Pyranodipyridine compound

Patent metadata

Field	Value
Publication number	US-9738656-B2
Application number	US-201615346912-A
Country	US
Kind code	B2
Filing date	Nov 9, 2016
Priority date	Nov 13, 2015
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

Compounds represented by formulae (I) to (XXII) or pharmaceutically acceptable salts thereof:

First claim

What is claimed is:

1. A compound selected from the group consisting of:
9-(2-chlorophenyl)-7-(pyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

2-fluoro-6-(7-(5-methoxypyridin-3-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

2-fluoro-6-(7-(6-methylpyridin-3-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

9-(2-chloro-3-fluorophenyl)-7-(6-methylpyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

2-fluoro-6-(7-(2-methoxypyrimidin-5-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

7-(pyridin-3-yl)-9-(2,3,5,6-tetrafluorophenyl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

3-(8-oxo-7-(thiophen-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

3-(8-oxo-7-(thiophen-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)pyrazine-2-carbonitrile:

9-(2-fluorophenyl)-7-phenyl-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

2-(7-(4-fluorophenyl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

3-(7-(4-fluorophenyl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

3-(7-(2-fluorophenyl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

3-(3-fluoro-8-oxo-7-phenyl-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

2-fluoro-6-(3-fluoro-8-oxo-7-(pyridin-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

2-fluoro-6-(7-(5-fluoropyridin-3-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

9-(2-chloro-3-fluorophenyl)-7-(5-fluoropyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

2-fluoro-6-(8-oxo-7-(pyrimidin-5-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

3,6-difluoro-2-(8-oxo-7-(pyridin-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

2-(7-(5-chloropyridin-3-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)-6-fluorobenzonitrile:

2-fluoro-6-(7-(2-methylpyrimidin-5-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

and
9-(3-fluoro-2-methylphenyl)-7-(pyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

or a pharmaceutically acceptable salt thereof.

2. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 9-(2-Chlorophenyl)-7-(pyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

3. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 2-Fluoro-6-(7-(6-methylpyridin-3-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′] dipyridin-9-yl)benzonitrile:

4. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 9-(2-Chloro-3-fluorophenyl)-7-(6-methylpyridin-3-yl)-6H-pyrano[3,2-b:5,4-b′]dipyridin-8(7H)-one:

5. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 2-Fluoro-6-(7-(2-methoxypyrimidin-5-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

6. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 3-(7-(4-Fluorophenyl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

7. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 3-(3-Fluoro-8-oxo-7-phenyl-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)picolinonitrile:

8. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 2-Fluoro-6-(3-fluoro-8-oxo-7-(pyridin-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

9. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 2-Fluoro-6-(8-oxo-7-(pyrimidin-5-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

10. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 3,6-Difluoro-2-(8-oxo-7-(pyridin-3-yl)-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

11. The compound or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is 2-Fluoro-6-(7-(2-methylpyrimidin-5-yl)-8-oxo-7,8-dihydro-6H-pyrano[3,2-b:5,4-b′]dipyridin-9-yl)benzonitrile:

12. A phar

Assignees

• Eisai R&D Man Co Ltd

Inventors

• Kurokawa Toshiki
• Yoshida Yu
• Shin Kogyoku
• Kobayashi Yoshihisa
• Fukumoto Hironori
• Takeda Kunitoshi
• Ohashi Yoshiaki
• Kotake Makoto
• SHIBUGUCHI Tomoyuki
• Watanabe Toru
• Kita Yoichi
• Hirota Shinsuke
• Fukuyama Takashi
• KAMADA Yasuaki

Classifications

• A61P43/00

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

• A61P25/30

  for treating abuse or dependence · 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