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US 4,226,775 AGranted
Substituted thio-substituted benzyl-propionyl-L-prolines
AssigneeAmerican Cyanamid Company
InventorsFrancis J. McEvoy, Jay D. Albright
Life of this patent
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Abstract
This disclosure describes novel substituted .omega.-aroyl(propionyl or butyryl)-L-prolines and the esters and cationic salts thereof which are useful as hypotensive agents in mammals.
Claims26
A compound selected from the group consisting of those of the formulae:
- ##STR22## wherein n is zero or one;
- R.sub.1 is hydrogen or alkyl having up to 3 carbon atoms;
- R.sub.2 is hydrogen, phenyl or alkyl having up to 3 carbon atoms;
- R.sub.3 is mercapto, formylthio, benzoylthio, alkanolythio having from 2 to 4 carbon atoms or moieties of the formulae:
- ##STR23## wherein R.sub.9 is phenyl;
- R.sub.4 is hydrogen, phenyl or alkyl having up to 4 carbon atoms;
- R.sub.5 is hydrogen or alkyl having up to 4 carbon atoms;
- and ARYL is selected from the group consisting of 1-naphthyl, 2-naphthyl, 4-chloro-1-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 4-methoxy-1-naphthyl, 5-acenaphthyl, 4-biphenylyl, 5-indanyl, 4-indanyl and moieties of the formula:
- ##STR24## wherein R.sub.6 is selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl, cyano, amnio, phenoxy, halophenoxy, phenylthio, halophenylthio, p-cyclohexylphenoxy, alkyl having up to 4 carbon atoms, alkoxy having up to 4 carbon atoms, alkylamino having up to 4 carbon atoms, alkanoylamino having from 2 to 4 carbon atoms and alkoxycarbonyl having from 2 to 4 carbon atoms, R.sub.7 is selected from the group consisting of chloro, fluoro, bromo, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms, and m is zero, one or two;
- and the pharmacologically acceptable cationic salts thereof when R.sub.5 is hydrogen.
7 more elements
The compound according to clai 1, formula (III) thereof, wherein n is zero, R.sub.3 is acetylthio, ARYL is 4-chlorophenyl, R.sub.4 is methyl and R.sub.5 is hydrogen;
- 1-[3-acetylthio-3-(4-chlorobenzoyl)-2-methylpropionyl]-L-proline.
Dependencies are inferred from the claim text.