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US 4,289,878 AGranted
2-Decarboxy-2-tetrazolyl-trans-2,3,4,5-tetradehydro-PGI.sub.1 compounds
AssigneeThe Upjohn Company
InventorRoy A. Johnson
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel 2-decarboxy-2-tetrazolyl-trans-2,3,4,5-tetradehydro-PGI.sub.1 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.
Claims18
A 4Z compound of the formula ##STR3## wherein W.sub.1 is .alpha.-OH:.beta.-H, .alpha.-H:.beta.-OH, oxo, methylene, .alpha.-H:.beta.-H, .alpha.-CH.sub.2 OH:.beta.-H;
- wherein Q is oxo, .alpha.-H:.beta.-H, .alpha.-OH:.beta.-R.sub.8 or .alpha.-R.sub.8 :.beta.-OH
- wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- and
- wherein R.sub.4 is
- (1) --CR.sub.5 R.sub.6 --C.sub.g H.sub.2g .dbd.CH.sub.3
- (2) --CR.sub.5 R.sub.6 --Z--(Ph)
- (3) cis--CH.sub.2 --CH.dbd.CH--CH.sub.2 CH.sub.3
- wherein C.sub.g H.sub.2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR.sub.5 R.sub.6 -- and terminal methyl, 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 the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--);
- wherein Z represents an oxa atom (--O--) or C.sub.j H.sub.2j wherein C.sub.j H.sub.2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 -- and the (Ph);
- wherein (Ph) is phenyl or phenyl substituted by (T)s, wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7 --, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different;
- 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 --;
- including the lower alkanoates thereof.
14 more elements
A 4E compound of the formula ##STR4## wherein W.sub.1 is .alpha.-OH:.beta.-H, .alpha.-H:.beta.-OH, oxo, methylene, .alpha.-H:.beta.-H, .alpha.-CH.sub.2 OH:.beta.-H;
- wherein Q is oxo, .alpha.-H:.beta.-H, .alpha.-OH:.beta.-R.sub.8 or .alpha.-R.sub.8 :.beta.-OH
- wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- and
- wherein R.sub.4 is
- (1) --CR.sub.5 R.sub.6 --C.sub.g H.sub.2g .dbd.CH.sub.3
- (2) --CR.sub.5 R.sub.6 --Z--(Ph)
- (3) cis--CH.sub.2 --CH.dbd.CH--CH.sub.2 CH.sub.3
- wherein C.sub.g H.sub.2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR.sub.5 R.sub.6 -- and terminal methyl, 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 the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--);
- wherein Z represents an oxa atom (--O--) or C.sub.j H.sub.2j wherein C.sub.j H.sub.2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 -- and the (Ph);
- wherein (Ph) is phenyl or phenyl substituted by (T)s, wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7 --, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different;
- 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 --;
- including the lower alkanoates thereof.
14 more elements
Dependencies are inferred from the claim text.