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US 4,225,508 AGranted
19-Hydroxy-PGI.sub.2 compounds
AssigneeThe Upjohn Company
InventorJohn C. Sih
Life of this patent
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Abstract
Prostacyclin and prostacyclin-type derivatives having a 19-hydroxy feature are disclosed, including processes for preparing them and the appropriate intermediates. The compounds are useful for pharmacological purposes such as inhibition of blood platelate aggregation.
Claims12
A prostacyclin-type compound of the formula
- wherein A.sub.1 is --O--(oxa) and E.sub.1 is --CH.sub.2 --
- wherein L.sub.1 is
- (1) --(CH.sub.2).sub.n -- wherein n is one to 5, inclusor
- (2) --(CH.sub.2).sub.p --CF.sub.2 -- wherein P is 2, 3, or 4,
- wherein M.sub.1 is ##STR48## wherein .about. indicates attachment in alpha or beta configuration, wherein Q is ##STR49## wherein R.sub.4 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.1 is
- (1) --COOR.sub.3
- (2) --CH.sub.2 OH
- (3) --CH.sub.2 N(R.sub.7)(R.sub.8) ##STR50## wherein R.sub.3 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;
- ##STR51## wherein R.sub.16 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, or
- (o) a pharmacologically acceptable cation;
- wherein R.sub.7 and R.sub.8 are hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl, being the same or different, and wherein R.sub.15 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl groups of one to 3 carbon atoms, inclusive, or phenyl substituted with hydroxycarbonyl or alkoxycarbonyl of one to 4 carbon atoms, inclusive,
- wherein R.sub.2 is hydrogen, hydroxyl, or hydroxymethyl,
- wherein R.sub.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro, and wherein X is
- (1) trans-CH.dbd.CH--
- (2) cis-CH.dbd.CH--
- (3) -C.tbd.C-- or
- (4) --CH.sub.2 CH.sub.2 --.
14 more elements
Dependencies are inferred from the claim text.