US 10,138,234 B2
2-phenyl or 2-hetaryl imidazol[1,2-a]pyridine derivatives
Edilio Borroni, Basel (CH); Luca Gobbi, Muttenz (CH); Michael Honer, Zurich (CH); Henner Knust, Rheinfelden (DE); Matthias Koerner, Grenzach-Wyhlen (DE); and Dieter Muri, Basel (CH)
Assigned to Hoffmann-La Roche Inc., Little Falls, NJ (US)
Filed by Hoffmann-La Roche Inc., Little Falls, NJ (US)
Filed on Oct. 28, 2015, as Appl. No. 14/925,574.
Application 14/925,574 is a continuation of application No. PCT/EP2014/058415, filed on Apr. 25, 2014.
Claims priority of application No. 13165676 (EP), filed on Apr. 29, 2013.
Prior Publication US 2016/0244441 A1, Aug. 25, 2016
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 51/00 (2006.01); A61M 36/14 (2006.01); C07D 471/04 (2006.01); A61K 49/00 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 49/0002 (2013.01)] 7 Claims
 
1. A compound selected from the group consisting of:
N-(2-fluoroethyl)-2-phenylimidazo[1,2-a]pyridin-7-amine,
N-(2-fluoroethyl)-N-methyl-2-phenylimidazo[1,2-a]pyridin-7-amine,
N,N-dimethyl-2-phenylimidazo[1,2-a]pyridin-7-amine,
N-methyl-2-phenylimidazo[1,2-a]pyridin-7-amine,
[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
(2-[4-(2-fluoro-ethoxy)-phenyl]-imidazo[1,2-a]pyridin-7-yl}-dimethyl-amine,
[2-(4-fluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
[2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
N-methyl-2-m-tolylimidazo[1,2-a]pyridin-7-amine,
N,N-dimethyl-(2-m-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
N,N-dimethyl-(2-p-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
N-methyl-(2-p-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
N-(2-fluoroethyl)-N-methyl-(2-p-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
2-(4-(dimethylamino)phenyl)-N-(2-fluoroethyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
[2-(3-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
(2-fluoro-ethyl)-methyl-(2-m-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine
[2-(3-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
[2-(4-fluoromethoxy-phenyl)-imidazo[1,2-a]pyri din-7-yl]-methyl-amine,
(2-fluoro-ethyl)-(2-p-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
(2-fluoro-ethyl)-(2-m-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
(2-fluoro-ethyl)-[2-(4-fluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
[2-(3,4-dimethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
[2-(3,4-dimethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
[3H]-[2-(4-fluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
[3H]—N-methyl-2-phenyl-imidazo[1,2-a]pyridin-7-amine,
[3H]—N-(2-fluoroethyl)-2-phenyl-imidazo[1,2-a]pyridin-7-amine,
[3H]—N-methyl-(2-p-tolyl-imidazo[1,2-a]pyridin-7-yl)-amine,
(2-fluoro-ethyl)-[2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
[2-(3,4-dimethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
cyclopropyl-[2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
methyl-[2-(4-methyl sulfanyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
[2-(3,4-dimethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-(2-fluoro-ethyl)-amine,
[2-(3,4-dimethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-(2-fluoro-ethyl)-amine,
[2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
(2-fluoro-ethyl)-[2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
(2-fluoro-ethyl)-[2-(3-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
[2-(3-fluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-dimethyl-amine,
(2-fluoro-ethyl)-[2-(4-methyl sulfanyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
cyclopropyl-[2-(4-fluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
2-methoxy-4-(7-methylamino-imidazo[1,2-a]pyridin-2-yl)-phenol,
3-(7-dimethylamino-imidazo[1,2-a]pyridin-2-yl)-phenol,
[4-[7-(methylamino)imidazo[1,2-a]pyridin-2-yl]phenyl]methanol,
[4-[7-(dimethylamino)imidazo[1,2-a]pyridin-2-yl]phenyl]methanol,
2-(3,5-dimethoxyphenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
N-[2-(4-ethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
methyl-[2-(4-pyrrolidin-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
N-[2-(3-fluoro-4-methoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
N-[2-(4-diethylamino-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
N-[2-(4-ethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
2-[4-(methoxymethyl)phenyl]-N,N-dimethyl-imidazo[1,2-a]pyridin-7-amine,
methyl-[2-(4-morpholin-4-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
2-[4-(2-fluoroethoxymethyl)phenyl]-N,N-dimethyl-imidazo[1,2-a]pyridin-7-amine,
2-(3-methoxy-4-methylphenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
2-[4-(2-fluoroethoxy)phenyl]-N-methylimidazo[1,2-a]pyridin-7-amine,
2-(4-(benzyl(methyl)amino)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
N-[2-(4-difluoromethoxy-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
N-[2-(4-bromo-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methyl-amine,
methyl-[2-(4-piperidin-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-amine,
2-(7-methylamino-imidazo[1,2-a]pyridin-2-yl)-phenol,
methyl 3-[7-(methylamino)imidazo[1,2-a]pyridin-2-yl]benzoate,
[3-[7-(methylamino)imidazo[1,2-a]pyridin-2-yl]phenyl]methanol,
N-cyclopropyl-2-[4-(2-fluoroethoxy)phenyl]imidazo[1,2-a]pyridin-7-amine,
7-(azetidin-1-yl)-2-[4-(3-fluoropropoxy)phenyl]imidazo[1,2-a]pyridine,
4-methyl-2-(7-methylamino-imidazo[1,2-a]pyridin-2-yl)-phenol,
2-[3-(methoxymethyl)phenyl]-N-methyl-imidazo[1,2-a]pyridine-7-amine,
2-(4-(2-fluoroethylamino)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
N-(3-fluoropropyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-amine,
2-(3-(fluoromethoxy)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
2-(2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-ylamino)propan-1-ol,
N-(2-fluoroethyl)-2-(3-methoxy-4-methylphenyl)imidazo[1,2-a]pyridin-7-amine,
N-methyl-2-(3-(methylthio)phenyl)imidazo[1,2-a]pyridin-7-amine,
2-(3-(2-fluoroethoxy)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
2-(3-(3-fluoropropoxy)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
2-(4-(4-fluoropiperidin-1-yl)phenyl)-N-methylimidazo[1,2-a]pyridin-7-amine,
4-(7-(2-fluoroethylamino)imidazo[1,2-a]pyridin-2-yl)-2-methoxyphenol,
4-(7-(2-fluoroethylamino)imidazo[1,2-a]pyridin-2-yl)phenol,
3-(7-(2-fluoroethylamino)imidazo[1,2-a]pyridin-2-yl)phenol,
N-(2-fluoroethyl)-2-(4-morpholin-4-ylphenyl)imidazo[1,2-a]pyridin-7-amine, and
N-cyclopropyl-2-[4-(3-fluoropropoxy)phenyl]imidazo[1,2-a]pyridin-7-amine, or a pharmaceutically acceptable salt thereof.