Laboratoire Theramex

Laboratoire Theramex S.a.

Claude Tchernatinsky

Alain Piasco

Robert Bucourt

A 3-keto-19-nor-pregnene of the formula ##STR1## wherein R is selected from the group consisting of hydroxy, acyloxy of an organic carboxylic acid, lower alkoxy, halogen and lower alkyl, R' is selected from the group consisting of hydrogen and halogen, or R and R' together form oxygen, R.sub.3 is selected from the group consisting of methyl, --OH and lower acyloxy of an organic carboxylic acid and the dotted line is an optional double bond in the 6,7-position useful for treating the symptoms of menopause in females.

3-keto-nor-pregnenes substituted in the 6-position and treatment of

A process for making a known 6-methyl, 19-nor-pregna-4, 6-diene, 3.20-dione which begins with formylating a 3-alcoxy, 19-nor-pregna-3,5,17(20)-triene at the 6 position. The 6-formylated derivative is reduced to yield a 6-hydroxy methylated derivative, which is in turn dehydrated to a 3-keto, 6-methylenic derivative. The 3-keto derivative is then isomerized to a 3-keto, 4,6,17-pregnatriene. This latter triene is then coverted to the known product by reaction with a bis-hydroxylating agent and a catalyst based on osmium tetroxide. Optionally, the product can be acylated at the 17-alpha position. The process reduces the cost of producing the known product by allowing it to be manufactured from starting materials less costly than those previously required.

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Beausoleil, France

Claude Tchernatinsky