US 11,702,419 B2
Heterocyclic compound and use thereof
Yuya Oguro, Fujisawa (JP); Shigemitsu Matsumoto, Fujisawa (JP); Takeshi Wakabayashi, Fujisawa (JP); Norihito Tokunaga, Fujisawa (JP); Taku Kamei, Fujisawa (JP); Mitsuhiro Ito, Fujisawa (JP); Satoshi Mikami, Fujisawa (JP); Masaki Seto, Fujisawa (JP); Shinji Morimoto, Fujisawa (JP); Shinji Nakamura, Fujisawa (JP); Sachie Takashima, Fujisawa (JP); Masataka Murakami, Fujisawa (JP); Masaki Daini, Fujisawa (JP); Makoto Kamata, Fujisawa (JP); Minoru Nakamura, Fujisawa (JP); Yasufumi Wada, Fujisawa (JP); Hiroyuki Kakei, Fujisawa (JP); Kazuaki Takami, Fujisawa (JP); Taisuke Tawaraishi, Fujisawa (JP); Jumpei Aida, Fujisawa (JP); Kouichi Iwanaga, Fujisawa (JP); and Satoshi Yamamoto, Fujisawa (JP)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (JP)
Filed by Takeda Pharmaceutical Company Limited, Osaka (JP)
Filed on Mar. 15, 2021, as Appl. No. 17/201,878.
Application 17/201,878 is a continuation of application No. 17/010,666, filed on Sep. 2, 2020, abandoned.
Application 17/010,666 is a continuation of application No. 16/366,710, filed on Mar. 27, 2019, granted, now 10,807,987, issued on Oct. 20, 2020.
Claims priority of application No. 2018-062939 (JP), filed on Mar. 28, 2018.
Prior Publication US 2021/0332053 A1, Oct. 28, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 487/04 (2006.01); A61K 9/20 (2006.01); A61K 9/48 (2006.01); C07D 471/04 (2006.01); A61P 25/00 (2006.01)
CPC C07D 487/04 (2013.01) [A61K 9/2095 (2013.01); A61K 9/4833 (2013.01); A61P 25/00 (2018.01); C07D 471/04 (2013.01)] 18 Claims
 
1. A compound or salt selected from:
N-((6-fluoro[1,2,3]triazolo[1,5-a]pyridin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
N-((4(4-methyl[1,2,3]triazolo[1,5-a]pyridin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
3-chloro-4-(difluoromethoxy)-N-((4-methyl[1,2,3]triazolo[1,5-a]pyridin-3-yl)methyl)benzamide;
5-fluoro-6-methoxy-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
3-fluoro-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
3-chloro-4-(difluoromethoxy)-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)benzamide;
5-chloro-6-(difluoromethoxy)-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
5-chloro-6-methoxy-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
3-fluoro-N-((2-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((6-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
3,5-difluoro-4-methoxy-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)benzamide;
3-fluoro-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)nicotinamide;
4-(difluoromethoxy)-3-fluoro-N-(pyrazolo[1,5-b]pyridazin-3-ylmethyl)benzamide;
3-fluoro-N-(pyrazolo[1,5-a]pyrazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N-((2-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
3-fluoro-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((4-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((5-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
5-chloro-6-(difluoromethoxy)-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
6-(difluoromethoxy)-5-fluoro-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)nicotinamide;
6-(difluoromethoxy)-N-((2-ethoxypyrazolo[1,5-b]pyridazin-3-yl)methyl)-5-fluoronicotinamide;
4-(difluoromethoxy)-N-((2-ethoxypyrazolo[1,5-b]pyridazin-3-yl)methyl)-3-fluorobenzamide;
6-(difluoromethoxy)-N-((2-ethylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-5-fluoronicotinamide;
4-(difluoromethoxy)-N-((2-ethylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-3-fluorobenzamide;
N-((2-cyclopropylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-6-(difluoromethoxy)-5-fluoronicotinamide;
N-((2-cyclopropylpyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(difluoromethoxy)-3-fluorobenzamide;
3-chloro-4-(difluoromethoxy)-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)benzamide;
6-(difluoromethoxy)-5-fluoro-N-((2-(methoxymethyl)pyrazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
3-fluoro-N-((2-(methoxymethyl)pyrazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
4-(difluoromethoxy)-3-fluoro-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)benzamide;
3-chloro-4-(difluoromethoxy)-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)benzamide;
4-(difluoromethoxy)-3-fluoro-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)benzamide;
4-(difluoromethoxy)-3-fluoro-N-((4-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)benzamide;
6-(difluoromethoxy)-5-fluoro-N-((4-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
4-(difluoromethoxy)-3-fluoro-N-((5-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)benzamide;
6-(difluoromethoxy)-5-fluoro-N-((5-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
3-chloro-N-([1,2,3]triazolo[1,5-b]pyridazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
3,5-difluoro-4-methoxy-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)benzamide;
3-fluoro-N-([1,2,3]triazolo[1,5-a]pyrazin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-N-((2-(difluoromethyl)pyrazolo[1,5-b]pyridazin-3-yl)methyl)-5-fluoronicotinamide;
4-(difluoromethoxy)-3-fluoro-N-(pyrazolo[1,5-a]pyrazin-3-ylmethyl)benzamide;
6-(difluoromethoxy)-5-fluoro-N-(pyrazolo[1,5-a]pyrazin-3-ylmethyl)nicotinamide;
5-chloro-6-(difluoromethoxy)-N-((2-methylpyrazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
3-fluoro-N-(pyrazolo[1,5-b][1,2,4]triazin-8-ylmethyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((2-methylpyrazolo[1,5-c]pyrimidin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((5-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N((5-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
5-chloro-6-(difluoromethoxy)-N((5-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
3-fluoro-N-((4-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N((4-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
5-chloro-6-(difluoromethoxy)-N((4-methyl[1,2,3]triazolo[1,5-b]pyridazin-3-yl)methyl)nicotinamide;
6-(difluoromethoxy)-5-fluoro-N-((2-methylpyrazolo[1,5-c]pyrimidin-3-yl)methyl)nicotinamide;
5-chloro-6-(difluoromethoxy)-N-((2-methylpyrazolo[1,5-c]pyrimidin-3-yl)methyl)nicotinamide;
3-fluoro-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)nicotinamide;
5-chloro-6-(difluoromethoxy)-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)nicotinamide;
4-(cyclopropyloxy)-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)benzamide;
5-fluoro-6-methoxy-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)nicotinamide;
3,5-difluoro-4-methoxy-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)benzamide;
4-chloro-3-fluoro-N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)benzamide;
N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)-6-(trifluoromethoxy)nicotinamide;
N-((1-methyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl)-5-(trifluoromethyl)thiophene-2-carboxamide;
N-((1-methyl-1H-imidazo[1,2-1D]pyrazol-7-yl)methyl)-4-(trifluoromethoxy)benzamide;
3-fluoro-N-((1-methyl-1H-imidazo[1,2-1D]pyrazol-7-yl)methyl)-4-(trifluoromethyl)benzamide;
3-fluoro-N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)-4-(trifluoromethyl)benzamide;
N-([1,2,3]triazolo[1,5-a]pyridin-3-ylmethyl)-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-N-[(1,2-dimethyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl)methyl]-5-fluoropyridine-3-carboxamide;
N-[(1,2-dimethyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl)methyl]-3-fluoro-4-(trifluoromethoxy)benzamide;
5-chloro-6-(difluoromethoxy)-N-[(1,2-dimethyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl)methyl]pyridine-3-carboxamide;
6-(difluoromethoxy)-N-[(1,6-dimethyl-1H-imidazo[1,2-1D]pyrazol-7-yl)methyl]-5-fluoropyridine-3-carboxamide;
6-(difluoromethoxy)-N-{[1-(difluoromethyl)-2-methyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl]methyl}-5-fluoropyridine-3-carboxamide;
5-chloro-6-(difluoromethoxy)-N-{[1-(difluoromethyl)-2-methyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl]methyl}pyridine-3-carboxamide;
6-(difluoromethoxy)-N-{[1-(difluoromethyl)-1H-imidazo[1,2-1D]pyrazol-7-yl]methyl}-5-fluoropyridine-3-carboxamide;
5-chloro-N-{[1-(2,2-difluoroethyl)-2-methyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl]methyl}-6-(difluoromethoxy)pyridine-3-carboxamide;
N-{[1-(2,2-difluoroethyl)-2-methyl-1H-pyrazolo[1,5-b][1,2,4]triazol-7-yl]methyl}-3-fluoro-4-(trifluoromethoxy)benzamide;
N-{[1-(2,2-difluoroethyl)-1H-imidazo[1,2-1D]pyrazol-7-yl]methyl}-6-(difluoromethoxy)-5-fluoropyridine-3-carboxamide;
5-chloro-N-{[1-(2,2-difluoroethyl)-1H-imidazo[1,2-1D]pyrazol-7-yl]methyl}-6-(difluoromethoxy)pyridine-3-carboxamide;
N-{[1-(2,2-difluoroethyl)-1H-imidazo[1,2-1D]pyrazol-7-yl]methyl}-3-fluoro-4-(trifluoromethoxy)benzamide;
6-(difluoromethoxy)-5-fluoro-N-{[1-(2,2,2-trifluoroethyl)-1H-imidazo[1,2-b]pyrazol-7-yl]methyl}pyridine-3-carboxamide;
6-(difluoromethoxy)-N-[(1-ethyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl]-5-fluoropyridine-3-carboxamide;
5-chloro-6-(difluoromethoxy)-N-[(1-ethyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl]pyridine-3-carboxamide;
6-(difluoromethoxy)-N-[(1,2-dimethyl-1H-imidazo[1,2-b]pyrazol-7-yl)methyl]-5-fluoropyridine-3-carboxamide;
and salts of any of the foregoing.