Schering Aktiengesellschaft

Hoffmann-la Roche Inc.

Other

Schering, A.g. Patentabteilung

Ulrich Kerb

Rudolf Wiechert

Marcel Muller

Andor Furst

Leo Alig

Klaus Kieslich

Peter Keller

Otto Engelfried

Dieter Bittler

Jorge Casals-Stenzel

Wolfgang Losert

Robert C Nickolson

Helmut Wachtel

Karl Petzoldt

Yukishige Nishino

David A Henderson

Wolfgang Kehr

Reinhard Horowski

Dieter Palenschat

Gert Paschelke

Paul-Eberhard Schulze

Klaus Prezewowsky

Jurg Albert Gutzwiller

Gerhard Sauer

Sybille Beier

Ulrich Eder

Bob Nieuweboer

Hansjorg Krahmer

Rainer Philippson

Bernhard Krieger

Klaus Lubke

Manfred Stahnke

1-Methyl-15.alpha.-(1-oxyalkyl)androsta-1,4-diene-3,17-diones of general Formula I ##STR1## wherein R.sup.1 is a hydrogen atom or an acyl group of 1-10 carbon atoms,

1-methyl-15.alpha.-(1-oxyalkyl)androsta-1,4-diene-3,17-diones, processes

1-Alkyl androsta-1,4-diene-3,17-diones of the formula ##STR1## wherein R.sub.1 is a methyl, ethyl, hydroxymethyl, C.sub.1 -C.sub.3 -alkoxymethyl, or C.sub.1 -C.sub.4 -alkanoyloxymethyl group, R.sub.6 is a hydrogen atom or a methyl group, and R.sub.7 is a hydrogen atom or a methyl group in the 7.alpha.- or 7.beta.-position, are useful for fertility control and for the treatment of estrogen-triggered diseases.

1-alkyl-androsta-1,4-diene-3,17-diones their production and

New hexanor-brassinolid-22-ethers are disclosed, of the formula ##STR1## wherein Z is the group ##STR2## OR.sub.2 and OR.sub.3 are oriented cis 2.alpha., 3.alpha. or 2.beta., 3.beta., R.sub.2 and R.sub.3 are the same or different and are each hydrogen formyl, C.sub.2 -C.sub.7 -alkyl-CO--, C.sub.2 -C.sub.7 -alkoxy-C.sub.1 -C.sub.3 -alkyl-CO-- or aryl-CO--, and R.sub.23 is straight-chain or branched C.sub.1 -C.sub.7 -alkyl or C.sub.1 -C.sub.7 -alkoxy-C.sub.1 -C.sub.3 -alkyl. Also disclosed are processes for the production of these compounds as well as compositions containing the same having growth-regulatory activity for plants.

Hexanor-brassinolid-22-ethers

The novel D-homosteroids of the formula ##STR1## wherein R.sup.1 represents a --CN, .dbd.NOH or .dbd.CH--NHOH group; R.sup.2 represents oxo or, where R.sup.1 represents a --CN group, R.sup.2 represents oxo or a --OAc group; or R.sup.1 and R.sup.2 together with carbon atoms 2 and 3 of the steroid skeleton represents a [2,3-d]-fused isoxazole ring, a [3,2-c]-fused pyrazole ring, a [3,2-c]-fused N-acylated pyrazole ring or a [2,3-c]-fused furazan ring; Ac represents an acyl group; R.sup.3 and R.sup.4 represent methyl and R.sup.5 and R.sup.6 together represent an additional bond between carbon atoms 5 and 6 of the steroid skeleton; or R.sup.4 and R.sup.5 together represent --O--, R.sup.3 represents hydrogen or methyl, and R.sup.6 represents hydrogen; R.sup.7 represents hydrogen, lower-alkyl or ethynyl; R.sup.8 represents hydroxy or acyloxy; or R.sup.7 and R.sup.8 together represent a spiroether group of the formula ##STR2## or a spirolactone group of the formula ##STR3## the dotted 16,17-bond is an optional additional carbon-carbon bond; and the dotted 2,3-bond is an additional carbon-carbon bond when R.sup.1 and R.sup.2 together with carbon atoms 2 and 3 form the isoxazole or pyrazole ring or when R.sup.2 represents a --OAc group, inhibit the synthesis of progesterone in organisms and can be used for fertility control. The novel D-homosteroids can be manufactured by molecular modifications of other D-homosteroids.

Novel D-homosteroids

The invention is directed to 3-oxo-D-homosteroids and derivatives thereof which are useful as antiantigens.

D-Homosteroids

17.alpha.-hyroxy- and 17a.alpha.-hydroxy-D-homoetiocarboxylic acids of the formula ##STR1## wherein n is 1 or 2,

Process for the preparation of 17.alpha.-hydroxy- and

A process for preparing an 11-keto steroid consists essentially of heating the corresponding 9.alpha.-halo-11.beta.-hydroxy steroid, to 180.degree.-350.degree. C. in an inert, aprotic, high-boiling solvent.

Process for preparing 11-keto steroids

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

A process for preparing a .DELTA..sup.9(11) - and/or .DELTA..sup.16 -unsaturated steroid comprises heating the corresponding steroid of the pregnane series substituted by 9.alpha.-chloro- and/or 16.alpha.-chloro- or 17.alpha.-acyloxy, in an inert, aprotic high-boiling solvent at 180.degree.-350.degree. C.

Process for preparing .DELTA..sup.9(11) and/or .DELTA..sup.16

The present invention is directed to 3-oxo, 6,9-hydro or halo, 11-oxo or (.alpha.--H,.beta.--OH), 17a-alkanoyloxy, 17a.beta.-carboxylate D-homosteroids which are useful as antiinflammatory agents.

Novel 17.alpha.-(3-iodobenzoyloxy)-9.alpha.-chloro-4-pregnene-3,20-diones and the D-homo homologs thereof, of the formula ##STR1## wherein n is 1 or 2;

Process for the preparation of

The present disclosure is concerned with 9.alpha.-chloro-17-(m-iodobenzyloxy) steroids and a process for their manufacture. The subject compounds are useful as intermediates in the synthesis of pharmacologically-active substances and have themselves been found to exhibit pharmacological activity.

Steroids and process for their manufacture

D-Homopregnanes of the formula ##STR1## wherein the dotted line in the 1,2-position together with the corresponding solid line denotes a single or double carbon-carbon bond; R.sup.6 is hydrogen, fluoro, chloro or methyl; R.sup.9 is hydrogen, fluoro, chloro or bromo; R.sup.11 is hydroxyl, acyloxy, fluoro or chloro; and R.sup.17a is hydroxyl or acyloxy with the proviso that when R.sup.9 is fluoro, chloro or bromo and R.sup.11 is fluoro or chloro, the atomic number of R.sup.11 is less than or equal to that of R.sup.9 ; and with the further proviso that when R.sup.6 is hydrogen, and R.sup.11 and R.sup.17a are hydroxy or when R.sup.6 is fluoro, R.sup.11 and R.sup.17a are hydroxyl and the dotted line in the 1,2-position together with the corresponding solid line denotes a single carbon-carbon bond, R.sup.9 is fluoro, chloro or bromo and processes for the preparation thereof are disclosed.

D-Homopregnanes

The present disclosure is concerned with 17a-(m-iodobenzoyloxy) substituted D-homosteroids and a process for their manufacture. The compounds are useful as intermediates and also as hormonal agents, particularly progestational agents.

Compounds of the formula I ##STR1## wherein R.sub.2 is hydrogen or an organic acid residue;

Growing community of inventors

Berlin, Germany

Ulrich Kerb