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

US4248790A · kind A · utility

Assignee

• VEB Jenapharm · DE

Inventors

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

Key dates

• Filing date: Feb 13, 1979
• Grant date: Feb 3, 1981
• Expiry date: Feb 13, 1999

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 preparation, 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-methoxy-13.beta.-R-gona-2,5(10)-diene-17.beta.-spiro-1,`2`-ox iranes to 17.beta.-hydroxy-17.alpha.-CH.sub.2 -13.beta.-R-gona-4,9(10)-diene-3-ones to the 17.alpha.-CH.sub.2 X-14.beta.-ols which are hydrolyzed to the 17.beta.-OH which latter are then converted to the compounds of formula I.