Cyclopentanone derivatives

Abstract

Novel prostanoic acid derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 7 carbon atoms, R 1 is selected from the group consisting of hydrogen and carbalkoxy of 1 to 7 alkyl carbon atoms, R 2 is selected from the group consisting of hydrogen, carboxy and carbalkoxy of 1 to 7 alkyl carbon atoms, R 3 is selected from the group consisting of hydrogen and α-tetrahydropyranyl .Iadd.and at least one of R 1 , R 2 and R 3 is other than hydrogen.Iaddend., m is 3, 4 or 5 and n is 2, 3 or 4 with the proviso that when R 1 is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R 2 is hydrogen and R 3 is α-tetrahydropyranyl; when R 2 is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R 1 is hydrogen and R 3 is α-tetrahydropyranyl and when R 2 is carboxy, R and R 1 are hydrogen and R 3 is α-tetrahydropyranyl, which possess the physiological activity of prostaglandins .[. , and salts thereof when R, R 1 , R 2 and R 3 are hydrogen, with non-toxic, pharmaceutically acceptable bases.]. and their preparation.

We claim: 
     
       1. A prostanoic acid compound of the formula ##STR19## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 7 carbon atoms, R 1  is selected from the group consisting of hydrogen and carbalkoxy of 1 to 7 alkyl carbon atoms, R 2  is selected from the group consisting of hydrogen, carboxy and carbalkoxy of 1 to 7 alkyl carbon atoms, R 3  is selected from the group consisting of hydrogen, and α-tetrahydropyranyl, .Iadd.and at least one of R 1 , R 2  and R 3  is other than hydrogen, .Iaddend.m is 3, 4 or 5 and n is 2, 3 or 4 with the proviso that when R 1  is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R 2  is hydrogen and R 3  is α-tetrahydropyranyl; when R 2  is carbalkoxy, R is alkyl of 1 to 7 carbon atoms, R 1  is hydrogen and R 3  is α-tetrahydropyranyl and when R 2  is carboxy, R and R 1  are hydrogen and R 3  is α-tetrahydropyranyl .[.and when R is hydrogen, at least one of R 1 , R 2  and R 3  is other than hydrogen.].. 
     
     
       2. A compound of claim 1 having the formula ##STR20## wherein AlK and AlK' are alkyl of 1 to 7 carbon atoms, m is 3,4 or 5 and n is 2,3 or 4. 
     
     
       3. A compound of claim 2 which is ethyl 15α-(α -tetrahydropyranyloxy)-9-oxo-8-carbethoxy-5-cis 13-trans prostadienoate. 
     
     
       4. A compound of claim 1 having the formula ##STR21## wherein AlK and AlK' are alkyl of 1 to 7 carbon atoms, n is 2,3 or 4 and m is 3,4 or 5. 
     
     
       5. A compound of claim 4 which is ethyl 15α-(α-tetrahydropyranyloxy)-10-carbethoxy-9-oxo-5-cis 13-trans prostadienoate. 
     
     
       6. A compound of claim 1 having the formula ##STR22## wherein n is 2,3 or 4 and m is 3,4 or 5. 
     
     
       7. A compound of claim 6 which is 15α-(α-tetrahydropyranyloxy)-10-carboxy-9-oxo-5-cis 13-trans prostadienoic acid. 
     
     
       8. A compound of claim 1 which 15α-(α-tetrahydropyranyloxy)-9-oxo-5-cis 13-trans-prostadienoic acid. .[.9. A process for the preparation of the compound of claim 2 comprising condensing in the presence of an alkaline agent an alkyl 3-alkenyl-cyclopentanone-2-carboxylate of the formula ##STR23##  wherein AlK is alkyl of 1 to 7 carbon atoms and m is 3,4 or 5 with an alkyl haloalkenoate of the formula   Hal-- CH.sub.2 --CH = CH = (CH.sub.2).sub.n --COOAlK'     wherein Hal is chlorine or bromine and Alk' is alkyl of 1 to 7 carbon atoms   
     
     
        to form the said prostadienoate..]. .[.10.  The process of claim 9 wherein the prostadienoate is reacted with an alkali metal alcoholate to form the corresponding 10-carboalkoxy-prostadienoate of claim 4..]. .[.11. The process of claim 10 wherein the said 10-carboalkoxy-prostadienoate is saponified with a basic agent to form the corresponding acid of claim 6..]. .[.12. A process for the preparation of a compound of claim 4 comprising reacting a compound of the formula ##STR24##  wherein AlK' is alkyl of 1 to 7 carbon atoms, n is 2,3 or 4 and m is 3,4 or 5 with an alkali metal alcoholate..].