Process of making 3-aryloxy, 4-aryl furan-2-ones useful as inhibitors of COX-2
US6140515A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 15, 1998 |
| Grant date | Oct 31, 2000 |
| Priority date | — |
| Expiry date | Sep 15, 2018 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D307/60
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Described is a process of preparing 3-aryl, 4-aryloxy furan-5-ones which are useful as inhibitors of cyclooxygenase-2 (COX-2). Such compounds are useful as anti-inflammatory agents. The process is directed to an asymmetric synthesis which involves: a trisubstituted styrene derivative preparation via Horner-Wadsworth-Emmons reaction and subsequent one pot trifluoromethylation of the allylic alcohol; preparation of the .alpha.-hydroxyl ketone using Sharpless asymmetric dihydroxylation and Swern oxidation; the esterification of the .alpha.-hydroxyl ketone with the phenoxy acetic acid; and the Dieckman condensation of the resulting ester.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.