Veb Jenapharm

Michael Oettell

Kurt Ponsold

Michael Hubner

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.

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Jena, Germany

Michael Oettell