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US 4,227,011 AGranted
15-Deoxy-16-hydroxy-16-chloromethyl or bromomethyl prostaglandins of the E and F series
AssigneeAmerican Cyanamid Company
InventorsSow-Mei L. Chen, Charles V. Grudzinskas
Life of this patent
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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 chloromethyl or bromomethyl as well as the pharmacologically acceptable, nontoxic lower alkyl esters and salts thereof, and to the intermediates and processes for producing such compounds.
Claims5
An optically active compound of the formula:
- ##STR15## wherein Y is ##STR16## X 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 chloromethyl and bromomethyl;
- R.sub.4 is hydrogen and 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.
2 more elements
The racemic compounds according to claim 2, 11.alpha.,16-dihydroxy-9-oxo-16-chloromethyl-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.