Bicyclo lactone intermediates for prostaglandin analogs
AssigneeThe Upjohn Company
InventorNorman A. Nelson
Life of this patent
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Abstract
Prostaglandin-type compounds with a phenoxy or substituted-phenoxy substituent at the C-16 position are disclosed, with processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
Claims9
An optically active compound of the formula:
- ##STR57## or a racemic compound of that formula and the mirror image thereof, wherein M" is ##STR58## wherein R.sub.8 is hydrogen or tetrahydropyranyl;
- wherein R.sub.2 and R.sub.3 are hydrogen, methyl, or ethyl, being the same or different;
- wherein T is alkyl of one to 3 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.4 wherein R.sub.4 is alkyl of one to 3 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.
The compound of the formula:
- ##STR60## wherein R.sub.1 and R.sub.2 are hydrogen or lower alkyl and wherein R.sub.3 is hydrogen, methyl, fluoro, chloro, trifluoromethyl, or methoxy.
An optically active compound of the formula ##STR61## or a racemic compound of that formula and the mirror image thereof, wherein M is ##STR62## wherein R.sub.1 and R.sub.2 are hydrogen or lower alkyl, and wherein R.sub.3 is hydrogen, methyl, fluoro, chloro, trifluoromethyl, or methoxy.
A prostanoic acid derivative of the formula ##STR63## wherein R.sup.a is carboxy or alkoxycarbonyl of up to 11 carbon atoms;
- R.sup.b is hydroxy;
- R.sup.c is hydrogen;
- R.sup.3 is hydrogen, methyl, fluoro, chloro, trifluoromethyl, or methoxy;
- wherein R.sup.1 and R.sup.2 are hydrogen or lower alkyl.
A prostanoic acid derivative of the formula ##STR64## wherein R.sup.a is carboxy or alkoxycarbonyl of up to 11 carbon atoms;
- R.sup.b and R.sup.c together are oxo;
- R.sup.3 is hydrogen, methyl, fluoro, chloro, trifluoromethyl, or methoxy;
- and wherein R.sup.1 and R.sup.2 are hydrogen or lower alkyl.
Dependencies are inferred from the claim text.