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US 4,284,792 AGranted
19-Hydroxy-19-methyl-inter-phenylene-PG.sub.1 compounds
AssigneeThe Upjohn Company
InventorJohn C. Sih
Life of this patent
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Abstract
The present invention provides novel 19-hydroxy-19-methyl-inter-phenylene-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
Drawings
Claims2
A compound of the formula ##STR2## wherein D is (1) --(m--Ph)--(CH.sub.2).sub.2 --, or
- (2) --(m--Ph)--O--CH.sub.2 --,
- wherein --(m--Ph)-- is inter-meta-phenylene, and
- wherein Q is .alpha.-OH:.beta.-R.sub.5 or .alpha.-R.sub.5 :.beta.-OH, wherein R.sub.5 is hydrogen or methyl;
- wherein R.sub.6 is
- (a) hydrogen,
- (b) alkyl of one to 12 carbon atoms, inclusive,
- (c) cycloalkyl of 3 to 10 carbon atoms, inclusive,
- (d) aralkyl of 7 to 12 carbon atoms, inclusive,
- (e) phenyl,
- (f) phenyl substituted with one, 2, or 3 chloro or alkyl groups of one to 3 carbon atoms, inclusive,
- (g) --(p--Ph)--CO--CH.sub.3,
- (h) --(p--Ph)--NH--CO--(p--Ph)--NH--CO--CH.sub.3,
- (i) --(p--Ph)--NH--CO--(p--Ph),
- (j) --(p--Ph)--NH--CO--CH.sub.3,
- (k) --(p--Ph)--NH--CO--NH.sub.2,
- (l) --(p--Ph)--CH.dbd.N--NH--CO--NH.sub.2,
- (m) .beta.-naphthyl,
- (n) --CH.sub.2 --CO--R.sub.28,
- wherein (p--Ph) is para-phenyl or inter-para-phenylene,
- wherein R.sub.28 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, or
- (o) a pharmacologically acceptable cation;
- wherein R.sub.2 is hydrogen, hydroxyl, or hydroxymethyl;
- wherein R.sub.3 and R.sub.4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R.sub.3 and R.sub.4 is fluoro only when the other is hydrogen or fluoro;
- wherein W is oxo, methylene, .alpha.-OH:.beta.-H, or .alpha.-H:.beta.-OH;
- and
- wherein X is cis- or trans--CH.dbd.CH-- or --C.tbd.C--.
23 more elements
Dependencies are inferred from the claim text.