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US 4,289,893 AGranted
2,5-Inter-O-phenylene-3,4-dinor-PGF.sub.2 compounds
AssigneeThe Upjohn Company
InventorsUdo F. Axen, John C. Sih
Life of this patent
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Abstract
The present invention provides 2,5-inter-o-phenylene-3,4-dinor-PGF.sub.2 compounds. These compounds are intermediates for preparing 2,5-inter-o-phenylene-3,4-dinor-prostacyclin analogs, which are useful for pharmacological purposes, e.g., as antithrombotic agents.
Claims1
A prostacyclin intermediate of formula VII
- wherein
- R.sub.8 is hydrogen, hydroxy, or hydroxymethyl;
- wherein Y.sub.1 is
- (1) trans--CH.dbd.CH--,
- (2) cis--CH.dbd.CH--,
- (3) --CH.sub.2 CH.sub.2 --, or
- (4) --C.tbd.C--,
- wherein M.sub.1 is .alpha.-R.sub.5 :.beta.-OH or .alpha.OH-.beta.-R.sub.5, wherein R.sub.5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive,
- wherein L.sub.1 is .alpha.R.sub.3 :.beta.-R.sub.4, .alpha.-R.sub.4 :.beta.-R.sub.3, or a mixture of .alpha.-R.sub.3 :.beta.-R.sub.4 and .alpha.R.sub.4 :.beta.-R.sub.3, 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 R.sub.7 is
- (1) --(CH.sub.2).sub.m -CH.sub.3, wherein m is an integer from one to 5, inclusive;
- (2) phenoxy;
- (3) phenoxy substituted by one, 2 or 3 chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, with the proviso that not more than two substituents are other than alkyl;
- (4) phenyl;
- (5) phenyl substituted by one, 2 or 3 chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, with the proviso that not more than two substituents are other than alkyl;
- (6) phenylmethyl, phenylethyl, or phenylpropyl;
- or
- (7) phenylmethyl, phenylethyl, or phenylpropyl substituted by one, two or three chloro, fluoro, trifluoromethyl, alkyl or one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, with the proviso that not more than two substituents are other than alkyl;
- with the proviso that R.sub.7 is phenoxy or substituted phenoxy, only when R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different;
- wherein R.sub.1 is
- (1) hydrogen;
- (2) alkyl of one to 12 carbon atoms, inclusive;
- (3) cycloalkyl of 3 to 10 carbon atoms, inclusive;
- (4) aralkyl of 7 to 12 carbon atoms, inclusive;
- (5) phenyl;
- (6) phenyl substituted with one, 2 or 3 chloro or alkyl of one to 3 carbon atoms;
- (7) phenyl substituted in the para position by
- (a) --NH--CO--R.sub.25,
- (b) --CO--R.sub.26,
- (c) --O--CO--R.sub.27, or
- (d) --CH.dbd.N--NH--CO--NH.sub.2,
- wherein R.sub.25 is methyl, phenyl, acetamidophenyl, benzamidophenyl, or --NH.sub.2 ;
- R.sub.26 is hydroxy, methyl, phenyl, --NH.sub.2, or methoxy;
- and R.sub.27 is phenyl or acetaminophenyl, inclusive, or a pharmacologically acceptable salt thereof when R.sub.1 is hydrogen.
31 more elements
Dependencies are inferred from the claim text.