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US 4,052,552 AGranted
Thromboxane B analogs
AssigneeThe Upjohn Company
InventorWilliam P. Schneider
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.
Claims49
A thromboxane alanog of the formula ##STR158## wherein Z.sub.5 is ##STR159## or ##STR160## wherein g is 1, 2, or 3;
- 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;
- wherein R.sub.6 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;
- wherein Y.sub.1 is trans--CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --;
- wherein M.sub.1 is ##STR161## or ##STR162## wherein R.sub.5 is hydrogen or methyl;
- wherein L.sub.1 is ##STR163## or a mixture of ##STR164## and ##STR165## 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 R.sub.7 is
- 1. --(CH.sub.2).sub.m --CH.sub.3, ##STR166## or ##STR167## wherein l is 0, 1, 2, or 3, wherein m is 1 to 5, inclusive, T is alkyl of 1 to 3 carbon atoms, inclusive, alkoxy of one to 3 carbon atoms, inclusive, chloro, fluoro, or trifluoromethyl, and s is 1, 2, or 3, the various T's being the same or different, with the proviso that not more tha two T'S are other than alkyl, with the further proviso that R.sub.7 is ##STR168## only when R.sub.3 and R.sub.4 are hydrogen or methyl, being the same or different.
6 more elements
Dependencies are inferred from the claim text.