Azolecarboxamide compound or salt thereof

An azolecarboxamide compound represented by the following formula (I) or a salt thereof:

• (the symbols in the formula have the following meanings:
• X:
• S or O,
• R1:
• halogen, aryl, heteroaryl, cycloalkyl, 4-piperidyl, 4-tetrahydropyranyl, -Alk-aryl, -Alk-O-aryl, -Alk-O-lower alkyl, -Alk-NH—CO-lower alkyl, -Alk-NH—CO—O-lower alkyl, —NH-aryl, —NH-(4-piperidyl), a group represented by the formula (II), or a group represented by the formula (III):
• wherein in R1, each aryl may be substituted with group(s) selected from the group consisting of halogen and halogeno-lower alkyl, the heteroaryl may be substituted with amino or —NH—CO—O-lower alkyl, the cycloalkyl may be substituted with —O-Alk-aryl or —O-heteroaryl, and the N atom of each 4-piperidyl may be substituted with lower alkyl, heteroaryl, —CO-lower alkyl, or —CO—O-lower alkyl,
• Alk:
• the same as or different from each other, each representing lower alkylene,
• R1a:
• lower alkyl substituted with one or two —OH, -Alk-O-lower alkyl, -Alk-SO2-lower alkyl, -Alk-O—SO2-lower alkyl, -Alk-aryl, -Alk-O-aryl, -Alk-heteroaryl, -Alk-O-heteroaryl, -Alk-CO-saturated hetero ring group, -Alk-NRARB, -Alk-CO—NRARB, saturated hetero ring group, wherein the saturated hetero ring group may be substituted with lower alkyl, lower alkenyl, -Alk-O-lower alkyl or -Alk-aryl, or -Alk-saturated hetero ring group, wherein the saturated hetero ring group in the -Alk-saturated hetero ring group may be substituted with lower alkyl or —OH,
• RA and RB:
• the same as or different from each other, each representing —H or lower alkyl,
• R1b:
• lower alkyl or -Alk-aryl,
• Q:
• cyclic amino which may be substituted with group(s) selected from Group G1 below:
• Group G1:
• halogen, —OH, —CN, lower alkyl, halogeno-lower alkyl, -Alk-OH, —O-lower alkyl, —O-halogeno-lower alkyl, -Alk-O-lower alkyl, —O-Alk-O-lower alkyl, —O-cycloalkyl, —O-Alk-cycloalkyl, —CO2H, —CO—O-lower alkyl, —CO-lower alkyl, —CO—NRARB, —CO—NH-Alk-OH, -Alk-CO—NRARB, —SO2-lower alkyl, —SO2—NRARB, aryl, —O-aryl, heteroaryl which may be substituted with (—O-lower alkyl), -Alk-heteroaryl, —O-(heteroaryl which may be substituted with group(s) selected from the group consisting of halogen, lower alkyl, —O-lower alkyl, —CN and —OH), -Alk-O-heteroaryl, —SO2-heteroaryl, —S-(heteroaryl which may be substituted with lower alkyl), oxo, —NRCRD, and -Alk-aryl,
• wherein, in -Alk-aryl of Group G1, the Alk may be substituted with —OH, and the aryl may be substituted with —CO2H or —CO—O-lower alkyl,
• and two substituents on the ring group Q may be combined to form -Alk-,
• saturated hetero ring which may be substituted with group(s) selected from the group consisting of lower alkyl and oxo, or cycloalkane, may be spiro bonded on the ring group Q,
• heteroarene which may be substituted with lower alkyl, arene, or cycloalkane, may be condensed with the ring group Q,
• RC:
• —H or lower alkyl,
• RD:
• lower alkyl, —CO-lower alkyl, —CO—O-lower alkyl, -Alk-CO—NRARB, or heteroaryl,
• R2:
• a group selected from (i) or (ii) below,
• (i) a group represented by the formula (IV) or (V),
• R2a:
• —O—RE, —CH2—RF, —NRGRH, or heteroaryl,
• RE:
• —H or lower alkyl,
• RF:
• —H, heteroaryl, or saturated hetero ring group,
• RG:
• —H or lower alkyl,
• RH:
• (1) —H, (2) —O-lower alkyl, (3) cycloalkyl which may be substituted with group(s) selected from the group consisting of —OH, —NRARB, —NH—CO—O-lower alkyl, —CN, —CO2H, —CO—O-lower alkyl and —CONH2, (4) cycloalkenyl which may be substituted with -Alk-OH or —CONH2, (5) saturated hetero ring group which may be substituted with group(s) selected from the group consisting of —OH, lower alkyl, -Alk-cycloalkyl, —CO-lower alkyl and oxo, (6) aryl which may be substituted with group(s) selected from the group consisting of —OH, —CN and halogen, (7) heteroaryl, or (8) lower alkyl which may be substituted with group(s) selected from Group G2 below:
• Group G2:
• halogen, halogeno-lower alkyl, —OH, cycloalkyl, —O-lower alkyl, —O-cycloalkyl, —O-Alk-OH, —CN, —S-lower alkyl, —SO2-lower alkyl, —CONH2, —CONH-lower alkyl, —NHCO-lower alkyl, —CO2H, —CO—O-lower alkyl, —NRARB, saturated hetero ring group, —CO-saturated hetero ring group, aryl, and heteroaryl,
• wherein, in Group G2, the cycloalkyl may be substituted with —OH, —CO—O-lower alkyl, -Alk-OH or -Alk-NRARB, the saturated hetero ring group may be substituted with —OH, lower alkyl, -Alk-OH, -Alk-O-lower alkyl, -Alk-aryl, —NRARB, —CO—O-lower alkyl or oxo, and the heteroaryl may be substituted with —OH, lower alkyl, —CO2H or —CO—O-lower alkyl,
• and RG and RH may be combined with the N atom to which they are bonded to form nitrogen-containing saturated hetero ring which may be substituted with group(s) selected from the group consisting of —OH, lower alkyl, —CO—O-lower alkyl, -Alk-aryl and —CO-saturated hetero ring group,
• R2b:
• lower alkyl, halogeno-lower alkyl, -Alk-RK, —NRLRM, aryl or saturated hetero ring group, wherein the saturated hetero ring group may be substituted with —CO—O-Alk-aryl,
• RK:
• —CN, —OH, —N3, —CONH2, —O—CO-lower alkyl, —NRARB, —NH—CO-lower alkyl, —O—SO2-lower alkyl, heteroaryl or saturated hetero ring group,
• RL:
• —H or lower alkyl,
• RM:
• heteroaryl or saturated hetero ring group,
• (ii) —H, halogen, —OH, lower alkyl, halogeno-lower alkyl, —CN, —O-lower alkyl, —O-halogeno-lower alkyl, heteroaryl which may be substituted with lower alkyl, -Alk-OH, -Alk-CONH2, -Alk-saturated hetero ring group or —S—RN,
• RN:
• (1) -Alk-OH, (2) -Alk-CONH2, (3) -Alk-heteroaryl, (4) -Alk-saturated hetero ring group, or (5) saturated hetero ring group which may be substituted with (—CO—O-Alk-aryl),
• A:
• R3:
• —H, halogen, lower alkyl, —O-lower alkyl or —CN,
• R4:
• —H, halogen, —OH, —O-Alk-R4a, cycloalkyl which may be substituted with —CN, —CN, —CO2H, —CO—O-lower alkyl, —CO—NH-heteroaryl, —CO—NH—SO2-lower alkyl, —CO—NH—SO2—NRARB, saturated hetero ring group, —O-saturated hetero ring group, —CO-saturated hetero ring group, —SO2-saturated hetero ring group, —CO—NR4bR4c, or lower alkyl which may be substituted with group(s) selected from Group G3 below,
• R4a:
• —H, —OH, —O-lower alkyl, —O-Alk-aryl, —S-lower alkyl, —SO2-lower alkyl or —NH—RO,
• RO:
• —H, —CO—O-lower alkyl, —CO-lower alkyl or —SO2-lower alkyl,
• R4b:
• the same as or different from each other, each representing —H or lower alkyl,
• R4c:
• the same as or different from each other, each representing —H, lower alkyl, -Alk-O-lower alkyl, -Alk-NRARB, -Alk-aryl, -Alk-saturated hetero ring group, cycloalkyl, aryl or saturated hetero ring group,
• Group G3:
• halogen, —OH, —O-lower alkyl, —O—CO-lower alkyl, —O-Alk-O-lower alkyl, —CN, —CO2H, —CO—O-lower alkyl, —NR4b, cyclic amino and —CO-saturated hetero ring group,
• wherein each saturated hetero ring group in R4, the saturated hetero ring group in the —CO-saturated hetero ring group of Group G3, and the cyclic amino in Group G3 may be substituted with group(s) selected from Group G4 below,
• and two substituents on the cyclic amino in Group G3 may be combined to form -Alk-,
• saturated hetero ring which may be substituted with group(s) selected from the group consisting of lower alkyl and oxo, or cycloalkane, may be Spiro bonded on the cyclic amino,
• and arene which may be substituted with group(s) selected from the group consisting of halogen, lower alkyl, and —O-lower alkyl, heteroarene, cycloalkane or saturated hetero ring, may be condensed with the cyclic amino,
• Group G4:
• halogen, lower alkyl, halogeno-lower alkyl, —OH, —O-lower alkyl, —O-aryl, —O—CO-lower alkyl, —CO—O-lower alkyl, —NRARB, —NH—CO-lower alkyl, -Alk-OH, -Alk-O-lower alkyl, —CO-lower alkyl, —CO—NRARB, -Alk-aryl, -Alk-heteroaryl, -Alk-NRARB, -Alk-CO—NRARB, -Alk-cyclic amino, -Alk-NH-aryl, -Alk-S-lower alkyl, -Alk-halogeno-lower alkyl, cycloalkyl, aryl, heteroaryl, cyclic amino, —SO2-lower alkyl, —SO2—NRARB, oxo and —CN,
• wherein each aryl and each heteroaryl in Group G4 may be substituted with group(s) selected from Group G5 below,
• Group G5:
• halogen, lower alkyl, halogeno-lower alkyl, —O-lower alkyl, —NRARB and -Alk-O-lower alkyl,
• R5:
• —H, halogen, lower alkyl, —OH, —O-lower alkyl, —CN, halogeno-lower alkyl, -Alk-OH, -Alk-O-lower alkyl, -Alk-CN, —O-Alk-NH2, —O-Alk-NH—CO—O-lower alkyl, —O-Alk-aryl or —CONH2,
• wherein R4 and R5 may be combined with the carbon atom on the benzene ring to which they are bonded to form (1) pyrazole ring, (2) 2,3-dihydro-1,4-dioxine ring, or (3) cyclopentene ring which may be substituted with —OH or oxo,
• R6:
• —H, halogen, lower alkyl, or —O-lower alkyl,
• R7:
• —H, lower alkyl, —CO2H, —CO—O-lower alkyl, —CO-saturated hetero ring group or -Alk-saturated hetero ring group,
• R8:
• —H or lower alkyl, and
• R9:
• —H, lower alkyl or -Alk-saturated hetero ring group,
• provided that 1) in the case where R2 is a group selected from (ii), R1 is a group represented by the formula (II) or (III), 2) in the case where R2 is —H, any one group of R3 to R6 and R7 are a group other than —H, and 3) in the case where R1 is heteroaryl, A is phenylene which may be substituted.)