Pyrazole compound
The present invention relates to a novel serotonin reuptake inhibitor which also exhibits 5-HT 2C antagonistic action (antidepressive and anxiolytic effects), in particular, 5-HT 2C inverse agonistic action comprising Compound (1): or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen or C 1-6 alkyl etc.; R 5 is C 4-7 alkyl or —(CR 8 R 9 ) r -E; R 6 , R 7 , R 8 and R 9 are independently hydrogen, fluorine or C 1-6 alkyl; A is C 6-10 aryl or heteroaryl etc.; r is 1, 2, 3 or 4; E is C 3-8 cycloalkyl or C 6-10 aryl etc.; L is oxygen, sulfur or —NR 10 —; n is 1, 2 or 3; R 10 is hydrogen or C 1-6 alkyl etc.; and X is hydrogen or halogen etc.
1. A compound of Formula (A-10):
or a salt thereof wherein
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,
n is 1, 2 or 3, and
LG is a leaving group.
2. A compound of Formula (B-9):
or a salt thereof wherein
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.
3. A compound of Formula (A-13):
or a salt thereof wherein
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,
n is 1, 2 or 3, and
R a is hydrogen atom or a C 1-6 alkyl group.