Verfahren zur Herstellung von 3-Carbalkoxymethylen-20-oxo-delta?,?-pregnadienderivaten

摘要

1,165,174. 3 - Carboxymethylene - steroids. FARBWERKE HOECHST A.G. 22 Aug., 1966 [21 Aug., 1965(2)], No. 37583/66. Heading C2U. The invention comprises (a) a process for preparing a 3-esterified carboxy)-methylene steroid of the androstene, estrane or pregnane series by reaction of a 3-oxo-#4- or -#4,6-steroid with a compound of formula in which R 3 is methyl or ethyl and R 4 1 is a C 1-12 saturated or unsaturated aliphatic, cycloaliphatic or araliphatic hydrocarbon group in the presence of an anhydrous base and in an anhydrous organic solvent, followed if desired by esterification of any hydroxyl groups, and (b) the products of formulae wherein R 1 1 is a #-hydroxy or acyloxy group, a (#-hydroxy-α-methyl or ethyl) group, a (#-hydroxy or acyloxy-α-vinyl or ethynyl) group, a carbony or etherylenedioxy group, a (#-COCH 3 -α-H, -OH, -O Alk or -OCO Alk) group, a (#-CH 2 OH or -CH 2 O Acyl- α-OH) group or a group. Alk having the same meanings as R 4 1 above, R 2 1 is a hydrogen, fluorine or chlorine atom or a methyl or ethyl group, R 3 1 a hydrogen atom or a methyl group, R 4 1 is as defined above, R 6 1 represents a 9(11) double bond, two 11-hydrogen atoms, an 11 #-hydroxy or keto group or the 11 #-hydroxy-9 α-fluoro grouping, and R1 8 is a hydrogen atom or a methyl group or in combination with R 2 1 forms a 6α, 7α- oxido-group. The compounds of the invention have gestagenic activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral or parenteral administration.