# US 10,870,647 B2 · Imidazopyridine derivative, method for preparing same, and pharmaceutical composition containing same as active ingredient for preventing or treating cancer

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,870,647 B2
- Document ID: US10870647B2
- Status: Granted
- Kind: B2
- Application number: 16/311,654
- Filed: 2017-06-20
- Published: 2019-10-17
- Granted: 2020-12-22
- Earliest claimed: 2016-06-20
- Assignees: Daegu-Gyeongbuk Medical Innovation Foundation
- Applicants: Daegu-Gyeongbuk Medical Innovation Foundation
- Inventors: Hwan Geun Choi; Jung Beom Son; Shinae Kim; Seungyeon Lee; Eunhwa Ko; Joongheui Cho; Seock Yong Kang; So Young Kim; Jin-Hee Park; Yi Kyung Ko; Hee Yoon Ryu; Nam Doo Kim; Hyunkyoung Kim; Younho Lee; Sun-Hwa Lee; Dayea Kim; Sun Joo Lee; Seongho Hong; Sang Hyun Min; Sungwoo Lee; Dong Kyu Choi; Jae Hyun Bae; Eunmi Hong; Tae-Ho Jang; Jaeyoung Song; Sangbum Kim; Suk Kyoon Yoon
- Web page: https://patentgrep.com/patent/US10870647B2

## CPC

- A61P 35/00: Antineoplastic agents
- C07D 471/04: Ortho-condensed systems
- A23L 29/045: {containing nitrogen as heteroatom}
- A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21)
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)

## Abstract

The present invention relates to a novel imidazopyridine derivative, a method for preparing the same, and a pharmaceutical composition containing the same as an active ingredient for preventing or treating cancer. The novel imidazopyridine derivative according to the present invention, a stereoisomer thereof and a pharmaceutically acceptable salt thereof can effectively inhibit cancer-related kinases, are excellent in inhibiting proliferation of cancer cells in a cancer cell line, and effectively inhibit proliferation of cancer cells (cancer cell apoptosis) in a cancer cell heterograft model, and thus can be useful as a pharmaceutical composition containing the same as an active ingredient for preventing or treating cancer. Also, the novel imidazopyridine derivative according to the present invention, the stereoisomer thereof, and the pharmaceutically acceptable salt thereof can effectively inhibit Src and Fyn, thereby being useful as a pharmaceutical composition for preventing or treating the Src and Fyn related diseases, and in particular, have been confirmed to be useful in diabetic nephropathy in animal model experiments. Therefore, the compound of the present invention can be effective as a pharmaceutical composition containing the same as an active ingredient for preventing or treating diabetic nephropathy.

## Claims

### Claim 1

A compound represented by formula 1, an optical isomer thereof or a pharmaceutically acceptable salt thereof:
in formula 1,
V is hydrogen, halogen, or methyl;
X is —NHR1;
R1 is nonsubstituted or substituted 5 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S,
wherein, the substituted 5 membered heteroaryl can be substituted with nonsubstituted C1-10 straight or branched alkyl;
C1-10 straight or branched alkyl substituted with one or more substituents selected from the group consisting of halogen, methoxy and dimethylamino;
halogen;
amino; or
5-6 membered heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, O and S, or
the substituted 5 membered heteroaryl is fused with a 5-6 membered ring containing one or more heteroatoms selected from the group consisting of N, O and S to form a fused ring;
Y is —(C═O)NHR2, —NH(C═O)R2, —NH(C═O)NHR2 or
R2 is nonsubstituted or substituted C6-10 aryl or nonsubstituted or substituted 5-10 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S,
wherein, the substituted C6-10 aryl or the substituted 5-10 membered heteroaryl can be substituted with one or more substituents selected from the group consisting of
halogen;
—CH2—R3;
nonsubstituted C1-10 straight or branched alkyl or C1-10 straight or branched alkyl substituted with halogen;
nonsubstituted C1-2 alkoxy or C1-2 alkoxy substituted with halogen;
nonsubstituted C6-10 cycloalkyl or C6-10 cycloalkyl substituted with halogen;
substituted or nonsubstituted 5-10 membered heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, O and S;
nonsubstituted or substituted 5-10 membered heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S; or
nonsubstituted or substituted amino,
wherein, the substituted heteroaryl, the substituted heterocycloalkyl, and the substituted amino can be substituted with substituted or nonsubstituted C1-3 straight or branched alkyl,
wherein, the substituted C1-3 straight or branched alkyl can be substituted with dimethyl amino; and
R3 is 5-10 membered heterocycloalkyl containing one or more heteroatoms selected from the group consisting of N, O and S,
wherein, the 5-10 membered heterocycloalkyl can be nonsubstituted 5-10 membered heterocycloalkyl or 5-10 membered heterocycloalkyl substituted with one or more substituents selected from the group consisting of methyl, ethyl, dimethyl amino, and halogen.

### Claim 2 (depends on 1)

The compound represented by formula 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof according to claim 1, wherein the R1 is oxazolyl or pyrazolyl.

### Claim 3 (depends on 1)

The compound represented by formula 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof according to claim 1, wherein the X is

### Claim 4

A compound, the optical isomer thereof, or the pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:
(1) 4-methyl-3-((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;
(2) N-(2-fluorophenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(3) N-(3,5-dimethoxyphenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(4) N-(3-fluoro-4-methoxyphenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(6) N-(3-fluorophenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(7) N-(4-chlorophenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(8) N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(9) 4-methyl-3-((8-((1-methyl-1H-pyrazol-3-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(10) N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-3-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(11) 4-methyl-3-((8-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(trifluoromethyl)phenyl)benzamide;
(12) 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;
(13) 4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(trifluoromethyl)phenyl)benzamide;
(14) 3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(22) 3-((8-((1-ethyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(23) 3-((8-((1-ethyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(26) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(27) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide;
(28) 4-methyl-3-((8-((5-methylisoxazol-3-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(29) (R)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(30) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(31) (R)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(32) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(33) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(34) (R)-3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(35) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(36) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(37) N-(benzo[d]thiazol-6-yl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(38) 3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methyl-1,4-diazepin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(39) 3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methyl-1,4-diazepin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(40) (R)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(41) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(42) (R)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(3-methoxypropyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(43) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(3-methoxypropyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(44) (S)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(45) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((5-methylisoxazol-3-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(46) (S)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(3-methoxypropyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(47) (S)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(48) (S)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(49) (S)-3-((8-((1-(3-(dimethylamino)propyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(50) (R)—N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(51) (S)—N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(52) N-(4-((4,4-difluoropiperidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(53) (R)—N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-ethyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(54) (S)—N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-ethyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(55) N-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(56) 3-((8-((1-ethyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-fluoro-4-morpholinophenyl)-4-methylbenzamide;
(57) 3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(58) 3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)benzamide;
(59) N-(5-(tert-butyl)isoxazol-3-yl)-3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(60) 3-((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;
(61) 4-fluoro-3-((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;
(62) N-(4-chloro-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]ethynyl)benzamide;
(63) N-(4-chloro-3-(trifluoromethyl)phenyl)-4-methyl-3-((8-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(65) 3-((8-(1-(3-methoxypropyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide;
(66) 4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(67) 4-methyl-3-((8-((4,5,6,7-tetrahydropyrazolo[1, 5-a]pyrazin-2-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-N-(3-(trifluoromethyl)phenyl)benzamide;
(68) N-(5-(tert-butyl)isoxazol-3-yl)-4-methyl-3-((8-((4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(69) N-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(70) 3-((8-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-((trifluoromethyl)phenyl)benzamide;
(71) 3-((8-(1-(2-methoxyethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methyl-N-((4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
(72) 4-methyl-3-((8-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)-N-(3-(trifluoromethyl)phenyl)benzamide;
(73) 3-((8-(2-(dimethylamino)ethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)-ethynyl)-N-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-4-methylbenzamide;
(74) 3-((8-(2-(dimethylamino)ethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl) N-(3-(trifluoromethyl)phenyl)benzamide;
(75) 3-((8-(2-(dimethylamino)ethyl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl) N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide;
(76) (3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-((8-((1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)benzamide;
(77) N-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide;
(78) N-(4-fluorophenyl)-N-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)cyclopropan-1,1-dicarboxamide;
(79) N-(4-fluorophenyl)-N-(4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)phenyl)cyclopropan-1,1-dicarboxamide;
(80) N-(4-methyl-3-((8-((1-methyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)phenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide;
(81) (R)—N-(4-((3,4-dimethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylbenzamide;
(82) 1-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)-3-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)urea;
(83) 1-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)-3-(3-(trifluoromethyl)phenyl)urea;
(84) 1-(5-(tert-butyl)isoxazol-3-yl)-3-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)urea; and
(85) 1-(3-((8-((1-isopropyl-1H-pyrazol-4-yl)amino)imidazo[1,2-a]pyridin-3-yl)ethynyl)-4-methylphenyl)-3-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)urea.

### Claim 5 (depends on 1)

A preparation method of the compound represented by formula 1 of claim 1 comprising, as shown in reaction formula 1 below:
preparing the compound represented by formula 4 by reacting the compound represented by formula 2 with the compound represented by formula 3 (step 1);
preparing the compound represented by formula 6 by reacting the compound represented by formula 4 prepared in step 1 above with the compound represented by formula 5 (step 2);
preparing the compound represented by formula 7 from the compound represented by formula 6 prepared in step 2 above (step 3); and
preparing the compound represented by formula 1 by reacting the compound represented by formula 7 prepared in step 3 above with the compound represented by formula 8 (step 4);
wherein
V, X and Y are as defined in formula 1 of claim 1; and
Z′ is —NH2 when Z is —NO2 and Z′ is
when Z is

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the compound represented by formula 1 of claim 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for the prevention or treatment of cancer.

### Claim 7 (depends on 6)

The pharmaceutical composition according to claim 6, wherein the compound inhibits Rearranged during transfection (Ret), ABL1(E255K)-phosphorylated, ABL1(F317I)-nonphosphorylated, ABL1(F317I)-phosphorylated, ABL1(F317L)-nonphosphorylated, ABL1(F317L)-phosphorylated, ABL1(H396P)-nonphosphorylated, ABL1(H396P)-phosphorylated, ABL1(M351T)-phosphorylated, ABL1(Q252H)-nonphosphorylated, ABL1(Q252H)-phosphorylated, ABL1(T315I)-nonphosphorylated, ABL1(T315I)-phosphorylated, ABL1(Y253F)-phosphorylated, ABL1-nonphosphorylated, ABL1-phosphorylated, ABL2, ALK(L1196M), AMPK-alpha1, AMPK-alpha2, ANKK1, AURKB, AURKC, AXL, BLK, BMX, BRAF, BRAF(V600E), BRK, BTK, CAMK1, CAMKK1, CAMKK2, CDC2L1, CDCl2L2, CDC2L5, CDK11, CDK2, CDK5, CDK7, CDK8, CDKL1, CDKL2, CDKL3, CHEK2, CIT, CLK1, CLK4, CSF1R, CSK, CTK, DDR1, DDR2, DLK, EGFR, EGFR(E746-A750del), EGFR(G719C), EGFR(G719S), EGFR(L747-E749del, A750P), EGFR(L747-S752del, P753S), EGFR(L747-T751del,Sins), EGFR(L858R), EGFR(L858R,T790M), EGFR(L861Q), EGFR(S752-I759del), EGFR(T790M), EPHA1, EPHA2, EPHA3, EPHA4, EPHA5, EPHA6, EPHA7, EPHA8, EPHB1, EPHB2, EPHB4, EPHB6, ERBB2, ERBB4, ERK8, FAK, FER, FES, FGFR1, FGFR2, FGFR3, FGFR3(G697C), FGFR4, FGR, FLT1, FLT3, FLT3(D835H), FLT3(D835V), FLT3(D835Y), FLT3(ITD), FLT3(ITD,D835V), FLT3(ITD,F691L), FLT3(K663Q), FLT3(N841I), FLT3(R834Q), FLT4, FRK, FYN, GAK, GCN2(Kin.Dom.2,S808G), HCK, HIPK4, HPK1, IKK-alpha, IKK-beta, IRAK1, IRAK4, ITK, JAK1(JH1domain-catalytic), JAK2(JH1domain-catalytic), JAK3(JH1domain-catalytic), JNK1, JNK2, JNK3, KIT, KIT(A829P), KIT(D816H), KIT(D816V), KIT(L576P), KIT(V559D), KIT(V559D,T670I), KIT(V559D,V654A), LCK, LIMK1, LIMK2, LOK, LRRK2, LRRK2(G2019S), LTK, LYN, MAK, MAP3K2, MAP3K3, MAP4K2, MAP4K3, MAP4K4, MAP4K5, MEK5, MELK, MERTK, MET, MET(M1250T), MINK, MKNK2, MLK1, MLK2, MLK3, MST1, MST1R, MST2, MUSK, MYLK2, MYO3A, MYO3B, NDR2, NEK1, NEK11, NEK4, NEKS, NEK9, NLK, p38-alpha, p38-beta, p38-delta, p38-gamma, PCTK2, PDGFRA, PDGFRB, PFCDPK1(P.falciparum), PFTAIRE2, PFTK1, PKAC-alpha, PKAC-beta, PYK2, RAF1, RET, RET(M918T), RET(V804L), RET(V804M), RIPK1, RIPK2, RIPK4, ROCK2, RPS6KA4(Kin.Dom.1-N-terminal), RSK2(Kin.Dom.1-N-terminal), RSK3(Kin.DoN-terminal), S6K1, SIK, SLK, SRC, SRMS, SRPK1, STK33, STK35, STK36, SYK, TAK1, TAOK2, TAOK3, TEC, TESK1, TGFBR2, TIE1, TIE2, TNIK, TNK1, TNK2, TNNI3K, TRKA, TRKB, TRKC, TTK, TXK, TYK2(JH1domain-catalytic), TYRO3, ULK3, VEGFR2, YES, YSK4, ZAK, ZAP70 or fibroblast growth factor receptor (FGFR) to prevent or treat cancer.

### Claim 8 (depends on 6)

The pharmaceutical composition according to claim 6, wherein the cancer is at least one selected from the group consisting of pseudomyxoma, intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, lip cancer, mycosis fungoides, acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, ovarian epithelial cancer, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, biliary cancer, colon cancer, chronic myelogenous leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, diffuse large B cell lymphoma, ampulla of Vater cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal gland cancer, sinunasal cancer, non-small cell lung cancer, non-Hodgkin's lymphoma, tongue cancer, astrocytoma, small cell lung cancer, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small bowel cancer, meningioma, esophagus cancer, glioma, neuroblastoma, renal cancer, kidney cancer, heart cancer, duodenal cancer, malignant soft tissue tumor, malignant bone cancer, malignant lymphoma, malignant mesothelioma, malignant melanoma, eye cancer, vulvar cancer, ureteral cancer, urethral cancer, cancer of unknown primary site, gastric lymphoma, gastric cancer, gastric carcinoid, gastrointestinal stromal cancer, Wilms' tumor, breast cancer, sarcoma, penile cancer, pharyngeal cancer, getstational trophoblatic disease, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid, vaginal cancer, spinal cord cancer, vestibular schwannoma, pancreatic cancer, salivary gland cancer, Kaposi's sarcoma, Paget's disease, tonsil cancer, squamous cell carcinoma, adenocarcinoma of lung, lung cancer, squamos cell carcinoma of lung, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, and thymus cancer.

### Claim 9 (depends on 1)

A health functional food composition comprising the compound represented by formula 1 of claim 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for preventing or ameliorating cancer.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the compound represented by formula 1 of claim 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for the prevention or treatment of diabetic nephropathy.

### Claim 11 (depends on 10)

The pharmaceutical composition according to claim 10, wherein the compound inhibits SRC or Fyn to prevent or treat diabetic nephropathy.

### Claim 12 (depends on 10)

The pharmaceutical composition according to claim 10, wherein the compound of the pharmaceutical composition is used for the prevention and/or treatment of diabetic microalbuminuria characterized by decreasing albuminuria in the early microalbuminuria stage of diabetic nephropathy and reducing the ratio of albumin-creatinine.

### Claim 13 (depends on 1)

A health functional food composition comprising the compound represented by formula 1 of claim 1, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for preventing or ameliorating diabetic nephropathy.

### Claim 14 (depends on 4)

A pharmaceutical composition comprising the compound of claim 4, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for the prevention or treatment of cancer.

### Claim 15 (depends on 14)

The pharmaceutical composition according to claim 14, wherein the compound inhibits Rearranged during transfection (Ret), ABL1 (E255K)-phosphorylated, ABL1 (F317I)-nonphosphorylated, ABL1 (F317I)-phosphorylated, ABL1 (F317L)-nonphosphorylated, ABL1 (F317L)-phosphorylated, ABL1 (H396P)-nonphosphorylated, ABL1 (H396P)-phosphorylated, ABL1 (M351T)-phosphorylated, ABL1 (Q252H)-nonphosphorylated, ABL1 (Q252H)-phosphorylated, ABL1 (T315I)-nonphosphorylated, ABL1 (T315I)-phosphorylated, ABL1 (Y253F)-phosphorylated, ABL1-nonphosphorylated, ABL1-phosphorylated, ABL2, ALK (L1196M), AMPK-alpha1, AMPK-alpha2, ANKK1, AURKB, AURKC, AXL, BLK, BMX, BRAF, BRAF (V600E), BRK, BTK, CAMK1, CAMKK1, CAMKK2, CDC2L1, CDC2L2, CDC2L5, CDK11, CDK2, CDK5, CDK7, CDK8, CDKL1, CDKL2, CDKL3, CHEK2, CIT, CLK1, CLK4, CSF1R, CSK, CTK, DDR1, DDR2, DLK, EGFR, EGFR (E746-A750del), EGFR (G719C), EGFR (G719S), EGFR (L747-E749del, A750P), EGFR (L747-S752del, P753S), EGFR (L747-T751del, Sins), EGFR (L858R), EGFR (L858R,T790M), EGFR (L861Q), EGFR(S752-I759del), EGFR (T790M), EPHA1, EPHA2, EPHA3, EPHA4, EPHA5, EPHA6, EPHA7, EPHA8, EPHB1, EPHB2, EPHB4, EPHB6, ERBB2, ERBB4, ERK8, FAK, FER, FES, FGFR1, FGFR2, FGFR3, FGFR3 (G697C), FGFR4, FGR, FLT1, FLT3, FLT3 (D835H), FLT3 (D835V), FLT3 (D835Y), FLT3 (ITD), FLT3 (ITD,D835V), FLT3 (ITD,F691L), FLT3 (K663Q), FLT3 (N841I), FLT3 (R834Q), FLT4, FRK, FYN, GAK, GCN2 (Kin.Dom.2,S808G), HCK, HIPK4, HPK1, IKK-alpha, IKK-beta, IRAK1, IRAK4, ITK, JAK1 (JH1domain-catalytic), JAK2 (JH1domain-catalytic), JAK3 (JH1domain-catalytic), JNK1, JNK2, JNK3, KIT, KIT (A829P), KIT (D816H), KIT (D816V), KIT (L576P), KIT (V559D), KIT (V559D,T670I), KIT (V559D,V654A), LCK, LIMK1, LIMK2, LOK, LRRK2, LRRK2 (G2019S), LTK, LYN, MAK, MAP3K2, MAP3K3, MAP4K2, MAP4K3, MAP4K4, MAP4K5, MEK5, MELK, MERTK, MET, MET (M1250T), MINK, MKNK2, MLK1, MLK2, MLK3, MST1, MST1R, MST2, MUSK, MYLK2, MYO3A, MYO3B, NDR2, NEK1, NEK11, NEK4, NEK5, NEK9, NLK, p38-alpha, p38-beta, p38-delta, p38-gamma, PCTK2, PDGFRA, PDGFRB, PFCDPK1 (P. falciparum), PFTAIRE2, PFTK1, PKAC-alpha, PKAC-beta, PYK2, RAF1, RET, RET (M918T), RET (V804L), RET (V804M), RIPK1, RIPK2, RIPK4, ROCK2, RPS6KA4 (Kin.Dom.1-N-terminal), RSK2 (Kin.Dom.1-N-terminal), RSK3 (Kin.DoN-terminal), S6K1, SIK, SLK, SRC, SRMS, SRPK1, STK33, STK35, STK36, SYK, TAK1, TAOK2, GG:cms 06/22/20 {{2018FPO-12-003/US}}TAOK3, TEC, TESK1, TGFBR2, TIE1, TIE2, TNIK, TNK1, TNK2, TNNI3K, TRKA, TRKB, TRKC, TTK, TXK, TYK2 (JH1domain-catalytic), TYRO3, ULK3, VEGFR2, YES, YSK4, ZAK, and ZAP70 or fibroblast growth factor receptor (FGFR) to prevent or treat cancer.

### Claim 16 (depends on 14)

The pharmaceutical composition according to claim 14, wherein the cancer is at least one selected from the group consisting of pseudomyxoma, intrahepatic cholangiocarcinoma, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, lip cancer, mycosis fungoides, acute myelogenous leukemia, acute lymphocytic leukemia, basal cell carcinoma, ovarian epithelial cancer, ovarian germ cell carcinoma, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, biliary cancer, colon cancer, chronic myelogenous leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, diffuse large B cell lymphoma, ampulla of Vater cancer, bladder cancer, peritoneal cancer, parathyroid cancer, adrenal gland cancer, sinunasal cancer, non-small cell lung cancer, non-Hodgkin's lymphoma, tongue cancer, astrocytoma, small cell lung cancer, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small bowel cancer, meningioma, esophagus cancer, glioma, neuroblastoma, renal cancer, kidney cancer, heart cancer, duodenal cancer, malignant soft tissue tumor, malignant bone cancer, malignant lymphoma, malignant mesothelioma, malignant melanoma, eye cancer, vulvar cancer, ureteral cancer, urethral cancer, cancer of unknown primary site, gastric lymphoma, gastric cancer, gastric carcinoid, gastrointestinal stromal cancer, Wilms' tumor, breast cancer, sarcoma, penile cancer, pharyngeal cancer, getstational trophoblatic disease, cervical cancer, endometrial cancer, uterine sarcoma, prostate cancer, metastatic bone cancer, metastatic brain cancer, mediastinal cancer, rectal cancer, rectal carcinoid, vaginal cancer, spinal cord cancer, vestibular schwannoma, pancreatic cancer, salivary gland cancer, Kaposi's sarcoma, Paget's disease, tonsil cancer, squamous cell carcinoma, adenocarcinoma of lung, lung cancer, squamos cell carcinoma of lung, skin cancer, anal cancer, rhabdomyosarcoma, laryngeal cancer, pleural cancer, and thymus cancer.

### Claim 17 (depends on 4)

A health functional food composition comprising the compound of claim 4, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for preventing or ameliorating cancer.

### Claim 18 (depends on 4)

A pharmaceutical composition comprising the compound of claim 4, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for the prevention or treatment of diabetic nephropathy.

### Claim 19 (depends on 18)

The pharmaceutical composition according to claim 18, wherein the compound inhibits SRC or Fyn to prevent or treat diabetic nephropathy.

### Claim 20 (depends on 18)

The pharmaceutical composition according to claim 18, wherein the compound of the pharmaceutical composition is used for the prevention and/or treatment of diabetic microalbuminuria characterized by decreasing albuminuria in the early microalbuminuria stage of diabetic, nephropathy and reducing the ratio of albumin-creatinine.

### Claim 21 (depends on 4)

A health functional food composition comprising the compound of claim 4, the optical isomer thereof or the pharmaceutically acceptable salt thereof as an active ingredient for preventing or ameliorating diabetic nephropathy.