GB2089808A — 5 alpha - and 5 beta -androstane-17 beta - carboxylates and -thiocarboxylates

USPTO Abstract

Compounds of the formula <IMAGE> wherein Q is O or S; R2 is hydrogen or methyl; R6 is hydrogen, fluorine or methyl; either R9 is hydrogen, fluorine or chlorine, R11 is beta -chlorine, beta -hydroxyl or oxo, and the 9,11-bond is a single bond, or R9 and R11 are each hydrogen and the 9,11-bond is a double bond; either R16 is hydrogen, hydroxy or methyl and R17 is COR17 alpha or R16 and R17 together form an acetonide; R17 alpha if present, is hydrogen, C1-4 alkyl, phenyl or p-tolyl; QR20 is hydroxyl, C1-4 alkoxy optionally substituted by 1 or 2 halogen atoms, benzyloxy, C5-7 cycloalkoxy, C6H11-CH2-O-, C6H11-CH2-CH2O-, HOCH2CH2O-, (C1-4 alkyl)-COOCH2CH2O-, PhCOOCH2CH2O-, C1-6 alkylthio, optionally ring-substituted phenylthio or optionally ring-substituted benzylthio, in which any ring substituent is selected from C1-4 alkyl, C1-4 alkoxy, fluorine, chlorine and bromine; and SIMILAR indicates alpha or beta configuration. Certain of the above compounds have antiinflammatory activity.