Heterocyclic compounds, their production and use

A compound of the formula:

• wherein ring A is an unsubstituted benzene ring or a substituted benzene ring
• wherein said substituted benzene ring is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a C3-7cycloalkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• ring B′ is a non-aromatic heterocyclic ring represented by the following formulae:
• wherein R6 is (1) a hydrogen atom, (2) a C1-7 alkyl or a C7-10 aralkyl group which may be substituted with a C1-4 alkyl group, a halogen atom, a nitro group, a C1-4 alkoxy group or a hydroxyl group, (3) a formyl group or (4) a C2-8 alkylcarbonyl group;
• R1 is a hydrogen atom or, an unsubstituted hydrocarbon group or a substituted hydrocarbon group, which may be different from one another in the repetition of n,
• wherein said substituted hydrocarbon group is substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C1-4alkyl group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C3-7cycloalkyl-carbonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C3-3alkyl group, a phenoxy group a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4akylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an ammo group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• n denotes an integer of 2;
• and
• Z2 is a leaving group, or a salt thereof.

A method of producing a compound of the formula:

• wherein ring A is an unsubstituted benzene ring or a substituted benzene ring,
• wherein said substituted benzene ring is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alklamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and slfur atoms, a C1-4alkyl-carbonylamino group, an aminocarbonyloxy group, a mono- or di-C1-4alklamino-carbonyloxy group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a C3-7cycloalkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4 alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• ring B′ is a non-aromatic heterocyclic ring represented by the following formulae:
• wherein R6 is (1) a hydrogen atom, (2) a C1-7 alkyl or a C7-10 aralkyl group which may be substituted with a C1-4 alkyl group, a halogen atom, a nitro group, a C1-4 alkoxy group or a hydroxyl group, (3) a formyl group or (4) a C2-8 alkylcarbonyl group;
• R1 is a hydrogen atom, an unsubstituted hydrocarbon group or a substituted hydrocarbon group, which may be different from one another in the repetition of n,
• wherein said substituted hydrocarbon group is substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-4alkylsulfonyl group, a C1-4alkyl group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C3-7cycloalkyl-carbonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• Y is an unsubstituted amino group, a substituted amino group, an unsubstituted N-containing saturated heterocyclic group, or a substituted N-containing saturated heterocyclic group,
• wherein said substituted amino group is substituted with 1 to 2 substituents selected from the group consisting of a hydrogen atom, an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group and a substituted acyl group,
• wherein said substituted acyl group is substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, a nitro group, a hydroxy group, an amino group, a mono- or di-C1-6alkylamino group and a C1-4alkoxy group, and
• said substituted N-containing saturated heterocyclic group is substituted with 1 to 5 substituents selected from the group consisting of an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group, said substituted acyl group for said substituted amino group of Y, a halogen atom, a nitro group, a cyano group, an oxo group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 of hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a phenyl-C1-4alkyl-oxycarbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, benzoyl group, a substituted benzoyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group and a C1-6alkylsulfonyl group
• wherein said substituted benzoyl group is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a C1-4alkoxy group, a mono- or di-C1-4alkylamine, a 5- to 7-membered cyclic amino group, a nitro group and a hydroxyl group;
• n denotes an integer of 2, or a salt thereof, which comprises reacting a compound of the formula:
• wherein the ring A and the ring B′ have the same meanings as defined above, or a salt thereof, with a compound of the formula:
• wherein Z1 is a leaving group;
• and R1, Y and n have the same meanings as defined above, or a salt thereof.

A method of producing a compound of the formula:

• wherein ring A is an unsubstituted benzene ring or a substituted benzene ring,
• wherein said substituted benzene ring is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a C3-7cycloalkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• ring B′ is a non-aromatic heterocyclic ring represented by the following formulae:
• wherein R6 is (1) a hydrogen atom, (2) a C1-7 alkyl or a C7-10 aralkyl group which may be substituted with a C1-4 alkyl group, a halogen atom, a nitro group, a C1-4 alkoxy group or a hydroxyl group, (3) a formyl group or (4) a C2-8 alkylcarbonyl group;
• R1 is a hydrogen atom, an unsubstituted hydrocarbon group or a substituted hydrocarbon group, which may be different from one another in the repetition of n,
• wherein said substituted hydrocarbon group is substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino groups a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group a C1-6alkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C1-4alkyl group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C3-7cycloalkyl-carbonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• n denotes an integer of 2;
• and
• R2 and R3 are respectively H, an unsubstituted hydrocarbon group, a hydrocarbon group substituted with 1 to 5 substituents selected from the group consisting of said substituent for said hydrocabon of R1, an unsubstituted acyl group or a substituted acyl group,
• wherein said substituted acyl group is substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, a nitro group, a hydroxy group, an amino group, a mono- or di-C1-6alklamino group and a C1-4alkoxy group, and
• R2 and R3 may form an unsubstituted N-containing saturated heterocyclic group or a substituted N-containing saturated heterocyclic group,
• wherein said substituted N-containing saturated heterocyclic group is substituted with 1 to 5 substituents selected from the group consisting of said substituted hydrocarbon group of R1, an unsubstituted acyl group, said substituted acyl group for R2 and R3, a halogen atom, a nitro group, a cyano group, an oxo group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 of hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a phenyl-C1-4alkyl-oxycarbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, benzoyl group, a substituted benzoyl group, a carbamoyl group, a mono or di-C1-4alkyl-carbamoyl group and a C1-6alkylsulfonyl group,
• wherein said substituted benzoyl group is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a C1-4alkoxy group, a mono- or di-C1-4alkylamine, a 5- to 7-membered cyclic amino group, a nitro group and a hydroxyl group,
• or a salt thereof, which comprises reacting a compound of the formula:
• wherein the ring A, the ring B′, R1 and n are as defined above;
• and Z2 represents a leaving group, or a salt thereof, with a compound of the formula:
• wherein Z3 is a leaving group which can be left with Z2;
• R2 and R3 are as defined above, or a salt thereof.

A pharmaceutical composition, which contains a compound of the formula:

• wherein ring A is an unsubstituted benzene ring or a substituted benzene ring
• wherein said substituted benzene ring is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, an aminocarbonyloxy group, a mono- or di-C1-4alkyl-carbonyloxy group, a C1-4alkylsulfonylamino group, a C1-4alkoxycarbonyl group, a carboxyl group, a C1-4alkyl-carbonyl group, a C3-7cycloalkyl carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group, and a benzoyl group;
• ring B is a non-aromatic heterocyclic ring represented by the following formulae:
• wherein R6 is (1) a hydrogen atom, (2) a C1-7 alkyl or a C7-10 aralkyl group which may be substituted with a C1-4 alkyl group, a halogen atom, a nitro group, a C1-4 alkoxy group or a hydroxyl group, (3) a formyl group or (4) a C2-8 alkylcarbonyl group;
• R1 is a hydrogen atom, an unsubstituted hydrocarbon group or a substituted hydrocarbon group, which may be different from one another in the repetition of n,
• wherein said substituted hydrocarbon group is substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C1-4alkyl group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C3-7cycloalkyl-carbonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfonyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from a C1-4alkyl group, C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• Y is an unsubstituted amino group, a substituted amino group, an unsubstituted N-containing saturated heterocyclic group, or a substituted N-containing saturated heterocyclic group,
• wherein said substituted amino group is substituted with 1 to 2 substituents selected from a hydrogen atom, an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group and a substituted acyl group,
• wherein said substituted acyl group is substituted with 1 to 3 substituents selected from a halogen atom, a nitro group, a hydroxy group, an amino group, a mono- or di-C1-6alkylamino group, and a C1-4alkoxy group, and
• said substituted N-containing saturated heterocyclic group is substituted with 1 to 5 substituents selected from an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group, said substituted acyl group for said substituted amino group of Y, a halogen atom, a nitro group, a cyano group, an oxo group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 of hetero atoms selected from nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a phenyl-C1-4alkyl-oxycarbonyl group, a carboxyl group, a C1-6-carbonyl group, benzoyl group, a substituted benzoyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, and a C1-6alkylsulfonyl group
• wherein said substituted benzoyl group is substituted with 1 to 3 substituents selected from a C1-4alkyl group, a halogen atom, a C1-4alkoxy group, a mono- or di-C1-4alkylamine, a 5- to 7-membered cyclic amino group, a nitro group, and a hydroxyl group;
• and
• n denotes an integer of 2, or a pharmaceutically acceptable salt thereof.

A method for inhibiting acetylcholinesterase activity comprising administering to a mammal in need thereof a therapeutically effective amount of a compound of the formula:

• wherein ring A is an unsubstituted benzene ring or a substituted benzene ring,
• wherein said substituted benzene ring is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carbonyloxy group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a C3-7cycloalkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• ring B is a non-aromatic heterocyclic ring represented by the following formulae:
• wherein R6 is (1) a hydrogen atom, (2) a C1-7 alkyl or a C7-10 aralkyl group which may be substituted with a C1-4 alkyl group, a halogen atom, a nitro group, a C1-4 alkoxy group or a hydroxyl group, (3) a formyl group or (4) a C2-8 alkylcarbonyl group;
• R1 is a hydrogen atom, an unsubstituted hydrocarbon group or a substituted hydrocarbon group, which may be different from one another in the repetition of n,
• wherein said substituted hydrocarbon group is substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a nitro group, a cyano group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylamino group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group, a C1-6alkylsulfonyl group, a C1-4alkyl group, an aminocarbonyloxy group, a mono- or di-C1-4alkylamino-carboxyhexyl group, a C3-7cycloalkylcarbonyl group, a C3-7cycloalkylsulfonyl group, phenyl group, naphthyl group, a mono- or di-phenyl-C1-3alkyl group, a phenoxy group, a benzoyl group, a phenoxycarbonyl group, a benzylcarbonyl group, a phenyl-C1-4alkyl-carbamoyl group, a phenylcarbamoyl group, a phenyl-C1-4alkyl-carbonylamino, benzoylamino group, a phenyl-C1-4alkylsulfonyl group, a phenylsulfonyl group, a phenyl-C1-4alkylsulfinyl group, a phenyl-C1-4alkylsulfonylamino group, and a phenylsulfonylamino group,
• wherein each phenyl group or naphthyl group in the substituents may be substituted with 1 to 4 substituents selected from the group consisting of a C1-4alkyl group, a C1-4alkoxy group, a halogen atom, a hydroxyl group, a benzyloxy group, an amino group, a mono- or di-C1-4alkylamino group, a nitro group, a C1-6alkyl-carbonyl group and a benzoyl group;
• Y is an unsubstituted amino group, a substituted amino group, an unsubstituted N-containing saturated heterocyclic group, or a substituted Ncontaining saturated heterocyclic group,
• wherein said substituted amino group is substituted with 1 to 2 substituents selected from the group consisting of a hydrogen atom, an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group, and a substituted acyl group,
• wherein said substituted acyl group is substituted with 1 to 3 substituents selected from the group consisting of a halogen atom, a nitro group, a hydroxy group, an amino group, a mono- or di-C1-6alkylamino group, and a C1-4alkoxy group, and said substituted N-containing saturated heterocyclic group is substituted with 1 to 5 substituents selected from the group consisting of an unsubstituted hydrocarbon group, said substituted hydrocarbon group of R1, an unsubstituted acyl group, said substituted acyl group for said substituted amino group of Y, a halogen atom, a nitro group, a cyano group, an oxo group, a hydroxyl group, a C1-4alkoxy group, a C1-4alkylthio group, an amino group, a mono- or di-C1-4alkylamino group, a 5- to 7-membered cyclic amino group which may have, other than carbon atoms and one nitrogen atom, 1 to 3 of hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, a C1-4alkyl-carbonylaminmo group, a C1-4alkylsulfonylamino group, a C1-4alkoxy-carbonyl group, a phenyl-C1-4alkyl-oxycarbonyl group, a carboxyl group, a C1-6alkyl-carbonyl group, benzoyl group, a substituted benzoyl group, a carbamoyl group, a mono- or di-C1-4alkyl-carbamoyl group and a C1-6alkylsulfonyl group
• wherein said substituted benzoyl group is substituted with 1 to 3 substituents selected from the group consisting of a C1-4alkyl group, a halogen atom, a C1-4alkoxy group, a mono- or di-C1-4alklamine, a 5- to 7-membered cyclic amino group, a nitro group, and a hydroxyl group;
• and
• n denotes an integer of 2, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier to a mammal.