Oral compositions containing 3-substituted 17-ª--methyl testosterones

The invention comprises inter alia the 3-enol alkyl or cycloalkyl ethers of free or acylated 17a -methyl testosterone having from 4-8 carbon atoms in the alkyl or cycloalkyl group. The compounds are prepared by (a) reacting methyl magnesium bromide with the corresponding enol ether of androstene-3,17-dione or (b) reacting the appropriate alcohol with the 3-enol ethyl ether of 17a -methyl testerone free or acylated in the presence of an acid catalyst, e.g. p-toluene sulphonic acid. The above process (b) may be used to prepare other 3-enol alkyl and benzyl ethers of 17a -methyltestosterone especially those substituted with functional substituents such as nitro and halo substituents. 3-Alkylene ketals of 17a -methyltestosterone are prepared by reacting 3-alkylene ketals of D 4-androstene-3,17-dione with methyl magnesium halide.ALSO:An oral composition having a high androgenic and anobolic activity comprises a 3-enol ether or a 3-glycol ketal of 17a methyl tertosterone or a 17b ester thereof, mixed with an orally ingestible pharmaceutical carrier. The 3-enol ether of tertosterone has at the 3 position a residue of an aliphatic, alicyclic arylaliphatic, aromatic or heterocyclic alcohol. The residue may contain a straight or branch chain alkyl group, which may be substituted e.g. by halogen; an alkylene group e.g. ethylene, a tetrahydropyraryl group or maybe a sugar residue such as that of glucose, galactose or maltose. Preferred ethers have a straight alkyl chain of 4 to 8 carbon atoms with or without methyl or ethyl substituents, at the 3 position. Preferred glycol ketals are alkylene glycol ketals having 2 to 4 carbon atoms in the glycol group. The compositions may be in the form of coated or uncoated tablets, powders, syrups and capsules e.g. keratin or gelatin capsules and are stabilised by adding an alkaline oxide e.g. MgO or an alkaline carbonate. The preferred carrier is a lipid from animal or vegetable sources, specified lipid carriers are (a) oils e.g. coconut, corn, cottonseed, lard, linseed, olive, sunflower seed, palm, peanut, sesame, soya bean, wheat germ and egg yolk oil. (b) Fats e.g. butter fat, lard, cocoa butter or margarine fat; (c) esters of glycerol with high molecular weight long chain fatty acids of 10-22 C atoms; (d) the free fatty acids contained in fats or oils having 10 to 22 carbon atoms e.g. decenoic, decosanoic lauric, palmitic, stearic, archidic, oleic, linoleic and linolenic acids. Other adjuvants specified are magnesium stearate