Improved synthesis of 2-substituted adenosines

Details Improved synthesis of 2-substituted adenosines Improved synthesis of 2-substituted adenosines

C - Chemistry, Metallurgy

07

H

C07H 1/00 (2006.01) C07H 19/16 (2006.01)

Patent

CA 2552583

Synthesis of 2-substituted adenosines of formula (I) using 2-nitro pentabenzoyl adenosine, or 2-nitro pentaacetyl adenosine, as intermediate is described: Formula (I) wherein R = C1-6 alkoxy (straight or branched), a phenoxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3- , cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), a benzyloxy group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-, cyano, nitro, C1-6 alkyl, or C1-6 alkoxy), or a benzoyl group (unsubstituted, or mono-, or di-substituted by halo, amino, CF3-,cyano, nitro, C1-6 alkyl, or C1-6 alkoxy). The methods provide improved yield and purity of product.

L'invention concerne la synthèse d'adénosines substituées en 2 de formule I, au moyen de 2-nitro pentabenzoyl adénosine, ou de 2-nitro pentaacétyl adénosine, en tant qu'intermédiaire. Dans ladite formule (I), R = C¿1-6? alcoxy (linéaire ou ramifié), un groupe phénoxy (non substitué, ou mono-, or di-substitué par halo, amino, CF¿3?-, cyano, nitro, C¿1-6? alkyle, or C¿1-6? alcoxy), un groupe benzyloxy (non substitué, ou mono-, ou bi-substitué par halo, amino, CF¿3?-, cyano, nitro, C¿1-6? alkyle, ou C¿1-6? alcoxy), ou un groupe benzoyle (non substitué, ou mono-, or di-substitué par halo, amino, CF¿3?-,cyano, nitro, C¿1-6? alkyle, or C¿1-6? alcoxy). Les procédés de l'invention permettent une production à rendement élevé de produit pur.

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