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US 3,944,593 AGranted
3-Oxa prostaglandin E-type compounds
AssigneeThe Upjohn Company
InventorNorman A. Nelson
Life of this patent
Estimating the term…
Abstract
This invention is a group of 3-oxa PGE-type compounds, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including antiulcer, inhibition and platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
Claims70
An optically active compound of the formula:
- ##SPC34##
- or a racemic compound of that formula and the mirror image thereof, wherein C.sub.n H.sub.2n is alkylene of one to 10 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, between --CH.sub.2 -- and --O--;
- wherein Q is ##EQU95## wherein R.sub.3 is hydrogen or methyl;
- wherein R.sub.1 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro;
- wherein R.sub.2 is ##EQU96## wherein R.sub.4 is hydrogen or fluoro and g is one, 2, 3, 4, or 5;
- and wherein R.sub.5, R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- including the lower akanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
4 more elements
An optically active compound of the formula:
- ##SPC35##
- or a racemic compound of that formula and the mirror image thereof, wherein C.sub.p H.sub.2p is alkylene of one to 8 carbon atoms, inclusive, with one, 2, or 3 carbon atoms, between --CH=CH-- and --O--;
- wherein Q is ##EQU99## wherein R.sub.3 is hydrogen or methyl;
- wherein R.sub.1 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro;
- wherein R.sub.2 is ##EQU100## wherein R.sub.4 is hydrogen or fluoro and g is one, 2, 3, 4, or 5;
- and wherein R.sub.5 and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
4 more elements
An optically active compound of the formula:
- ##SPC36##
- or a racemic compound of that formula and the mirror image thereof, wherein C.sub.p H.sub.2p is alkylene of one to 8 carbon atoms, inclusive, with one, 2, or 3 carbon atoms, between --C.tbd.C-- and --O--;
- wherein Q is ##EQU103## wherein R.sub.3 is hydrogen or methyl;
- wherein R.sub.1 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro;
- wherein R.sub.2 is ##EQU104## wherein R.sub.4 is hydrogen or fluoro and g is one, 2, 3, 4, or 5;
- and wherein R.sub.5 and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms inclusive;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
4 more elements
An optically active compound of the formula:
- ##SPC37##
- or a racemic compound of that formula and the mirror image thereof, wherein C.sub.n H.sub.2n is alkylene of one to 10 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, between --CH.sub.2 -- and --O--;
- wherein Q is ##EQU107## wherein R.sub.3 is hydrogen or methyl;
- wherein R.sub.1 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro;
- wherein R.sub.2 is ##EQU108## wherein R.sub.4 is hydrogen or fluoro and g is one, 2, 3, 4, or 5;
- and wherein R.sub.5 and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive, including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
3 more elements
An optically active compound of the formula:
- ##SPC38##
- or a racemic compound of that formula and the mirror image thereof, wherein C.sub.j H.sub.2j is alkylene of one to 4 carbon atoms, inclusive;
- wherein C.sub.p H.sub.2p is alkylene of one to 8 carbon atoms, inclusive, with one, 2, or 3 carbon atoms between ##EQU111## and --O--;
- wherein Q is ##EQU112## wherein R.sub.3 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.1 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the beta position with 3 chloro;
- wherein R.sub.9 is alkyl of one to 4 carbon atoms, inclusive, substituted with zero, one, 2, or 3 fluoro;
- and wherein R.sub.5 and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
4 more elements
Dependencies are inferred from the claim text.