Hydroxylated 15-deoxy derivatives of 9-hydroxyl-13-trans-prostenoic acid
AssigneeAmerican Cyanamid Company
InventorsMiddleton Brawner Floyd, Jr., William James McGahren, Robert Eugene Schaub, Martin Joseph Weiss
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Abstract
This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators; hypotensive agents, anti-ulcer agents, or as intermediates.
Claims48
An optically active compound of the formula:
- ##STR57## or a racemic compound of that formula and the mirror image thereof wherein R.sub.1 is selected from the group consisting of hydroxy, [lower alkoxy, tetrahydropyranyloxy, lower alkanoyloxy,] methoxy, ethoxy and .omega.-hydroxy substituted [lower] alkoxy [and .omega.-tetrahydropyranyloxy substituted lower alkoxy] having from 2 to 4 carbon atoms;
- R.sub.2 is a moiety selected from the group consisting of those of the formulae:
- ##STR58## wherein R' is selected from the group consisting of [a straight chain alkyl group having from 2 to 10 carbon atoms and a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms] n-propyl, n-butyl and n-pentyl , and R" is a moiety selected from the group consisting of [a straight chain alkyl group having from 2 to 10 carbon atoms and substituted with an hydroxy group, a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms and substituted with an hydroxy group, a straight chain alkenyl group having from 2 to 10 carbon atoms and substituted with an hydroxy group and a straight chain alkenyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms and substituted with an hydroxy group;] those of the formulae:
- ##STR59## wherein m is an integer from 3 to 5, inclusive, p is an integer from 1 to 3, inclusive, q is zero, 1 or 2, and y is ##STR60## R.sub.3 is selected from the group consisting of hydroxy [,] and alkoxy having from 1 to [12] 4 carbon atoms [and tetrahydropyranyloxy];
- and Z is a divalent radical selected from the group consisting of those of the formulae:
- ##STR61## wherein n is an integer from [3] 6 to 8, inclusive [, R.sub.4 is an alkyl group having up to 3 carbon atoms, and R.sub.5 is selected from the group consisting of an alkyl group having up to 3 carbon atoms, a fluorine atom and a phenyl group];
- and the pharmacologically acceptable cationic salts thereof when R.sub.3 is hydroxy.
The optically active compound ethyl l-9-oxo-11.alpha.,16-dihydroxy-17-methyl-13-transprostenoate.
The racemic compound ethyl dl-9-oxo-11.alpha.,16-dihydroxy-17-methyl-13-transprostenoate.
The optically active compound l-9-oxo-11.alpha.,16-dihydroxy-17-methyl-13-trans-prostenoic acid.
The racemic compound dl-9-oxo-11.alpha.,16-dihydroxy-17-methyl-13-trans-prostenoic acid.
The optically active compound l-9-oxo-11.alpha.-hydroxy-16-hydroxy-17-methyl-19,20-dinor-13-trans-proste noic acid.
The racemic compound dl-9-oxo-11.alpha.-hydroxy-16-hydroxy-17-methyl-19,20-dinor-13-trans-prost enoic acid.
The optically active compound l-9-oxo-11.alpha.-hydroxy-16-hydroxy-17-ethyl-20-nor-13-trans-prostenoic
- acid.
The racemic compound dl-9-oxo-11.alpha.-hydroxy-16-hydroxy-17-ethyl-20-nor-13-trans-prostenoic acid.
Dependencies are inferred from the claim text.