Phenacyl-type esters of PGE-types compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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C07C17700

Patent

active

043049265

ABSTRACT:
Phenacyl-type esters of PGE.sub.2, PGE.sub.1, and 13,14-dihydro-PGE.sub.1 and their 15-methyl, 16,16-dimethyl, and 17-phenyl analogs, including the respective 15(R)epimers, are disclosed, represented by the formula ##STR1## wherein M is ##STR2## wherein R.sub.3 is hydrogen or methyl; wherein Q is ##STR3## wherein each of R.sub.4 and R.sub.5 is hydrogen or methyl, being the same or different, or ##STR4## wherein the moiety--C.sub.t H.sub.2t -- represents a valence bond or alkylene of one to 10 carbon atoms, inclusive, with one to 7 carbon atoms, inclusive, between ##STR5## and the phenyl ring; wherein R.sub.1 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl; wherein R.sub.2 is hydrogen or benzoyl; and wherein (a) X is --CH.sub.2 CH.sub.2 -- or trans--CH.dbd.CH-- and Y is --CH.sub.2 CH.sub.2 --, or (b) X is trans--CH.dbd.CH-- and Y is cis--CH.dbd.CH--. The products are useful for the same pharmacological and medical purposes as the corresponding prostaglandins and analogs, and are also useful as a means for obtaining highly purified products.

REFERENCES:
patent: 3812179 (1974-05-01), Bundy
patent: 3984454 (1976-10-01), Skubulla et al.
Shriner et al., Organic Compounds, p. 197 (1950).
Fieser et al., Reagent for Organic Synthesis, p. 1201.
McOmie, Protective Groups in Organic Chemistry, p. 199 (1972).

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