Nitrogen-containing heterocyclic compounds and benzamide compounds and drugs containing the same

A compound represented by formula (I) or a pharmacologically acceptable salt or solvate thereof:

• wherein
• R1 represents
• alkyl having 1 to 6 carbon atoms which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom,
• alkoxy having 1 to 6 carbon atoms which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom,
• cycloalkyl having 3 to 8 carbon atoms which is optionally substituted by alkyl having 1 to 6 carbon atoms;
• hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• benzyl;
• or alkylcarbonyloxy having 2 to 5 carbon atoms,
• phenyl which is optionally substituted by alkyl having 1 to 6 carbon atoms;
• hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkylcarbonyl having 2 to 5 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom;
• trifluoromethyl;
• or nitro, alkenyl having 2 to 6 carbon atoms which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom,
• alkynyl having 2 to 6 carbon atoms which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom, or
• a heterocyclic ring which is selected from the group consisting of pyridine, thiophene, pyrrole, furan, pyrazole, imidazole, oxazole, thiazole, pyran, pyridazine, pyrimidine, pyrazine, and oxane, wherein one of more hydrogen atoms on the ring are optionally substituted by alkyl having 1 to 6 carbon atoms;
• hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• and benzyl,
• R2 and R3 are attached to each other to form a 1,2-diazine ring;
• R4 represents
• a hydrogen atom,
• alkyl having 1 to 6 carbon atoms which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom,
• a halogen atom,
• hydroxyl,
• nitrile,
• alkoxycarbonyl having 2 to 5 carbon atoms,
• alkoxy having 1 to 6 carbon atoms, or
• carboxyl,
• A, D, E, and G each represent a carbon atom,
• Q represents a nitrogen atom or a carbon atom,
• q, when Q represents a nitrogen atom, represents a single bond and, when Q represents a carbon atom, represents a single bond or a double bond;
• Y represents a group represented by formula (II):
• wherein
• X represents a hydrogen atom;
• group —C(═O)N(R5)R6 wherein R5 and R6, which may be the same or different, represent a hydrogen atom, alkyl having 1 to 6 carbon atoms (which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom), cycloalkyl having 3 to 8 carbon atoms (which is optionally substituted by alkyl having 1 to 6 carbon atoms;
• hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• benzyl;
• or alkylcarbonyloxy having 2 to 5 carbon atoms), phenyl (which is optionally substituted by alkyl having 1 to 6 carbon atoms;
• hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkylcarbonyl having 2 to 5 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom;
• trifluoromethyl;
• or nitro), alkenyl having 2 to 6 carbon atoms (which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom), or alkynyl having 2 to 6 carbon atoms (which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom);
• or group —C(═O)OR7 wherein R7 represents a hydrogen atom or alkyl having 1 to 6 carbon atoms (which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom),
• R8 represents two hydrogen atoms to make the group of formula (II) diphenylmethyl or represents a bond, an oxygen atom, a sulfur atom, —SO2—, —SO—, —CH2—CH2—, or —CH═CH—, and
• R9 and R10, which may be the same or different, represent a hydrogen atom, alkyl having 1 to 6 carbon atoms (which is optionally substituted by hydroxyl;
• halogen;
• amino;
• alkoxy having 1 to 6 carbon atoms;
• alkoxycarbonyl having 2 to 5 carbon atoms;
• C3-8 cycloalkyl;
• phenyl;
• biphenyl;
• amino substituted by alkyl having 1 to 6 carbon atoms;
• or five- or six-membered saturated or unsaturated heteroaromatic ring containing one hetero-atom), alkoxy having 1 to 6 carbon atoms, a halogen atom, or hydroxyl;
• and
• Z represents —(CH2)n—, wherein n is an integer of 0 to 6, —O—(CH2)i—, or —C(═O)NH—(CH2)i— wherein i is an integer of 1 to 6.