13-Ethinyl-steroids and processes for their manufacture

Details 13-Ethinyl-steroids and processes for their manufacture 13-Ethinyl-steroids and processes for their manufacture

1976-01-20

1977-10-04

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

26023955C, 2603973, 2603974, C07J 100

Patent

active

040524213

ABSTRACT:
A new class of 13-ethinyl-steroids is prepared by a novel process comprising Wittig reaction of a 13-formyl steroid with a chloro- or bromomethylenephosphorane and dehydrohalogenation of the intermediate 13-(2-halogenovinyl)steroid with an extremely strong base. Preferred products are those of the formula ##STR1## wherein R denotes a hydrogen atom or the methyl group, R.sub.3 denotes a hydrogen atom or a lower alkyl or lower alkanoyl group, R.sub.4 denotes a hydrogen atom or a lower aliphatic hydrocarbon radical, or R.sub.3 and R.sub.4 together denote a C--O linkage, R.sub.5 denotes the oxo group, a hydrogen atom together with an esterified or free hydroxyl group, or two hydrogen atoms, R.sub.6 denotes a hydrogen atom or a lower alkyl group, and R.sub.7 denotes a hydrogen atom or the methyl group, it also being possible for an additional 1,2-double bond to be present in compounds in which R is the methyl group. These compounds are pharmacologically active in a manner analogous to that of natural sexual hormones, and are distinguished as blockers of the secretion of pituitary gonadotrophins; accordingly, they are useful in medicine for the corresponding indications and for fertility control.

REFERENCES:
patent: 3267005 (1966-08-01), Foell et al.
patent: 3798215 (1974-03-01), Galantay et al.
patent: 3959322 (1976-05-01), Hughes et al.

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