11-deoxyprostaglandin derivatives and process therefor

Abstract

Abstract 1. A PROCESS FOR PREPARING A COMPOUND OF FORMULA I 1-(O=),2-(R-OOC-(CH2)P-(A)-CH2-),3-(H3C-(C)-CH(-O-R1)- (B)-),4-R2-CYCLOPENTANE IN WHICH (A) IS CH2CH2, CIS CH=CH OR C$C, P IS AN INTEGER FROM 2 TO 4, (B) IS TRANS CH=CH, (C) IS EITHER (CH2)Q WHEREIN Q IS AN INTEGER FROM 1 TO 6 OR CIS CH2CH=CH8CH2)R WHEREIN R IS AN INTEGER FROM 0 TO 3, R AND R1 IS EACH HYDROGEN AND R2 IS HYDROGEN, LOWER ALKYL OR CH2 OR3 WHEREIN R3 IS HYDROGEN WHICH COMPRISES SUBJECTING A COMPOUND OF FORMULA II 1,1-DI(R4-OOC-),2-(H3C-(C)-CH(-O-R5)-CH=CH-),3-R2- CYCLOPROPANE IN WHICH R2 IS HYDROGEN, LOWER ALKYL OR CH2OR3 IN WHICH R3 IS LOWER ALKANOYL, R4 IS LOWER ALKYL, R5 IS HYDROGEN OR TETRAHYDROPYRAN-2-YL AND (C) IS AS DEFINED HEREIN TO A BASE CATALYZED CONDENSATION AT A TEMPERATURE OF 100* TO 150* C. FOR 30 MINUTES TO THREE HOURS IN THE PRESENCE OF, AS THE BASE, AN ALKALI METAL ALKOXIDE OR AN ALKALI METAL HYDROXIDE WITH APPROXIMATELY AN EQUIMOLAR AMOUNT OF A TRIESTER OF FORMULA III R-OOC-(CH2)P-(A)-CH2-CH(-COO-R6)2 IN WHICH R AND R6 ARE LOWER ALKYL AND (A) AND P ARE AS DEFINED HEREIN TO YIELD THE CORRESPONDING CYCLOPENTANONETRIESTER SELECTED FROM THE GROUP CONSISTING OF FORMULA IVA AND FORMULA IVB 1-(O=),2-(R6-OOC-),2-(R-OOC-(CH2)P-(A)-CH2-),3-(H3C-(C)- CH(-O-R5)-CH=CH-),4-R7,5-(R-OOC-)-CYCLOPENTANE 1,6-DI(O=),4-(H3C-(C)-CH(-O-R5)-CH=CH-),5-(R-OOC-(CH2)P- (A)-CH2-),5-(R6-OOC-)-TETRAHYDRO-1H-CYCLOPENTA(C)FURAN IN WHICH (A), (C), P, R4, R5 AND R6 ARE AS DEFINED HEREIN, R IS LOWER ALKYL AND R7 IS HYDROGEN OR LOWER ALKYL, SAID CYCLOPENTANONETRIESTER OF FORMULA IVA BEING OBTAINED WHEN R2 OF THE COMPOUND OF FORMULA II IS HYDROGEN OR LOWER ALKYL AND SAID CYCLOPENTANONETRIESTER OF FORMULA IVB BEING OBTAINED WHEN R2 OF THE COMPOUND OF FORMULA II IS CH2 OR3 IN WHICH R3 IS LOWER ALKANOYL; IN THE INSTANCE WHEN R5 OF THE CYCLOPENTANONETRIESTER IS TETRAHYDROPYRAN-2-YL SUBJECTING THE CYCLOPENTANONETRIESTER TO TREATING WITH AN ACID IN AN INERT SOLVENT IN THE PRESENCE OF WATER TO REMOVE THE TETRAHYDROPYRAN-2-YL PROTECTING GROUP TO OBTAIN THE CORRESPONDING CYCLOPENTANONETRIESTER IN WHICH R5 IS HYDROGEN, AND THEREAFTER TREATING THE INSTANT CYCLOPENTANONETRIESTER INTERMEDIATE WITH AN ALKALI METAL HYDROXIDE TO GIVE THE CORRESPONDING COMPOUND OF FORMULA I IN WHICH R AND R1 ARE HYDROGEN AND R2 IS HYDROGEN, LOWER ALKYL OR CH2OR3 WHEREIN R3 IS HYDROGEN.

Inventors

• 👤 N Abraham
• 👤 J Bagli
• 👤 T Bogri

Bibliographic Details