Schering Aktiengesellschaft

Bayer Pharma Aktiengesellschaft

Jenapharm Gmbh

Bernd Erhart

Sven Ring

Gerd Schubert

Sigfrid Schwarz

Detlef Grawe

Sabine Gliesing

Bernd Undeutsch

Hagen Gerecke

Gerd Mueller

Peter Hoesel

Michael Sander

Uwe Mueller

Thomas Michel

Ulf Tilstam

Robert Eilers

Harald Raethe

Peter Moellmann

Dieter Wehmeier

Uwe Knabe

Michael Mosebach

David Voigtlaender

Gisela Weber

Gerhard Teichmueller

Hans-Joachim Palme

Jürgen Jacke

Carmen Pfeiffer

Klaus Bahl

Ulf Bohlmann

The present invention relates to a method for the reliable and reproducible preparation of 4-[17&#x3b2;-methoxy-17&#x3b1;-methoxymethyl-3-oxoestra-4,9-dien-11&#x3b2;-yl]benzaldehyde (E)-oxime (asoprisnil) on the pilot and manufacturing scale. Asoprisnil, which is prepared by this method, is distinguished by a very good physical stability and is therefore particularly suitable for the manufacture of solid pharmaceutical forms (tablets, coated tablets, etc.).

Method for preparing 4-[17&#x3b2;-methoxy-17&#x3b1;-methoxymethyl-3-oxoestra-4,9-dien-11&#x3b2;-yl]benzaldehyde (E)-oxime (asoprisnil)

The invention relates to a process for the production of 4-(17&#x3b1;-methyl-substituted 3-oxoestra-4,9-dien-11&#x3b2;-yl)benzaldehyde-(1E or 1Z)-oximes of general formula (I), in which Ris a hydrogen atom, a C-alkyl radical or a CFradical, whereby n is 1, 2 or 3, Ris a C-alkyl radical, X is an OH group in E- or Z-position, and Y is an OC-alkyl group, an SC-alkyl group or an OCHCFgroup, whereby n is 1, 2 or 3, which provides the target compounds of formula (I) with a high yield and good selectivity 

Method for the production of 4-(17$g(a)-methyl substituted 3-oxoestra-4 9-dien-11$g(b)-yl)benzaldehyd-(1e or 1z)-oximes

The invention relates to a method for the production of 4-(17&#x3b1; substituted 3-oxoestra-4,9-dien-11&#x3b2;-yl)benzaldehyd-(1E or 1Z)-oximes of general formula (I), where R&#x2550;H, Calkyl or a CFgroup; R&#x2550;Calkyl, X=E- or Z-OH; and Y&#x2550;O&#x2014;Calkyl, S&#x2014;Calkyl or O&#x2014;CHCF, where n=1, 2 or 3, which produces the target compounds of formula (I) with high yield and selectivity.

Method for the production of 4-(17&#x3b1;-substituted-3-oxoestra-4,9-dien-11&#x3b2;-yl)benzaldehyde-(1E)-oximes

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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Kahla, Germany

Bernd Erhart