Quinolinone derivatives
The present invention relates to compounds of the formula (I), salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds as activators of AMPK.
1. A compound of formula (I) or a salt thereof:
wherein:
R 1 is a) a 5-membered heteroaryl optionally substituted with 1, 2, or 3 groups independently selected from —CH 3 , —OCH 3 , —OH, —CH 2 OH, —CF 3 , —OCF 3 , —CN, —CO 2 H, —CH 2 CO 2 H, —CONH 2 , —NH 2 and halogen;
b) O-phenyl optionally substituted with a group selected from methyl, methoxy, fluoro, and CO 2 H;
c) selected from the group consisting of H, CO 2 H, CO 2 Et, and NO 2 ;
d) phenyl optionally substituted with a group selected from CO 2 H, Cl, F, methyl, —CN, -NMe 2 and methoxy;
e) selected from the group consisting of 3-pyridinyl, 4-pyridinyl, and —S(O) n -phenyl; or
f) selected from the group consisting of O-pyridin-2-yl, O-(4-methyl-pyridin-2-yl), O-(5-methoxy-pyridin-2-yl) and O-(5-methyl-pyridin-2-yl);
n=0 or 2;
R 2 is H;
R 3 is
R 4 is Cl;
R 5 is H; and
R 7 is H and R 6 is selected from a group consisting of, —NHMe, —NMe 2 , —NHC(O)OMe, —OMe, —OEt, Et, iPr, —CH 2 OH, and —CH 2 CH 2 OH or is a group selected from
or
R 6 and R 7 taken together form a group selected from
or
wherein:
i) R 1 =3-methoxyphenyl, R 4 is F and R 3 =4-(4-morpholino)phenyl;
ii) R 1 =3-methylisoxazol-5-yl, and R 3 =3-dimethylaminophenyl; or
iii) R 1 =3-methoxyphenyl, and R 3 =3-dimethylaminophenyl.
2. The compound or salt thereof according to claim 1 wherein R 1 represents 5-membered heteroaryl optionally substituted by a group selected from —CH 3 , —OCH 3 , —OH, —CH 2 OH, —CF 3 , —OCF 3 , —CN, —CO 2 H, —CH 2 CO 2 H, —CONH 2 , —NH 2 and halogen.
3. The compound or salt thereof according to claim 1 wherein R 1 represents 5-membered heteroaryl optionally substituted with 1, 2, or 3 groups independently selected from methyl, chloro, bromo, CO 2 H and methoxy.
4. The compound or salt thereof according to claim 1 wherein R 3 represents
5. The compound or salt thereof according to claim 1 wherein R 3 represents
6. A compound of formula (A) or a salt thereof:
wherein
R 1 represents 5-membered heteroaryl optionally substituted by —CH 3 , —OCH 3 , —OH, —CH 2 OH, —CF 3 , —OCF 3 , —CN, —CO 2 H, —CH 2 CO 2 H, —CONH 2 , —NH 2 or halogen;
R 2 represents H;
R 3 is
R 4 represents chloro;
R 5 represents H; and
R 7 is H and R 6 is selected from a group consisting of —NHMe, —NMe 2 , —NHC(O)OMe, Et, and iPr, or is a group selected from
7. The compound or salt thereof according to claim 1 , selected from the group consisting of:
7-Chloro-4-hydroxy-6-(2′-hydroxy-3′-methoxy-[1,1′-biphenyl]-4-yl)-3-phenylquinolin-2(1H)-one;
3-{7-Chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-2-oxo-1,2-dihydro-3-quinolinyl}benzoic acid;
7-chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-morpholinophenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-[4-(4-morpholinyl)phenyl]-3-phenylquinolin-2(1H)-one;
4-{7-Chloro-4-hydroxy-3-[3-(methyloxy)phenyl]-2-oxo-1,2-dihydro-6-quinolinyl}-N-cyclopentylbenzamide;
7-Fluoro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-morpholinophenyl)quinolin-2(1H)-one;
3-[7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydro-3-quinolinyl]benzoic acid;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-[3-(methyloxy)phenyl]quinolin-2(1H)-one;
N-{4-[4-(7-Chloro-4-hydroxy-2-oxo-3-phenyl-1,2-dihydro-6-quinolinyl)phenyl]-1,3-thiazol-2-yl}acetamide;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-phenylquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4′-fluoro-[1,1′-biphenyl]-4-yl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(3′-methoxy-[1,1′-biphenyl]-4-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-6-(4-(5-methylthiophen-2-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4′-methoxy-[1,1′-biphenyl]-4-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(2′-fluoro-[1,1′-biphenyl]-4-yl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
3-(7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)benzonitrile;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(3-methyl-1,2,4-oxadiazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-3,6-bis(4-(dimethylamino)phenyl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-3-(4-cyanophenyl)-6-(4-(dimethylamino)phenyl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(2-methylthiazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(2,4-dimethylthiazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-3-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxo-6-(4-(piperidin-1-yl)phenyl)-1,2-dihydroquinolin-4-olate;
Ethyl 7-chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-1,2-dihydro-3-quinolinecarboxylate;
Ethyl 7-chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-2-oxo-1,2-dihydro-3-quinoline carboxylate;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-nitroquinolin-2(1H)-one;
Ethyl 7-chloro-4-hydroxy-6-[4-(4-morpholinyl)phenyl]-2-oxo-1,2-dihydro-3-quinolinecarboxylate;
7-Chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-6-(4-morpholino phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(1-methyl-1H-benzo [d]imidazol-6-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
Methyl (4-(7-chloro-4-hydroxy-3-(3-methoxyphenyl)-2-oxo-1,2-dihydroquinolin-6-yl)phenyl) carbamate;
7-Chloro-6-[4-(dimethylamino)phenyl]-4-hydroxy-3-[3-(methyloxy)phenyl]quinolin-2(1H)-one;
7-Chloro-6-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-3-(3-methoxyphenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-ethylphenyl)-4-hydroxy-3-(3-methoxyphenyl)quinolin-2(1H)-one;
7-Chloro-6-[3-(dimethylamino) phenyl]-4-hydroxy-3-[3-(methyloxy)phenyl]-2(1H)-quinolinone;
7-Chloro-6-(3-(dimethylamino)phenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-ethylphenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(2′-hydroxy-3′-methoxy-[1,1′-biphenyl]-4-yl)-3-(3-methylisoxazol-5-yl) quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-morpholinophenyl)-3-phenoxyquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-phenylquinolin-2(1H)-one;
6-(4-(1H-Pyrazol-1-yl)phenyl)-7-chloro-4-hydroxy-3-phenylquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-methoxyphenyl)-3-phenylquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-morpholinophenyl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-phenoxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-phenyl-6-(4-(piperidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(2-hydroxyethyl)phenyl)-3-phenylquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(3-hydroxypiperidin-1-yl)phenyl)-3-(3-methoxyphenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(2′-hydroxy-3′-methoxy-[1,1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenyl)-6-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-phenyl-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(2′-hydroxy-3′-methoxy-[1,1′-biphenyl]-4-yl)-3-phenoxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(2′-hydroxy-3′-methoxy-[1,1′-biphenyl]-4-yl)quinolin-2(1H)-one;
N-(4-(4-(7-Chloro-4-hydroxy-2-oxo-3-phenoxy-1,2-dihydroquinolin-6-yl)phenyl)thiazol-2-yl) acetamide;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(o-tolyloxy)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(4-methoxyphenoxyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(hydroxymethyl)phenyl)-3-phenylquinolin-2(1H)-one;
7-Chloro-3-(3-fluorophenoxy)-4-hydroxy-6-(4-isopropylphenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(3-fluorophenoxy)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(methylamino)phenyl)-3-phenylquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(1H-pyrazol-1-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-ethoxyphenyl)-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-phenoxy-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-ethylphenyl)-4-hydroxy-3-phenoxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-isopropylphenyl)-3-phenoxyquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methoxyphenoxyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenoxy)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-isopropylphenyl)-3-(3-methoxyphenoxyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(cyclopropylmethoxy)phenyl)-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-3-(1H-pyrazol-1-yl) quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indazol-5-yl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-isopropylphenyl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(p-tolyloxy)quinolin-2(1H)-one;
7-Chloro-6-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(4-methyl-1,2,5-oxadiazol-3-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(pyridin-4-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(pyridin-2-yloxy)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(1H-1,2,4-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(2-methoxyphenoxyl)quinolin-2 (1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(1H-1,2,3-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(4-methyl-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(m-tolyloxy)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(pyridin-3-yl)quinolin-2(1H)-one;
3-((7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)oxy) benzoic acid;
1-(7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-1H-pyrazole-4-carboxylic acid;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(4-fluorophenoxy)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(2′-hydroxy-[1, 1′-biphenyl]-4-yl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-3-(1,3-dimethyl-1H-pyrazol-5-yl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(piperidin-1-yl)phenyl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-((4-methylpyridin-2-yl)oxy)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-methoxyphenyl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(pyridin-3-yl)quinolin-2(1H)-one;
1-(7-Chloro-4-hydroxy-2-oxo-6-(4-(pyrrolidin-1-yl)phenyl)-1,2-dihydroquinolin-3-yl)-1H-pyrazole-4-carboxylic acid;
7-Chloro-4-hydroxy-3-(pyridin-3-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methyl-1,2,5-oxadiazol-3-yl)-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methyl-1,2,5-oxadiazol-3-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2 (1H)-one;
7-Chloro-4-hydroxy-3-(pyridin-4-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(4-methyl-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(pyridin-4-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-phenoxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(2-methoxyphenoxy)-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(p-tolyloxy)quinolin-2(1H)-one;
7-Chloro-3-(3-fluorophenoxy)-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
6-([1,1′-Biphenyl]-4-yl)-7-chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-cyclohexylphenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(5-methyl-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(5-methyl-1H-pyrazol-1-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2 (1H)-one;
7-Chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-6-(naphthalen-2-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(3-hydroxypiperidin-1-yl)phenyl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(phenylthio)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-morpholinophenyl)-3-(phenylthio)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(hydroxymethyl)phenyl)-3-(phenylthio)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(6-methoxynaphthalen-2-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-methoxyphenyl)-3-phenoxyquinolin-2(1H)-one;
6-(4-(1H-Pyrazol-1-yl)phenyl)-7-chloro-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1H-indol-5-yl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-3-(1,3-dimethyl-1H-pyrazol-5-yl)-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-3-(4-chloro-1H-pyrazol-1-yl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(3-methoxyphenoxy)-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-3-(1,3-dimethyl-1H-pyrazol-5-yl)-4-hydroxy-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(1H-1,2,4-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(1-methyl-1H-pyrazol-4-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-((5-methylpyridin-2-yl)oxy)quinolin-2(1H)-one;
7-Chloro-3-(4-chloro-1H-pyrazol-1-yl)-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(pyrrolidin-1-yl)phenyl)-3-(1H-1,2,4-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(piperidin-1-yl)phenyl)-3-(1H-1,2,4-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(3-fluorophenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(methylamino)phenyl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methyl-1H-pyrazol-1-yl)-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methyl-1H-pyrazol-1-yl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2 (1H)-one;
7-Chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(1-ethyl-1H-indol-5-yl)-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methyl-1,2,5-oxadiazol-3-yl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2 (1H)-one;
7-Chloro-4-hydroxy-6-(4-(piperidin-1-yl)phenyl)-3-(pyridin-3-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-nitroquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(phenylsulfonyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)-3-(phenylsulfonyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(4-fluorophenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(o-tolyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(2-methoxyphenyl)quinolin-2(1H)-one;
7-Chloro-3-(4-chlorophenyl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-3-(3-chlorophenyl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-3-(2-chlorophenyl)-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-3-(2-fluoro phenyl)-4-hydroxyquinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-6-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methylindolin-5-yl)-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methoxy-1H-pyrazol-1-yl)-6-(4-(piperidin-1-yl)phenyl)quinolin-2 (1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(m-tolyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(p-tolyl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)-3-(2-methoxyphenoxy) quinolin-2(1H)-one;
7-chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclopropyl)phenyl)-3-(4-methoxy-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclopentyl)phenyl)-3-(3-methylisoxazol-5-yl) quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(4-methoxyphenyl) quinolin-2(1H)-one;
Methyl 1-(4-(7-chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-6-yl)phenyl)cyclopropane carboxylate;
7-Chloro-3-(3-chlorophenyl)-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-3-(3-chlorophenyl)-4-hydroxy-6-(4-(pyrrolidin-1-yl)phenyl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(4-methoxy-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(1-(hydroxymethyl)cyclobutyl)phenyl)-3-(3-methylisoxazol-5-yl) quinolin-2(1H)-one;
7-Chloro-6-(4-(1-hydroxycyclobutyl)phenyl)-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(1-ethyl-1H-indol-5-yl)-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-ethoxyphenyl)-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-(3-hydroxyoxetan-3-yl)phenyl)-3-(3-methylisoxazol-5-yl)-2-oxo-1,2-dihydroquinolin-4-olate;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methyl-1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-((4-methoxypyridin-2-yl)oxy)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-3-(4-methoxyphenoxy)-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-((5-methylpyridin-2-yl)oxy)quinolin-2(1H)-one;
7-Chloro-6-(2′-fluoro-[1,1′-biphenyl]-4-yl)-4-hydroxy-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(4-(5-methylthiophen-2-yl)phenyl)-3-(1H-pyrazol-1-yl)quinolin-2(1H)-one;
3-(4-Bromo-1H-pyrazol-1-yl)-7-chloro-6-(4-(dimethylamino)phenyl)-4-hydroxyquinolin-2(1H)-one;
3-(4-Bromo-1H-pyrazol-1-yl)-7-chloro-4-hydroxy-6-(4-(piperidin-1-yl)phenyl)quinolin-2 (1H)-one;
6-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]-7-chloro-4-hydroxy-3-phenylquinolin-2(1H)-one;
6-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]-7-chloro-4-hydroxy-3-[3-(methyloxy)phenyl]quinolin-2(1H)-one;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(3-methoxyphenyl)quinolin-2(1H)-one;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(pyridin-3-yl)quinolin-2(1H)-one;
6-[4-(2-Amino-1,3-thiazol-4-yl)phenyl]-7-chloro-4-hydroxy-3-(1H-pyrazol-1-yl)-2(1H)-quinolinone;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(pyridin-4-yl)quinolin-2(1H)-one;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(4-methyl-1H-pyrazol-1-yl) quinolin-2(1H)-one;
6-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)-7-chloro-4-hydroxy-3-(1H-1,2,3-triazol-1-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-(1-methyl-1H-indol-5-yl)quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-[4-(4-morpholinyl)phenyl]quinolin-2(1H)-one;
7-Chloro-4-hydroxy-6-[2′-hydroxy-3′-(methyloxy)-4-biphenylyl]-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid;
1-(4-(7-Chloro-3-(3-methylisoxazol-5-yl)-4-oxido-2-oxo-1,2-dihydroquinolin-6-yl)phenyl)cyclopropanecarboxylate;
1-(7-Chloro-4-oxido-2-oxo-6-(4-(piperidin-1-yl)phenyl)-1,2-dihydroquinolin-3-yl)-1H-pyrazole-4-carboxylate; and
7-Chloro-3-(3-chlorophenyl)-4-hydroxy-6-(4-(piperidin-1-yl)phenyl) quinolin-2(1H)-one;
or a pharmaceutically acceptable salt thereof.
8. The compound or salt thereof according to claim 1 wherein the salt is a pharmaceutically acceptable salt.
9. A compound which is 7-chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one, represented by the formula:
or a pharmaceutically acceptable salt thereof.
10. The compound according to claim 9 which is 7-chloro-6-(4-(dimethylamino)phenyl)-4-hydroxy-3-(3-methylisoxazol-5-yl)quinolin-2(1H)-one, represented by the formula:
11. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 8 and a pharmaceutically acceptable carrier.
12. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 9 and a pharmaceutically acceptable carrier.
13. A pharmaceutical composition comprising the compound according to claim 10 and a pharmaceutically acceptable carrier.