7-oxabicycloheptyl substituted heterocyclic thioamide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

A compound having the formula ##STR191## including all stereoisomers thereof, wherein m is 1, 2 or 3;

• n is 0, 1, 2, 3 or 4;
• Z is ##STR192## wherein Y is O, a single bond or vinyl (--CH.dbd.CH--), with the provisos that when n is 0, if Z is ##STR193## then Y cannot be O;
• and when Y=vinyl, n=0;
• R is CO.sub.2 H, CO.sub.2 alkali metal, CO.sub.2 lower alkyl, CH.sub.2 OH, CONHSO.sub.2 R.sup.3, CONHR.sup.3a or --CH.sub.2 -5-tetrazolyl, with the proviso that when R is --CH.sub.2 -5-tetrazolyl, and Z is other than --(CH.sub.2).sub.2 --, n is 1, 2, 3 or 4;
• X is O, S is NH;
• R.sup.1 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, cycloheteroalkyl, cycloheteroalkylalkyl, heteroaryl or heteroarylalkyl, each of R.sup.1 being unsubstituted or optionally substituted with a lower alkyl, aryl, cycloalkyl or cycloalkylalkyl group;
• R.sup.2 is hydrogen, lower alkyl, aryl, or aralkyl, or
• R.sup.1 and R.sup.2 together with the N to which they are linked form a 5- to 8-membered ring which contains only the single N heteroatom;
• and
• R.sup.3 is lower alkyl, aryl or aralkyl;
• and
• R.sup.3a is hydrogen, lower alkyl, aryl or aralkyl, wherein the term "aryl" by itself or as part of another group refers to a monocyclic or bicyclic aromatic group containing from 6 to 10 carbons in the ring portions, which is unsubstituted or substituted with 1 or 2 substituents which are lower alkyl, trifluoromethyl, halogen, lower alkoxy, arylalkoxy, hydroxy, alkylthio, alkylsulfinyl, alkylsulfonyl, arylthio, arylsulfinyl and/or arylsulfonyl;
• the term "cycloalkyl" by itself or as part of another group refers to a saturated cyclic hydrocarbon group containing 3 to 12 carbons, which is unsubstituted or substituted with halogen, lower alkyl, alkoxy and/or hydroxy;
• the term "cycloheteroalkyl" by itself or as part of another group refers to a 5-, 6- or 7-membered saturated ring which includes 1 or 2 heteroatoms which are nitrogen, oxygen and/or sulfur;
• the term "heteroaryl" by itself or as part of another group refers to 5- or 6-membered aromatic ring which includes 1 or 2 heteroatoms which are nitrogen, oxygen or sulfur;
• the term "lower alkyl" or "alkyl" by itself or as part of another group refers to a straight or branched chain radical of up to 18 carbons which is unsubstituted or substituted with 1, 2 or 3 halogen, aryl, alkyl-aryl, haloaryl, cycloalkyl, alkylcycloalkyl, hydroxy or carboxy substituents;
• The term "lower alkenyl" or "alkenyl" by itself or as part of another group refers to a carbon chain of up to 16 carbons containing one double bond and which is unsubstituted or substituted with a halogen substituent;
• and
• the term "lower alkynyl" or "alkynyl" by itself or as part of another group refers to a carbon chain of up to 16 carbons containing one triple bond.