Method of preparation of ethers tetrahydropyranyl in 17 and bis - tetrahydropyranyl in 3 and 17 of estradiol or its derivatives, and products thus obtained

摘要

Novel steroids of the formulae FORM:1087585/C2/1 (wherein R is H or CH3; R1 is OH, Oacyl or tetrahydropyranyloxy; R2 is H, C1- 8 alkyl, C2- 8 alkenyl or C2- 8 alkynyl, or R1h + R2 is keto; R3 is H, OH, Oacyl or CH3; R4 is H or a - or b -CH3; X is H, CH3, Cl or F; and Z is a double or single bond) and other 3-tetrahydropyranyloxy - D 4 - steroids of the androstane, 19 - norandrostane and pregnane series are prepared from the free 3b -ols and an excess of dihydropyran in the presence of an arylsulphonyl halide catalyst. Free 17-ols are converted to the 3,17-bistetrahydropyranyl ethers. Products which are 17-acylates can be hydrolysed and 17 ols acylated. 3 - Hydroxy - D 4 - and D 4, 6 - steroids used a starting materials are prepared by reduction of the corresponding D 4-3-keto-steroids, with, if necessary, protection of other OH groups e.g. at C-17, by esterification. The steroid tetrahydropyranyl ethers of the invention are stated to promote nitrogen retention when administered orally, variously to possess anti-estrogenic, blood cholesterol lowering, gonadotrophin inhibiting and progestational properties, and to be useful in fertility control, and they may be made up into pharmaceutical compositions with suitable carriers.