Gona-4,9(10)-dienes and process of producing the same

US4167517A · kind A · utility

Assignee

• VEB Jenapharm · DE

Inventors

• Kurt Ponsold · Jena, DE
• Michael Hübner · Weinheim, DE
• Michael Oettel · Jena, DE

Key dates

• Filing date: Jul 18, 1977
• Grant date: Sep 11, 1979
• Expiry date: Jul 18, 1997

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J41/0094
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

New gona-4,9(10)-dienes of formula I ##STR1## where R is alkyl of 1 to 3 carbon atoms and X is Cl, Br, F, N.sub.3, SCN, CN, OH, OR'(R'=alkyl), NH.sub.2, a substituted amino group or a heterocyclic compound including nitrogen in the ring. The compounds have valuable biological properties, especially hormonal and antihormonal effects, and can be used to advantage in pharmaceutical preparations for the treatment of endocrinopathies and for reproduction control in human beings and livestock. The invention also embraces a process for making the compounds by converting 3-methyoxy-13.beta.-R-gona-2,5(10)-diene-17.beta.-spiro-1',2'-o xiranes first to 17.beta.-hydroxy-17.alpha.-CH.sub.2 X-13.beta.-R-gon-5(10)-en-3-one, then to the 17.beta.-hydroxy-17.alpha.-CH.sub.2 X-13.beta.-R-gona-4,9(10)-diene-3-ones of formula I.