GB1043047A - Estadiol derivatives - Google Patents

Abstract

The invention comprises compounds of formula <FORM:1043047/C2/1> wherein Q is a hydrogen atom or a methyl group, R and R1 are hydrogen atoms or alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, phenyl, phenylalkyl, phenylalkenyl, carboxylic acyl or nitro groups and R11 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, alkylcycloalkyl, phenylalkyl, phenylalkenyl, carboxylic acyl or nitro group, wherein the alkyl groups have 1 to 10 carbon atoms, the alkenyl groups have 2 to 10 carbon atoms, the cycloalkyl groups have 5 or 6 ring members, the phenyl groups may be substituted, and the acyl groups have 1 to 10 carbon atoms and a molecular weight less than 200, and 6 (7) dehydro, 9 (11) dehydro and 6 (7), 8 (9) didehydro derivatives thereof, provided that, in compounds having no additional double bond, when Q is a hydrogen atom and R1 is a methyl group, at least one of R and R11 is other than a hydrogen atom, and their preparation by (a) reaction of the corresponding 17-keto compound with an alkali metal or halo-magnesium derivative of a compound of formula HC­C.CH2OR, (b) esterification or ester hydrolysis, both of which may be selective, or (c) etherification by reaction of an alkali metal salt with the appropriate organic halide. The compounds of the invention have hypocholesteremic and estrogenic activity. 3 - Methoxy - 17a - (3 - hydroxy - 1 - propynyl)-1,3,5(10) - estratrien - 17b - ol is prepared by process (a) above.