15-Deoxy-16-hydroxy-17-methylene prostaglandins of the E and F series
AssigneeAmerican Cyanamid Company
InventorAllan Wissner
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Abstract
The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E and F series wherein C-16 is substituted with hydroxy and methyl and a double bond is introduced between C-19 and C-20. These compounds are active as bronchodilators, anti-ulcer agents and fertility control agents.
Claims11
An optically active compound of the formula:
- ##STR15## wherein X is:
- ##STR16## Y is:
- ##STR17## 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 hydrogen, methyl or ethyl;
- R.sub.4 is hydrogen or C.sub.1 to C.sub.3 alkyl;
- Z is selected from the group consisting of a divalent moiety of the formula--(CH.sub.2).sub.n --,--(CH.sub.2).sub.m OCH.sub.2 --, and--(CH.sub.2).sub.m SCH.sub.2 --, wherein n is 5 to 7, and m is 3 to 5, and the racemic mixture thereof, and when R.sub.1 is hydrogen, the pharmaceutically acceptable salts thereof.
The racemic compounds according to claim 3, 11.alpha.,16.alpha./.beta.-dihydroxy-9-oxo-17-methylene-13-trans-prostenoi c acid, the individual 16.alpha.- and 16.beta.-hydroxy racemates, and the methyl esters thereof.
The racemic compounds according to claim 4, 11.alpha.,16.alpha./.beta.-dihydroxy-9-oxo-16-methyl-17-methylene-13-trans -prostenoic acid, the individual 16.alpha.- and 16.beta.-hydroxy racemates and the methyl esters thereof.
The racemic compounds according to claim 4, 11.alpha.,16.alpha./.beta.-dihydroxy-9-oxo-16-ethyl-17-methylene-13-trans- prostenoic acid, the individual 16.alpha.- and 16.beta.-hydroxy racemates and the methyl esters thereof.
Dependencies are inferred from the claim text.