Pyrazolone compounds and thrombopoietin receptor activator

A pyrazolone compound represented by the following formula (1):

• wherein
• A is a C2-14 aryl group,
• wherein the C2-14 aryl group may be optionally substituted with one or more C1-6 alkyl groups, one or more C1-3 alkyl groups substituted with one or more fluorine atoms, one or more halogen atoms, one or more nitro groups, one or more C1-6 alkylcarbonyl groups, one or more hydroxyl groups or one or more amino groups, and
• wherein the hydroxyl group and the amino group may be substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group;
• B is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group;
• D is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group;
• and
• E is a C2-14 aryl group,
• wherein the C2-14 aryl group is optionally substituted with one or more hydroxyl groups, one or more nitro groups, one or more halogen atoms, one or more cyano groups, one or more C1-3 alkyl groups substituted with one or more fluorine atoms, NG1G2,
• wherein G1 and G2 are independently hydrogen atoms, formyl groups, C1-6 alkyl groups or C1-6 alkylcarbonyl groups, one or more carboxyl groups, one or more sulfonic acid groups, one or more phosphonic acid groups, one or more carbamido groups,
• wherein the carbamido group may be substituted with a C1-6 alkyl group, one or more sulfamido groups, one or more hydroxycarbamido groups, one or more hydroxysulfamido groups, one or more tetrazole groups, and one or more C1-6 alkoxycarbonyl groups or X(CYZ)nCO2H,
• wherein X is CH2, O, S or NG3,
• wherein G3 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group,
• wherein Y and Z are independently hydrogen atoms or C1-3 alkyl groups, and n is 0, 1, 2 or 3, and
• wherein the sulfamido group may be substituted with a C1-6 alkyl group;
• a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

A pyrazolone compound represented by the following formula (2):

• wherein
• R1 is a C2-14 aryl group,
• wherein the C2-14 aryl group may be optionally substituted with one or more C1-6 alkyl groups, one or more C1-3 alkyl groups substituted with one or more fluorine atoms, one or more halogen atoms, one or more nitro groups, one or more C1-6 alkylcarbonyl groups, one or more hydroxyl groups or one or more amino groups, and
• wherein the hydroxyl group and the amino group may be substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group;
• R2 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group;
• R3 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group, and R4 is a C2-14 aryl group,
• wherein the C2-14 aryl group is optionally substituted with one or more hydroxyl groups, one or more nitro groups or NR5R6, and
• wherein R5 and R6 are independently hydrogen atoms, formyl groups, C1-6 alkyl groups or C1-6 alkylcarbonyl groups;
• a tautomer prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

A pyrazolone compound represented by the following formula (3):

• wherein
• R7 is a C2-14 aryl group,
• wherein the C2-14 aryl group may be optionally substituted with one or more C1-6 alkyl groups, one or more C1-3 alkyl groups substituted with one or more fluorine atoms, one or more halogen atoms, one or more nitro groups, one or more C1-6 alkylcarbonyl groups, one or more hydroxyl groups or one or more amino groups, and
• wherein the hydroxyl group and the amino group may be substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group;
• R8 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group;
• R9 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group, and R10 is a C2-14 aryl group,
• wherein the C2-14 aryl group is optionally substituted with one or more carboxyl groups, one or more sulfonic acid groups, one or more phosphonic acid groups, one or more carbamido groups, one or more sulfamido groups, one or more hydroxycarbamido groups, one or more hydroxysulfamido groups, one or more tetrazole groups, one or more C1-6 alkoxycarbonyl groups or X(CYZ)nCO2H,
• wherein X is CH2, O, S or NR11,
• wherein R11 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group, and
• wherein Y and Z are independently hydrogen atoms or C1-3 alkyl groups, and n is 0, 1, 2 or 3;
• a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

A pyrazolone compound represented by the following formula (4):

• wherein
• R12 is a C2-14 aryl group,
• wherein the C2-14 aryl group may be optionally substituted with one or more C1-6 alkyl groups, one or more C1-3 alkyl groups substituted with one or more fluorine atoms, one or more halogen atoms, one or more nitro groups, one or more C1-6 alkylcarbonyl groups, one or more hydroxyl groups or one or more amino groups, and
• wherein the hydroxyl group and the amino group may be substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group;
• R13 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group;
• R14 is a hydrogen atom, a C1-6 alkyl group, a C1-3 alkyl group substituted with one or more fluorine atoms or a C2-14 aryl group, and R15 is a C2-14 aryl group,
• wherein the C2-14 aryl group is substituted with a substituent selected from the group consisting of a hydroxyl group, an amino group, a nitro group, a halogen atom, a cyano group, a C1-3 alkyl group substituted with one or more fluorine atoms, a carbamido group and a sulfamido group,
• wherein the carbamido group and the sulfamido group may be substituted with a C1-6 alkyl group, and with a substituent selected from the group consisting of a carboxyl group, a sulfonic acid group, a phosphonic acid group, a carbamido group, a sulfamido group, a hydroxycarbamido group, a hydroxysulfamido group, a tetrazole group, a C1-6 alkoxycarbonyl group and X(CYZ)nCO2H,
• wherein X is CH2, O, S or NR16,
• wherein R16 is a hydrogen atom, a C1-6 alkyl group, a formyl group or a C1-6 alkylcarbonyl group, and
• wherein Y and Z are independently hydrogen atoms or C1-3 alkyl groups, and n is 0, 1, 2 or 3;
• a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.