Processes for production of nucleosides

Details Processes for production of nucleosides Processes for production of nucleosides

C - Chemistry, Metallurgy

07

H

C07H 19/167 (2006.01) C07H 19/06 (2006.01) C07H 19/067 (2006.01) C07H 19/16 (2006.01)

Patent

CA 2513545

A process for the production of nucleosides represented by the general formula [II], characterized by subjecting a 2~, 3~, 5~-triacyloxynucleoside represented by the general formula [I] to deacylation with 0.01 to 0.5 time by mole as much alkali metal hydroxide as the 2~, 3~, 5~-triacyloxynucleoside. The invention provides a process for the production of nucleosides [II] which little suffers from the formation of by-products and a process for the production of nucleoside derivatives according to the process. Further, the invention also relates to a process of oxidizing a nucleoside represented by the general formula (1) in the presence of a 2,2,6,6-tetramethylpyridine-1- oxyl catalyst and a hypochlorite or hypobromite while controlling the pH within the range of 5 to 9, and a process which comprises extracting a carboxylic acid nucleoside represented by the general formula (2) with an organic solvent under acidic conditions, subjecting the obtained organic solution to back extraction with an aqueous alkaline solution, and neutralizing the obtained aqueous solution by the addition of an acid to crystallize the carboxylic acid nucleoside. According to these processes, specific carboxylic acid nucleosides or salts thereof can be produced at high purity by processes suitable for industrial production. [I] [II] (1) (2) (In the formulae, each symbol is as defined in the description.)

L'invention concerne un procédé de production de nucléosides représenté par la formule générale (II), qui consiste à soumettre un 2',3',5'-triacyloxynucléoside de formule générale (I) à une désacylation utilisant 0,01 à 0,5 fois par mole autant d'hydroxyde de métal alcalin que du 2',3',5'-triacyloxynucléoside. L'invention concerne un procédé de production de nucléosides (II) peu susceptibles de formation de produits inutiles; et une méthode de production de dérivés de nucléosides selon le procédé de l'invention. L'invention concerne également un procédé d'oxydation d'un nucléoside de formule générale (1), en présence d'un catalyseur de 2,2,6,6-tétraméthylpyridine-1-oxyle et d'hypochlorite ou d'hypobromite, le pH étant maintenu dans une plage comprise entre 5 et 9. L'invention concerne en outre un procédé qui consiste à: extraire un nucléoside d'acide carboxylique de formule générale (2) avec un solvant organique, dans des conditions d'acidité; soumettre la solution organique obtenue à une extraction par désorption avec une solution alcaline aqueuse; et neutraliser la solution aqueuse obtenue par adjonction d'un acide propre à cristalliser le nucléoside d'acide carboxylique. Ces procédés permettent de produire des nucléosides d'acide carboxylique spécifiques, ou leurs sels, de grande pureté, grâce à des processus qui conviennent pour la production industrielle. (Dans lesdites formules, chaque symbole est tel que défini dans le mémorandum descriptif).

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