ES254059A1 - Fluorinated steroids - Google Patents

Abstract

The invention comprises a compound having the formula: <FORM:0933867/IV(a)/1> wherein -C1-C2 and -C4-C5- are -CH2-CH2- or -CH=CH- -C9-C11- is <FORM:0933867/IV(a)/2> different and are hydrogen atoms, alkyl radicals, alkaryl radicals, aryl radicals, cycloalkyl radicals or heterocyclic radicals or taken together are cycloalkyl or heterocyclic radicals and Y is hydrogen, fluoro, OH or OR, in which R is a lower alkanoyl radical, a tetrahydropyran-2-yl-oxy radical or a tetrahydrofuran-2-yl-oxy radical, and the preparation thereof by treating a steroid of formula I lacking one or more of the above specified substituents or structures in accordance with one or more of the following reactions performed in any desired order (1) forming the D 1 and/or D 4 unsaturation by use of a dehydrogenating agent such as SeO2 or by use of a microorganism such as the Nocardia type (2) treating the 9,11-oxide with HF preferably in a suitable inert solvent to form the 9a -fluoro-11b -hydroxy steroid, and, if desired, oxidising the 11-hydroxy to 11-keto at any time in the reaction sequence (3) reacting the 16a -17a -dihydroxy steroid in the presence of an acidic agent with a carbonyl compound <FORM:0933867/IV(a)/3> wherein R1 and R11 are as defined above (4) introducing the 6a -fluoro atom by treating the corresponding 5a ,6a -epoxy steroid with HF and then dehydrating (5) where the 6a -mono-fluoro compounds are prepared forming the 11b -hydroxy group microbiologically, employing for example Botrytus cinerea. The 16a ,17a -dihydroxy steroid may be obtained by treating the corresponding 17a -hydroxy steroid with an organism such as Streptomyces roseochromogenus, Streptomyces viridus, Streptomyces olivaceous, and Streptomyces argenteolus.