stereoisomerisch pure 17 alpha ethynyl est 2 en - 17beta ol and its esters.

摘要

Stereoisometrically pure DELTA 2 compound of formula (I) wherein R1 is hydrogen or -(C=O)-R2, wherein R2 is an organic substituent selected from the group consisting of alkyls, alkenyls, alkynyls, cycloalkyls, cycloalkylalkylenes, haloalkyls, aryls, haloaryls and arylalkylenes, and their product by the process of: (a) reacting the 17 beta -hydroxy group of 17 beta -hydroxy-5 alpha -ester-1-en-3-one with dihydropyran to produce the 3-keto-17 beta -ether; (b) reducing the 3-keto-17 beta -ether product of step (a) with lithium in ammonia; (c) reacting the product of step (b) with dialkyl chlorophosphate to produce the 3-substituted phosphate; (d) reducing the product of step (c) with lithium and ammonia to produce the DELTA 2-protected-17 beta -ether product; (e) hydrolysis of the produce of step (d) to produce the DELTA 2-17 beta -hydroxy compound; (f) oxidizing the 17 beta -hydroxy product of step (e) to produce the 17-keto compound; (g) reacting the 17-keto derivative of step (f) with acetylene magnesium halide to produce the compound of formula (I) where R1 is hydrogen; and (h) optionally reacting the product of step (g) with an acyl halide or acyl anhydride to produce the compound of formula (I) wherein R1 is acyl. The invention also relates to a pharmaceutical composition for oral administration comprising a compound of formula (I) and to a method of achieving contraception (fertility-control) in a female mammal. The compound of formula (I) has antiprogestational activity in a female mammal and is useful in the control of fertility, having substantially no undesirable side effects.