Process for preparing antiviral nucleoside derivatives

Details Process for preparing antiviral nucleoside derivatives Process for preparing antiviral nucleoside derivatives

C - Chemistry, Metallurgy

07

H

C07H 19/056 (2006.01)

Patent

CA 2537849

Process and novel intermediates for preparing 2-aminocarboxylic acid esters of the 5~- hydroxymethyl group of levovirin (1-(3S, 4R-dihydroxy-5S-hydroxymethyl- tetrahydro furan-2S-yl)-IH-[1,2,4]triazole-3-carboxylic acid amide; Id: R1=R2 =R3 =H) and acid addition salts thereof. The present process provides the monoesters selectively in high purity with increased efficiency with reduced number of production steps. The process involves condensation of a cyclopentylidene levovirin compound with a N-urethane-N~-carboxylic anhydride and subsequent deprotection to directly provide the hydrochloride salt of the product. The mono esters are useful for treatment of viral diseases and are absorbed more efficiently than the parent compound.

L'invention concerne des procédés et de nouveaux intermédiaires permettant d'obtenir des esters 2-aminocarboxyliques du groupe 5-- hydroxyméthyle de l'amide levovirine (1-(3S, 4R-dihydroxy-5S-hydroxyméthyl-tétrahydro furan-2S-yl)-IH-[1,2,4]de l'acide triazole-3-carboxylique; Id: R?1¿=R?2¿ =R?3¿ =H) et des sels d'addition acides de ces composés. Ce procédé permet d'obtenir des monoesters sélectivement avec une grande pureté, un rendement accru et un nombre réduit d'opérations de fabrication. Le procédé consiste à condenser un composé de cyclopentylidène levovirine avec un anhydride N-uréthane-N--carboxylique avec déprotection subséquente permettant d'obtenir directement le sel de chlorhydrate du produit. Ces monoesters conviennent pour le traitement de maladies virales et sont absorbés plus efficacement que le composé d'origine.

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