Oxidation of glycoside substituted taxanes to taxol or taxol precursors and new taxane compounds formed as intermediates
US5412116A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 7, 1993 |
| Grant date | May 2, 1995 |
| Priority date | — |
| Expiry date | Oct 7, 2013 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/256
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
A process for the conversion of glycoside substituted taxanes to taxol and related compounds that can serve as precursors to taxol. The process includes the oxidation of glycoside substituted taxanes to convert the glycoside to the hydroxyl group. The oxidation can occur in the presence of an acid or followed by treatment with acid. Application of the process to 7-xylosyl taxol ("XT") yields taxol; application to other glycoside substituted taxanes forms compounds that can serve as precursors for taxol. The process includes the formation of certain new taxol related intermediate compounds having a hemialdal at the C-7 site on the taxane ring, which hemialdal can then be converted to taxol or taxol precursors. Since glycoside substituted taxanes are isolated with taxol from naturally occurring biomass, their conversion to taxol using the process of the present invention significantly improves the total yield of taxol from natural sources.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.