13-Ethinyl-steroids and processes for their manufacture
US4052421A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jan 20, 1976 |
| Grant date | Oct 4, 1977 |
| Priority date | — |
| Expiry date | Jan 20, 1996 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J51/00
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.