Heterocyclic compound and use thereof

Patent metadata

Field	Value
Publication number	US-9493484-B2
Application number	US-201314377106-A
Country	US
Kind code	B2
Filing date	Feb 7, 2013
Priority date	Feb 8, 2012
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

Provided is a compound having an AMPA receptor function enhancing action, and useful as a prophylactic or therapeutic drug for depression, schizophrenia, Alzheimer's disease, attention deficit hyperactivity disorder (ADHD) and the like. The compound represented by formula (I):

wherein each symbol is as defined in the DESCRIPTION, or a salt thereof has an AMPA receptor function enhancing action, and is useful as a prophylactic or therapeutic drug for depression, schizophrenia, Alzheimer's disease or attention deficit hyperactivity disorder (ADHD) and the like.

First claim

The invention claimed is:

1. A compound represented by the formula (I)

wherein
R 1 is

(1) C 1-6 alkyl optionally substituted by 1 to 3 substituents selected from a halogen atom and C 1-6 alkoxy;
(2) C 3-7 cycloalkyl;
(3) phenyl optionally substituted by 1 to 3 substituents selected from a halogen atom, cyano, C 1-6 alkyl optionally substituted by 1 to 3 halogen atoms and C 1-6 alkoxy;
(4) dihydrobenzofuranyl;
(5) benzodioxolyl substituted by 1 to 3 halogen atoms;
(6) pyridyl optionally substituted by 1 to 3 substituents selected from a halogen atom and C 1-6 alkyl optionally substituted by 1 to 3 halogen atoms;
(7) pyrimidinyl;
(8) isoxazolyl substituted by 1 to 3 C 1-6 alkyls;
(9) tetrahydrofuranyl; or
(10) pyrazolyl;
L 1 is a bond, —O— or CH 2 —O—;
ring D is a benzene ring;
a partial structure:

wherein
L 2A is a bond or —O—CH 2 —; or
L 2B is a bond,

or a salt thereof.

2. The compound according to claim 1 , wherein R 1 is
(1) C 1-6 alkyl;
(2) phenyl optionally substituted by 1 to 3 substituents selected from a halogen atom, cyano and C 1-6 alkyl optionally substituted by 1 to 3 halogen atoms;
(3) pyridyl substituted by 1 to 3 substituents selected from C 1-6 alkyl substituted by 1 to 3 halogen atoms;
(4) pyrimidinyl; or
(5) tetrahydrofuranyl;
L 1 is —O— or —CH 2 —O—;
ring D is a benzene ring;
the partial structure:

 wherein,
L 2A is a bond; or
L 2B is a bond,

or a salt thereof.

3. 9-(4-(4-Chlorophenoxy)phenyl)-3,4,6,7,8,9-hexahydro-6,9-ethanopyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide or a salt thereof.

4. 9-(4-(4-Chlorophenoxy)phenyl)-3,4,6,7,8,9-hexahydropyrimido[2,1-c][1,2,4]thiadiazine 2,2-dioxide or a salt thereof.

5. 9-(4-((6-(Trifluoromethyl)pyridin-2-yl)oxy)phenyl)-3,4,6,7,8,9-hexahydro-6,9-ethanopyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide or a salt thereof.

6. A pharmaceutical composition comprising the compound according to claim 1 or a salt thereof and a pharmaceutically acceptable carrier.

7. The pharmaceutical composition according to claim 6 , which is an AMPA receptor function enhancer.

8. The pharmaceutical composition according to claim 6 , which is a therapeutic drug for depression, schizophrenia or attention deficit hyperactivity disorder.

9. A method of treating depression, schizophrenia or attention deficit hyperactivity disorder in a mammal, comprising administering an effective amount of the compound according to claim 1 or a salt thereof to the mammal.

Assignees

• Takeda Pharmaceuticals Co

Inventors

• Toyofuku Masashi
• Nakamura Shinji
• Honda Eiji

Classifications

• A61P43/00

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

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P25/24

  Antidepressants · CPC title

• A61P25/18

  Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia · CPC title

• C07D513/18

  Bridged systems · CPC title