Sterling Drug Inc.

Robert G Christiansen

Malcolm R Bell

Virendra Kumar

Chester J Opalka, Jr

John L Herrmann, Jr

Harry P Schane, Jr

5'-Alkylsulfonylsteroido[3,2-b]furans, for example 5'-methylsulfonyl-5.alpha.-pregn-2-en-20-yno[3,2-b]furan-17.beta.-ol having the structural formula, ##STR1## which are useful as antiandrogenic agents, and processes for preparation, method of use and compositions thereof are disclosed.

Antiandrogenic sulfonylsteroidofurans

1'-Sulfonylsteroido[3,2-c]pyrazoles, for example, (5.alpha.,17.alpha.)-1'-(methylsulfonyl)-1'H-pregn-20-yno[3,2-c]pyrazol-17 -ol, which are useful as antiandrogenic agents, and processes for preparation, method of use and compositions thereof are disclosed.

Antiandrogenic sulfonylsteroidopyrazoles and processes for preparation

4.alpha.,5.alpha.-Epoxy-3,20-dioxopregnane-2.alpha.,16.alpha.-dicarbonitril e is prepared by decyclizing 4.alpha.,5.alpha.-epoxy-20-oxopregn-2-eno-[2,3-d]isoxazole-16.alpha.-carbo nitrile with strong base and is useful as an inhibitor of mineralocorticoid production and/or action without concomitant glucocorticoid inhibition in primates.

4.alpha.,5.alpha.-Epoxy-3,20-dioxopregnan

2.alpha.-Cyano-3-oxosteroids having a 4.alpha.,5.alpha.-epoxy group and alkylated in the 4- and/or 6-position, useful as interceptive agents, are prepared by alkaline cleavage of the corresponding steroido[2,3-d]isoxazoles.

Steroid cyanoketones and intermediates

A process for preparing 17.beta.-hydroxysteroido[2,3-d]isoxazoles substituted at the 17.alpha.-position by an ethynyl or substituted ethynyl group comprising reacting a 17-oxosteroido[2,3-d]isoxazole with the appropriate ethynylmagnesium halide, substituted ethynylmagnesium halide, monolithium acetylide or substituted monolithium acetylide. The process affords a novel compound, 21-trifluoromethyl-17.alpha.-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol, which has estrogenic activity.

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Schodack, NY, United States of America

Robert G Christiansen