Method for making 3.alpha.-hydroxy, 3.beta.-substituted-pregnanes
US5319115A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Mar 4, 1992 |
| Grant date | Jun 7, 1994 |
| Priority date | — |
| Expiry date | Mar 4, 2012 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J71/001
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
This invention provides a simplified method for converting pregnan-3,20-dione compounds to 3.alpha.-hydroxy,3.beta.-substituted-pregnanes. By selective use of reagents the unprotected dione is converted chemoselectively and diastereoselectively into a 3(R)-pregnan-3-spiro-2'oxirane-20-one intermediate. This intermediate can then be converted regioselectively by a second set of reactions to the 3.alpha.-hydroxy,3.beta.-substituted-20-one form, which can be further modified at the 20-keto position. Through this method, each ketone group is independently treated. By modifying the ketones one at a time, one can obtain the desired stereo-specificity at each site.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.