US 12,435,051 B2
Dual modulator of mGluR5 and 5-HT2A receptor, and use thereof
Dae Kyu Choi, Yongin-si (KR); Hyo Jin Kim, Yongin-si (KR); Mi Seon Bae, Yongin-si (KR); Jin Choi, Seoul (KR); Hyun Jin Heo, Yongin-si (KR); Yong Seok Lee, Yongin-si (KR); Geon Ho Lee, Yongin-si (KR); Mi Yon Shim, Yongin-si (KR); Jin Sun Park, Yongin-si (KR); and Han Mi Lee, Yongin-si (KR)
Assigned to Vivozon, Inc., Yongin-si (KR)
Filed by Vivozon Inc., Yongin-si (KR)
Filed on Jul. 1, 2024, as Appl. No. 18/760,458.
Application 18/760,458 is a continuation of application No. 17/631,212, granted, now 12,060,339, previously published as PCT/KR2021/009826, filed on Jul. 28, 2021.
Claims priority of application No. 10-2020-0094236 (KR), filed on Jul. 29, 2020.
Prior Publication US 2024/0360092 A1, Oct. 31, 2024
Int. Cl. C07D 295/135 (2006.01); A61P 25/04 (2006.01); C07C 233/66 (2006.01); C07C 233/70 (2006.01); C07C 233/72 (2006.01); C07C 233/78 (2006.01); C07C 233/86 (2006.01); C07C 237/34 (2006.01); C07D 213/40 (2006.01); C07D 213/56 (2006.01); C07D 305/06 (2006.01); C07D 307/14 (2006.01); C07D 309/06 (2006.01); C07D 309/14 (2006.01); C07D 319/12 (2006.01)
CPC C07D 295/135 (2013.01) [A61P 25/04 (2018.01); C07C 233/66 (2013.01); C07C 233/70 (2013.01); C07C 233/72 (2013.01); C07C 233/78 (2013.01); C07C 233/86 (2013.01); C07C 237/34 (2013.01); C07D 213/40 (2013.01); C07D 213/56 (2013.01); C07D 305/06 (2013.01); C07D 307/14 (2013.01); C07D 309/06 (2013.01); C07D 309/14 (2013.01); C07D 319/12 (2013.01)] 3 Claims
 
1. A compound selected from the group consisting of:
N-((1-(cyclopropylamino)cycloheptyl)methyl)-4-(pyridin-2-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclopentyl)methyl)-4-(pyridin-4-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclobutyl)methyl)-4-(pyridin-4-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclobutyl)methyl)-3-fluoro-4-(pyridin-4-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclobutyl)methyl)-4-(pyridin-2-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclobutyl)methyl)-2-fluoro-4-(pyridin-4-ylethynyl)benzamide;
N-((1-(cyclopropylamino)cyclohexyl)methyl)-4-((4-fluorophenyl)ethynyl)benzamide;
N-((1-(cyclopropylamino)cyclohexyl)methyl)-4-((2-fluorophenyl)ethynyl)benzamide;
N-((1-(cyclopropylamino)cyclopentyl)methyl)-4-((2-methylpyridin-4-yl)ethynyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-(isopropylamino)cyclohexyl)methyl)benzamide;
N-((1-(cyclopropylamino)-4-methylcyclohexyl)methyl)-4-((2-fluorophenyl)ethynyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-(neopentylamino)cyclohexyl)methyl)benzamide;
4-(pyridin-4-ylethynyl)-N-((1-((2,2,2-trifluoroethyl)amino)cyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-hydroxycyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-(hydroxymethyl)cyclohexyl)methyl)benzamide;
N-((4,4-difluorocyclohexyl)methyl)-4-((2-fluorophenyl)ethynyl)benzamide;
4-(phenylethynyl)-N-((tetrahydro-2H-pyran-4-yl)methyl)benzamide;
N-((1-(isopropylamino)cyclohexyl)methyl)-4-(phenylethynyl)benzamide;
methyl 3-(1-((4-((2-fluorophenyl)ethynyl)benzamido)methyl)cyclohexyl)propanoate;
3-(1-((4-((2-fluorophenyl)ethynyl)benzamido)methyl)cyclohexyl)propanoic acid;
4-((2-fluorophenyl)ethynyl)-N-((1-(3-hydroxypropyl)cyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((2-hydroxycyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((3-hydroxycyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-methoxycyclohexyl)methyl)benzamide;
4-((2,4-difluorophenyl)ethynyl)-N-((1-fluorocyclohexyl)methyl)benzamide;
methyl 2-(1-((4-((2-fluorophenyl)ethynyl)benzamido)methyl)cyclohexyl)acetate;
2-(1-((4-((2-fluorophenyl)ethynyl)benzamido)methyl)cyclohexyl)acetic acid;
4-((2-fluorophenyl)ethynyl)-N-((1-(2-(hydroxyamino)-2-oxoethyl)cyclohexyl)methyl)benzamide;
4-((2-fluorophenyl)ethynyl)-N-((1-(2-(methylamino)-2-oxoethyl)cyclohexyl)methyl)benzamide;
N-((1-(2-(dimethylamino)-2-oxoethyl)cyclohexyl)methyl)-4-((2-fluorophenyl)ethynyl)benzamide;
N-((4,4-difluorocyclohexyl)methyl)-4-(pyridin-4-ylethynyl)benzamide;
N-((3,3-difluorocyclobutyl)methyl)-4-(pyridin-4-ylethynyl)benzamide; and
N-((3,3-difluorocyclobutyl)methyl)-4-(phenylethynyl)benzamide;
or a pharmaceutically acceptable salt thereof.