Veb Jenapharm

Michael Oettel

Kurt Ponsold

Michael Hubner

Herbert Hoffmann

Joachim Strecke

Richard Prousa

Compounds of the general formula ##STR1## in which R' is hydrogen or a methyl radical; R is a hydroxyl, acetoxy, arylaminocarbonyloxy, alkylaminocarbonyloxy radical;

14,15-Methylene derivatives of the estrane series and methods for

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.

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Jena, Germany

Michael Oettel