IP Library › Granted Patent US 10,407,419
Granted Patent B2
US 10,407,419 · App. 15/568,072 · Granted Sep 10, 2019

Quinolinone five-membered heterocyclic compounds as mutant-isocitrate dehydrogenase inhibitors

Inventors: Jian Lin (Acton, MA); Anna Ericsson (Shrewsbury, MA); Ann-Marie Campbell (Monroe, CT); Gary Gustafson (Ridgefield, CT); Zhongguo Wang (Lexington, MA); R. Bruce Diebold (Waltham, MA); Susan Ashwell (Carlisle, MA); David R. Lancia, Jr. (Boston, MA); Justin Andrew Caravella (Cambridge, MA); Wei Lu (Newton, MA)
Assignee: Forma Therapeutics, Inc.
C07D417/12A61P35/00C07D417/14C07D471/04
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Quick Facts
Patent No.
US 10,407,419
App. No.
15/568,072
Granted
Sep 10, 2019
Kind
B2
Abstract

The invention relates to inhibitors of mutant isocitrate dehydrogenase (mt-IDH) proteins with neomorphic activity useful in the treatment of cell-proliferation disorders and cancers, having the Formula: (I) where Y 1 , X 1 , X 2 , Y 2 , W 1 , W 2 , W 3 , and R 1 -R 5 are described herein.

Claims (279)

1. A pharmaceutical composition comprising a compound selected from the group consisting of:

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1R)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

N-(2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)acetamide,

ethyl 2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxylate,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,2,4-thiadiazol-3-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-({[4-(pyridin-2-yl)-1,3-thiazol-2-yl]amino}methyl)-1,2-dihydroquinolin-2-one,

6-chloro-3-({[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]amino}methyl)-1,2-dihydroquinolin-2-one,

3-{[(1,3-benzothiazol-2-yl)amino]methyl}-6-methoxy-1,2-dihydroquinolin-2-one,

2-{[(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-4-ethyl-5-methylthiophene-3-carbonitrile,

3-{[(dimethyl-1,3-thiazol-2-yl)amino]methyl}-6-methoxy-1,2-dihydroquinolin-2-one,

2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-7-fluoro-3-(1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

methyl N-(2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-7-fluoro-3-(1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-(1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

3-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-(1-({5-[1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-[1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-fluoro-1,2-dihydroquinolin-2-one,

3-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-7-fluoro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-7-fluoro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-fluoro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-fluoro-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-(6-chloro-7-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-[(1R)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-[(1R)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1R)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1R)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1R)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-7-methoxy-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-7-methoxy-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-methoxy-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-methoxy-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-methoxy-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-methoxy-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-methoxy-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-4-methyl-1,3-thiazole-5-carbonitrile,

2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-(1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

methyl N-[2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1,3-thiazol-5-yl]carbamate,

2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-(1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-(1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-7-(pyridin-2-ylmethoxy)-3-(1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

6-chloro-7-(pyridin-2-ylmethoxy)-3-(1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl)-1,2-dihydroquinolin-2-one,

3-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-(1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl)-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

3-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1-methyl-1H-pyrazole-5-carboxamide,

2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1H-imidazole-5-carboxamide,

N-[2-({1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl}amino)-1,3-oxazol-4-yl]acetamide,

2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-7-(pyridin-2-ylmethoxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(pyridin-2-ylmethoxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-[6-chloro-2-oxo-7-(pyridin-2-ylmethoxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-7-[(1R)-1-(pyridin-2-yl)ethoxy]-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-[(1R)-1-(pyridin-2-yl)ethoxy]-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-{6-chloro-2-oxo-7-[(1R)-1-(pyridin-2-yl)ethoxy]-1,2-dihydroquinolin-3-yl}ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(cyclopropylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(cyclopropylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(cyclopropylmethoxy)-1,2-dihydroquinolin-2-one,

6-chloro-7-(cyclopropylmethoxy)-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-[6-chloro-7-(cyclopropylmethoxy)-2-oxo-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-8-fluoro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-8-fluoro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-8-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-8-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-8-fluoro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-8-fluoro-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-8-fluoro-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-(6-chloro-8-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-7-(propan-2-yloxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-(propan-2-yloxy)-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-7-(propan-2-yloxy)-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-[6-chloro-2-oxo-7-(propan-2-yloxy)-1,2-dihydroquinolin-3-yl]ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carboxamide,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-7-cyclopropyl-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-7-cyclopropyl-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide,

N-(2-{[(1S)-1-(6-chloro-7-cyclopropyl-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methoxy-1,3-thiazole-5-carbonitrile,

6-chloro-3-[(1S)-1-{[5-(2-oxo-1,3-oxazolidin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

methyl N-(2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)carbamate,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[5-(5-cyclopropyl-1H-1,2,3-triazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3-triazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(5-methyl-1H-1,2,3,4-tetrazol-1-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one

6-chloro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-{[4-(pyridin-3-yl)-1,3-oxazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-1,2,4-triazole-5-carboxamide,

6-chloro-3-[(1S)-1-{[5-(1-cyclopropyl-1H-imidazol-5-yl)-1,3-thiazol-2-yl]amino}ethyl]-1,2-dihydroquinolin-2-one,

6-chloro-3-[(1S)-1-({5-[1-(cyclopropylmethyl)-1H-imidazol-5-yl]-1,3-thiazol-2-yl}amino)ethyl]-1,2-dihydroquinolin-2-one,

3-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1-methyl-1H-pyrazole-5-carboxamide,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1H-imidazole-5-carboxamide, and

N-(2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-oxazol-4-yl)acetamide;

or a pharmaceutically acceptable salt thereof.

2. The pharmaceutical composition of claim 1 , wherein the compound is selected from the group consisting of:

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[1-(6-chloro-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl)ethyl]amino}-1,3-thiazole-5-carbonitrile,

2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-4-methyl-1,3-thiazole-5-carbonitrile, and

N-(2-{[(1S)-1-(6-chloro-2-oxo-1,2-dihydroquinolin-3-yl)ethyl]amino}-1,3-thiazol-5-yl)acetamide;

or a pharmaceutically acceptable salt thereof.

3. The pharmaceutical composition of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

4. The pharmaceutical composition of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

5. The pharmaceutical composition of claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2019
From: FORMA TM2, INC.
To: FORMA THERAPEUTICS, INC.
Reel/Frame 049598/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2018
From: FORMA THERAPEUTICS, INC.
To: FORMA TM2, INC.
Reel/Frame 047457/0946 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2018
From: LIN, JIAN; ERICSSON, ANNA; CAMPBELL, ANN-MARIE; GUSTAFSON, GARY; WANG, ZHONGGUO; DIEBOLD, R. BRUCE; ASHWELL, SUSAN; LANCIA, DAVID R., JR.; CARAVELLA, JUSTIN ANDREW; LU, WEI
To: FORMA THERAPEUTICS, INC.
Reel/Frame 046226/0409 →
Continuity (2)
Provisional Application 62150816 · Apr 21, 2015
Related Publication 20180118732A1 · May 3, 2018
Cited By (1)
US 12,275,715