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US 4,366,313 AGranted
2-Decarboxy-2-tetrazolyl-6-keto-PGE.sub.1 compounds
AssigneeThe Upjohn Company
InventorUdo F. Axen
Life of this patent
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Abstract
Prostaglandin E (PGE)-type derivatives and analogs having a 6-keto feature are disclosed, including processes for preparing them and the appropriate intermediates, said derivatives having pharmacological activity.
Claims1
A compound of the formula ##STR2## wherein W.sub.1 is .alpha.--OH:.beta.--H, .alpha.--H:.beta.--OH, .alpha.--H:.beta.--H, methylene, or .alpha.--CH.sub.2 OH:.beta.--H;
- wherein
- Q is oxo, .alpha.--H:.beta.--H, .alpha.--R.sub.8 :.beta.--OH, or .alpha.--OH:.beta.--R.sub.8,
- wherein
- R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- wherein
- R.sub.4 is
- (1) --C(R.sub.5)(R.sub.6)--C.sub.g H.sub.2g .dbd.CH.sub.3
- (2) --C(R.sub.5)(R.sub.6)--Z--(Ph) or
- (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 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
- wherein
- 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;
- wherein
- D is
- (1) --(CH.sub.2).sub.d --C(R.sub.2).sub.2 --
- (2) --CH.sub.2 --O--CH.sub.2 --Y-- or
- (3) --CH.sub.2 --C.dbd.CH--
- wherein d is zero to 5, R.sub.2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R.sub.2 is not methyl when the other is fluoro, and Y is a valence bond, --CH.sub.2 -- or --(CH.sub.2).sub.2 --,
- wherein
- R.sub.9 is hydrogen, methyl or ethyl and R.sub.28 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbon atoms, inclusive;
- and
- wherein
- X is
- (2) trans--CH.dbd.CH--
- (2) cis--CH.dbd.CH--
- (3) --C.tbd.C--
- (4) --CH.sub.2 CH.sub.2 --
29 more elements
Dependencies are inferred from the claim text.