Pyrazole compound

Patent metadata

Field	Value
Publication number	US-11312688-B2
Application number	US-202016903646-A
Country	US
Kind code	B2
Filing date	Jun 17, 2020
Priority date	Jul 15, 2010
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

The present invention relates to a novel serotonin reuptake inhibitor which also exhibits 5-HT2C antagonistic action (antidepressive and anxiolytic effects), in particular, 5-HT2C inverse agonistic action comprising Compound (1):or a pharmaceutically acceptable salt thereofwherein R1, R2, R3 and R4 are independently hydrogen or C1-6 alkyl etc.; R5 is C4-7 alkyl or —(CR8R9)r-E; R6, R7, R8 and R9 are independently hydrogen, fluorine or C1-6 alkyl; A is C6-10 aryl or heteroaryl etc.; r is 1, 2, 3 or 4; E is C3-8 cycloalkyl or C6-10 aryl etc.; L is oxygen, sulfur or —NR10—; n is 1, 2 or 3; R10 is hydrogen or C1-6 alkyl etc.; and X is hydrogen or halogen etc.

First claim

The invention claimed is:

1. 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 a hydrogen atom and a C 1-6 alkyl group,
R 3 and R 4 are independently selected from the group consisting of a hydrogen atom and a methyl group,
R 5 is an optionally-substituted C 4-7 alkyl group or —(CR 8 R 9 ) r -E,
R 6 and R 7 are hydrogen atoms,
R 8 and R 9 are independently selected from the group consisting of a hydrogen atom, a 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 or 2,
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 an oxygen atom and a 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 an oxygen atom or a sulfur atom,
n is 1, and
X is a hydrogen atom, a C 1-6 alkyl group optionally substituted with a fluorine atom, or a halogen atom.

2. 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 the compound of Formula (1) according to claim 1 .

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

4. The method of claim 2 , wherein the disease is (i) a depressive disorder, (ii) depression, (iii) seasonal affective disorder, or (iv) a major depressive episode in bipolar disorder.

5. The method of claim 2 , wherein the disease is selected from the group consisting of (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) a substance-induced anxiety disorder, (viii) agoraphobia, (ix) social phobia, (x) avoidant personality disorder, or (xi) psychophysiological disorder.

6. The method of claim 2 , wherein the disease is a symptom of depression or anxiety associated with schizophrenia or dementia.

7. The method of claim 2 , wherein the disease is selected from the group consisting of (i) memory impairment, (ii) eating behavior disorder, (iii) obesity, (iv) sleep disorder, (v) schizophrenia, (vi) an addiction to a drug, (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, and (xviii) sexual dysfunction.

Assignees

• Sumitomo Dainippon Pharma Co Ltd

Inventors

• Sasaki Izumi
• Toyoda Tomohiro
• Yoshinaga Hidefumi
• Natsutani Itaru
• Takahashi Yoko

Classifications

• C07D231/20 Primary

  One oxygen atom attached in position 3 or 5 · CPC title

• C07D405/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title

• C07D493/08

  Bridged systems · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title