Process for the production of unsaturated 17 .alpha.-cyanomethyl-17 .beta.- h

US5438134A · kind A · utility

Assignee

• Jenapharm GmbH · DE

Inventors

• Gerhard Teichmuller · Jena, DE
• Gerd Muller · Jena, DE

Key dates

• Filing date: Jun 1, 1993
• Grant date: Aug 1, 1995
• Expiry date: Jun 1, 2013

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P15/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The unsaturated 17.alpha.-cyanomethyl-17.beta.-hydroxy steroids of the formula I, ##STR1## in which R.sub.1 =Me, Eth; R.sub.2 =H, Me; R.sub.3 =H, OH, an acetoxy or alkoxy group; R.sub.4 =H, R.sub.5 =OH, an acetoxy, alkoxy group of R.sub.4 and R.sub.5 together represent a keto- or ketal group and double bonds are contained in the basic structure of the steroid, particularly between the 15 and 16 position in the steroid ring, from unsaturated 17-ketosteroids of the general formula II as described herein with the aforementioned meanings of R.sub.1 to R.sub.5 by reacting the unsaturated 17-ketosteroids with LiCH.sub.2 CN and subsequently hydrolyzing. The compounds of formula I are pharmacologically interesting steroid compounds or also intermediate products for the synthesis of highly-effective steroid products which can be used in human and veterinary medicine for the treatment of endocrine disorders and for reproductive control based on their specific hormonal/anti-hormonal actions. The compounds are suitable for the treatment of endometriosis and also in combination with preparations with ethinylestradiol for fertility control.