Thiadiazoles and their use as antipicornaviral agents

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 285/04 (2006.01) A61K 31/425 (2006.01) A61K 31/44 (2006.01) A61K 31/495 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2190130

Compounds of formula (I) wherein Thi is thiadiazolyl or thiadiazolyl substituted with alcoxy, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1- difluoroethyl, halo, alkyl, cycloalkyl, hydroxyalkyl, or alkoxyalkyl; Y is alkylene bridge of 3-9 carbon atoms; R1 and R2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl, or cyano; R3 is alkoxycarbonyl, phenyl, alkyltetrazolyl or heterocyclyl chosen from benzoxazolyl, benzathiazolyl, thiadioazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, furyl, triazolyl, thienyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or substituted phenyl, or substituted heterocyclyl wherein the substitution is with alkyl, alkoxyalkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxy, hydroxy, furyl, thienyl, or fluoroalkyl; or a pharmaceutically acceptable salt thereof are effective antipicornaviral agents.

L'invention se rapporte à des composés de la formule (I) dans laquelle Thi représente thiadiazolyle ou thiadiazolyle substitué par alcoxy, fluorométhyle, difluorométhyle, trifluorométhyle, 1,1-difluoroéthyle, halo, alkyle, cycloalkyle, hydroxyalkyle ou alcoxyalkyle; Y représente un pont alkylène de 3 à 9 atomes de carbone; R¿1? et R¿2? sont chacun indépendamment sélectionnés parmi hydrogène, halo, alkyle, alcényle, amino, alkylthio, hydroxy, hydroxyalkyle, alcoxyalkyle, alkylthioalkyle, alkylsulfinyle, alkyle, alkylsulfonylalkyle, alcoxy, nitro, carboxy, alcoxycarbonyle, dialkylaminoalkyle, alkylaminoalkyle, aminoalkyle, difluorométhyle, trifluorométhyle ou cyano; R¿3? représente alcoxycarbonyle, phényle, alkyltétrazolyle ou hétérocyclyle sélectionnés parmi benzoxazolyle, benzathiazolyle, thiadioazolyle, imidazolyle, dihydroimidazolyle, oxazolyle, thiazolyle, oxadiazolyle, pyrazolyle, isoxazolyle, isothiazolyle, furyle, triazolyle, thiényle, pyridyle, pyrimidinyle, pyrazinyle, pyridazinyle ou phényle substitué, ou hétérocyclyle substitué dans lesquels la substitution est réalisée avec alkyle, alcoxyalkyle, cycloalkyle, haloalkyle, hydroxyalkyle, alcoxy, hydroxy, furyle, thiényle ou fluoroalkyle; ou à un sel pharmaceutiquement acceptable de ces composés qui sont utilisés comme agents antipicornaviraux.

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