Preparation of 5-deazariboflavins
US4277603A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Mar 12, 1979 |
| Grant date | Jul 7, 1981 |
| Priority date | — |
| Expiry date | Mar 12, 1999 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H15/18
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
This invention relates generally to a novel process for preparing 5-deazariboflavins by the cyclization of the corresponding 6-(N-substituted arylamino)uracils with trialkylorthoformate in the presence of a strong acid catalyst. An improved process for preparing the uracil intermediate is also disclosed. More particularly, it is concerned with the process for preparing 5-deazariboflavin by cyclizing 6-[3,4-dimethyl-N-(D-ribityl)anilino[uracil with trialkylorthoformate in the presence of a strong acid catalyst and hydrolyzing the resulting alkoxymethylene derivative. The corresponding uracil intermediate is prepared by reacting 6-chlorouracil with N-D-ribityl-3,4-xylidine. 5-Deazariboflavins having the general Formula (I) herein below: ##STR1## wherein R.sub.7 is hydrogen or methyl, R.sub.8 is methyl, hydroxy or acyloxy and R.sub.10 is a ribityl group and the corresponding acyl and alkoxymethylene derivatives are useful as riboflavin antagonists with particular utility for the chemotherapy of coccidiosis in chickens or as intermediates for the preparation of said antagonists. The bis(alkoxymethylene) derivatives described herein are useful as prodrug forms of 5-deazariboflavins. Whe…
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.