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US 4,054,737 AGranted
Thromboxane B analogs
AssigneeThe Upjohn Company
InventorsRobert C. Kelly, Norman A. Nelson
Life of this patent
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Abstract
The present specification provides novel intermediates and novel processes for the synthesis of various side chain and skeletal analogs of Thromboxane B.sub.2 (11.beta.-homo-11a-oxa-PGF.sub.2.alpha.). These analogs are particularly and especially useful as reproductive cycle control agents.
Claims54
A thromboxane analog of the formula. ##STR89## wherein R.sub.6 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- wherein M.sub.1 is ##STR90## wherein R.sub.5 is hydrogen or methyl;
- wherein L.sub.1 is ##STR91## 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 methyl only when the other is hydrogen or methyl;
- wherein Y.sub.1 is trans -- CH.dbd.CH-- or --CH.sub.2 CH.sub.2 -;
- wherein R.sub.7 is ##STR92## wherein 1 is zero, one, two, or three;
- wherein m is one to 5, inclusive, T is alkyl of one to 3 carbon atoms. inclusive, alkoxy of one to 3 carbon atoms, inclusive, chloro, fluoro, or trifluoroethyl, and s is one, two, or 3, the various T's being the same or different, with the proviso that not more than two T's are other then alkyl, with the further proviso that R.sub.7 is ##STR93## only when R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different;
- wherein Z.sub.4 is
- (1) cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --,
- (2cis--CH.dbd.CH--CH.sub.2 --(CH.sub.2).sub.g --CF.sub.2 --,
- (3) cis--CH.sub.2 --CH.dbd.CH--(CH.sub.2).sub.g --CH.sub.2 --,
- (4) --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CH.sub.2 --,
- (5) --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CF.sub.2 --,
- (6) --ch.sub.2 --o--ch.sub.2 --(ch.sub.2).sub.g --CH.sub.2 --,
- wherein g is one, or 3;
- and
- wherein X.sub.1 is
- (1) --CH.sub.2 OH, or
- (2) --COOR.sub.1, wherein R.sub.1 is 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 or two chloro, fluoro, or alkyl of one to 4 carbon atoms, inclusive, or a pharmacologically acceptable cation,
- with the overal proviso that Z.sub.4 is cis--CH.dbd.CH--(CH.sub.2).sub.3 --Y.sub.1 is trans--CH.dbd.CH--, R.sub.3, R.sub.4, and R.sub.5 are all hydrogen, and R.sub.7 is n-butyl, only when X.sub.1 is --CH.sub.2 OH.
15 more elements
Dependencies are inferred from the claim text.