Schering Aktiengesellschaft

Hermann Steinbeck

Rudolf Wiechert

Henry Laurent

Helmut Hofmeister

Klaus Annen

Walter Elger

Karl Petzoldt

Gerhard Sauer

Gunter Neef

Gregor Haffer

Ulrich Eder

Klaus Prezewowsky

11-Methylene-.DELTA..sup.15 -steroids of Formula I ##STR1## wherein R.sup.1 is hydrogen or acyl and

11-Methylene-.DELTA..sup.15 -steroids, their preparation and use in

Steroids of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical or different and each is hydrogen or the residue of an organic or inorganic acid, and for the esters (R.sub.1 or R.sub.2 is not H) capable of salt formation, the salts thereof, possess valuable pharmacoligical properties, e.g., good antiandrogenic activity with low progestational activity.

15 Hydroxylation of 1.alpha.,2.alpha.-methylene steroids

16 .alpha.-Alkyl steroids of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl,

16 .alpha.-Alkyl steroids, their preparation, and pharmaceutical

1-Hydroxy steroids of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or alkanoyl of 1-8 carbon atoms are distinguished by strong progestational activity and only very minor androgenic side effects.

1-Hydroxy steroids, a process for the production thereof, and

11-Methylene steroids of Formula I ##STR1## wherein R is hydrogen or acyl, and

11-Methylene steroids, their preparation and pharmaceutical preparations

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

Steroids of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical or different and each is hydrogen or the residue of an organic or inorganic acid, and for the esters (R.sub.1 or R.sub.2 is not H) capable of salt formation, the salts thereof, possess valuable pharmacological properties, e.g., good antiandrogenic activity with low progestational activity.

Hydroxylated 1 alpha, 2 alpha-methylene steroids

.DELTA..sup.15 -Steroids of the formula ##STR1## wherein R.sub.1 is a hydrogen atom, trialkylsilyl or acyl; R.sub.2 is ethynyl, chloroethynyl or propinyl; and X is an oxygen atom, ##STR2## or NOR.sub.4 wherein R.sub.3 is a hydrogen atom or acyl and R.sub.4 is a hydrogen atom, acyl, alkyl or tetrahydropyranyl, possess progestational and ovulation and nidation inhibiting activities.

.DELTA..sup.15 -Steroids and pharmaceutical compositions thereof

11.beta.-Fluoropregnenes of the formula ##STR1## wherein 6 7 IS A SINGLE OR DOUBLE BOND,

11.beta.-FLUOROPREGNENES

15.alpha.,16.alpha.-METHYLENE-4-ESTREN-17.beta.-OLS OF THE Formula ##SPC1## Wherein R.sub.1 is lower alkyl, R.sub.2 is hydrogen or an acyl residue, R.sub.3 is hydrogen or a substituted or unsubstituted, saturated or unsaturated monovalent lower aliphatic hydrocarbon, and X is oxygen or the group H,OR.sub.4, wherein R.sub.4 is hydrogen or an acyl residue, have useful anabolic, androgenic, and/or gestagenic activity.

15.alpha.,16.alpha.-Methylene-4-estren-17.beta.-ols

11.beta.-Fluoroandrostenes of the formula ##SPC1## Wherein R.sub.1 and R.sub.2 are hydrogen atoms, methylene or another C--C bond; R.sub.3 is H or Cl, R.sub.4 is H, F or Cl; and X is carbonyl, .beta.-hydroxymethylene, or an ester or ether thereof or .alpha.-alkyl-.beta.-hydroxymethylene or an ester thereof, possess androgenic activity and can be prepared by the dehalogenation of a corresponding 9.alpha.-halo-11.beta.-F steroid.

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Berlin, Germany

Hermann Steinbeck