Process for the synthesis of the hydroxyacetyl side-chain of steroids of the pregnane type, novel 21-hydroxy-20-oxo-17.alpha.-pregnane compounds and pharmaceutical preparations containing them
US4424159A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Feb 3, 1982 |
| Grant date | Jan 3, 1984 |
| Priority date | — |
| Expiry date | Feb 3, 2002 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J63/008
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention relates to a novel general process for synthesizing a .alpha.- or .beta.-oriented hydroxyacetyl side chain of steroids of the pregnane type, which comprises treating a corresponding steroid carbaldehyde in succession with formaldehyde dimethylmercaptal-S-oxide in the form of an alkali metal salt thereof, and with a strongly acid hydrolysing agent. Preferred final products are compounds of the formula ##STR1## wherein n is 1 or 2, R.sup.2 represents methyl or difluoromethyl, and R.sup.1 represents hydroxymethyl, methoxymethyl, acetoxymethyl or hydrogen, and, if n is 2 and/or R.sup.2 is difluoromethyl, R.sup.1 also represents methyl. These compounds act as agonists or antagonists of natural steroid hormones. The antigestagenic 19,21-dihydroxy-17.alpha.-pregn-4-ene-3,20-dione and its 6,7-dehydro derivatives and diacetates are of particular interest.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.