Preparation of diacyl derivatives of 2'-deoxy-5-fluorouridine via novel intermediate compound
US5013828A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 21, 1989 |
| Grant date | May 7, 1991 |
| Priority date | — |
| Expiry date | Apr 21, 2009 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
2'-Deoxy-3',5'-diacyl-5-fluorouridines useful as antitumor medicines or intermediates thereof are easily and efficiently obtained by first fluorinating 2'-deoxyuridine in aqueous solution with fluorine gas to thereby form 2'-deoxy-5,6-dihydro-5-fluoro-6-hydroxyuridine, which is a novel compound, and reacting this compound with a carboxylic acid anhydride or halide R--CO--X, where R is an aliphatic group having not more than 20 carbon atoms or a substituted or unsubstituted phenyl group, and X is an acyloxy group RCO.sub.2 or a halogen atom. In the initial fluorination reaction the aqueous solution may contain a carbonate (or a hydrogen carbonate) or a lower fatty acid or its salt to capture hydrogen fluoride formed by the reaction. The next acylating reaction can be promoted by carrying out the reaction in the presence of an organic base such as pyridine.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.