Nitrogen-containing heterocyclic compound

Patent metadata

Field	Value
Publication number	US-10214508-B2
Application number	US-201515318552-A
Country	US
Kind code	B2
Filing date	Jun 11, 2015
Priority date	Jun 13, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

The present invention provides a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity and useful as a medicament such as a prophylactic or therapeutic drug for Alzheimer's disease, schizophrenia, pain, sleep disorder, Parkinson's disease dementia, dementia with Lewy bodies and the like, and the like. The present invention relates to a compound represented by the formula (I) or a salt thereof.

wherein each symbol is as described in the attached DESCRIPTION.

First claim

The invention claimed is:

1. A compound represented by the formula (I):

wherein
A is

a C 3-10 cycloalkyl group
which is optionally further substituted by 1 to 3 substituents selected from
(1) a halogen atom,
(2) a C 1-6 alkyl group optionally substituted by 1 to 3 hydroxy groups, and
(3) a C 1-6 alkoxy group;
R 1 is a hydrogen atom or a hydroxyl group;
R 2 is a hydrogen atom, a C 1-6 alkyl group or a C 1-6 alkoxy group;
R 3 is a hydrogen atom, a halogen atom, a cyano group, a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 2-6 alkenyl group, a C 3-6 cycloalkyl group, or a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;
R 4 is a hydrogen atom or a halogen atom;
R 5 is a pyrazolyl group optionally substituted by 1 to 3 C 1-6 alkyl groups; and
X is CH,

or a salt thereof.

2. The compound according to claim 1 , wherein A is
a C 3-10 cycloalkyl group;
R 1 is a hydroxyl group;
R 2 is a hydrogen atom or a C 1-6 alkyl group;
R 3 is a halogen atom, a cyano group, a C 1-6 alkyl group, or a C 1-6 alkoxy group;
R 4 is a hydrogen atom;
R 5 is a pyrazolyl group optionally substituted by 1 to 3 C 1-6 alkyl groups; and
X is CH,

or a salt thereof.

3. The compound according to claim 1 , wherein A is a C 3-10 cycloalkyl group;
R 1 is a hydroxyl group;
R 2 is a hydrogen atom or a C 1-6 alkyl group;
R 3 is a C 1-6 alkyl group;
R 4 is a hydrogen atom;
R 5 is a pyrazolyl group optionally substituted by 1 to 3 C 1-6 alkyl groups; and
X is CH,

or a salt thereof.

4. N-((1S,2S)-2-hydroxycyclopentyl)-5-methyl-4-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)pyridine-2-carboxamide or a salt thereof.

5. N-((1S,2S)-2-hydroxycyclopentyl)-5,6-dimethyl-4-(4-(1-methyl-1H-pyrazol-3-yl)benzyl)pyridine-2-carboxamide or a salt thereof.

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

Assignees

• Takeda Pharmaceuticals Co

Inventors

• Ogino Masaki
• Kimura Eiji
• Suzuki Shinkichi
• Ashizawa Tomoko
• Imaeda Toshihiro
• Fujimori Ikuo
• Arai Ryosuke

Classifications

• A61P43/00

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

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P37/04

  Immunostimulants · CPC title

• A61P9/12

  Antihypertensives · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title