Anti-viral aromatic o-alkylated oximes, ethers and thioethers

C - Chemistry – Metallurgy – 07 – D

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C07D 307/68 (2006.01) A61K 31/27 (2006.01) A61K 31/33 (2006.01) A61P 31/12 (2006.01) C07C 251/38 (2006.01) C07C 333/08 (2006.01) C07D 207/34 (2006.01) C07D 263/34 (2006.01) C07D 277/56 (2006.01) C07D 307/30 (2006.01) C07D 309/32 (2006.01) C07D 319/12 (2006.01) C07D 327/06 (2006.01) C07D 333/38 (2006.01)

Patent

CA 2163175

Compounds of the formula (see formula I) wherein Q is (see formula II) or -XR' ; X is oxygen or sulphur; R1 is hydrogen, halogen, C1-C4 alkyl or C1-C4 alkoxy; R2 is hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C3-C4 alkenyloxy, C3-C4 alkynyloxy, mono-, di- or tri- halomethyl, trifuluoromethoxy, C1-C4 alkylthio, C3-C4 branched alkylthio, nitro, or cyano; R3 is hydrogen or C1-C4 alkyl; R 4 is C3-C6 alkenyl, C3-C6 alkynyl, C1-C8 haloalkyl, C1-C8 alkoxyalkyl, C1-C8 alkylthioalkyl, C1-C8 hydroxyalkyl, C1-C8 acyloxyalkyl, C1-C8 aroyloxyalkyl, C1-C8 carboxyalkyl, C1-C8 alkylcarboxyalkyl, C6-C12 arylcarboxyalkyl, C1-C8 aminoalkyl, C1-C8 alkylaminoalkyl, C1-C8 dialkylaminoalkyl, C1-C8 trialkylsilylalkyl, wherein each of the aforementioned alkyl moieties may be straight-chain or branched; C3-C8 cycloalkyl, C1-C6 alkylphenyl, C7-C12 arylalkyl, C7-C12 alkarylalkyl, or heterocyclylalkyl, wherein the heterocyclic moiety is morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, oxiranyl, oxetanyl, furanyl, tetrahydropyranyl or tetrahydrofuranyl; R' is C1-C8 haloalkyl, C1-C8 alkoxyalkyl, C1-C8 alkylthioalkyl, C1-C8 hydroxyalkyl, C1-C8 acyloxyalkyl, C1-C8 aroyloxyalkyl, C1-C8 aminoalkyl, C1-C8 alkylaminoalkyl, C1-C8 dialkylaminoalkyl, C1-C8 trialkylsilylalkyl, wherein each of the aforementioned alkyl moieties may be straight-chain or branched; C1-C6 alkylphenyl, C7-C12 arylalkyl, C7-C12 alkarylalkyl, or heterocyclylalkyl, wherein the heterocyclic moiety is morpholinyl, piperidinyl, pyrrolidinyl, piperazinyl, oxiranyl, oxetanyl, furanyl, tetrahydropyranyl or tetrahydrofuranyl; R5 is hydrogen, halo, methyl, mono-, di- or tri-halomethyl; and R6 is an aliphatic or cyclic side chain as defined herein. These compounds are useful for inhibiting the growth or replication of retroviruses such as HIV.

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