Quinoline- and isoquinoline-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof

1. A compound or Formula 1 or a

pharmaceutically acceptable salt thereof, wherein:

Ar is chosen from aryl, substituted aryl, heteroaryl, and substituted heteroaryl;

A is —N— and B is —CH—, or A is —CH— and B is —N—;

L is chosen from NR 1 and O;

R 1 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, and substituted heterocycloalkyl;

X and Y are independently chosen from CH and N;

G is chosen from a covalent bond and NR 6 ;

R 6 is chosen from hydrogen and optionally substituted alkyl; and

R is chosen from optionally substituted heterocycloalkyl,

with the proviso that when Ar is phenyl, A is —N—, B is —CH—, L is NR 1 , R 1 is H, X is CH,

Y is CH, and G is a covalent bond, then R is not 4-methylpiperazin-1-yl.

2. The compound of claim 1 wherein A is —N— and B is —CH—.

3. The compound of claim 1 wherein A is —CH— and B is —N—.

4. The compound of claim 1 wherein R is chosen from optionally substituted piperidinyl, optionally substituted pyrrolidinyl, and optionally substituted piperazinyl.

5. The compound of claim 1 wherein G is a covalent bond.

6. The compound of claim 1 wherein G is NR 6 .

7. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 2:

wherein

m is an integer chosen from 1, 2, and 3; and

R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

8. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 3:

wherein

R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

9. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 4:

wherein

m is an integer chosen from 1, 2, and 3; and

R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

10. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 5:

wherein

R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

11. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 6:

wherein

R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

12. The compound of claim 7 wherein R 2 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, and —NR 4 R 5 , wherein

R 4 and R 5 are independently chosen from H, alkyl, and substituted alkyl; and

when R 2 is attached to a carbon α to the ring nitrogen, then R 2 is not —NR 4 R 5 .

13. The compound of claim 12 wherein R 2 is chosen from alkyl, and substituted alkyl.

14. The compound of claim 12 wherein R 2 is independently chosen from —NR 4 R 1 and —CH 2 —NR 4 R 5 .

15. The compound of claim 14 wherein

R 2 is —NR 4 R 5 and

R 4 and R 5 are independently chosen from C 1-4 alkyl, and substituted C 1-4 alkyl.

16. The compound of claim 15 wherein R 2 is —N(CH 3 ) 2 .

17. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 7:

wherein

m is an integer chosen from 1, 2, and 3; and

R 3 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

18. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 8:

wherein

m is an integer chosen from 1, 2, and 3; and

R 3 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

19. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 9:

wherein

m is an integer chosen from 1, 2, and 3; and

R 3 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

20. The compound of claim 1 wherein the compound of Formula 1 is chosen from compounds of Formula 10:

wherein

m is an integer chosen from 1, 2, and 3; and

R 3 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

21. The compound of claim 19 wherein R 6 is chosen from hydrogen and lower alkyl.

22. The compound of claim 17 wherein R 3 is chosen from H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl.

23. The compound of claim 22 wherein R 3 is chosen from H, alkyl, and substituted alkyl.

24. The compound of claim 23 wherein R 3 is chosen from C 1-4 alkyl, and substituted C 1-4 alkyl.

25. The compound of claim 1 wherein R 1 is chosen from hydrogen, alkyl, and substituted alkyl.

26. The compound of claim 25 wherein R 1 is hydrogen.

27. The compound of claim 1 wherein Ar is chosen from aryl and substituted aryl.

28. The compound of claim 27 wherein Ar is chosen from phenyl, substituted phenyl, and naphthyl.

29. The compound of claim 28 wherein Ar is chosen from phenyl and substituted phenyl.

30. The compound of claim 29 wherein Ar is substituted phenyl.

31. The compound of claim 27 wherein the substituent groups are selected from halogen, —CN, —OH, —COOH, —NO 2 , C 1-8 alkoxy, substituted C 1-8 alkoxy, C 1-8 alkyl, substituted C 1-8 alkyl, C 5-10 aryl, substituted C 5-10 aryl, C 5-10 cycloalkyl, substituted C 5-10 cycloalkyl, C 1-8 alkylthio, substituted C 1-8 alkylthio, C 1-8 alkylsulfinyl, substituted C 1-8 alkylsulfinyl, C 1-8 alkylamino, substituted C 1-8 alkylamino, C 1-8 aminocarbonyl, substituted C 1-8 aminocarbonyl, C 1-8 alkylcarbonylamino, substituted C 1-8 alkylcarbonylamino, C 1-8 alkylsulfonyl, substituted C 1-8 alkylsulfonyl, C 1-8 alkylcarbonyl, and substituted C 1-8 alkylcarbonyl.

32. The compound claim 1 wherein X is CH and Y is CH.

33. The compound of claim 1 wherein X is CH and Y is N.

34. The compound of claim 1 wherein X is N and Y is N.

35. The compound of claim 1 wherein the at least one chemical entity inhibits at least one ATP-utilizing enzyme.

36. The compound of claim 35 , wherein the at least one ATP-utilizing enzyme is a human protein kinase.

37. The compound of claim 36 , wherein the human protein kinase is chosen from ABL1, AKT1, AKT2, AKT3, AURORA-A, BMX, c-TAK1, CDK1, CDK1/cyclinB, CDK2/cyclinA, CDK2/cyclinE, CDK5, CHEK1, CHEK2, CK2, CSK, DAPK1, DYRK2, FLT-3, FYN, GSK3-α, GSK3-β, HCK, INSR, KIT, LCK, LYNA, MAPKAPK2, MAPKAPK3, MSK1, MSK2, NEK2, p38-α, p38-β, p38-δ, p38-γ, P70S6K1, PAK2, PDGFR-α, PAK1, PKA, PRAK, ROCK2, SGK1, SRC, SYK, PIM-1-kinase, PDK1, and RSK2.

38. The compound of claim 37 , wherein the human protein kinase is MAPKAPK2.

39. The compound of claim 1 chosen from:

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

6-(3-chlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-chlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-o-tolylquinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-m-tolylquinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-p-tolylquinolin-4-amine;

6-(2-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(3-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

2-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzamide;

3-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

6-(3,4-dimethoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2,4-difluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-fluoro-3-methylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

(3-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenyl)methanol;

6-(5-fluoro-2-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

3-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenol;

6-(3-chloro-4-fluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

4-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenol;

6-(2,3-dimethylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2,5-dimethoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2-ethylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

4-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzamide;

6-(4-(ethylthio)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2,5-difluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(fluorophenyl)-N-(4-(4-methylpiperazin-1yl)phenyl)quinolin-4-amine;

6-(2,3-dichlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2,5-dimethylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

3-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzoic acid;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-(methylthio)phenyl)quinolin-4-amine;

6-(3-ethoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(2-(trifluoromethyl)phenyl)quinolin-4-amine;

6-(3-(benzyloxy)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-vinylphenyl)quinolin-4-amine;

6-(2,4-dimethoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(3,4,5-trifluorophenyl)quinolin-4-amine;

(4-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenyl)methanol;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-phenoxyphenyl)quinolin-4-amine;

6-(4-ethoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(3,4-dichlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-(trifluoromethyl)phenyl)quinolin-4-amine;

6-(2,5-dichlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2,4-dichlorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(3-isopropylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-isopropylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-fluoro-2-methylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(3,4-difluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(biphenyl-3-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(5-isopropyl-2-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(3-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenyl)acetamide;

6-(2,4-bis(trifluoromethyl)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-(methylsulfinyl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-pentylphenyl)quinolin-4-amine;

6-(3,5-bis(trifluoromethyl)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-butylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

3-(4-(4-(4-(4-methylpiperazin-1-yl)phenylamino)quinolin-6-yl)phenyl)propanoic acid;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(3-nitrophenyl)quinolin-4-amine;

6-(3-fluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2-fluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-tert-butylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(3-(trifluoromethoxy)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(4-(trifluoromethoxy)phenyl)quinolin-4-amine;

6-(2,6-difluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-methylpiperazin-1-yl)phenyl)-6-(3-(trifluoromethyl)phenyl)quinolin-4-amine;

6-(4-(benzyloxy)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(2-((dimethylamino)methyl)phenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-(benzyloxy)-3-fluorophenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(4-cyclohexylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-(3,4-dimethylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-amine;

6-phenyl-N-(4-(piperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-ethylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

6-phenyl-N-(4-(4-propylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-butylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

N-(4-(4-isopropylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

N-(4-(4-(pentan-3-yl)piperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

2-(4-(4-(6-phenylquinolin-4-ylamino)phenyl)piperazin-1-yl)ethanol;

N-(4-(4-(2-methoxyethyl)piperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

3-(4-(4-(6-phenylquinolin-4-ylamino)phenyl)piperazin-1-yl)propan-1-ol;

N-(4-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

3-(4-(4-(6-phenylquinolin-4-ylamino)phenyl)piperazin-1-yl)propanenitrile;

2-(4-(4-(6-phenylquinolin-4-ylamino)phenyl)piperazin-1-yl)acetic acid;

6-(4-methoxyphenyl)-N-(4-(piperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-ethylpiperazin-1-yl)phenyl)-6-(4-methoxyphenyl)quinolin-4-amine;

6-(4-methoxyphenyl)-N-(4-(4-propylpiperazin-1-yl)phenyl)quinolin-4-amine;

N-(4-(4-butylpiperazin-1-yl)phenyl)-6-(4-methoxyphenyl)quinolin-4-amine;

N-(4-(4-isopropylpiperazin-1-yl)phenyl)-6-(4-methoxyphenyl)quinolin-4-amine;

2-(4-(4-(6-(4-methoxyphenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)ethanol;

3-(4-(4-(6-(4-methoxyphenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)propan-1-ol;

N-(4-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)phenyl)-6-(4-methoxyphenyl)quinolin-4-amine;

3-(4-(4-(6-(4-methoxyphenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)propanenitrile;

2-(4-(4-(6-(4-methoxyphenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)-N,N-dimethylacetamide;

2-(4-(4-(6-(4-methoxyphenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)acetic acid;

4-(4-(4-(piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-propylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-butylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-sec-butylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(pentan-3-yl)piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-allylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-cyclohexylpiperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(3-hydroxypropyl)piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(2-(dimethylamino)ethyl)piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(2-cyanoethyl)piperazin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

2-(4-(4-(6-(4-cyanophenyl)quinolin-4-ylamino)phenyl)piperazin-1-yl)acetic acid;

N-(4-(4-sec-butylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

N-(4-(4-cyclopentylpiperazin-1-yl)phenyl)-6-phenylquinolin-4-amine;

4-(4-(4-(4-methylpiperidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-(dimethylamino)piperidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(2-((dimethylamino)methyl)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(3-((dimethylamino)methyl)piperidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-((dimethylamino)methyl)piperidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(3-(dimethylamino)piperidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(3-(methylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

6-(3-chlorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

6-(4-chlorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-m-tolylquinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-p-tolylquinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(3-methoxyphenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(4-methoxyphenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(4-fluoro-3-methylphenyl)quinolin-4-amine;

6-(3-(benzyloxy)phenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(4-vinylphenyl)quinolin-4-amine;

6-(3,4-dichlorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(3,4-dimethylphenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(naphthalen-2-yl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(4-isopropylphenyl)quinolin-4-amine;

6-(benzo[b]thiophen-3-yl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(5-methylpyridin-2-yl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(1H-indol-5-yl)quinolin-4-amine;

6-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzo[d]thiazol-2 (3H)-one;

5-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)-2,3-dihydroinden-1-one;

5-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)nicotinic acid;

6-(6-chloropyridin-3-yl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(1H-indol-4-yl)quinolin-4-amine;

6-(6-chloro-5-methylpyridin-3-yl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(thiazol-2-yl)quinolin-4-amine;

1-(5-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)indolin-1-yl)ethanone;

4-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)-2-methylbenzonitrile;

6-(4-(difluoromethoxy)phenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

6-(4-(diethylamino)phenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(1H-indol-6-yl)quinolin-4-amine;

4-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)-2-fluorobenzonitrile;

6-(4-chloro-3-methoxyphenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

6-(4-chloro-3-fluorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

6-(benzo[d][1,3]dioxol-5-yl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(3-fluoro-4-methylphenyl)quinolin-4-amine;

6-(3-chloro-4-methylphenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(3-fluoro-4-methoxyphenyl)quinolin-4-amine;

6-(4-chloro-3-methylphenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

6-(4-chlorophenyl)-N-(4-(3-(diethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

4-(4-(4-(3-(diethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

N-(4-(3-(diethylamino)pyrrolidin-1-yl)phenyl)-6-(naphthalen-2-yl)quinolin-4-amine;

(R)-6-(4-chlorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

(R)-4-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

(R)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(naphthalen-2-yl)quinolin-4-amine;

(S)-6-(4-chlorophenyl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)quinolin-4-amine;

(S)-4-(4-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

(S)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-6-(naphthalen-2-yl)quinolin-4-amine;

4-(4-(4-(3-(benzyl(methyl)amino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(3-(methyl(3,3,3-trifluoropropyl)amino)pyrrolidin-1-yl)phenylamino)quinolin-6-yl)benzonitrile;

6-(4-chlorophenyl)-N-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)quinolin-4-amine;

4-(4-(6-(4-methylpiperazin-1-yl)pyridazin-3-ylamino)quinolin-6-yl)benzonitrile;

4-(4-(6-(4-methylpiperazin-1-yl)pyridin-3-ylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(4-methylpiperazin-1-yl)phenoxy)quinolin-6-yl)benzonitrile;

6-(4-chlorophenyl)-4-(4-(4-methylpiperazin-1-yl)phenoxy)quinoline;

4-(4-(4-(1-methylpiperidin-4-yl)phenylamino)quinolin-6-yl)benzonitrile;

4-(4-(4-(piperidin-4-yl)phenylamino)quinolin-6-yl)benzonitrile;

N1-(3,6′-biquinolin-4′-yl)-N-4-methyl-N-4-(1-methylpyrrolidin-3-yl)benzene-1,4-diamine;

4-(4-(4-(methyl(1-methylpyrrolidin-3-yl)amino)phenylamino)quinolin-6-yl)benzonitrile; and

N1-methyl-N-4-(6-(5-methylpyridin-2-yl)quinolin-4-yl)-N-1-(1-methylpyrrolidin-3-yl)benzene-1,4-diamine.

40. A pharmaceutical composition comprising at least one pharmaceutically acceptable excipient, and a therapeutically effective amount of a compound of claim 1 .

41. The pharmaceutical composition of claim 40 , wherein the compound is present in an amount effective for the treatment in a patient of a disease chosen from Alzheimer's disease, stroke, diabetes, obesity, inflammation, and cancer.

42. The pharmaceutical composition of claim 41 , wherein inflammation is chosen from Crohn's disease, rheumatoid arthritis, psoriasis, and inflammatory bowel disease.