Synthesis and purification of valacyclovir

Details Synthesis and purification of valacyclovir Synthesis and purification of valacyclovir

C - Chemistry, Metallurgy

07

D

C07D 473/18 (2006.01) C07D 473/00 (2006.01)

Patent

CA 2465928

The present invention relates to protected valacyclovir, N-tert-butoxycarbonyl- L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy] ethyl ester, and a method of making it. The present invention further relates to a method of making valacyclovir including the steps of coupling an amine protected valine selected from N-tbutoxycarbonyl valine and N-formyl valine with acyclovir using a coupling agent to form a protected valacyclovir, and deprotecting the protected valacyclovir to form valacyclovir or a pharmaceutically acceptable salt thereof. The present invention further relates to valacyclovir in pure form, a method of making pure valacyclovir, and to compositions containing pure valacyclovir.

L'invention concerne du valacyclovir protégé, un ester de N-tert-butoxycarbonyl-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)méthoxy] éthyle, ainsi qu'un procédé de préparation associé. L'invention concerne également un procédé de préparation de valacyclovir. Ce procédé consiste à coupler une valine protégée par une amine, cette valine étant choisie entre une valine N-t-butoxycarbonyle et une valine N-formyle, à de l'acyclovir, au moyen d'un agent de couplage, de sorte à former du valacyclovir protégé; et à déprotéger le valacyclovir protégé, de sorte à former du valacyclovir ou un sel pharmaceutiquement acceptable de celui-ci. L'invention concerne également du valacyclovir sous forme pure, un procédé de fabrication de valacyclovir pur et des compositions contenant du valacyclovir pur.

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