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AssigneeSchering Corporation
InventorsHelmut Hofmeister, Klaus Annen, Rudolf Wiechert, Henry Laurent
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Novel estrogenic 17.alpha.-hydroxy-1,3,5(10),15-estratetraenes of the formula ##STR1## wherein R.sub.1 is H, lower alkyl or lower acyl, R.sub.2 is lower alkyl and R.sub.3 is H, lower alkyl, lower acyl or tetrahydropyranyloxy, are produced by (a) reacting a 16.alpha.,17.alpha.-epoxy-estratriene with lithium halide or HCl in glacial acetic acid; converting the resulting halohydrin into a 16-halo-17-tetrahydropyranyl ether; and splitting off hydrogen halide from therefrom; or (b) reacting the 16.alpha.,17.alpha.-epoxy-estratriene with diphenylselenide and alkali metal borohydride; oxidizing the thus-produced 17.alpha.-hydroxy-16.beta.-phenylselenide to the corresponding phenylselenide oxide; and forming the .DELTA..sup.15 double bond by heating with removal of phenyl--Se--OH.
A 17.alpha.-oxy-1,3,5(10),15-estratetraene of the formula ##STR7## wherein R.sub.1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms;
A compound of claim 1, 17.alpha.-acetoxy-3-methoxy-18-methyl-1,3,5(10),15-estratetraene.
A 16.beta.-halo-17.alpha.-tetrahydropyranyloxy estratriene of the formula ##STR11## wherein R.sub.1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R.sub.2 is alkyl of 1-5 carbon atoms.
A 16.alpha.,17.alpha.-epoxy-estratriene of the formula ##STR12## wherein R.sub.1 is a hydrogen atom or alkanoyl of 1-5 carbon atoms and R.sub.2 is ethyl.
A compound of the formula ##STR13## wherein R.sub.1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R.sub.2 is alkyl of 1-5 carbon atoms.
A 17.alpha.-tetrahydropyranyloxy-1,3,5(10),15-estratetraene of the formula ##STR14## wherein R.sub.1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and THP is tetrahydropyranyl.
Dependencies are inferred from the claim text.