EP0004773A2 — 17-Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes, their pharmaceutical use and processes for their preparation

USPTO Abstract

17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula: wherein X' is fluoro, chloro or bromo; X 2 is fluoro, chloro or hydrogen; X 3 is fluoro, chloro, bromo or hydrogen; X 4 is =C=O or or may also be when X 3 is chloro; R is alkyl or 1 to 6 carbon atoms or phenyl or benzyl optionally substituted with one substituent on the phenyl ring chosen from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo; R 1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R 2 is hydrogen, a-methyl or β-methyl, or OR' and R 2 together are isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or a single bond; are useful as anti-inflammatory agents. They can be prepared by treating the corresponding 17β-carboxylic acid with a suitable base salt of RSH. The 17β-hydroxy compounds can be esterified to produce the 17β-alkanoyloxy compound. The double bond at the 4,5 position can be produced by contacting the corresponding Δ 5 compound with a base.