15-Deoxy-16-hydroxy-16-fluoromethyl, difluoromethyl or trifluoromethyl prostaglandins of the E and F series
AssigneeAmerican Cyanamid Company
InventorsSow-Mei L. Chen, Charles V. Grudzinskas
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Abstract
The invention disclosed herein relates to pharmacologically active prostaglandins of the E and F series in which C-16 is substituted with hydroxyl and fluoromethyl, difluoromethyl or trifluoromethyl as well as the pharmacologically acceptable, non-toxic lower alkyl esters and salts thereof, and to the intermediates and processes for producing such compounds.
Claims12
An optically active compound of the formula:
- ##STR18## wherein Y is ##STR19## X is:
- ##STR20## R.sub.1 is hydrogen or hydroxyl;
- R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl;
- R.sub.3 is --CH.sub.2 F, --CHF.sub.2, and --CF.sub.3 ;
- R.sub.4 is hydrogen, and C.sub.1 to C.sub.3 alkyl;
- Z is ##STR21## wherein p is 3 to 5, and the racemic mixture thereof;
- and when R.sub.1 is hydrogen, the pharmaceutically acceptable salts thereof.
The racemic compound according to claim 2, 11.alpha., 16.alpha./.beta.-dihydroxy-9-oxo-16-fluoromethyl-5-cis-13-transprostadieno ic acid, the individual 16.alpha. and 16.beta.-hydroxy racemates and the methyl esters thereof.
The racemic compounds according to claim 2, 11.alpha.,16.alpha./.beta.-dihydroxy-9-oxo-16-difluoromethyl-5-cis-13-tran s-prostadienoic acid, the individual 16.alpha.and 16.beta.-hydroxy racemates, and the methyl esters thereof.
The racemic compounds according to claim 2, 11.alpha.,16.alpha./.beta.-dihydroxy-9-oxo-16-trifluoromethyl-5-cis-13-tra ns prostadienoic acid, the individual 16.alpha. and 16.beta.-hydroxy racemates, and the methyl esters thereof.
Dependencies are inferred from the claim text.