Jenapharm Gmbh & Co. Kg

Jenapharm Gmbh

Bernd Undeutsch

Michael Oettel

Gunter Kaufmann

Sigfrid Schwarz

Peter Droescher

Bernd Menzenbach

Kurt Ponsold

Jens Schroder

Wolfgang Romer

Sven Ring

Guenter Kaufmann

Bernd Erhart

Ina Thieme

Doris Hubler

Gerd Muller

Wolfgang Roemer

Jens Schroeder

Gerhard Teichmuller

Harald Raethe

Peter Moellmann

Gisela Weber

Gerhard Teichmueller

Hans-Joachim Palme

Carmen Pfeiffer

Harry Henkel

Ronald Gebuhr

Wolfgang R&ouml;mer

14, 15-.&agr;.-methylene equilenine derivatives, methods for producing the same and medicaments containing them

The method of prophylaxis and therapy of radical-mediated cell damage includes administering an effective amount of at least one steroid and at least one pharmaceutical adjuvant to a human being. The at least one steroid is selected from the group consisting of ent-estradiol, 17&agr;-estradiol, 8-dehydro-estradiol, 8-dehydro-17&agr;-estradiol, 8(14)-dehydroestradiol, 6,8-didehydro-17&agr;-estradiol, 6-dehydroestriol, 9(11)-dehydroestriol, 20-hydroxymethyl-3-hydroxy-19-norpregna-1,3,5(10)-triene, 14&agr;, 15&agr;-methylene-8-dehydroestradiol, 14&agr;, 15&agr;-methylene-estradiol, 2-hydroxy-estradiol-3-methyl ether, 3-hydroxy-1,3,5(10)-estratriene-17S-spirooxirane, 3-hydroxy-1,3,5(10),9(11)-estratetraene-17S-spirooxirane, and 14&bgr;,15&bgr;-methylene-8-dehydroestradiol. This method strongly inhibits changes in cells and tissues, such as lipid peroxidation and oxidation of low-density lipoprotein (LDL) cholesterol, triggered by reaction oxygen species, free oxygen radicals and other forms of radicals and thus reduces attendant irreversible membrane and endothelial damage.

Pharmaceutical compositions and method for prophylaxis and therapy of radical-mediated cell damage

Novel substituted steroid compounds are disclosed which are more effective than known radical-trapping agents in methods of prophylaxis and therapy of radical-mediated cell damage and of treatment of diseases due to radical-mediated cell damage. The novel substituted steroid compounds can be made from steroids having an estrane, androstane, pregnane or cholestane basic skeleton and have a radical-attracting aromatic substituent of the general formula --(CH.sub.2).sub.n X, or .dbd.CH--(CH.sub.2).sub.m X at the 17 or 6 position of the steroid nucleus, wherein X=Y, OY, SY, SeY or NHY; n=0 to 5; m=n-1 and Y is a phenyl group having five substituents A, B, C, D and E, wherein A to E is independently H, alkyl, Oalkyl, Oacyl, OH, or one of the substituents B, C or D is NR.sub.2 wherein R=alkyl and each of the other substituents is hydrogen. Pharmaceutical compositions containing the novel substituted steroid compounds and methods of making them are also part of the invention.

Steroids with radical-attracting aromatic substituents, process for the

The 17.alpha.-cyanomethylestra-4,9-diene derivative compounds are of formula I: ##STR1## wherein R.sub.1 is an alkyl group having from 1 to 2 carbon atoms; R.sub.2 is an alkyl group with 1 to 10 carbon atoms, an acyl group with 1 to 10 carbon atoms or a trialkylsilyl group; and R.sub.3 is an oxygen atom or a R--O--N group, wherein R is a hydrogen atom, an acyl group with 1 to 10 carbon atoms, an alkyl group with 1 to 10 carbon atoms, a sulfamoyl group, an alkylsilyl group or a trialkylsilyl group. These compounds, particularly in combination with at least one suitable estrogen, are suitable for treatment of endometrioses or gestagen-dependent tumors and for hormonal contraception and climacteric hormone replacement therapy (HRT). Processes for making the new steroids are described as well as methods of making the pharmaceutical compositions containing them.

17.alpha.-cyanomethylestra-4,9-dien derivatives and pharmaceutical

The invention is directed to novel steroid intermediate products of general formula I ##STR1## The steroid intermediate products which can be isolated according to the invention are suitable for the synthesis of 13-ethyl-11-methylene-18,19-bisnor-17.alpha.-pregn-4-en-20-in-17-ol (desogestrel). Further, processes for producing the steroid intermediate products of general formula I are described. The olefination of the 11-oxo steroids is carried out under the influence of ultrasound.

Steroid intermediate products and method of their production

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Jena, Germany

Bernd Undeutsch