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| [1-Hydroximino-2,2-disubstituted-5-indanyloxy-(or thio)]alkanoic acids |
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Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids
| Details |
Inventors: Hoefle, Milton L.; Bobowski, George;
Assignee: Warner-Lambert Company (Morris Plains, NJ)
Primary Examiner: Daus; Donald G.
Assistant Examiner: Turnipseed; James H.
Attorney, Agent or Firm: Patton; Walter
Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acid and the pharmaceutically acceptable salts thereof are produced by acylating a suitably substituted octahydro-1H-indole with a suitably activated substituted carboxylic acid and when desired hydrolyzing the resulting product. The compounds of the invention, their salts and pharmaceutical compositions thereof are useful as antihypertensive agents. |
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DETAILED DESCRIPTION The invention relates to octahydro-1-(.
omega.
-mercaptoalkanoyl)-1H-indole-2-carboxylic acid compounds having the formula ##STR1## wherein R is hydrogen or lower alkyl; R.
sub.
1 is hydrogen, lower alkyl, or benzyl; R.
sub.
2 is hydrogen or ##STR2## where R.
sub.
3 is lower alkyl, heteroaryl containing 4 to 9 carbon atoms and one or two nitrogen, oxygen or sulfur atoms; phenyl having 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, lower alkyl, or lower alkoxy; and n is 0 or 1 and pharmaceutically acceptable salts of the compounds when R is hydrogen and when R.
sub.
3 is heteroaryl containing 1 or 2 nitrogen atoms.
The terms lower alkyl and lower alkoxy include groups having straight or branched chains and containing 1 to 4 carbon atoms.
The invention further relates to substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acid compounds having the formula ##STR3## and pharmaceutically acceptable salts thereof therein R.
sub.
4 and R.
sub.
6 are hydrogen or lower alkyl, R.
sub.
5 is hydrogen, lower alkyl or benzyl; Ar is phenyl or phenyl substituted with 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, lower alkyl, lower alkoxy, hydroxy or amino; and m is 0 to 3.
The terms lower alkyl and lower alkoxy include groups having straight or branched chains and containing 1 to 4 carbon atoms.
Preferred compounds of the invention are octahydro-1-(.
omega.
-mercaptoalkanoyl)-1H-indole-2-carboxylic acids having the formula ##STR4## and pharmaceutically acceptable salts thereof; where R.
sub.
1 is hydrogen or lower alkyl containing 1 to 3 carbon atoms; R.
sub.
2 is hydrogen or ##STR5## where R.
sub.
3 is lower alkyl containing 1 to 3 carbon atoms, phenyl, furyl, benzo(b)furyl, thienyl, benzo(b)thienyl, pyridyl, quinolyl or isoquinolyl; and n is 0 or 1.
Further preferred compounds of the invention are octahydro-1-(3-mercaptopropanoyl)-1H-indole-2-carboxylic acids having the formula ##STR6## and pharmaceutically acceptable basic salts thereof; where R
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