Pyrazole compound

1. A method for treating a disease mediated by serotonin nervous system which comprises administering to a patient in need thereof a therapeutically effective amount of a compound of Formula (1):

or a pharmaceutically acceptable salt thereof wherein

R 1 and R 2 are independently selected from the group consisting of hydrogen atom, a C 1-6 alkyl group and a C 3-8 cycloalkyl group,

R 3 and R 4 are independently selected from the group consisting of hydrogen atom and a C 1-6 alkyl group,

R 5 is an optionally-substituted C 4-7 alkyl group or —(CR 8 R 9 ) r -E,

R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen atom, fluorine atom and an optionally-substituted C 1-6 alkyl group,

A is an optionally-substituted C 6-10 aryl group or an optionally-substituted 5- to 10-membered heteroaryl group,

r is 1, 2, 3 or 4,

E is an optionally-substituted C 3-8 cycloalkyl group, an optionally-substituted C 4-8 cycloalkenyl group, an optionally-substituted 5- to 10-membered saturated heterocyclic group which comprises 1 to 3 heteroatoms independently selected from the group consisting of oxygen atom and sulfur atom as a constituent atom of the ring, an optionally-substituted C 6-10 aryl group or an optionally-substituted 5- to 10-membered heteroaryl group,

L is oxygen atom, sulfur atom or —NR 10 —,

n is 1, 2 or 3,

R 10 is hydrogen atom, a C 1-6 alkyl group or a C 3-8 cycloalkyl group, and

X is hydrogen atom, a C 1-6 alkyl group optionally-substituted with fluorine atom or a halogen atom.

2. The method of claim 1 wherein the disease is (i) depression or (ii) anxiety.

3. The method of claim 1 wherein the disease is (i) depressive disorders such as major depressive disorder, dysthymic disorder, and depressive disorders not otherwise specified, (ii) depression, (iii) seasonal affective disorder, or (iv) major depressive episode in bipolar disorder.

4. The method of claim 1 wherein the disease is (i) panic disorder, (ii) obsessive-compulsive disorder, (iii) posttraumatic stress disorder, (iv) acute stress disorder, (v) generalized anxiety disorder, (vi) anxiety disorder due to a general medical condition, (vii) anxiety disorder comprising substance-induced anxiety disorder, (viii) agoraphobia, (ix) social phobia, (x) avoidant personality disorder, or (xi) psychophysiological disorder.

5. The method of claim 1 wherein the disease is a symptom of depression or anxiety associated with schizophrenia or dementia.

6. The method of claim 1 wherein the disease is (i) memory impairment, (ii) eating behavior disorder, (iii) obesity, (iv) sleep disorder, (v) schizophrenia, (vi) addiction to drugs, (vii) cluster headache, (viii) migraine, (ix) pain, (x) Alzheimer's disease, (xi) chronic paroxysmal hemicrania, (xii) headache associated with vascular disorder, (xiii) Parkinson's disease, (xiv) endocrine abnormality, (xv) vasospasm, (xvi) hypertension, (xvii) gastrointestinal disorder associated with motility and secretory change, or (xviii) sexual dysfunction.

7. The method of claim 1 wherein R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen atom and methyl group, and R 4 is hydrogen atom.

8. The method of claim 1 wherein A is an optionally-substituted C 6-10 aryl group.

9. The method of claim 1 wherein X is hydrogen atom.

10. The method of claim 1 wherein L is oxygen atom.

11. The method of claim 1 wherein n is 1.

12. The method of claim 1 wherein R 1 , R 3 and R 4 are hydrogen atom, and R 2 is methyl group.

13. The method of claim 1 wherein R 6 , R 7 , R 8 and R 9 are hydrogen atom.

14. The method of claim 1 wherein E is an optionally-substituted C 3-8 cycloalkyl group, an optionally-substituted 5- to 10-membered saturated heterocyclic group which comprises 1 to 3 oxygen atoms as a constituent atom of the ring, or an optionally-substituted phenyl group.

15. The method of claim 1 wherein E is an optionally-substituted C 3-8 cycloalkyl group.

16. The method of claim 1 wherein r is 1 or 2.

17. The method of claim 1 wherein R 5 is an optionally-substituted C 4-7 alkyl group.

18. The method of claim 1 wherein the compound of Formula (1) is any one of the following compounds, or a pharmaceutically acceptable salt thereof:

1-[5-(benzyloxy)-1-(cyclohexylmethyl)-1H-pyrazol-3-yl]-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(3-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(4-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chlorobenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(3-chlorobenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(3-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2,4-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-4-fluorobenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(4-fluoro-2-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2,5-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2-fluoro-5-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-5-fluorobenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2,5-dichlorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-5-methylbenzyl)oxy]-1-(cyclohexylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-[5-(benzyloxy)-1-(cyclopentylmethyl)-1H-pyrazol-3-yl]-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(3-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(4-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chlorobenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(3-chlorobenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(3-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2,4-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-4-fluorobenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(4-fluoro-2-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2,5-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2-fluoro-5-methylbenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-5-fluorobenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2,5-dichlorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-chloro-5-methylbenzyl)oxy]-1-(cyclopentylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-[5-(benzyloxy)-1-(3,3-dimethylbutyl)-1H-pyrazol-3-yl]-N-methylmethanamine;

1-{5-[(3-chlorobenzyl)oxy]-1-(3,3-dimethylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(3,3-dimethylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(3,3-dimethylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-[5-(benzyloxy)-1-(3-methylbutyl)-1H-pyrazol-3-yl]-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(3-methoxy-3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(3-methoxy-3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclopentylmethyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(cyclohexylmethyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(2-cyclopentylethyl)-5-[(2,5-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylethanamine;

N-methyl-1-{1-(3-methylbutyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}methanamine;

1-{1-(3,3-dimethylbutyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(4-fluorobenzyl)-5-[(2-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(4-fluorobenzyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(4-fluorobenzyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-fluorobenzyl)oxy]-1-(4-methylbenzyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(4-methylbenzyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

N-methyl-1-{1-(4-methylbenzyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}methanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(4-methoxybenzyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(4-methoxybenzyl)-5-[(2,4,5-trifluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(cyclopropylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(4-fluorobenzyl)oxy]-1-(2-methylpropyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(2-methylpropyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{1-(2,2-dimethylpropyl)-5-[(4-fluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(2-fluorobenzyl)oxy]-1-(3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-{5-[(4-fluorobenzyl)oxy]-1-(3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

1-(5-[(4-fluorobenzyl)oxy]-1-{[1-(trifluoromethyl)cyclopentyl]methyl}-1H-pyrazol-3-yl)-N-methylmethanamine;

1-(5-[(2,5-difluorobenzyl)oxy]-1-{[1-(trifluoromethyl)cyclopentyl]methyl}-1H-pyrazol-3-yl)-N-methylmethanamine;

1-(5-[(5-chloro-2-fluorobenzyl)oxy]-1-{[1-(trifluoromethyl)cyclopentyl]methyl}-1H-pyrazol-3-yl)-N-methylmethanamine;

(−)-1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

(+)-1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(tetrahydro-2H-pyran-2-ylmethyl)-1H-pyrazol-3-yl}-N-methylmethanamine;

(−)-1-{1-(2-cyclopentylethyl)-5-[(2,5-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylethanamine;

(+)-1-{1-(2-cyclopentylethyl)-5-[(2,5-difluorobenzyl)oxy]-1H-pyrazol-3-yl}-N-methylethanamine;

1-{5-[(2,5-difluorobenzyl)oxy]-1-(3-fluoro-3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine; or

1-{5-[(5-chloro-2-fluorobenzyl)oxy]-1-(3-fluoro-3-methylbutyl)-1H-pyrazol-3-yl}-N-methylmethanamine.

19. A process for preparing a compound of Formula (A-12):

or a pharmaceutically acceptable salt thereof which comprises the following Steps (i) to (v):

Step (i): reacting a compound of Formula (B-7):

with a compound of Formula (B-4):

or a salt thereof to give a compound of Formula (B-8):

Step (ii): reacting the compound of Formula (B-8) with a compound of Formula (A-2):

to give a compound of Formula (A-13):

Step (iii): converting the compound of Formula (A-13) to a compound of Formula (B-9):

Step (iv): converting the compound of Formula (B-9) to a compound of Formula (A-10):

 and

Step (v): reacting the compound of Formula (A-10) with a compound of Formula (A-11):

or a salt thereof to give the compound of Formula (A-12)

wherein

R 1 and R 2 are independently selected from the group consisting of hydrogen atom, a C 1-6 alkyl group and a C 3-8 cycloalkyl group,

R 3 and R 4 are independently selected from the group consisting of hydrogen atom and a C 1-6 alkyl group,

R 5 is an optionally-substituted C 4-7 alkyl group or —(CR 8 R 9 ) r -E,

R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen atom, fluorine atom and an optionally-substituted C 1-6 alkyl group,

A is an optionally-substituted C 6-10 aryl group or an optionally-substituted 5- to 10-membered heteroaryl group,

r is 1, 2, 3 or 4,

E is an optionally-substituted C 3-8 cycloalkyl group, an optionally-substituted C 4-8 cycloalkenyl group, an optionally-substituted 5- to 10-membered saturated heterocyclic group which comprises 1 to 3 heteroatoms independently selected from the group consisting of oxygen atom and sulfur atom as a constituent atom of the ring, an optionally-substituted C 6-10 aryl group or an optionally-substituted 5- to 10-membered heteroaryl group, and

n is 1, 2 or 3,

R a is hydrogen atom or a C 1-6 alkyl group,

M 1 is an alkali metal or an alkaline earth metal, and

LG is a leaving group.

20. The process of claim 19 wherein R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen atom and methyl group, and R 4 is hydrogen atom.

21. The process of claim 19 wherein A is an optionally-substituted C 6-10 aryl group.

22. The process of claim 19 wherein n is 1.

23. The process of claim 19 wherein R 1 , R 3 and R 4 are hydrogen atom, and R 2 is methyl group.

24. The process of claim 19 wherein R 6 , R 7 , R 8 and R 9 are hydrogen atom.

25. The process of claim 19 wherein E is an optionally-substituted C 3-8 cycloalkyl group, and r is 1 or 2.

26. The process of claim 19 wherein R 5 is an optionally-substituted C 4-7 alkyl group.

27. The process of claim 19 wherein LG is iodine atom, bromine atom, chlorine atom, p-toluenesulfonyloxy group, benzenesulfonyloxy group or methanesulfonyloxy group.