Anti-inflammatory 1-substituted-4,5-diaryl-2-...

C - Chemistry – Metallurgy – 07 – D

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260/305, 260/315

C07D 405/00 (2006.01) C07D 233/84 (2006.01) C07D 317/56 (2006.01)

Patent

CA 1107286

ABSTRACT OF THE DISCLOSURE Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted- thio) imidazoles and their corresponding sulfoxides and sul- fones useful for treating arthritis and related disease are disclosed. The imidazoles are of the formula Image - R1 where n = 0, 1, or 2; R1 = C1 - C6 alkyl; allyl: vinyl; -CH2COCH3; -CH2S(O)mCH3, where m = 0, 1, or 2; mono- and poly- halo- C1 - C4 alkyl; R2 and R3, the same or different = Image Y1 and Y2, the same or different = hydrogen, C1 - C4 alkoxy, C1 - C4 alkyl, Cl, F, CF3, NH2, -N(CH3)2, NO2, CH3S-, CH3SO2-, or Y1 and Y2 taken together forming a dioxymethylene bridge; provided, when R1 = C1 - C4 alkyl, C3 - C4 haloalkyl with halogen substituted at the 3 or 4 position, allyl, or acetonyl, both Y1 and Y2 cannot be H; R4 = C1 - C6 alkyl, allyl, CH2CH2N(R5)2, Image , 2-tetrahydropyranyl; 2-tetrahydrofuranyl, Image , Image , Image , Image , Image , Image ; Image ; -SO2R15 or -SO2Ar, where R5 = methyl or ethyl, R6 = H or methyl; R7 = C1 - C3 alkyl, benzyl, -CH2CH2OCH or Image ; R8 = C1 - C4 alkyl or benzyl; R9 = C1 - C4 alkyl or benzyl; R10 = C1 - C6 alkyl; R11 = H, methyl or ethyl, R12 = H, methyl or ethyl, R13 = C1 - C6 alkyl; R14 = C1 - C6 alkyl; R15 = C1 - C4 alkyl; Ar = Image where Y3 = H, F, Cl, Br, C1 - C4 alkyl, C1 - C4 alkoxy or nitro; provided when R4 = Image , Image , Image , Image , Image , Image , Image , -SO2R15 or -SO2Ar, then n must be 0.

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