Patent ID: 6362342
Filing Date: 2002-03-26
Classification: A01N,A61P,C07D

Abstract:
A single triazole compound of the formula: wherein:R1 is selected from the group consisting of â€”NHC(O)NR6R7, â€”CO2R6, â€”OR6, â€”NR6R7, â€”C(O)NR6R7, and â€”CH2NR6R7, wherein R6 is a hydrogen atom or a functionalized resin, and R7 is selcted from the group consisting of a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, C2 to C7 alkenyl, C2 to C7 substituted alkenyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, heteroaryl, substituted heteroaryl, heterocycle and substituted heterocycle; R2 is selected from the group consisting of C1 to C12 alkylene, C1 to C12 substituted alkylene, C2 to C7 alkenylene, C2 to C7 substituted alkenylene, C2 to C7 alkynylene, C5 to C7 cycloalkylene, C5 to C7 substituted cycloalkylene, C5 to C7 cycloalkenylene, C5 to C7 substituted cycloalkenylene, phenylene, substituted phenylene, naphthylene, substituted naphthylene, heterocyclene, substituted heterocyclene, heteroarylene, substituted heteroarylene, C7 to C12 phenylalkoxy, C7 to C12 substituted phenylalkoxy, the formula: â€”(CH2)mâ€”Gâ€”(CH2)nâ€”wherein m and n are integers independently selected from 0 to 6, provided that m and n are not together 0; and G is selected from phenylene and substituted phenylene, the formula: â€”(CH2)mâ€”NXâ€”(CH2)nâ€”wherein m and n are integers independently selected from 0 to 6, provided that m and n are not together 0; and X is selected from the group consisting of a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, C1 to C7 acyl, C1 to C7 substituted acyl, C1 to C4 alkyl sulfonyl, C1 to C4 substituted alkyl sulfonyl, phenylsulfonyl, substituted phenylsulfonyl, C1 to C6 alkylaminocarbonyl, C1 to C6 substituted alkylaminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl, C1 to C6 alkylaminothiocarbonyl, C1 to C6 substituted alkylaminothiocarbonyl, phenylaminothiocarbonyl, substituted phenylaminothiocarbonyl, C1 to C7 alkoxycarbonyl, C1 to C7 substituted alkoxycarbonyl, phenoxycarbonyl and substituted phenoxycarbonyl, the formula: wherein n is an integer selected from 0 to 6; Y and Z are together or independently a hydrogen atom, C6 to C1 alkyl, C1 to C6 substituted alkyl, C2 to C7 alkenyl, C2 to C7 alkynyl, C2 to C7 substituted alkenyl, C2 to C7 substituted alkynyl, C1 to C7 acyl, C1 to C7 substituted acyl, C3 to C7 cycloalkyl, C3 to C7 substituted cycloalkyl, C5 to C7 cycloalkenyl, C5 to C7 substituted cycloalkenyl, a heterocyclic ring, substituted heterocyclic ring, heteroaryl, substituted heteroaryl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, C7 to C12 phenylalkoxy, C7 to C12 substituted phenylalkoxy, phenyl, substituted phenyl, naphthyl, substituted naphthyl, cyclic C2 to C7 alkylene, substituted cyclic C2 to C7 alkylene, cyclic C2 to C7 heteroalkylene, substituted cyclic C2 to C7 heteroalkylene, carboxy, protected carboxy, hydroxymethyl and protected hydroxymethyl; and G is selected from phenylene and substituted phenylene, and the formula: wherein J and K are each selected from the group consisting of phenylene and substituted phenylene, and m and n are independently selected from 0 and 1; R3 is selected from the group consisting of a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, heteroaryl, substituted heteroaryl, carboxy, protected carboxy, cyano, (monosubstituted)amino, protected (monosubstituted)amino, (disubstituted)amino, C1 to C7 acyl, C1 to C7 substituted acyl, C1 to C7 alkoxycarbonyl, C1 to C7 substituted alkoxycarbonyl, C1 to C7 alkylaminocarbonyl, C1 to C7 substituted alkylaminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl, heterocycle, substituted heterocycle, naphthyl, substituted naphthyl, C5 to C7 cycloalkyl, C5 to C7 substituted cycloalkyl, C5 to C7 cycloalkenyl and C5 to C7 substituted cycloalkenyl; R4 is selected from the group consisting of the formula: â€”D-phenylene-Eâ€”â€ƒwherein: D is directly attached to the triazole ring and D and E are independently selected from the group consisting of C1 to C6 alkylene, C2 to C7 alkenylene, C2 to C7 alkynylene, C1 to C6 substituted alkylene, C2 to C7 substituted alkenylene, C2 to C7 substituted alkynylene, C5 to C7 cycloalkylene, C5 to C7 substituted cycloalkylene, C5 to C7 cycloalkenylene, C5 to C7 substituted cycloalkenylene, C7 to C12 phenylalkylene, C7 to C12 substituted phenylalkylene, â€”R10â€”Oâ€”R11â€”, â€”NR10R11â€”, â€”R10â€”NHâ€”R11â€”and â€”C(O)NR10R11â€”, wherein R10 and R11 are independently absent or present and selected from the group consisting of C1 to C6 alkylene, C1 to C6 substituted alkylene, C7 to C12 phenylalkylene and C7 to C12 substituted phenylalkylene, provided that, when D is â€”NR10R11â€” or â€”C(O)NR10R11â€”, R11 is present and directly connected to the triazole ring; the formula: â€ƒwherein: R8 and R9 are together or independently selected from the group consisting of a hydrogen atom, C1 to C6 alkyl, C2 to C7 alkenyl, C2 to C7 alkynyl, C1 to C6 substituted alkyl, C2 to C7 substituted alkenyl, C2 to C7 substituted alkynyl, C1 to C7 acyl, C1 C7 substituted acyl, C5 to C7 cycloalkyl, C5 to C7 substituted cycloalkyl, C5 to C7 cycloalkenyl, C5 to C7 substituted cycloalkenyl, a heterocyclic ring, substituted heterocyclic ring, heteroaryl, substituted heteroaryl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, C7 to C12 phenylalkoxy, C7 to C12 substituted phenylalkoxy, phenyl, substituted phenyl, naphthyl, substituted naphthyl, cyclic C2 to C7 alkylene, substituted cyclic C2 to C7 alkylene, cyclic C2 to C7 heteroalkylene, substituted cyclic C2 to C7 heteroalkylene, carboxy, protected carboxy, hydroxymethyl, protected hydroxymethyl, amino and amino-protecting group; and m and n are independently 0, 1, 2, 3 or 4; and and the formulae: â€ƒwherein q is selected from 1 and 2; r is is selected from 0 and 1; s and t are independently selected from 0, 1 and 2; and R12 and R13 are independently selected from the group consisting of a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, C1 to C7 acyl, C1 to C7 substituted acyl, phenylsulfonyl, substituted phenylsulfonyl, C1 to C4 alkylsulfonyl, C1 to C4 substituted alkylsulfonyl, C1 to C6 alkylaminocarbonyl, C1 to C6 substituted alkylaminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl, C1 to C6 alkylaminothiocarbonyl, C1 to C6 substituted alkylaminothiocarbonyl, phenylaminothiocarbonyl and substituted phenylaminothiocarbonyl; and R14 is selected from a hydrogen atom, â€”OH, hydroxy-protecting group, C1 to C6 alkyl, C1 to C6 substituted alkyl, C1 to C7 alkoxy, C1 to C7 phenylalkoxy, phenyl, substituted phenyl, heteroaryl and substituted heteroaryl; and R5 is absent or is selected from the group consisting of a hydrogen atom, a halide, â€”OH, â€”CO2H, â€”CHO, â€”CO2R15, â€”C(O)NR15R16 and â€”NR15R16, wherein R15 and R16 are independently selected from a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, phenyl, substituted phenyl, heterocycle, substituted heterocycle, heteroaryl, substituted heteroaryl, C5 to C7 cycloalkyl, C5 to C7 substituted cycloalkyl, C5 to C7 cycloalkenyl, C5 to C7 substituted cycloalkenyl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, C1 to C7 acyl, C1 to C7 substituted acyl, phenylsulfonyl, substituted phenylsulfonyl, C1 to C4 alkylsulfonyl, C1 to C4 substituted alkylsulfonyl, C1 to C6 alkylaminocarbonyl, C1 to C6 substituted alkylaminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl, C1 to C6 alkylaminothiocarbonyl, C1 to C6 substituted alkylaminothiocarbonyl, phenylaminothiocarbonyl and substituted phenylaminothiocarbonyl, and the formulae: â€ƒwherein R17 and R18 are independently selected from a hydrogen atom, C1 to C6 alkyl, C1 to C6 substituted alkyl, C7 to C12 phenylalkyl, C7 to C12 substituted phenylalkyl, C7 to C12 phenylalkoxy, C7 to C12 substituted phenylalkoxy C1 to C7 acyl, C1 to C7 substituted acyl, phenylsulfonyl, substituted phenylsulfonyl, C1 to C4 alkylsulfonyl, C1 to C4 substituted alkylsulfonyl, C1 to C6 alkylaminocarbonyl, C1 to C6 substituted alkylaminocarbonyl, phenylaminocarbonyl, substituted phenylaminocarbonyl, C1 to C6 alkylaminothiocarbonyl, C1 to C6 substituted alkylaminothiocarbonyl, phenylaminothiocarbonyl and substituted phenylaminothiocarbonyl; and s is an integer selected from 1 to 5; provided that, when (1) R8 and R9 are both hydrogen atoms; or (2) one of R8 and R9 is a hydrogen atom and the other is a C1 to C6 alkyl or C1 to C6 substituted alkyl where the substitution is one or more halides, R5 is not a hydrogen atom or a halide; and provided that, when one of R8 and R9 is a hydrogen atom and the other is a C2 to C7 alkenyl, R5 is not a hydrogen atom; or a pharmaceutically acceptable salt of a compound thereof.