Schering Aktiengesellschaft

Rainer Philippson

Rudolf Wiechert

Ulrich Kerb

Dieter Bittler

Jorge Casals-Stenzel

Wolfgang Losert

Klaus Prezewowsky

Bernhard Krieger

4-Androsten-3-ones of the formula ##STR1## wherein R.sub.1 is hydrogen or the acyl radical of an organic or inorganic acid, R.sub.2 is hydrogen, alkyl, or the acyl radical of an organic or inorganic acid, R.sub.3 is methyl or ethyl, R.sub.4 is hydrogen or methyl, ##STR2## and R.sub.5 is lower alkyl, have diuretic activity.

4-Androsten-3-ones and process for the preparation thereof

4-Androstene-3,17-dione and 1,4-androstadiene-3,17-dione are converted to 3-(17.beta.-hydroxy-4-androsten-3-on-17.alpha.-yl)-propionic acid lactone in three steps by reaction with propargyl alcohol in the presence of an alkali alcoholate of a tertiary alcohol, hydrogenating the thus-produced 17.alpha.-(3-hydroxy-propinyl)-17-.beta.-hydroxy compound with hydrogen in the presence of a complex metallic catalyst to produce 17.alpha.-(3-hydroxypropyl)-17.beta.-hydroxy-3-keto-androst-4-ene, which is oxidized with chromic acid to the desired lactone.

Process for the preparation of a .DELTA..sup.4 -3-keto steroid

Steroids containing both an isolated and an .alpha.,.beta.-unsaturated keto group are selectively reacted with dimethyl sulfonium methylide in a non-reactive polar solvent and in the presence of an alkali tertiary alcoholate to produce .alpha.,.beta.-unsaturated keto steroids containing the group ##EQU1##

Process for the preparation of steroid oxiranes

Growing community of inventors

Bergkamen, Germany

Rainer Philippson