Therapeutic phenoxyalkylpyridazines and intermediates therefor

C - Chemistry – Metallurgy – 07 – D

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C07D 413/12 (2006.01) A61K 31/33 (2006.01) C07D 237/08 (2006.01) C07D 307/42 (2006.01) C07D 307/54 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01) C07D 405/04 (2006.01) C07D 405/12 (2006.01) C07D 407/04 (2006.01) C07D 407/12 (2006.01) C07D 409/12 (2006.01) C07D 413/14 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2190129

Compounds of formula (A), Z is (B) or (C) wherein: R1 and R2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalcoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alcoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano; Y is alkylene of 3 to 9 carbon atoms; R3 and R4 are each independently chosen from hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalcoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo; R5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle chosen from benzoxazolyl, benzathiazolyl, thiadiazolyl, imidazolyl, dihydroimidazolyl, oxazolyl, thiazolyl, oxadiazolyl, pyrazolyl, oxazolinyl, isoxazolyl, isothiazolyl, furyl, triazolyl, thiophenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any of the above substituted with alkyl, alkoxyalkyl, cycloalkyl, halo, alkyl, hydroxyalkyl, alkoxy, hydroxy, halo, furyl, thienyl, fluoroalkyl; or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipicornaviral agents.

Composés répondant à la formule (A), où Z représente (B) ou (C), R¿1? et R¿2? sont chacun indépendamment choisis entre hydrogène, halo, alkyle, alcényle, alcoxy, hydroxy, hydroxyalkyle, hydroxyhaloalkyle, alcoxyalkyle, alkylthioalcynyle, hydroxyalcoxy, alkylthioalkyle, alkylsulfinylalkyle, alkylsulfonylalkyle, amino, aminoalkyle, alkylaminoalkyle, dialkylaminoalkyle, alcoxycarbonyle, carboxy ou cyanométhyle, nitro, diflurométhyle, trifluorométhyle ou cyano; Y représente alkylène contenant 3 à 9 atomes de carbone; R¿3? et R¿4? sont chacun indépendamment choisis entre hydrogène, alkyle, alcoxy, hydroxy, cycloalkyle, hydroxyalkyle, hydroxyhaloalkyle, alcoxyalkyle, hydroxyalcoxy, alkylthioalkyle, alcanoyle, alcanoyloxy, alkylsulfinylalkyle, alkylsulfonylalkyle, aminoalkyle, alkylaminoalkyle, dialkylaminoalkyle, alcoxycarbonyle, carboxy ou cyanométhyle, fluroalkyle, cyano, phényle, alcynyle, alcène ou halo; R¿5? représente alcoxycarbonyle, alkyltétrazolyle, phényle ou un hétérocycle choisi entre benzoxazolyle, benzathiazolyle, thiadiazolyle, imidazolyle, dihydro-imidazolyle, oxazolyle, thiazolyle, oxadiazolyle, pyrazolyle, oxazolinyle, isoxazolyle, isothiazolyle, furyle, triazolyle, thiophényle, pyridyle, pyrimidinyle, pyrazinyle, pyridazinyle, ou l'un quelconque des éléments précités substitués par alkyle, alcoxyalkyle, cycloalkyle, haloalkyle, hydroxyalkyle, alcoxy, hydroxy, halo, furyle, thiényle, fluoroalkyle. Ces composés, ou un de leurs sels d'addition d'acide pharmaceutiquement acceptables, et leurs N-oxydes, peuvent s'utiliser comme agents antipicornaviraux.

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