Schering Aktiengesellschaft

Klaus Prezewowsky

Rudolf Wiechert

Henry Laurent

Yukishige Nishino

Helmut Hofmeister

Ulrich Kerb

Dieter Bittler

Jorge Casals-Stenzel

Wolfgang Losert

Friedmund Neumann

Karl Petzoldt

Hermann Steinbeck

Hans-Jorg Vidic

Rainer Philippson

Bernhard Krieger

Klaus Engel

Compounds of the formula ##STR1## wherein the 15,16-methylene group is in the .alpha.- or .beta.-position, and

6.beta.,7.beta.;15,16-Dimethylene-1,4-androstadien-3-ones, their

1,3-Dibenzoic acid esters of 17.alpha.-ethynyl-7.alpha.-methyl-1,3,5(10)-estratriene-1,3,17.beta.-triol possess strong estrogenic and ovulation-inhibiting activities. As compared to the corresponding diacetic acid ester, these dibenzoic acid esters remain stable over 2-7 months even in the desired, low dosage at a thermal load of up to 60.degree. C.

1,3-Dibenzoic acid esters of

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

7-Hydroxyestradiols of the formula ##STR1## wherein R.sub.1 is hydrogen, acyl, alkyl, cycloalkyl, an oxygenated saturated heterocyclic group or hydrocarbylsulfonyl; R.sub.2 and R.sub.3 each are hydrogen, acyl, oxygenated saturated heterocyclic group or R.sub.2 is hydrocarbylsulfonyl and R.sub.4 is alkyl, alkenyl, chlorinated alkenyl, alkynyl or chlorinated alkynyl, are useful for treating estrogen deficiency symptoms.

7-Hydroxyestradiols

3,17,18-Trihydroxy-1,3,5(10)-estratrienes of the formula ##SPC1## Wherein R is H or substituted or unsubstituted saturated or unsaturated hydrocarbon, and esters and ethers thereof, possess strong vaginotropic and only weak utertropic activity and are useful in the treatment of estrogenic deficiency conditions where uteral effects are not desired.

3,17,18-Trihydroxy-1,3,5(10)-estratrienes

8.alpha.-Estratrienes of the formula ##SPC1## Wherein R is lower alkyl and X is an oxygen atom, a .beta.-hydroxy or .beta.-hydroxy-.alpha.-substituted or unsubstituted saturated or unsaturated hydrocarbon group, and the esters and ethers thereof, possess strong vaginotropic but only weak utertropic activity and are useful in the treatment of estrogenic deficiency conditions where uteral effects are not desired.

1,3-Oxygenated 8.alpha.-estratrienes

1,3-Dihydroxy-8.alpha.-estratrienes of the formula ##SPC1## Wherein R is lower-alkyl and --A--B is ##SPC2## Wherein R' is a saturated or unsaturated hydrocarbon group and R' is lower-alkyl, aralkyl or phenyl, and the esters and ethers thereof, possess strong vaginotropic but only weak utertropic activity and are useful in the treatment of estrogenic deficiency conditions where uteral effects are not desired.

Growing community of inventors

Berlin, Germany

Klaus Prezewowsky