Preparation of phenacyl esters of prostanoic acids

Details Preparation of phenacyl esters of prostanoic acids Preparation of phenacyl esters of prostanoic acids

C - Chemistry, Metallurgy

07

C

260/235.01

C07C 405/00 (2006.01)

Patent

CA 1059506

ABSTRACT OF THE DISCLOSURE Phenacyl-type esters of PGE2, PGEl, and 13,14-dihydro- PGE1 and their 15-metnyl, 16,16-dimethyl, and 17-phenyl analogs, including the respective 15(R)epimers, are dis- closed, represented by the formula Image wherein M is Image or Image wherein R3 is hydrogen or methyl; wherein Q is (1) Image wherein each of R4 and R5 is hydrogen or methyl, being the same or different, or (2) Image wherein the moiety -CtH2t- represents a valence bond or alkylene of one to 10 carbon atoms, inclusive, with one to 7 carbon atoms, inclusive, between Image and the phenyl ring; wherein R1 is phenyl, p-bromophenyl, p- biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl; wherein R2 is hydrogen or benzoyl; and wherein (a) X is -CH2CH2- or trans CH=CH- and Y is -CH2CH2-, or (b) X is trans-CH=CH- and Y is cis-CH=CH-. The products are use- ful for the same pharmacological and medical purposes as the corresponding prostaglandins and analogs, and are also use- ful as a means for obtaining highly purified products. -1-

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