- Patent JPS4856660

Document Type and Number:

Japanese Patent JPS4856660

Kind Code:

A

Abstract:

1367735 Silyl ethers of 11-alkyl-3-hydroxyestratrienes G D SEARLE & CO 6 April 1972 [7 April 1971] 15838/72 Heading C2U [Also in Division A5] Novel steroids of the formula (wherein R is H or a trialkylsilyl radical; R1 is a C 1-3 alkyl radical; and the alkynyl radical contains 2-7 carbon atoms) are prepared (i) when R is trialkylsilyl, by silylating the compounds wherein R is H or corresponding 3-ols, the compounds wherein R is H being in turn prepared by alkynylation of the corresponding 17-ones or by silylation in the 3-position only of corresponding 3-ols. Starting materials of the formula are prepared by silylation of the corresponding 3-ols. 11# - Ethyl - 17α - ethynylestra - 1,3,5(10)- triene - 3,17# - diol is prepared by oxidizing 3 - benzyloxy - 11 - hydroxy - estra - 1,3,5(10)- trien - 17 - one 17 - ethylene ketal (prepared by benzylation of the corresponding 3,11-diol) to the corresponding 11-one, reacting this with C 2 H 5 MgBr to give the corresponding 11#-ethyl- 11α-ol, refluxing this with concentrated hydrochloric acid in ethanol to give 3-benzyloxy- 11 - ethylestra - 1,3,5(10),9(11) - tetraen - 17- one, hydrogenating this to 11#-ethyl-3-hydroxyestra - 1,3,5(10) - trien - 17 - one and alkynylating this. 17α-Ethynyl-11#-(n-propyl)estra-1,3,5- (10) - triene - 3,17# - diol is prepared by reacting 3 - benzyloxy - 17# - hydroxy - estra - 1,3,5(10)- trien - 11 - one (prepared by benzylation of the 3,17 - diol) with allyl magnesium bromide to give 11 - allyl - 3 - benzyloxyestra - 1,3,5(10)- trien - 11,17# - diol, treating this with formic acid to give 11-allyl-3-benzyloxyestra-1,3,5(10),9- (11) - tetraen - 17# - ol 17 - formate, oxidizing this to the corresponding 17-one, hydrogenating this to 3 - hydroxy - 11# - (n - propyl) - estra- 1,3,5(10)-trien-17-one and ethynylating this. The novel steroids have use as chemosterilants for the control of nuisance animal populations, for which purpose they are conveniently incorporated in a bait containing an edible carrier. They may also be made up into pharmaceutical compositions with suitable carriers and used for their estrogenic, anti-fertility and pituitary inhibitory properties.

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