Polycyclic compound

Patent metadata

Field	Value
Publication number	US-9453000-B2
Application number	US-67187308-A
Country	US
Kind code	B2
Filing date	Aug 28, 2008
Priority date	Aug 31, 2007
Publication date	Sep 27, 2016
Grant date	Sep 27, 2016

Abstract

Disclosed is a compound represented by the formula (I):

or a pharmacologically acceptable salt thereof, which is effective as a therapeutic or prophylactic agent for a disease induced by Aβ, wherein Ar 1 represents an imidazolyl group which may be substituted with a C1-6 alkyl group, or the like; Ar 2 represents a phenyl group which may be substituted with a C1-6 alkoxy group, or the like; X 1 represents a double bond, or the like; and Het represents a triazolyl group or the like which may be substituted with a C1-6 alkyl group or the like, or the like.

First claim

The invention claimed is:

1. A compound or pharmacologically acceptable salt thereof, wherein the compound is:
(−)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine.

2. A pharmaceutical composition comprising:
the compound or pharmaceutically acceptable salt thereof according to claim 1 as an active ingredient; and
a pharmaceutically acceptable carrier.

3. A compound or pharmacologically acceptable salt thereof, wherein the compound is selected from the following group:
1) (−)-8-(3,4-difluorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
2) (−)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
3) (−)-8-(4-chlorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
4) (−)-8-(2,3-difluorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
5) (−)-8-(2-trifluoromethyl-4-fluorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
6) (−)-8-(2-bromophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
7) (−)-8-(5-fluoro-2-trifluoromethylphenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
8) (5R,8S)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5-methyl-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
9) (5S,8R)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5-methyl-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
10) (−)-8-(3-fluroro-2-methylphenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
11) (−)-8-(3,5-difluorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine,
12) (−)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(o-tolyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine, and
13) (−)-8-(2-fluorophenyl)-2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine.

4. A pharmaceutical composition comprising the compound or pharmacologically acceptable salt thereof according to claim 3 as an active ingredient and a pharmaceutically acceptable carrier.

Assignees

• Kimura Teiji
• Kitazawa Noritaka
• Kaneko Toshihiko
• Sato Nobuaki
• Kawano Koki
• Ito Koichi
• Takaishi Mamoru
• Sasaki Takeo
• Yoshida Yu
• Uemura Toshiyuki
• Doko Takashi
• Shinmyo Daisuke
• Hasegawa Daiju
• Miyagawa Takehiko
• Hagiwara Hiroaki
• Eisai R&D Man Co Ltd

Inventors

• Kimura Teiji
• Kitazawa Noritaka
• Kaneko Toshihiko
• Sato Nobuaki
• Kawano Koki
• Ito Koichi
• Takaishi Mamoru
• Sasaki Takeo
• Yoshida Yu
• Uemura Toshiyuki
• Doko Takashi
• Shinmyo Daisuke
• Hasegawa Daiju
• Miyagawa Takehiko
• Hagiwara Hiroaki

Classifications

• A61P43/00

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

• A61P25/00

  Drugs for disorders of the nervous system · 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

• C07D403/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07D487/04

  Ortho-condensed systems · CPC title