ES367281A1 - 09-alkyl steroids and a process for the preparation thereof - Google Patents

Abstract

The invention comprises compounds of Formul[mu] I and II wherein R 1 is H or C 1-6 alkyl R 2 is free, esterified or etherified hydroxy R 3 is H, C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl R is a 3 - oxo - #4,6/#1,4,6, 3 - hydroxy - #4,6, 3-acyloxy - #4/#4,6/#3,5/#2,4,6 or 3 - alkoxy - #4/#4,6/ #3,5/#3,5,7 system and R5 is alkoxy. Preparation of compounds I wherein R is a 3-alkoxy-#3,5 group is by reduction, alkylation, alkenylation or alkynylation of the 17-oxo group of compounds II. Subsequent dehydrogenation gives 3-oxo-#4,6 compounds which can also be obtained by dehydrogenation of the corresponding 3-oxo-#4 compounds as can also the 3-oxo-#1,4,6 compounds. Enol esterification/etherification then yields 3-alkoxy-#3.5/ #3,5,7 and 3 - acyloxy - #3,5/#2,4,6 compounds. The 3 - alkoxy/acyloxy - #4/#4,6 compounds are obtained conventionally from the corresponding 3-ols. The 17-hydroxy group can also be esterified and etherified. A 3-oxo-#4,6 group may be reduced to a 3-hydroxy-#4,6 group. Preparation of compounds II is by enol etherification of the corresponding 4-en-3-ones. 17[alpha] - Ethynyl - 19 - ethylandrost - 4 - ene- 3#,17#-diol and -3[alpha],17#-diol are prepared by NaBH 4 reduction of the corresponding 3-one. Compounds I are said to influence gonadotropin economy and to inhibit the action of progesterone, and may be made up with carriers into pharmaceutical compositions for oral, parenteral and rectal administration.