.DELTA..sup.9(11) - And .DELTA..sup.16 -21-chloro-20-keto steroids of the pregnane and D-homopregnane series, their preparation and use as intermediates for the synthesis of highly effective corticoids

US4404141A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Klaus Annen · Berlin, DE
• Henry Laurent
• Helmut Hofmeister · Berlin, DE

Key dates

• Filing date: Mar 9, 1982
• Grant date: Sep 13, 1983
• Expiry date: Mar 9, 2002

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J71/0031
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

.DELTA..sup.16 - and .DELTA..sup.17 -21-chloro-20-keto steroids of the formula ##STR1## wherein n is 1 or 2, PA1 C.sub.1 C.sub.2 and C.sub.9 C.sub.11 represent a CC-single or CC-double bond, PA1 R.sub.1 is H or OH, PA1 R.sub.2 is H or CH.sub.3, PA1 R.sub.3 is H or F wherein, when R.sub.3 =F, C.sub.9 C.sub.11 is a CC-single bond, and PA1 R.sub.4 is H, CH.sub.3, or F, are valuable intermediates for preparation of highly effective, known steroids. A process for preparing these compounds involves heating the corresponding 11.beta.- and/or 17.alpha.- or 17a.alpha.-nitrooxy-21-mesyloxy-20-keto steroids with lithium chloride in a dipolar aprotic solvent at temperatures above room temperature.