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US 4,363,817 AGranted
Enol acylate analogs of E.sub.1 and E.sub.2 prostaglandins
AssigneeMiles Laboratories, Inc.
InventorWilliam G. Biddlecom
Life of this patent
Estimating the term…
Abstract
Disclosed are C-9 enol acylate analogs of E.sub.1 and E.sub.2 prostaglandins which are variously useful as bronchodilators, gastric anti-secretory agents and cyto-protective agents.
Claims38
Prostaglandin C-9 enol acylate analogs characterized by the formula:
- ##STR39## wherein:
- the dashed line in the cyclopentyl ring represents the presence of a double carbon-carbon bond at either C.sub.8 -C.sub.9 or C.sub.9 -C.sub.10 ;
- Z is cis vinylene or ethylene;
- n is 0 or 1;
- A represents the presence of a single carbon-carbon bond between C.sub.7 and C.sub.8 which is in the .alpha. configuration when there is a double carbon-carbon bond between C.sub.9 and C.sub.10 and is in the plane of the 5 membered ring when there is a double carbon-carbon bond between C.sub.8 and C.sub.9 ;
- X is CH.sub.2 OH, CH.sub.2 OCOCH.sub.3, CONHR.sub.4, CO.sub.2 M where M is H.sup.+, K.sup.+, 1/2 Ca.sup.++, NH.sub.3.sup.+ C (C.sub.2 H.sub.5 OH).sub.3 or another pharmacologically acceptable salt cation, CH.sub.3 or C.sub.2 H.sub.5 ;
- R.sub.1 is n-alkyl of 1 to 20 carbon atoms which is optionally replaced with oxa groups, cyclic alkyl or 3 to 12 carbon atoms optionally replaced with nitrogen to form an imido group of the formula ##STR40## bicyclic alkyl of 7 to 12 carbon atoms, aryl of 6 to 12 carbon atoms optionally substituted with an n-alkyl group of 1 to 10 carbon atoms or one or more halogen atoms, alkenyl (Z and/or E) of 2 to 12 carbon atoms, alkenyl-alkyl of 3 to 12 carbon atoms or O-n-alkyl of 1 to 20 carbon atoms wherein all of the above are optionally substituted with CO.sub.2 M, CONHR.sub.4 or acetate;
- R.sub.2 is H, n-alkyl of 1 to 10 carbon atoms, branched alkyl of 3 to 10 carbon atoms, cyclic alkyl of 3 to 10 carbon atoms optionally substituted with n-alkyl of 1 to 10 carbon atoms, bicyclic alkyl of 7 to 12 carbon atoms, aryl of 6 to 12 carbon atoms optionally substituted with n-alkyl of 1 to 10 carbon atoms or halogen, R.sub.3 is a moiety coming within the definition of R.sub.2 except that R.sub.3 is not H;
- and R.sub.4 is H or a moiety coming within the definition of COR.sub.1.
6 more elements
A method of inhibiting the formation of lesions in the gastrointestinal tract of an individual which method involves introducing to the gastro-intestinal tract of such individual a lesion inhibiting (cytoprotective) amount of 9-acetoxy-16-methyl-1, 11.alpha.,16RS-trihydroxy-prosta-9,13E-diene.
Dependencies are inferred from the claim text.