Anthranilic acid derivative

The anthranilic acid derivative expressed by the following formula (1) or the following formula (2) or its pharmacologically permissible salt or solvate;

• 1289
• <<in the formulas, Y1 is the group of the following formula (3)-1 or (3)-2:
• 1290
• {in the formulas, Z is a straight-chain, branched or cyclic saturated, unsaturated or aromatic C1 to C12 hydrocarbon group substituted by one or more —NR1OR11, —COOR12, —(C═O)NR13R14, —(C═O)R15 or OR16 [the C1 to C12 hydrocarbon group is optionally substituted by a substituent L (is a C1 to C6 alkyl group, a halogen atom, —NO2 or —CN)],
• a 3 to 8-membered saturated ring containing one or plural —NR17—, —O— or —S— in the ring and optionally containing one or more —C(═O)— groups in the ring, a C1 to C4 straight or branched-chain saturated or unsaturated hydrocarbon group having one or two double bonds or triple bonds and optionally substituted by the above 3 to 8-membered ring, or a C5 to C10 straight or branched-chain saturated or unsaturated hydrocarbon group substituted by a monocyclic or bicyclic aromatic ring containing one or more hetero-atoms selected from oxygen, nitrogen and sulfur atom in the ring (the aromatic ring is optionally substituted by the substituent L)E)
• the groups R10, R11, R12, R13, R14, R15, R16, and R17 are each independently hydrogen atom, a straight or branched-chain C1 to C6 alkyl group which is optionally substituted, a C7 to C11 aralkyl group which is optionally substituted, a C6 to C10 aryl group which is optionally substituted (the substituent is a halogen atom, —OH, a C1 to C4 alkoxy group, —CN, —NO2 or —COOR18), or a group selected from the following formulas (4)-1, (4)-2 and (4)-3. The groups R10 and R11, or R13 and R14 may together form a 3 to 12-membered ring optionally containing one or more —O—, —S—, —NR18— or —(C═O)— groups.
• 1291
• [in the formulas, Q is a C1 to C10 alkyl group which is optionally substituted, a C2 to C6 alkenyl group which is optionally substituted, a C1 to C6 alkoxy group which is optionally substituted, a C7 to C11 aralkyl group which is optionally substituted, a C7 to C11 aralkyloxy group which is optionally substituted (the substituent is a halogen atom, —OH, —CN, —NO2, —COOR19 or phenoxy group), dimethylamino group, morpholino group or a monocyclic or bicyclic aromatic hydrocarbon group which may have one or more hetero-atoms selected from oxygen, nitrogen and sulfur atoms. [when a monocyclic or bicyclic aromatic hydrocarbon group which may have one or more hetero-atoms is selected in the above case, the ring is optionally substituted at arbitrary positions independently by one or plural substituents selected from halogen atom, —OH, —NO2, —CN, —COOR19, —NR19R20, straight or branched-chain C1 to C6 alkyl group, straight or branched-chain C1 to C6 alkoxy group (in this case, the substituents at adjacent positions may form an acetal bond), straight or branched-chain C1 to C6 alkylthio group, straight or branched-chain C1 to C6 alkylsulfonyl group, straight or branched-chain C1 to C6 acyl group, straight or branched-chain C1 to C6 acylamino group, trihalomethyl group, trihalomethoxy group, phenyl group, or phenoxy group which is optionally substituted by one or more halogen atoms],
• the groups R19 and R20 are each independently hydrogen atom or a C1 to C4 alkyl group],
• the group R18 is hydrogen atom or a C1 to C4 alkyl group,
• the group X3 is —(C═O)—, —O—, —S., —(S═O)—, SO2, —NR21—, *—NR21(C═O) or *—(C═O)NR21 (the sign (*—) representing a bond means the bonding to the benzene ring or the naphthalene ring in the formula (3)-1 or the formula (3)-2),
• the group R21 is hydrogen atom or a C1 to C4 hydrocarbon group which is optionally substituted by a halogen,
• the groups R5 and R6 are each independently hydrogen atom, a halogen atom, —NO2, —CO2H, —CN, —OR22, —NH(C═O)R22, —(C═O)NHR22 or a C1 to C4 straight or branched-chain saturated or unsaturated hydrocarbon group which is optionally substituted by halogen atom,
• the group R22 is a C1 to C3 hydrocarbon group which is optionally substituted by hydrogen atom or halogen atom},
• the group Y2 is the formula (3)-1, the formula (3)-2, the following formula (5)-1 or the following formula (5)-2,
• 1292
• <in the formulas, the group R7 is hydrogen atom or a substituted or unsubstituted straight-chain, branched or alicyclic saturated or unsaturated C1 to C12 hydrocarbon group having one or two double bonds or triple bonds [in this case, the substituent is a halogen atom, —NO2, —CN, a substituted or unsubstituted phenyl group (in this case, the substituent is a halogen atom, —NO2, —CN, —CF3 or a C1 to C4 hydrocarbon group), or a substituted or unsubstituted 5 to 8-membered cycloalkyl group (in this case, the substituent is a halogen atom or a C1 to C4 hydrocarbon group)],
• the group X4 is —(C═O)—, —O—, —S—, —(S═O)—, —(O═S═O)—, —NR23—, *—NR23CO or *—CONR23 (the group R23 is hydrogen atom or a C1 to C4 hydrocarbon group which is optionally substituted by halogen atom. In this case, the sign (*—) means the bonding to the benzene ring or the naphthalene ring of the formula (5)-1 or the formula (5)-2 The group R7 is not hydrogen atom when the group X4 is —(C═O)—, —(S═O)—, —(O═S═O)— or *—NR23(C═O)—,
• the groups R8 and R9 are each independently hydrogen atom, a halogen atom, —NO2, —CO2H, —CN, —OR24, —NH(C═O)R24, —(C═O)N—HR24 or a straight or branched-chain saturated or unsaturated C1 to C4 hydrocarbon group which is optionally substituted by halogen atom (the group R24 is hydrogen atom or a C1 to C3 hydrocarbon group which is optionally substituted by halogen atom)),
• the group X1 is —(C═O)—, —O—, —S—, —(S═O)—, —(O═S═O)— or —CH2—,
• the group X2 is O or S,
• the groups R1 and R2 are each independently hydrogen atom, a halogen atom, —NO2, —CO2H, —CN, —OR25, —NH(C═O)R25, —(C═O)NHR25 or a C1 to C4 straight or branched-chain saturated or unsaturated hydrocarbon group which is optionally substituted by halogen atom,
• the group R25 is hydrogen atom or a C1 to C3 hydrocarbon group which is optionally substituted by halogen atom,
• the groups R3 and R4 are each independently hydrogen atom or a C1 to C4 hydrocarbon group,
• the group A is N, N→O or N+—CH3, and
• n is an integer of 0 to 3.>>