Veb Jenapharm

Michael Hubner

Kurt Ponsold

Michael Oettel

Michael Oettell

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.

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

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.

Growing community of inventors

Jena, Germany

Michael Hubner