Antikonceptionsmiddel

1291150 6,6-Difluorosteroids E I DU PONT DE NEMOURS & CO 6 Nov 1970 [17 Nov 1969] 53042/70 Heading C2U The invention comprises d-, l- and dl-steroids of formula (wherein R1 is Me, Et, Prn or Pri; R2 is an alkyl, alkoxy, cycloalkyloxy or (cycloalkyl)alkoxy group of 4 to 15 carbon atoms or a cycloalkyl or (cycloalkyl)alkyl group of 6 to 11 carbon atoms; and R3 is H, Me or CF 3 ) and their preparation from the corresponding free 17#-ols by reaction with an appropriate carboxylic anhydride in the presence of a catalyst, preferably 4-(N,N-dimethylamino) pyridine, or by reaction with an appropriate chloroformate in the presence of a tertiary amine. dl - 6,6 - Difluoro - 13# - ethyl - 17α - ethynyl- 17# - hydroxygon - 4 - en - 3 - one (IV) is prepared from dl - 13# - ethyl - 17# -hydroxygon-4- en-3-one (III) by the sequence: III # dl- 3,17# - diacetoxy - 13# - ethylgona - 3,5 - diene # dl - 13# - ethyl - 17# - acetoxygon - 5 - en- 3#-ol # dl-3#, 17#-diacetory- 13#-ethylgon- 5 - ene # dl - 3#,17# - diacetoxy - 5 - fluoro- 6 - nitroimino - 13# - ethyl - 5α - gonane # dl- 3#, 17# - diacetoxy - 5 - fluoro - 13# - ethyl - 5#- gonan - 6 - one # dl - 3#, 17# - diacetoxy- 5,6,6 - trifluoro - 13# - ethyl - 5α - gonane # dl- 5,6,6 - trifluoro - 13# - ethyl - 5α - gonane - 3#, 17#- diol # dl - 5,6,6 - trifluoro - 13# - ethyl - 5α- gonane - 3,17 - dione # dl - 6,6 - difluoro- 13# - ethylgon - 4 - ene - 3,17 - dione # dl- 3,3 - ethylenedioxy - 6,6 - difluoro - 13# - ethylgon- 4 - en - 17 - one # dl - 3,3 - ethylenedioxy- 6,6 - difluoro - 13# - ethyl - 17α - ethynylgon - 4- en-17#-ol # IV. The inventive compounds are stated to possess progestational and antiestrogenic activities and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.