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US 4,206,151 AGranted
15-Deoxy-16-hydroxy-16-vinyl or cyclopropyl prostan-1-ols of the E, A and F series
AssigneeAmerican Cyanamid Company
InventorCharles V. Grudzinskas
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Abstract
This disclosure describes novel 15-deoxy-16 hydroxy-16-substituted prostanoic acid analogs in which the C-1 carboxyl is replaced by a primary alcohol and carboxylic acid esters, carbonates and carbomates thereof. The prostanoic carbinols and carboxylic acid esters thereof described herein have utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
Claims37
An optically active compound of the formula:
- ##STR23## wherein Q is a divalent cyclopentyl moiety selected from the group consisting of:
- ##STR24## wherein R.sub.1 is an alkyl (C.sub.3 -C.sub.7) optionally substituted with one or more alkyl groups of one to three carbon atoms;
- R.sub.2 is selected from the group comprising hydroxyl, alkoxyl, alkanoyloxy, a protecting group such as tetrahydropyran-2-yl-oxy, triloweralkylsilyloxy;
- or alkoxyalkoxy such as ##STR25## wherein R' is hydrogen or alkyl (C.sub.1 -C.sub.4) and R" is alkyl (C.sub.1 -C.sub.4);
- X is a divalent radical ##STR26## wherein R.sub.3 is selected from the group comprising vinyl and cyclopropyl;
- Z is selected from the group consisting --(CH.sub.2).sub.4 and ##STR27## and W is selected from the group consisting of --(CH.sub.2).sub.3 --OH and ##STR28## wherein R.sub.4 is selected from the group comprising alkyl (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4);
- dialkylamino (C.sub.1 -C.sub.4);
- phenyl and phenyl substituted with one or more substituents selected from the group consisting of hydrogen, hydroxyl, lower alkyl, loweralkoxy, loweralkylthia, fluoride or chloride, wherein loweralkyl is C.sub.1 -C.sub.4 ;
- the racemic mixtures thereof, the mirror images thereof.
6 more elements
Dependencies are inferred from the claim text.