6-Hydroxy-PGE.sub.1 compounds
AssigneeThe Upjohn Company
InventorHerman W. Smith
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Abstract
This invention relates to certain structural analogs of the prostaglandins which have been unexpectedly discovered to be pharmacological analogs of prostacyclin (PGI.sub.2), i.e., they exhibit the characteristic prostacyclin-type biological responses. These novel compounds are all 6-hydroxy-PGE-type compounds. They are useful for the pharmacological purposes for which prostacyclin is used, e.g., a antithromboti agents, smooth muscle stimulators, gastric antisecretory agents, antihypertensive agents, antiasthma agents, nasal decongestants, or regulators or fertility and procreation.
Claims36
A prostacyclin analog of the formula ##STR18## wherein Z.sub.1 is (1) --(CH.sub.2).sub.g --CH.sub.2 --CH.sub.2 --,
- (2) --(ch.sub.2).sub.g --CH.sub.2 --CF.sub.2 --, or
- (3) trans-(CH.sub.2).sub.g --CH.dbd.CH--,
- wherein g is the integer one, 2, or 3;
- wherein Y.sub.1 is
- (1) trans-CH.dbd.CH--,
- (2) cis-CH.dbd.CH--,
- (3) --ch.sub.2 ch.sub.2 --,
- (4) trans-CH.dbd.C(Hal)--, or
- (5) --C.tbd.C--
- wherein Hal is chloro or bromo;
- wherein M.sub.1 is ##STR19## wherein R.sub.5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive;
- wherein L.sub.1 is ##STR20## a mixture of ##STR21## 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.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, two, or three chloro or alkyl of one to 3 carbon atoms;
- phenyl substituted in the para position by ##STR22## wherein R.sub.25 is methyl, phenyl, acetamidophenyl, benzamidophenyl, or --NH.sub.2 ;
- R.sub.26 is methyl, phenyl, --NH.sub.2, or methoxy;
- and R.sub.27 is hydrogen or acetamido, inclusive;
- or a pharmacologically acceptable cation;
- wherein m is the integer one to 5, inclusive.
Dependencies are inferred from the claim text.