Substances stéroïdes dérivant de la 19-nortestostérone et leurs procédés de préparation

The invention comprises steroids of the formulae and wherein R is an alkyl group, R1 is an alkyl group of at least two carbon atoms, X is a hydroxymethylene, acyloxymethylene, carbonyl or ketalized carbonyl group, and the hydrogen atoms and group R1 at the junctions in ring C are in the trans-anti-trans configuration; the preparation of steroids of formula I, wherein R is more widely defined, as a substituted or unsubstituted aliphatic hydrocarbon group of the kind whose linkage to the oxygen atom is stable to the action of an alkali metal in liquid ammonia, R1 is as defined above and X is a hydroxymethylene or ketalized carbonyl group, by reducing, with an alkali metal in liquid ammonia in the presence of a proton donor a corresponding steroid of the formula wherein X is a hydroxymethylene, carbonyl or ketalized carbonyl group, ring C is saturated or contains an ethylenic bond terminating at the 9-position, the C : D ring junction is in the trans-configuration, the hydrogen atom at the 8-position where present is anti to the hydrogen atom at the 14-position, and the hydrogen atom at the 9-position where present is trans to the hydrogen atom at the 8-position; the preparation of the steroids of Formula I, wherein X is a carbonyl group by oxidation of the corresponding steroids, wherein X is a hydroxymethylene group; and the preparation of the 3-ketones of Formula II by mild hydrolysis of the steroids of Formula I. Products of Formula I, wherein X is an acyloxymethylene group are prepared by acylation of the corresponding 17-hydroxy compounds. The above structures include all states of resolution except the resolved 13a -enantiomers. Examples are given. Specification 975,596, 991,594, 1,010,051, 1,010,052 and 1,010,054 are referred to.