Quaternary ammonium compounds

A method for treating hyperlipidemia or arteriosclerosis in a subject, comprising administering to said subject an effective amount of a compound represented by formula (1):

• wherein R1 and R2, which may be mutually different, each represents an alkyl group having from 1 to 10 carbon atoms;
• m represents an integer of 1 or 2, and R3 and R4, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms;
• Y represents any one of —NHCS—, —NHCSNH—, and —NHCSO—where the —NH in the —NHCS— represents a bond which links with an adjacent benzene ring and the CS— in the —NHCS— represents a bond which links with an adjacent Z, and the —NH in the —NHCSO—represents a bond which links with an adjacent benzene ring and the CSO— in the —NHCSO— represents a bond which links with an adjacent Z;
• Z—(N+R5R6R7)n represents an alkyl group having from 2 to 10 carbon atoms or an alkenyl group having from 2 to 10 carbon atoms which is substituted with n (—N+R5R6R7)s, where at least one of methylenes which constitute Z may be replaced by any one of a phenylene and an —O—;
• n is an integer of 1 or 2;
• and N+R5R6R7 is any one of I), II), and III) given below which are mutually independent
• I) R5, R6, and R7, which may be mutually different, each represents any one of an alkyl group having from 1 to 10 carbon atoms, an alkenyl group having from 2 to 10 carbon atoms, and an alkynyl group having from 2 to 10 carbon atoms, where the alkyl group, the alkenyl group, and the alkynyl group may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH2 group, an —SO3H group, and further, at least one of methylenes which constitute the alkyl group, the alkenyl group, and the alkynyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO2—, an —NHCO—, an —NR8—, and an —N+W−R9R10— where R8 represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and the alkyl group and alkenyl group represented by R8 may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group;
• R9 and R10, which may be mutually different, each represents an alkyl group having from 1 to 5 carbon atoms or an alkenyl group having from 2 to 5 carbon atoms and may be substituted with at least one of a phenyl group, a cycloalkyl group having from 3 to 7 carbon atoms, and a hydroxyl group;
• and W− represents a counter anion,
• II) N+R5R6R7 represents a monocyclic ring or a bicyclic ring which is formed by 4 to 9 carbon atoms in addition to an ammonium nitrogen atom, provided that the position of its bonding with Z is the ammonium nitrogen atom, where one of the carbon atoms which constitute the ring in the monocyclic ring and the bicyclic ring may be replaced by any one atom of oxygen, nitrogen, and sulfur, and moreover, the monocyclic ring and the bicyclic ring may be substituted with at least one of a hydroxyl group, an oxo group, a thioxo group, a cyano group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a carboxyl group, a —CONH2 group, an —SO2H group, and an —R11 group;
• R11 represents an alkyl group having from 1 to 8 carbon atoms or an alkenyl group having from 2 to 8 carbon atoms, where the alkyl group and the alkenyl group represented by R11 may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a piperidyl group, a pyrrolidyl group, a morpholyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH2 group, and an —SO3H group;
• moreover, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —O—, an —S—, a —CO2—, an —NHCO—, an —NR8—, and an —N+W−R9R10—, where R8, R9 , R10, and W− are as described above;
• among R5, R6, and R7, a group which is not involved in formation of the monocyclic ring and the bicyclic ring is the same as that in I) described above,
• III) N+R5R6R7 represents a pyridinium ring, a quinolinium ring, or an isoquinolinium ring, provided that the position of its bonding with Z is an ammonium nitrogen atom;
• the pyridinium ring, the quinolinium ring, and the isoquinolinium ring may be substituted with at least one of a cyano group, a nitro group, a phenyl group, a naphthyl group, a thienyl group, a pyridyl group, a cycloalkyl group having from 3 to 7 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a carboxyl group, a —CONH2 group, an —SO3H group, and an —R12 group;
• R12 represents an alkyl group having from 1 to 9 carbon atoms or an alkenyl group having from 2 to 9 carbon atoms;
• and the alkyl group and the alkenyl group represented by R12 may be substituted with at least one of a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group, a thienyl group, a furyl group, a cycloalkyl group having from 3 to 7 carbon atoms, a cyano group, a nitro group, a hydroxyl group, an oxo group, a thioxo group, a carboxyl group, a —CONH2 group, and an —SO3H group;
• and further, at least one of methylenes which constitute the alkyl group and the alkenyl group may be replaced by any one of a phenylene, a thienylene, a furylene, a cyclohexylene, a cyclopentylene, an —S—, a —CO2—, an —NHCO—, an —NR8—, and an —N+W−R9R10—, where R8, R9, R10, and W− are as described above, and
• X− represents a counter anion.