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US 4,301,078 AGranted
Trans-4,5,13,14-tetradehydro-PGI.sub.1 compounds
AssigneeThe Upjohn Company
InventorHerman W. Smith
Life of this patent
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Abstract
This invention relates to certain structural and pharmacological analogs of prostacyclin (PGI.sub.2) wherein the C-5 to C-6 double bond is isomerized to the C-4 to C-5 position. These novel trans-4,5-didehydro-5,6-dihydro prostacyclin-type compounds are useful as smooth muscle stimulators.
Claims23
A prostacyclin analog of the formula ##STR31## wherein g is the integer zero, one, or 2;
- wherein M.sub.1 is ##STR32## wherein R.sub.5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive,
- wherein L.sub.1 is ##STR33## or a mixture of ##STR34## 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 ##STR35## 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, phenacyl, i.e., ##STR36## phenacyl substituted in the para position by chloro, bromo, phenyl, or benzamido;
- or a pharmacologically acceptable cation;
- and
- wherein m is the integer one to 5, inclusive.
12 more elements
Dependencies are inferred from the claim text.