3 acyloxy, amino, N-mono-C.sub.1 -C.sub.4 alkylamino, N-di-C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 thioalkyl, C.sub.1 -C.sub.3 alkylsulfonyl, nitro, and --NHCOR.sup.21 wherein R.sup.21 represents C.sub.1 -C.sub.3 alkyl, phenyl, C.sub.1 -C.sub.3 alkylphenyl, aminophenyl, or C.sub.1 -C.sub.4 alkylaminophenyl, and n is an integer of 1 to 6,
- R.sup.20 --C(O)-- wherein R.sup.20 is as defined above, or
- R.sup.20 --CH(OH)-- wherein R.sup.20 is as defined above;
- R.sup.2' represents amino, mono or di-C.sub.1 -C.sub.6 alkylamino, or 4- to 6-membered saturated N, S or O-containing heterocyclic amino;
- R.sup.3 represents --CH.sub.2 (phenyl), --CH(phenyl).sub.2, --CH(phenyl) CH.sub.3, --CH(phenyl)(cyclohexyl), --CH.sub.2 CH.sub.2 (phenyl), --CH.sub.2 (C.sub.1 -C.sub.6 alkoxyphenyl), or --CH.sub.2 (hydroxyphenyl);
- R.sup.4, R.sup.7, and R.sup.8 each represent independently hydrogen atom or C.sub.1 -C.sub.6 alkyl;
- and
- R.sup.6 represents nitro, (1-triphenylmethyl-1H-tetrazol-5-yl)phenyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano, or 2-cyanophenyl.
12 more elements
An angiotensin II AT.sub.1 receptor antagonist comprising a compound of the formula (I):
- ##STR54## or a pharmaceutically acceptable salt thereof;
- wherein R.sup.1 represents
- halogen atom,
- C.sub.1 -C.sub.6 alkyl,
- C.sub.3 -C.sub.6 alkenyl,
- C.sub.3 -C.sub.6 alkynyl,
- R.sup.20 (CH.sub.2).sub.n -- wherein R.sup.20 represents C.sub.3 -C.sub.8 cycloalkyl, naphthyl, phenyl, or phenyl substituted with one to five of C.sub.1 -C.sub.4 alkyl, halogen atom, trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.3 acyloxy, amino, N-mono-C.sub.1 -C.sub.4 alkylamino, N-di-C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 thioalkyl, C.sub.1 -C.sub.3 alkylsulfonyl, nitro, and --NHCOR.sup.21 wherein R.sup.21 represents C.sub.1 -C.sub.3 alkyl, phenyl, C.sub.1 -C.sub.3 alkylphenyl, aminophenyl, or C.sub.1 -C.sub.4 alkylaminophenyl, and n is an integer of 1 to 6,
- R.sup.20 --C(O)-- wherein R.sup.20 is as defined above, or
- R.sup.20 --CH(OH)-- wherein R.sup.20 is as defined above;
- R.sup.2 represents carbamoyl, mono- or di-C.sub.1 -C.sub.6 alkylcarbamoyl, or 4- to 6-membered saturated N, S, or O-containing heterocyclic carbamoyl;
- R represents amino, carboxy, (1H-tetrazol-5-yl)phenyl, carboxyphenyl, carboxybenzamido, (1H-tetrazol-5-yl)benzamido, carboxyphenylcarbamoyl, or (1H-tetrazol-5-yl)-phenylcarbamoyl;
- R.sup.3 represents --CH.sub.2 (phenyl), --CH(phenyl).sub.2, --CH(phenyl) CH.sub.3, --CH(phenyl)(cyclohexyl), --CH.sub.2 CH.sub.2 (phenyl), --CH.sub.2 (C.sub.1 -C.sub.6 alkoxyphenyl), or --CH.sub.2 (hydroxyphenyl);
- and
- R.sup.4 R.sup.7, and R.sup.8 each represent independently hydrogen atom or C.sub.1 -C.sub.6 alkyl.
11 more elements
An angiotensin II AT.sub.2 receptor antagonist comprising a compound of the formula (I):
- ##STR55## or a pharmaceutically acceptable salt thereof;
- wherein R.sup.1 represents hydrogen atom,
- R.sup.2 represents carbamoyl, mono- or di-C.sub.1 -C.sub.6 alkylcarbamoyl, or 4- to 6-membered saturated N, S, or O-containing heterocyclic carbamoyl;
- R represents amino, carboxy, (1H-tetrazol-5-yl)phenyl, carboxyphenyl, carboxybenzamido, (1H-tetrazol-5-yl)benzamido, carboxyphenylcarbamoyl, or (1H-tetrazol-5-yl)-phenylcarbamoyl;
- R.sup.3 represents --CH.sub.2 (phenyl), --CH(phenyl).sub.2, --CH(phenyl)CH.sub.3, --CH(phenyl)(cyclohexyl), --CH.sub.2 CH.sub.2 (phenyl), --CH.sub.2 (C.sub.1 -C.sub.6 alkoxyphenyl), or --CH.sub.2 (hydroxyphenyl);
- and
- R.sup.4, R.sup.7, and R.sup.8, each represent independently hydrogen atom or C.sub.1 -C.sub.6 alkyl.
4 more elements
Dependencies are inferred from the claim text.