Azole nucleosides and use as inhibitors of rna and dna viral...

Details Azole nucleosides and use as inhibitors of rna and dna viral... Azole nucleosides and use as inhibitors of rna and dna viral...

C - Chemistry, Metallurgy

07

H

C07H 19/056 (2006.01) A01N 43/04 (2006.01) A61K 31/7056 (2006.01) A61P 31/14 (2006.01) C07D 405/04 (2006.01) C07H 19/04 (2006.01) C07H 19/044 (2006.01)

Patent

CA 2663618

Azole nucleosides represented by the formulae (I) and (II); wherein A = C or N B = C or N X = H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, C1, Br and I; OH, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo); Z = H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo, halogen such as F, Cl, Br, I; OH, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo; E= (CH2)HONHR1; n is an integer from 0-6 and more typically 0-3; R1= aryl or heterocyclo; each of W, Y, R is individually selected from the group consisting of H; C1-C6 alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heterocyclo; halogen such as F, Cl, Br, and I; O, OH, Oalkyl, Oaryl, NH2, NH-(C1-C6 alkyl, cycloalkyl, aryl, or heterocyclo); provided that at least one of W, Y, and R is other than H and wherein both W and Y together can be =O; and each D individually is OH, Oalkyl, Oaryl, Fl and H;pharmaceutically acceptable salts thereof, prodrugs thereof and mixtures thereof are provided. Compounds of this disclosure are useful as inhibitors of viral RNA and DNA polymerases such as, but not limited to, Influenza, Hantaan Virus, Crimean Congo hemorrhagic fever virus, hepatitis B, hepatitis C, Polio, Coxsackie A and B, Rhino, Echo, orthopoxvirus (small pox), HIV, Ebola, and West Nile virus polymerases; and especially orthopoxvirus, HIV, and hepatitis B.

L'invention concerne des nucléosides d'azole représentés par les formules (I) et (II) ; dans lesquelles A = C ou N B = C ou N X = H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo, halogène tels que F, C1, Br et I ; OH, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; Z = H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo, halogène tels que F, Cl, Br, I ; OH, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; E= (CH2)HONHR1 ; n est un entier compris 0 et 6 et plus généralement entre 0 et 3 ; R1= aryle ou hétérocyclo ; W, Y, R sont choisis individuellement dans le groupe constitué par H ; alkyle, cycloalkyle, alcényle, cycloalcényle, alkynyle, aryle C1-C6, hétérocyclo ; halogène tels que F, Cl, Br et I ; O, OH, Oalkyle, Oaryle, NH2, NH-(alkyle, cycloalkyle, aryle C1-C6 ou hétérocyclo) ; à condition qu'au moins W, Y ou R soit autre que H, W et Y pouvant être ensemble =O ; et chaque D représente individuellement OH, Oalkyle, Oaryle, Fl et H ; des sels pharmaceutiquement acceptables, des promédicaments et des mélanges de ceux-ci. Les composés selon l'invention sont utiles en tant qu'inhibiteurs de polymérases d'ARN et d'ADN viral telles que, entre autres, les polymérases de la grippe, du virus Hantaan, du virus de la fièvre hémorragique de Crimée-Congo, de l'hépatite B, de l'hépatite C, de la polio, de Coxsackie A et B, de Rhino, d'Echo, de l'orthopoxvirus (variole), du VIH, d'Ebola et du virus du Nil occidental ; et en particulier de l'orthopoxvirus, du VIH et de l'hépatite B.

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