3-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethinyl)-n-phenylbenzamide derivative, method for preparing same, and pharmaceutical composition containing same as active ingredient for prevention or treatment of cancer
The present invention relates to a 3-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-phenylbenzamide derivative, a method for preparing the same, and a pharmaceutical composition comprising the same as an active ingredient for preventing or treating cancer. The derivative can significantly inhibit the proliferation of cancer cells by inhibiting kinases, particularly Bcr-Abl kinase or Bcr-Abl (T315I) kinase. Therefore, the derivative can be effectively used as a pharmaceutical composition for the prevention or treatment of cancer.
1 . A compound represented by formula 1, a solvate thereof or a pharmaceutically acceptable salt thereof:
in formula 1,
R 1 is hydrogen or C 1-10 alkyl;
X is halogen;
R 2 is
where, R 2a , R 2b and R 2c are independently hydrogen, halogen, cyano or C 1-10 alkyl;
L 1 is single bond, —O— or C 1-10 alkylene;
R 3 is 5-8 membered nonsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, 4-8 membered nonsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, O and S, nonsubstituted or substituted C 1-10 alkyl or NR 3a R 3b , wherein, R 3a and R 3b are independently hydrogen or nonsubstituted or substituted C 1-10 alkyl,
wherein, the substituted heteroaryl, substituted heterocycloalkyl and substituted alkyl are substituted with one or more substituents selected from the group consisting of C 1-10 alkyl nonsubstituted or substituted with one or more halogens, C 1-10 hydroxyalkyl, C 1-10 alkylsulfonyl, C 1-10 alkoxy, oxo, NR 3c R 3d and heterocycloalkyl substituted with 5-8 membered C 1-10 alkyl containing one or more heteroatoms selected from the group consisting of N, O and S, wherein, R 3c and R 3d are independently hydrogen or C 1-10 alkyl.
2 . The compound, the solvate thereof or the pharmaceutically acceptable salt thereof according to claim 1 , wherein:
R 1 is hydrogen or C 1-6 alkyl;
X is halogen;
R 2 is
where, R 2a , R 2b and R 2c are independently hydrogen, halogen, cyano or C 1-6 alkyl;
L 1 is single bond, —O— or C 1-6 alkylene;
R 3 is 5-6 membered nonsubstituted or substituted heteroaryl containing one or more heteroatoms selected from the group consisting of N and O, 4-7 membered nonsubstituted or substituted heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N and O, nonsubstituted or substituted C 1-6 alkyl or NR 3a R 3b , wherein, R 3a and R 3b are independently hydrogen or nonsubstituted or substituted C 1-6 alkyl,
wherein, the substituted heteroaryl, substituted heterocycloalkyl and substituted alkyl are substituted with one or more substituents selected from the group consisting of C 1-6 alkyl nonsubstituted or substituted with one or more halogens, C 1-6 hydroxyalkyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, oxo, NR 3c R 3d and heterocycloalkyl substituted with 5-6 membered C 1-6 alkyl containing one or more heteroatoms selected from the group consisting of N and O, wherein, R 3c and R 3d are independently hydrogen or C 1-6 alkyl.
3 . The compound, the solvate thereof or the pharmaceutically acceptable salt thereof according to claim 1 , wherein:
R 1 is hydrogen or methyl;
X is fluorine or chlorine;
R 2 is
where, R 2a , R 2b and R 2c are independently fluorine, cyano or methyl;
L 1 is single bond, —O— or methylene;
R 3 is nonsubstituted or substituted imidazolyl, pyridinyl, pyrimidinyl, substituted piperazinyl, substituted pyrazolyl, substituted diazepanyl, substituted piperidinyl, morpholinyl, substituted pyrrolidinyl, substituted azetidinyl, triazolyl, substituted ethyl, substituted propyl or NR 3a R 3b , wherein R 3a and R 3b are independently methyl, substituted ethyl or substituted propyl,
wherein the substituted imidazolyl, substituted piperazinyl, substituted pyrazolyl, substituted diazepanyl, substituted piperidinyl, substituted pyrrolidinyl, substituted azetidinyl, substituted ethyl and substituted propyl are substituted with one or more substituents selected from the group consisting of methyl, CF 3 , CH 2 CF 3 , isopropyl, methylsulfonyl, isopropylalkoxy, hydroxyethyl, piperazine substituted with methyl, piperidine substituted with methyl, oxo and NR 3c R 3d , wherein, R 3c and R 3d can be methyl.
4 . The compound of claim 1 , wherein the compound represented by formula 1 is a compound represented by formula 2, a solvate thereof or a pharmaceutically acceptable salt thereof:
5 . The compound, the solvate thereof or the pharmaceutically acceptable salt thereof according to claim 1 , wherein:
R 1 is hydrogen or methyl;
X is fluorine or chlorine;
R 2 is
L 1 -R 3 is
6 . The compound, the solvate thereof or the pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of the following compounds:
1) N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
2) 3-fluoro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
3) N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-2-fluoro-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
4) 2-fluoro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
5) 3-fluoro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
6) 2-fluoro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
7) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-4-yloxy)-5-(trifluoromethyl)phenyl)benzamide;
8) 3-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-4-yloxy)-5-(trifluoromethyl)phenyl)benzamide;
9) 2-fluoro-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-4-yloxy)-5-(trifluoromethyl)phenyl)benzamide;
10) N-(3-(2-cyanopropan-2-yl)-5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
11) N-(3-(2-cyanopropan-2-yl)-5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-3-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
12) N-(3-(2-cyanopropan-2-yl)-5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
13) 2-chloro-N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
14) 2-chloro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
15) 2-chloro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-4-yloxy)-5-(trifluoromethyl)phenyl)benzamide;
16) 2-chloro-N-(3-(2-cyanopropan-2-yl)-5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
17) N-(3-(2-cyanopropan-2-yl)-5-(pyridin-4-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
18) N-(3-(2-cyanopropan-2-yl)-5-(pyridin-3-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
19) N-(3-(2-cyanopropan-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
20) N-(3-(2-cyanopropan-2-yl)-5-(4-methylpiperazin-1-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
21) N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1,4-diazepan-1-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
22) N-(3-(2-cyanopropan-2-yl)-5-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
23) N-(3-(2-cyanopropan-2-yl)-5-((3-(dimethylamino)propyl)(methyl)amino)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
24) N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-3-oxopiperazin-1-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
25) N-(3-(2-cyanopropan-2-yl)-5-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
26) N-(3-(2-cyanopropan-2-yl)-5-(pyridin-4-yloxy)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
27) N-(3-(2-cyanopropan-2-yl)-5-((4-methylpiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
28) N-(3-(2-cyanopropan-2-yl)-5-(morpholinomethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
29) N-(3-(2-cyanopropan-2-yl)-5-((3-(dimethylamino)pyrrolidin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
30) N-(3-(2-cyanopropan-2-yl)-5-((4-methyl-1,4-diazepan-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
31) N-(3-(2-cyanopropan-2-yl)-5-((4-(trifluoromethyl)piperidin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
32) N-(3-(2-cyanopropan-2-yl)-5-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
33) N-(3-(2-cyanopropan-2-yl)-5-((4-isopropylpiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
34) N-(3-(2-cyanopropan-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
35) N-(3-(2-cyanopropan-2-yl)-5-((4-methyl-3-oxopiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
36) N-(3-(2-cyanopropan-2-yl)-5-((3-isopropoxyazetidin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
37) N-(3-((1H-imidazol-1-yl)methyl)-5-(2-cyanopropan-2-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
38) N-(3-((1H-1,2,4-triazol-1-yl)methyl)-5-(2-cyanopropan-2-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
39) N-(3-(2-cyanopropan-2-yl)-4-((4-methylpiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
40) N-(3-(2-cyanopropan-2-yl)-4-(morpholinomethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
41) N-(3-(2-cyanopropan-2-yl)-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
42) N-(3-(2-cyanopropan-2-yl)-4-((4-methyl-1,4-diazepan-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
43) N-(3-(2-cyanopropan-2-yl)-4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
44) N-(3-(2-cyanopropan-2-yl)-4-((4-methyl-3-oxopiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
45) N-(3-(2-cyanopropan-2-yl)-4-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
46) N-(4-((1H-imidazol-1-yl)methyl)-3-(2-cyanopropan-2-yl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
47) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
48) N-(3-((2-(dimethylamino)ethyl)(methyl)amino)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
49) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(4-methyl-3-oxopiperazin-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
50) N-(3-(2-(dimethylamino)ethoxy)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
51) N-(3-(3-(dimethylamino)propoxy)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
52) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)benzamide;
53) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(pyridin-3-yl)-5-(trifluoromethyl)phenyl)benzamide;
54) 2-fluoro-4-methyl-N-(3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
55) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
56) 2-fluoro-N-(4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
57) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-(morpholinomethyl)-3-(trifluoromethyl)phenyl)benzamide;
58) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-methyl-3-oxopiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
59) N-(4-((3-(dimethylamino)pyrrolidine-1-yl)methyl)-3-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
60) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
61) 2-fluoro-4-methyl-N-(4-((4-methyl-1,4-diazepan-1-yl)methyl)-3-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
62) 2-fluoro-N-(4-((3-isopropoxyazetidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
63) N-(4-((1H-imidazol-1-yl)methyl)-3-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
64) N-(4-((1H-1,2,4-triazol-1-yl)methyl)-3-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
65) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-(pyridin-4-yloxy)-3-(trifluoromethyl)phenyl)benzamide;
66) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(morpholinomethyl)-5-(trifluoromethyl)phenyl)benzamide;
67) 2-fluoro-4-methyl-N-(3-((4-methyl-1,4-diazepan-1-yl)methyl)-5-(trifluoromethyl)phenyl)-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
68) N-(3-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
69) 2-fluoro-N-(3-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
70) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide;
71) 2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-((4-methyl-3-oxopiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide;
72) 2-fluoro-N-(3-((3-isopropoxyazetidin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
73) N-(3-((1H-imidazol-1-yl)methyl)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
74) N-(3-((1H-1,2,4-triazol-1-yl)methyl)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methyl-5-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
75) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-2-fluoro-4-methylbenzamide;
76) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-chloro-N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methylbenzamide;
77) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)phenyl)-2-fluoro-4-methylbenzamide;
78) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(pyridin-4-yl)phenyl)-2-fluoro-4-methylbenzamide;
79) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(pyridin-3-yl)phenyl)-2-fluoro-4-methylbenzamide;
80) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(4-methylpiperazin-1-yl)phenyl)-2-fluoro-4-methylbenzamide;
81) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)-2-fluoro-4-methylbenzamide;
82) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(4-methyl-3-oxopiperazin-1-yl)phenyl)-2-fluoro-4-methylbenzamide;
83) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-(pyridin-4-yloxy)phenyl)-2-fluoro-4-methylbenzamide;
84) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((4-methylpiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
85) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((3-(dimethylamino)pyrrolidin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
86) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
87) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
88) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-5-((4-methyl-3-oxopiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
89) N-(3-((1H-1,2,4-triazol-1-yl)methyl)-5-(2-cyanopropan-2-yl)phenyl)-5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methylbenzamide;
90) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-4-((4-methylpiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
91) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
92) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
93) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-4-((4-methyl-3-oxopiperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
94) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-cyanopropan-2-yl)-4-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)-2-fluoro-4-methylbenzamide;
95) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
96) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)benzamide;
97) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(pyridin-4-yl)-5-(trifluoromethyl)phenyl)benzamide;
98) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(pyridin-3-yl)-5-(trifluoromethyl)phenyl)benzamide;
99) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
100) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(4-methyl-3-oxopiperazin-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
101) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-(pyridin-4-yloxy)-5-(trifluoromethyl)phenyl)benzamide;
102) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(2-(dimethylamino)ethoxy)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methylbenzamide;
103) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(3-(dimethylamino)propoxy)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methylbenzamide;
104) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-((4-methylpiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide;
105) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-2-fluoro-4-methylbenzamide;
106) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-N-(3-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)-4-methylbenzamide;
107) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(3-((4-methyl-3-oxopiperazin-1-yl)methyl)-5-(trifluoromethyl)phenyl)benzamide;
108) N-(3-((1H-1,2,4-triazol-1-yl)methyl)-5-(trifluoromethyl)phenyl)-5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methylbenzamide;
109) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
110) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-2-fluoro-4-methylbenzamide;
111) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-N-(4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
112) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(4-((4-methyl-3-oxopiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
113) 5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methyl-N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
114) N-(4-((1H-1,2,4-triazol-1-yl)methyl)-3-(trifluoromethyl)phenyl)-5-((8-((1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-2-fluoro-4-methylbenzamide.
7 . A method for preparing the compound represented by formula 1 of claim 1 , comprising a step of preparing a compound represented by formula 1 by reacting a compound represented by formula 2 with a compound represented by formula 3, as shown in reaction formula 1:
8 . A pharmaceutical composition containing an effective amount of the compound represented by formula 1 of claim 1 , a solvate thereof or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient.
9 . A method of treating cancer comprising administering the compound represented by formula 1 of claim 1 , a solvate thereof or a pharmaceutically acceptable salt thereof as an active ingredient to a subject in need thereof,
wherein the cancer is liver cancer, prostate cancer, rhabdomyosarcoma, colon cancer, non-small cell lung cancer or colorectal cancer.
10 . A method of treating leukemia, comprising administering the compound represented by formula 1 of claim 1 , a solvate thereof or a pharmaceutically acceptable salt thereof as an active ingredient to a subject in need thereof,
wherein the leukemia is acute myeloid leukemia, acute lymphocytic leukemia, chronic myelogenous leukemia or chronic lymphocytic leukemia.