Process for preparing inhibitors of nucleoside metabolism

Details Process for preparing inhibitors of nucleoside metabolism Process for preparing inhibitors of nucleoside metabolism

C - Chemistry, Metallurgy

07

F

C07F 7/18 (2006.01) C07D 487/04 (2006.01) C07D 519/00 (2006.01)

Patent

CA 2368095

A process of preparing a compound of formula (I), wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H, halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted alkyl, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of formula (II) with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX), to form a compound of formula (XX). The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

L'invention concerne un procédé qui permet de préparer un composé de formule (I), dans laquelle B représente OH, NH2, NHR, H ou halogène; D représente OH, NH2, NHR, H, halogène ou SCH3; R est un groupe alkyle, aralkyle ou aryle éventuellement substitué; et Z représente OH, hydrogène, halogène, hydroxy, SQ ou OQ, Q étant un groupe alkyle, aralkyle ou aryle éventuellement substitué; ou bien un tautomère, un sel pharmaceutiquement acceptable, un ester ou un promédicament dudit composé. Le procédé consiste à faire réagir un composé de formule (II) avec un anion produit par soustraction de l'atome de brome ou d'iode d'un composé de formule (XIX), de façon à former un composé de formule (XX); puis à déprotéger les atomes de N et de O du composé de formule (XX) afin d'obtenir le composé de formule (I).

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