Heterocyclic compound and use therefor

1. A compound represented by the formula (I)

wherein

R 1 is

(a) an amino group optionally substituted by 1 or 2 substituents selected from

(1) an amino group,

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from

(i) a hydroxyl group, (ii) a C 1-3 alkoxy group, (iii) a C 3-6 cycloalkyl group substituted by 1 to 3 hydroxyl groups, (iv) a phenyl group, (v) a furyl group, (vi) a tetrahydrofuranyl group, (vii) a piperidino group and (viii) a morpholino group,

(3) a C 3-6 cycloalkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom, a hydroxyl group and a hydroxymethyl group,

(4) a 4- to 10-membered cyclic amino group,

(5) a phenyl group optionally substituted by 1 to 3 substituents selected from a halogen atom, a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms and a hydroxymethyl group,

(6) a dihydroindenyl group substituted by 1 to 3 hydroxyl groups,

7) a pyrazolyl group,

(8) a tetrahydrofuranyl group, and

(9) a tetrahydropyranyl group substituted by 1 to 3 hydroxyl groups, or

(b) a 4- to 10-membered cyclic amino group optionally substituted by 1 to 3 substituents selected from a hydroxyl group and a hydroxymethyl group,

R 2 and R 3 are the same and each is a hydrogen atom or a halogen atom, or

R 2 is a hydrogen atom, and R 3 is a halogen atom, or a C 1-3 alkoxy group substituted by 1 to 3 halogen atoms,

X is —CH═ or —N═, and

ring A is a phenyl group wherein the 4-position is substituted by a substituent selected from

(i) a C 1-3 alkyl group substituted by 1 to 3 halogen atoms, (ii) a C 1-3 alkoxy group, (iii) a carbamoyl group, (iv) a pyrazolyl group optionally substituted by 1 to 3 C 1-3 alkyl groups and (v) a pyridyl group substituted by 1 to 3 C 1-3 alkyl groups,

or a salt thereof,

provided that

(1) R 1 is not an amino group substituted by a substituent selected from a saturated azabicyclo ring group and a tetrazolyl group;

(2) R 1 is not a group represented by the formula

wherein R a is a hydrogen atom; and

(3) the following compounds are excluded

(i) N-cyclohexyl-1,4-dihydro-1-[(4-methoxyphenyl)methyl]-4-oxo-3-quinolinecarboxamide, and

(ii) 1,4-dihydro-1-[(4-methoxyphenyl)methyl]-N-(2-methylphenyl)-4-oxo-3-quinolinecarboxamide.

2. 1,5-Anhydro-2,3-dideoxy-3-({[5,8-difluoro-1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinolin-3-yl]carbonyl}amino)-DL-threo-pentitol, or a salt thereof.

3. 5,8-Difluoro-N-[(1,2-trans)-2-hydroxycyclohexyl]-1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide, or a salt thereof.

4. 8-Fluoro-N-[(1,2-trans)-2-hydroxycyclopentyl]-4-oxo-1-[4-(1H-pyrazol-1-yl)benzyl]-1,4-dihydroquinoline-3-carboxamide, or a salt thereof.

5. 1-[4-(1,3-Dimethyl-1H-pyrazol-4-yl)benzyl]-N-[(1,2-trans)-2-hydroxycyclopentyl]-4-oxo-1,4-dihydroquinoline-3-carboxamide, or a salt thereof.

6. A medicament comprising the compound according to claim 1 , or a salt thereof.

7. The medicament according to claim 1 , which is a therapeutic drug for Alzheimer's disease, schizophrenia, pain, a sleep disorder or Lewy body dementia.

8. The compound according to claim 1 , wherein R 1 is an amino group optionally substituted by one substituent selected from

(1) an amino group,

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from

(i) a hydroxyl group, (ii) a C 1-3 alkoxy group and (iii) a C 3-6 cycloalkyl group substituted by 1 to 3 hydroxyl groups,

(3) a C 3-6 cycloalkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom, a hydroxyl group and a hydroxymethyl group,

(4) a piperidino group,

(5) a phenyl group optionally substituted by 1 to 3 substituents selected from a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, and

(6) a tetrahydropyranyl group substituted by 1 to 3 hydroxyl groups,

R 2 and R 3 are the same and each is a hydrogen atom or a halogen atom, or

R 2 is a hydrogen atom, and R 3 is a halogen atom,

X is —CH═ or —N═, and

ring A is a phenyl group wherein the 4-position is substituted by a substituent selected from

(i) a C 1-3 alkyl group substituted by 1 to 3 halogen atoms, (ii) a C 1-3 alkoxy group, (iii) a carbamoyl group, (iv) a pyrazolyl group optionally substituted by 1 to 3 C 1-3 alkyl groups and (v) a pyridyl group substituted by 1 to 3 C 1-3 alkyl groups,

or a salt thereof.

9. The compound according to claim 1 , wherein R 1 is

an amino group substituted by one substituent selected from

(1) an amino group,

(2) a C 3-6 cycloalkyl group substituted by 1 to 3 substituents selected from a halogen atom and a hydroxyl group, and

(3) a tetrahydropyranyl group substituted by 1 to 3 hydroxyl groups,

R 2 and R 3 are the same and each is a hydrogen atom or a halogen atom, or

R 2 is a hydrogen atom, and R 3 is a halogen atom,

X is —CH═ or —N═, and

ring A is a phenyl group wherein the 4-position is substituted by a substituent selected from

(i) a C 1-3 alkoxy group, (ii) a carbamoyl group, (iii) a pyrazolyl group optionally substituted by 1 to 3 C 1-3 alkyl groups and (iv) a pyridyl group substituted by 1 to 3 C 1-3 alkyl groups, or a salt thereof.

10. The medicament according to claim 6 , which is a cholinergic muscarinic M1 receptor positive allosteric modulator.

11. A method for the treatment of Alzheimer's disease, schizophrenia, pain, a sleep disorder or Lewy body dementia, comprising administering an effective amount of the compound according to claim 1 , or a salt thereof to a mammal.

12. The compound according to claim 1 or a salt thereof for use in cholinergic muscarinic M1 receptor positive allosteric modulation.

13. The compound according to claim 1 or a salt thereof for use in the treatment of Alzheimer's disease, schizophrenia, pain, a sleep disorder or Lewy body dementia.

14. A method of cholinergic muscarinic M1 receptor positive allosteric modulation, comprising administering an effective amount of the compound according to claim 1 or a salt thereof to a mammal.