Processes for stereoselective synthesis of trans ISATX247
US7799756B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jul 26, 2005 |
| Grant date | Sep 21, 2010 |
| Priority date | — |
| Expiry date | Oct 7, 2027 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07K7/645
- WIPO fieldBiotechnology
- WIPO sectorChemistry
Abstract
The present invention relates to a process for preparation of a trans ISATX247 compound of the formula: where R1═H or D; R2═H or D; and R3═H or D, by application of organozirconium chemistry. The process involves reacting an acetyl cyclosporin aldehyde with an organozirconium reagent to provide acetyl cyclosporin diene (the acetate of trans ISATX247) and deacetylating the acetyl cyclosporin diene to produce the trans-isomer of ISATX247. The present invention also relates to a process for preparing the same trans ISATX 247 compound, using olefin cross metathesis. The process involves: olefin cross metathesis of acetyl cyclosporin A to afford acetyl cyclosporin α,β-unsaturated aldehyde; Wittig reaction of the acetyl cyclosporin α,β-unsaturated aldehyde to provide acetyl cyclosporin diene; and deacetylation of the acetyl cyclosporin diene to produce the trans ISATX247 compound. Also disclosed are processes for preparing an acetyl cyclosporin α,β-unsaturated aldehyde compound and a cyclosporin triene analogue compound.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.