Novel heterocyclic compounds and pharmaceutical composition comprising the same

Abstract

The present disclosure relates to a novel heterocyclic compound represented by the Chemical Formula 1 and a pharmaceutical composition comprising the same, and the compound according to the present disclosure can be usefully used for the prevention or treatment of cancer. [Chemical Formula 1] in Chemical Formula 1, A, L1, R1, B, R2, R3, L2, R4, and R5 are as defined in the specification.

Description

[DESCRIPTION]

Invention Title

Technical Field

Background Art

Disclosure

Technical Problem

Technical Solution

Advantageous Effects

Best Mode

Claims

1. A compound represented by Chemical Formula 1 below, or a pharmaceutically acceptable salt thereof:[Chemical Formula 1]in Chemical Formula 1, A is a trivalent linker of C2-10 heteroaromatic ring containing one to three heteroatoms selected from N, O, or S; or pyridone,L1 is a bond; C1-4 alkylene; C2-4 alkenylene; C2-4 alkynylene; -S-; or -O-, R1 is hydrogen; C1-4 alkyl; -CONH2; -CONH(C1-4 alkyl); -CON(C1-4 alkyl)2; C2-10 heterocycloalkyl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl, or C1-4 haloalkyl; or C2-10 heteroaryl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl, or C1-4 haloalkyl,B is a bivalent linker of C6-10 aromatic ring; C2-10 heterocycloalkane ring containing one to three heteroatoms selected from N, O, or S; or C2-10 heteroaromatic ring containing one to three heteroatoms selected from N, O, or S,R2 and R3 are each independently, hydrogen; C1-4 alkyl; C2-4 alkenyl; C2-4 alkynyl; C1-4 haloalkyl; C1-4 alkoxy; halogen; cyano; or C2-6 heterocycloalkyloxy containing one oxygen; or R2 and R3 when on adjacent ring vertices, combine to form a C2-6 heterocycloalkyl containing one to three heteroatoms selected from N, O, or S ; or C2-6 heteroaryl containing one to three heteroatoms selected from N, O, or S, L2 is a bond; C1-4 alkylene; -CO-; -CONH-; -NHCO-; -S-; or -O-, R4 is -C≡C-R’; C6-10 aryl, which is unsubstituted or substituted by halogen, or C1-4 alkoxy; C3-6 cycloalkyl, which is unsubstituted or substituted by hydroxy; C2-10 heterocycloalkyl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl, C1-4 haloalkyl, or hydroxy; or C2-10 heteroaryl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by halogen, C1-4 alkyl, or C1-4 haloalkyl, R’ is hydrogen; C1-4 alkyl, which is unsubstituted or substituted by cyano; (C1-4 alkoxy)C1-4 alkyl; C1-4 hydroxyalkyl; C2-6 heterocycloalkyl containing one oxygen; C3-6 cycloalkyl, which is unsubstituted or substituted by one or two halogens; C6-10 aryl, which is unsubstituted or substituted by halogen; C2-10 heteroaryl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl; or C2-10 heterocycloalkyl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl, R5 is hydrogen; hydroxy; C1-4 alkyl; C3-6 cycloalkyl; or halogen,with the proviso that R4 is -C≡C-R’ when L2 is a bond.

2. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein A is a trivalent linker of 1,3-benzodioxole; 2,3-dihydrobenzofuran; 2-pyridone; imidazo[1,5-a]pyridine; imidazole; pyridazine; or pyridine.

3. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein L1 is a bond; -CH2-; -C≡C-; or -O-.

4. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R1 is hydrogen; CH3; -CONH2; -CONH(CH3); -CON(CH3)2; or any ring selected from the group consisting of 4,7-diazaspiro[2.5]octan-8-onyl, 7-azaspiro[3.5]nonan-6-onyl, 2-pyridonyl, oxadiazolyl, oxopyridazinyl, pyrazolyl, or thiazolyl, which ring is unsubstituted or substituted by CH3, or CF3.

5. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein B is a bivalent linker of 1,3-benzodioxole; 2-oxa-5-azabicyclo[4.1.0]heptane; 3,4-dihydro-2H-benzo[b][1,4]oxazine; 3-oxa-8-azabicyclo[3.2.1]octane; 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine; 4-oxa-7-azaspiro[2.5]octane; benzene; benzo[d]oxazole; benzo[d]thiazole; morpholine; piperazin-2-one; pyrazole; or pyridine.

6. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R2 and R3 are each independently, hydrogen; CH3; -C≡CH; CHF2; CF3; OCH3; F; Cl; cyano; or (oxetanyl)oxy.

7. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein L2 is a bond; -CH2-; -CO-; -CONH-; -NHCO-; -S-; or -O-.

8. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R4 is -C≡C-R’; R’ is hydrogen; methyl; ethyl, propyl; isopropyl; butyl; isobutyl; tert-butyl; -CH(CH3)(CN); -CH2-O-CH3; 2-hydroxyprop-2-yl; 1H-pyrrolo[2,3-b]pyridinyl, which is unsubstituted or substituted by CH3; oxetanyl; tetrahydrofuranyl; cyclopropyl, which is unsubstituted or substituted by one or two F; cyclobutyl, which is unsubstituted or substituted by one or two F; cyclopentyl, cyclohexyl; spiro[2.2]pentanyl; phenyl, which is unsubstituted or substituted by Cl; pyrazolyl, which is unsubstituted or substituted by CH3; or pyridinyl.

9. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R4 is phenyl, which is unsubstituted or substituted by Cl and OCH3; cyclohexyl, which is unsubstituted or substituted by hydroxy; hexahydrofuro[2,3-b]furanyl; bicyclo[2.2.2]octanyl, which is unsubstituted or substituted by hydroxy; 2,3-dihydrobenzofuranyl; 4-oxaspiro[2.4]heptanyl; tetrahydrofuranyl; 1,3-benzodioxolyl; or pyridinyl, which is unsubstituted or substituted by Cl.

10. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein R5 is hydrogen; hydroxy; CH3; cyclopropyl; or Cl.

11. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the Chemical Formula 1 is represented by Chemical Formula 2 below:[Chemical Formula 2]in Chemical Formula 2, X is N, or CH,R1 is C1-4 alkyl; or C2-10 heteroaryl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl, or C1-4 haloalkyl,R2 is C1-4 alkoxy,R3 is C1-4 haloalkyl; or halogen,R’ is hydrogen; C1-4 hydroxyalkyl; C2-6 heterocycloalkyl containing one oxygen; C3-6 cycloalkyl, which is unsubstituted or substituted by one or two halogens; or C2-10 heteroaryl containing one to three heteroatoms selected from N, O, or S, which is unsubstituted or substituted by C1-4 alkyl,R5 is hydrogen; hydroxy; C1-4 alkyl; C3-6 cycloalkyl; or halogen.

12. The compound or a pharmaceutically acceptable salt thereof according to claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of the following:1) 2'-chloro-N-(6-ethynylthiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,2) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,3) 2'-chloro-5'-methoxy-6-methyl-N-(6-((1-methyl-1H-pyrazol-4-yl)ethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,4) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-2'-(difluoromethyl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,5) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(5-(difluoromethyl)-2-methoxyphenyl)-6-methylnicotinamide,6) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-2'-(trifluoromethyl)-4,4'-bipyridine-3-carboxamide,7) 2'-chloro-N-(6-((3,3-difluorocyclobutyl)ethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,8) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(2-methoxy-5-(trifluoromethyl)phenyl)-6-(4-methyl-6-oxopyridazin-1(6H)-yl)nicotinamide,9) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(2-methoxy-5-(trifluoromethyl)phenyl)-6-(1-methyl-2-oxo-1,2-dihydropyridin-3-yl)nicotinamide,10) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(2-methoxy-5-(trifluoromethyl)phenyl)-6-(2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl)nicotinamide,11) 2'-chloro-N-(5-cyclopropyl-6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,12) 2'-chloro-N-(6-(cyclopropylethynyl)-5-methylthiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,13) 2'-chloro-5'-methoxy-6-methyl-N-(6-(oxetan-3-ylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,14) 2'-chloro-5'-methoxy-N-(6-(3-methoxyprop-1-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methyl-4,4'-bipyridine-3-carboxamide,15) 2'-chloro-5'-methoxy-6-methyl-N-(6-(pyridin-2-ylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,16) 2'-chloro-N-(6-((4-chlorophenyl)ethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,17) 2'-chloro-5'-methoxy-6-methyl-N-(6-(spiro[2.2]pentan-1-ylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,18) 2'-chloro-5'-methoxy-6-methyl-N-(6-((tetrahydrofuran-3-yl)ethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,19) 2'-chloro-5'-methoxy-6-methyl-N-(6-((1-methyl-1H-pyrrolo[2,3-b]pyridin-6-yl)ethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,20) 2'-chloro-N-(5-chloro-6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,21) 2'-chloro-N-(6-(cyclopropylethynyl)-5-hydroxythiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,22) 2'-chloro-5'-methoxy-6-methyl-N-(6-(tetrahydrofuran-3-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,23) 2'-chloro-N-(6-((5-chloropyridin-2-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,24) 2'-chloro-5'-methoxy-6-methyl-N-(6-((tetrahydrofuran-3-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,25) N-(6-(4-oxaspiro[2.4]heptan-6-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-2'-chloro-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,26) 2'-chloro-N-(6-(5-chloropyridin-2-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,27) 2'-chloro-N-(6-(4-chloro-3-methoxyphenoxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,28) 2-(2'-chloro-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamido)-N-(tetrahydrofuran-3-yl)thiazolo[4,5-b]pyrazine-6-carboxamide,29) 2'-chloro-5'-methoxy-6-methyl-N-(6-(tetrahydrofuran-3-carboxamido)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,30) 2'-chloro-5'-methoxy-6-methyl-N-(6-(morpholine-4-carbonyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,31) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(4-methyl-6-oxopyridazin-1(6H)-yl)-4,4'-bipyridine-3-carboxamide,32) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(5-(difluoromethyl)-2-methoxyphenyl)-6-(4-methyl-6-oxopyridazin-1(6H)-yl)nicotinamide,33) 2'-chloro-N-(6-(5-chloropyridin-2-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(4-methyl-6-oxopyridazin-1(6H)-yl)-4,4'-bipyridine-3-carboxamide,34) 2'-chloro-5'-methoxy-6-(4-methyl-6-oxopyridazin-1(6H)-yl)-N-(6-(tetrahydrofuran-3-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,35) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxamide,36) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(4-methyl-8-oxo-4,7-diazaspiro[2.5]octan-7-yl)-4,4'-bipyridine-3-carboxamide,37) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-2,3-dihydrobenzofuran-6-carboxamide,38) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-4-carboxamide,39) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(6-oxo-7-azaspiro[3.5]nonan-7-yl)-4,4'-bipyridine-3-carboxamide,40) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1-(5-methyl-1,3,4-oxadiazol-2-yl)-2-oxo-1,2-dihydropyridine-4-carboxamide,41) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)-2-oxo-1,2-dihydropyridine-4-carboxamide,42) 1-(2-amino-2-oxoethyl)-5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-2-oxo-1,2-dihydropyridine-4-carboxamide,43) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1-(2-(methylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridine-4-carboxamide,44) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1-(2-(dimethylamino)-2-oxoethyl)-2-oxo-1,2-dihydropyridine-4-carboxamide,45) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(thiazol-2-yloxy)-4,4'-bipyridine-3-carboxamide,46) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-(oxetan-3-ylethynyl)-4,4'-bipyridine-3-carboxamide,47) 2'-chloro-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-((1-methyl-1H-pyrazol-4-yl)ethynyl)-4,4'-bipyridine-3-carboxamide,48) 7-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)imidazo[1,5-a]pyridine-6-carboxamide,49) 1-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-1H-imidazole-5-carboxamide,50) 5-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)pyridazine-4-carboxamide,51) 6-(2-chloro-5-methoxypyridin-4-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)benzo[d][1,3]dioxole-5-carboxamide,52) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methyl-4-morpholinonicotinamide,53) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-2'-(difluoromethyl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,54) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-2'-(trifluoromethyl)-4,4'-bipyridine-3-carboxamide,55) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(5-(difluoromethyl)-2-methoxyphenyl)-6-methylnicotinamide,56) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(2-methoxy-5-(trifluoromethyl)phenyl)-6-methylnicotinamide,57) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(5-ethynyl-2-methoxyphenyl)-6-methylnicotinamide,58) 4-(5-cyano-2-methoxyphenyl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methylnicotinamide,59) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methyl-4-(2-(oxetan-3-yloxy)phenyl)nicotinamide,60) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)-6-methylnicotinamide,61) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(3,5-dimethyl-1H-pyrazol-4-yl)-6-methylnicotinamide,62) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(6,7-dihydropyrazolo[1,5-a]pyrimidin-4(5H)-yl)-6-methylnicotinamide,63) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methyl-4-(4-oxa-7-azaspiro[2.5]octan-7-yl)nicotinamide,64) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methyl-4-(2-methyl-3-oxopiperazin-1-yl)nicotinamide,65) 4-(2-oxa-5-azabicyclo[4.1.0]heptan-5-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methylnicotinamide,66) 4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methylnicotinamide,67) 4-(benzo[d]thiazol-7-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methylnicotinamide,68) 4-(benzo[d]oxazol-7-yl)-N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-6-methylnicotinamide,69) N-(6-(cyclopropylethynyl)thiazolo[4,5-b]pyrazin-2-yl)-4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-6-methylnicotinamide,70) 2'-chloro-5'-methoxy-6-methyl-N-(6-(prop-2-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,71) 2'-chloro-N-(6-(3-cyclopropylprop-2-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,72) 2'-chloro-5'-methoxy-6-methyl-N-(6-(3-(oxetan-3-yl)prop-2-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,73) 2'-chloro-5'-methoxy-6-methyl-N-(6-(3-(1-methyl-1H-pyrazol-4-yl)prop-2-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,74) 2'-chloro-N-(6-(3-cyanobut-1-ynyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,75) 2'-chloro-N-(5-chloro-6-((tetrahydrofuran-3-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,76) 2'-chloro-5'-methoxy-6-methyl-N-(5-methyl-6-((tetrahydrofuran-3-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,77) 2'-chloro-5'-methoxy-6-methyl-N-(5-methyl-6-(tetrahydrofuran-3-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,78) 2'-chloro-N-(6-((5-chloropyridin-2-yl)methyl)-5-methylthiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,79) 2'-chloro-N-(6-(5-chloropyridin-2-yloxy)-5-methylthiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,80) 2'-chloro-5'-methoxy-6-methyl-N-(6-(tetrahydrofuran-3-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,81) 2'-chloro-5'-methoxy-6-methyl-N-(5-methyl-6-(tetrahydrofuran-3-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-4,4'-bipyridine-3-carboxamide,82) 2'-chloro-N-(6-(5-chloropyridin-2-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,83) 2'-chloro-N-(6-(5-chloropyridin-2-ylthio)-5-methylthiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,84) 2'-chloro-N-(6-(4-hydroxycyclohexyloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,85) 2'-chloro-N-(6-(hexahydrofuro[2,3-b]furan-3-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,86) 2'-chloro-N-(6-(5-hydroxybicyclo[2.2.2]octan-2-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,87) N-(6-(benzo[d][1,3]dioxol-4-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-2'-chloro-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,88) 2'-chloro-N-(6-(2,3-dihydrobenzofuran-3-yloxy)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,89) 2'-chloro-N-(6-(4-chloro-3-methoxybenzyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,90) 2'-chloro-N-(6-((4-hydroxycyclohexyl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,91) N-(6-(4-oxaspiro[2.4]heptan-6-ylmethyl)thiazolo[4,5-b]pyrazin-2-yl)-2'-chloro-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,92) 2'-chloro-N-(6-((hexahydrofuro[2,3-b]furan-3-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,93) 2'-chloro-N-(6-((5-hydroxybicyclo[2.2.2]octan-2-yl)methyl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,94) 2'-chloro-N-(6-(4-chloro-3-methoxyphenylthio)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,95) 2'-chloro-N-(6-(4-hydroxycyclohexylthio)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,96) N-(6-(4-oxaspiro[2.4]heptan-6-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-2'-chloro-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,97) 2'-chloro-N-(6-(hexahydrofuro[2,3-b]furan-3-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide, 98) 2'-chloro-N-(6-(5-hydroxybicyclo[2.2.2]octan-2-ylthio)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-4,4'-bipyridine-3-carboxamide,99) 4-(2-chloro-5-methoxypyridin-4-yl)-N-[6-(cyclopentylethynyl)[1,3]thiazolo[4,5-b]pyrazin-2-yl]-6-methylpyridine-3-carboxamide,100) 4-(2-chloro-5-methoxypyridin-4-yl)-N-[6-(3,3-dimethylbut-1-ynyl)[1,3]thiazolo[4,5-b]pyrazin-2-yl]-6-methylpyridine-3-carboxamide,101) 2'-chloro-N-(6-(3-hydroxy-3-methylbut-1-yn-1-yl)thiazolo[4,5-b]pyrazin-2-yl)-5'-methoxy-6-methyl-[4,4'-bipyridine]-3-carboxamide, and102) 4-(2-chloro-5-methoxypyridin-4-yl)-N-[6-(cyclohexylethynyl)[1,3]thiazolo[4,5-b]pyrazin-2-yl]-6-methylpyridine-3-carboxamide.

13. A pharmaceutical composition for the prevention or treatment of cancer, comprising the compound of any one of claims 1 to 12, or a pharmaceutically acceptable salt thereof. 

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