Bicyclic heteroaryl derivatives having inhibitory activity for protein kinase

1. A bicyclic heteroaryl compound of formula (I), a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof:

wherein,

W is CH;

X is S;

Y is —(CH 2 ) 2 R 3 , —CHCR 2 R 3 , —CCR 3 , —C(O)OH, or —C(O)NR 2 R 3 ;

R 2 is H;

R 3 is selected from the group consisting of phenyl, 2-fluorophenyl, 2-hydroxyphenyl, 4-aminophenyl, 4-methoxyphenyl, 4-nitrophenyl, 2-(cyclopropylcarbamoyl)phenyl, 3-(cyclopropylcarbamoyl)phenyl, 4-(cyclopropylcarbamoyl)phenyl, 2,6-dimethylphenyl, 2-chloro-6-methylphenyl, 3,5-dimethoxyphenyl, 3-cyano-5-methoxyphenyl, 3-carbamoyl-5-methoxyphenyl, 4-chloro-3-fluorophenyl, 2,3-dichlorophenyl, 4-chloro-3-(trifluoromethyl)phenyl, 2-chloro-4-methylphenyl, 5-fluoro-2-methylphenyl, 5-fluoro-2-hydroxyphenyl, 2-methyl-5-nitrophenyl, 2-methyl-5-(cyclopropylcarbamoyl)phenyl, 2-methyl-5-(cyclopropylcarbonylamino)phenyl, 4-amino-3-fluorophenyl, 4-amino-2-methylphenyl, 4-amino-2-fluorophenyl, 2-chloro-3,5-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-bromo-3,5-dimethoxyphenyl, 5-chloro-2,4-dimethoxyphenyl, 2,6-dichloro-3,5-dimethoxyphenyl, 2,6-dichloro-3,5-dimethylphenyl, 2,6-difluoro-3,5-dimethoxyphenyl, 2,6-dichloro-3-hydroxy-5-methoxyphenyl, 2,6-dichloro-3,5-dihydroxyphenyl, 4-bromo-3,5-dimethoxyphenyl, 2,4,6-trichloro-3,5-dimethoxyphenyl, 4-bromo-2,6-dichloro-3,5-dimethoxyphenyl, 4-aminonaphthalen-1-yl, 2-chloropyridin-4-yl, 2,3-diaminopyridin-4-yl, 3-(cyclopropylcarbamoyl)cumarin-6-yl, 1H-pyrazol-4-yl, 6-methoxybenzofuran-4-yl, 6-methoxyquinolin-8-yl, 6-methylpyridin-3-yl, and benzo[d][1,3]dioxol-5-yl;

Z is H, halogen, C 1-6 alkyl, —OR 5 , —SR 5 , —S(O)R 5 , —S(O) 2 R 5 , —NR 4 C(O)NR 4 R 5 , —NR 4 C(S)NR 4 R 5 , —NR 4 S(O) 2 R 5 , 5-(4-ethylpiperazin-1-yl)pentylamino, 2,4-dimethoxybenzylamino, 4-(4-hydroxypiperidin-1-yl)phenylamino, 4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenylamino, 3-(4-ethylpiperazin-1-yl)phenylamino, 4-(4-ethylpiperazin-1-yl)phenylamino, 4-(4-propionylpiperazin-1-yl)phenylamino, 4-(4-(isopropylcarbamoyl)piperazin-1-yl)phenylamino, 4-(4-(ethoxycarbamoyl)piperazin-1-yl)phenylamino, 4-(4-ethylpiperazin-1-yl)-2-methoxyphenylamino, 4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methoxyphenylamino, 4-(4-ethylpiperazin-1-yl)-2-isopropoxyphenylamino, 4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-isopropoxyphenylamino, 4-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)phenylamino, 4-(4-(pyridin-2-yl)piperazin-1-yl)phenylamino, 4-((4-ethylpiperazin-1-yl)methyl)phenylamino, 4-(2-(4-ethylpiperazin-1-yl)-2-oxoethyl)phenylamino, 4-(2-(4-ethylpiperazin-1-yl)ethyl)phenylamino, 4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenylamino, 4-(1-benzylpiperidin-4-ylcarbamoyl)phenylamino, 4-(4-ethylpiperazine-1-carbonyl)phenylamino, 5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino, 5-((3-(4-ethylpiperazin-1-yl)propylamino)methyl)pyridin-2-ylamino, 5-((3-hydroxypyrrolidin-1-yl)methyl)pyridin-2-ylamino, 5-((4-methylpiperidin-1-yl)methyl)pyridin-2-ylamino, 5-((3-(trifluoromethyl)piperidin-1-yl)methyl)pyridin-2-ylamino, 5-((4-morpholinopiperidin-1-yl)methyl)pyridin-2-ylamino, 5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-ylamino, 5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)pyridin-2-ylamino, 5-((4-acetylpiperazin-1-yl)methyl)pyridin-2-ylamino, 5-(morpholinomethyl)pyridin-2-ylamino, 5-((3,5-dimethylmorpholino)methyl)pyridin-2-ylamino, 5-((1H-imidazol-1-yl)methyl)pyridin-2-ylamino, 5-(2-morpholino-2-oxoethyl)pyridin-2-ylamino, 5-((3-oxopiperazin-1-yl)methyl)pyridin-2-ylamino, 5-((2-methoxyethoxy)methyl)pyridin-2-ylamino, 4-(thiazolidin-3-ylmethyl)pyridin-2-ylamino, 5-(3-(4-ethylpiperazin-1-yl)propylcarbamoyl)pyridin-2-ylamino, 5-(morpholine-4-carbonyl)pyridin-2-ylamino, 6-(4-ethylpiperazin-1-yl)pyrimidin-4-ylamino, 6-(3-(4-ethylpiperazin-1-yl)propylamino)pyrimidin-4-ylamino, 6-(2-(dimethylamino)ethoxy)pyrimidin-4-ylamino, 6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino, 2-amino-5-(4-ethylpiperazin-1-yl)-6-fluoro-1H-benzo[d]imidazol-1-yl, 1-(4-methoxybenzyl)-1H-benzo[d]imidazol-2-ylamino, 3-(ethoxycarbonyl)thioureido, 4-((4-ethylpiperazin-1-yl)methyl)pyridin-2-ylamino, 4-(morpholinomethyl)pyridin-2-ylamino, 4-(piperidin-1-ylmethyl)pyridin-2-ylamino, 4-(4-ethylpiperazin-1yl)benzamido, amino, diethylamino, 2-hydroxyethylamino, cyclopropylamino, 2-(dimethylamino)ethylamino, 2-morpholinoethylamino, (hydroxycarbonyl)methylamino, (ethoxycarbonyl)methylamino, 2-(phenylamino)ethylamino, 3-(diethylamino)propylamino, 3-(1H-imidazol-1-yl)propylamino, 4-(diethylamino)butylamino, 4-(1H-imidazol-1-yl)butylamino, 5-(diethylamino)phenylamino, 5-(1H-imidazol-1-yl)phenylamino, piperidin-4-ylamino, 2,3,4-trifluorophenylamino, 3-chloro-4-fluorophenylamino, 3,4,5-trimethoxyphenylamino, 4-(dimethylamino)phenylamino, 4-morpholinophenylamino, 4-(piperazin-1-yl)phenylamino, 4-(4-methylpiperazin-1-ylamino)phenylamino, 4-(1H-imidazol-1-yl)phenylamino, 4-(piperidin-4-ylamino)phenylamino, 4-methoxyphenylamino, 4-(hydroxycarbonyl)phenylamino, 4-(2-hydroxyethyl)phenylamino, 4-(2-(diethylamino)ethoxy)phenylamino, pyridin-2-ylamino, pyridin-4-ylamino, 4-methylpyridin-2-ylamino, 5-methylpyridin-2-ylamino, 6-methylpyridin-3-ylamino, 5-chloropyridin-2-ylamino, 5-(2-(dimethylamino)acetamido)pyridin-2-ylamino, 5-(3-(diethylamino)propoxy)pyridin-2-ylamino, 4-(((2-hydroxyethyl)(methyl)amino)methyl)pyridin-2-ylamino, 4-((diethylamino)methyl)pyridin-2-ylamino, 4-((2-(diethylamino)ethylamino)methyl)pyridin-2-ylamino, 5-((diethylamino)methyl)pyridin-2-ylamino, 6-((diethylamino)methyl)pyridin-2-ylamino, 5-((3-(diethylamino)propylamino)methyl)pyridin-2-ylamino, 5-((2-(diethylamino)ethoxy)methyl)pyridin-2-ylamino, 5-((2-(piperidin-1-yl)ethoxy)methyl)pyridin-2-ylamino, 5-((3-(diethylamino)propoxy)methyl)pyridin-2-ylamino, 4-(diethylamino)pyridin-2-ylamino, 4-((2-(diethylamino)ethoxy)methyl)pyridin-2-ylamino, 4-(3-(diethylamino)propoxy)pyridin-2-ylamino, 4-(2-(diethylamino)-2-oxoethyl)pyridin-2-ylamino, 5-carbamoylpyridin-2-ylamino, 5-(3-(diethylamino)propylcarbamoyl)pyridin-2-ylamino, 5-(4-methylpiperazin-1-ylcarbamoyl)pyridin-2-ylamino, 6-(2-morpholinoethylamino)pyrimidin-4-ylamino, 6-(3-(diethylamino)propylamino)pyrimidin-4-ylamino, 4-methyl-6-(2-morpholinoethylamino)pyrimidine-2-ylamino, 5-nitrothiazol-2-ylamino, 2-amino-1H-benzo[d]imidazol-1-yl, 6-methylbenzo[d]thiazol-2-ylamino, 1H-indazol-6-ylamino, 5-methyl-1H-pyrazol-3-ylamino, 3-ethoxycarbonyl-1H-indazolyl-6-amino, acetamido, cyclopropanecarboxamido, benzamido, methylsulfonamido, or 3-(3-(trifluoromethyl)phenyl)ureido;

R 4 is H or C 1-6 alkyl;

R 5 is H, C 1-6 alkyl, C 3-7 cycloalkyl, C 3-14 aryl, C 2-13 heteroaryl, or C 2-7 heterocycloalkyl, wherein R 5 is optionally substituted with one or more substituents selected from the group consisting of halogen, —CF 3 , —NO 2 , —CN, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-14 aryl, C 2-13 heteroaryl, C 2-7 heterocycloalkyl, —(CH 2 ) m NR 8 R 9 , —(CH 2 ) m OR 9 , —(CH 2 ) m C(O)OR 9 , —(CH 2 ) m C(O)NR 8 R 9 , —(CH 2 ) m NR 8 C(O)R 9 , —(CH 2 ) m SR 9 , —(CH 2 ) m S(O)R 9 , and —(CH 2 ) m S(O) 2 R 9 ;

m is an integer of 0 to 3;

R 8 and R 9 are each independently H, —CF 3 , —NO 2 , —CN, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-14 aryl, C 2-13 heteroaryl, or C 2-7 heterocycloalkyl, wherein R 8 and R 9 are each independently optionally substituted with one or more substituents selected from the group consisting of halogen, —CF 3 , —NO 2 , —CN, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, —NR 10 R 10 , —OR 10 , C 3-14 aryl, C 2-13 heteroaryl, and C 2-7 heterocycloalkyl; and

R 10 is H or C 1-6 alkyl,

with proviso that when Y is C(O)OH, Z is not H, a halogen or 2,4-dimethoxybenzylamino; and when Y —C(O)NR 2 R 3 , Z is not H.

2. A compound selected from the group consisting of:

1) ethyl 3-((4-(2-hydroxyethylamino)thieno[3,2-d]pyrimidin-7-yl)ethynyl)-4-methyl benzoate;

1a) 4-(methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine;

1b) 7-ethynyl-4-(methylthio)thieno[3,2-d]pyrimidine;

1c) ethyl 4-methyl-3-((4-(methylthio)thieno[3,2-d]pyrimidin-7-yl)ethynyl)benzoate;

1d) ethyl 4-methyl-3-((4-(methylsulfinyl)thieno[3,2-d]pyrimidin-7-yl)ethynyl)benzoate;

2) ethyl 3-((4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethynyl)-4-methyl benzoate;

3) ethyl 4-methyl-3-((4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)ethynyl)benzoate;

4) ethyl 3-((4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethynyl)-4-methyl benzoate;

5) ethyl 4-methyl-3-((4-(4-morpholinophenylamino)thieno[3,2-d]pyrimidin-7-yl)ethynyl)benzoate;

6) N-cyclopropyl-7-((3,5-dimethoxyphenyl)ethynyl)thieno[3,2-d]pyrimidine-4-amine;

7) 7-((4-bromo-3,5-dimethoxyphenyl)ethynyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

8) 7-((4-bromo-2-chloro-3,5-dimethoxyphenyl)ethynyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

9) 7-((4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)ethynyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

10) 7-((2-chloro-3,5-dimethoxyphenyl)ethynyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

11) 7-(4-bromo-3,5-dimethoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

11a) 7-vinylthieno[3,2-d]pyrimidine-4-amine;

12) (E)-7-styrylthieno[3,2-d]pyrimidine-4-amine;

13) (E)-7-(4-methoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

14) (E)-2-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)phenol;

15) (E)-7-(4-aminostyryl)thieno[3,2-d]pyrimidine-4-amine;

16) (E)-ethyl 3-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methyl benzoate;

17) (E)-2-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-N-cyclopropylbenzamide;

18) (E)-3-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-N-cyclopropylbenzamide;

19) (E)-4-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-N-cyclopropylbenzamide;

20) (E)-3-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-N-cyclopropyl-4-methylbenzamide;

21) (E)-7-(4-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

22) (E)-2-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-4-fluorophenol;

23) (E)-7-(4-amino-2-fluorostyryl)thieno[3,2-d]pyrimidine-4-amine;

24) (E)-7-(2-(4-aminonaphthalen-1-yl)vinyl)thieno[3,2-d]pyrimidine-4-amine;

25) (E)-7-(2-(2-chloropyridin-4-yl)vinyl)thieno[3,2-d]pyrimidine-4-amine;

26) (E)-5-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)pyridine-2,3-diamine;

27) (E)-1-(5-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)thiophen-2-yl)ethanone;

28) (E)-6-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)vinyl)-N-cyclopropyl-2-oxo-2H-chromene-3-carboxamide;

29) (E)-7-(4-amino-3-fluorostyryl)thieno[3,2-d]pyrimidine-4-amine;

30) (E)-7-(2-methyl-5-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

31) (E)-N-cyclopropyl-7-styrylthieno[3,2-d]pyrimidine-4-amine;

32) (E)-N-cyclopropyl-7-(4-methoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

33) (E)-2-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)phenol;

34) (E)-7-(4-aminostyryl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

35) (E)-ethyl 3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methyl benzoate;

36) (E)-N-cyclopropyl-2-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

37) (E)-N-cyclopropyl-3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

38) (E)-N-cyclopropyl-4-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

39) (E)-N-cyclopropyl-3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methylbenzamide;

40) (E)-N-cyclopropyl-7-(4-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

41) (E)-2-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-fluorophenol;

42) (E)-7-(4-amino-2-fluorostyryl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

43) (E)-7-(2-(4-aminonaphthalen-1-yl)vinyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

44) (E)-7-(2-(2-chloropyridin-4-yl)vinyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

45) (E)-7-(2-(1H-pyrazol-4-yl)vinyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

46) (E)-5-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)pyridine-2,3-diamine;

47) (E)-1-(5-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)thiophen-2-yl)ethanone;

48) (E)-N-cyclopropyl-6-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-2-oxo-2H-chromene-3-carboxamide;

49) (E)-7-(4-amino-3-fluorostyryl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

50) (E)-N-cyclopropyl-7-(2-methyl-5-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

51) (E)-N-(3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methylphenyl)cyclopropanecarboxamide;

52) (E)-N-cyclopropyl-3-(2-(4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

53) (E)-N-cyclopropyl-4-methyl-3-(2-(4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

54) (E)-7-(2-(4-aminonaphthalen-1-yl)vinyl)-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidine-4-amine;

55) (E)-N-(4-methyl-3-(2-(4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)phenyl)cyclopropanecarboxamide;

56) (E)-N-cyclopropyl-4-methyl-3-(2-(4-(4-morpholinophenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

57) (E)-N-(4-methyl-3-(2-(4-(4-morpholinophenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)phenyl)cyclopropanecarboxamide;

58) (E)-N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-styrylthieno[3,2-d]pyrimidine-4-amine;

59) (E)-N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-(4-methoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

60) (E)-2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)phenol;

61) (E)-7-(4-aminostyryl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

62) (E)-ethyl 3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methyl benzoate;

63) (E)-N-cyclopropyl-2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

64) (E)-N-cyclopropyl-3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

65) (E)-N-cyclopropyl-4-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)benzamide;

66) (E)-N-cyclopropyl-3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methylbenzamide;

67) (E)-N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-(4-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

68) (E)-2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-fluorophenol;

69) (E)-7-(4-amino-2-fluorostyryl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

70) (E)-7-(2-(4-aminonaphthalen-1-yl)vinyl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

71) (E)-7-(2-(2-chloropyridin-4-yl)vinyl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

72) (E)-N-(3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)vinyl)-4-methylphenyl)cyclopropanecarboxamide;

73) (E)-N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-(2-methyl-5-nitrostyryl)thieno[3,2-d]pyrimidine-4-amine;

74) 7-(3,5-dimethoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

75) 7-(4-bromo-2,6-dichloro-3,5-dimethoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

76) 7-(2,6-dichloro-3,5-dimethoxystyryl)thieno[3,2-d]pyrimidine-4-amine;

77) 7-phenethylthieno[3,2-d]pyrimidine-4-amine;

78) 6-(2-(4-aminothieno[3,2-d]pyrimidin-7-yl)ethyl)-N-cyclopropyl-2-oxo-2H-chromene-3-carboxamide;

79) 7-(4-amino-2-methylphenethyl)thieno[3,2-d]pyrimidine-4-amine;

80) N-cyclopropyl-7-(4-methoxyphenethyl)thieno[3,2-d]pyrimidine-4-amine;

81) 2-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)phenol;

82) ethyl 3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-methyl benzoate;

83) N-cyclopropyl-2-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

84) N-cyclopropyl-3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

85) N-cyclopropyl-3-(2-(4-(cyclopropylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-methylbenzamide;

86) 7-(4-aminophenethyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

87) 7-(2-(2-chloropyridin-4-yl)ethyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

88) 7-(2-(1H-pyrazol-4-yl)ethyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

89) 7-(5-amino-2-methylphenethyl)-N-cyclopropylthieno[3,2-d]pyrimidine-4-amine;

90) N-cyclopropyl-3-(2-(4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

91) N-cyclopropyl-4-methyl-3-(2-(4-(3,4,5-trimethoxyphenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

92) N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-phenethylthieno[3,2-d]pyrimidine-4-amine;

93) N-(4-(4-ethylpiperazin-1-yl)phenyl)-7-(4-methoxyphenethyl)thieno[3,2-d]pyrimidine-4-amine;

94) 2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)phenol;

95) ethyl 3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-methyl benzoate;

96) N-cyclopropyl-2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

97) N-cyclopropyl-3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

98) N-cyclopropyl-4-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)benzamide;

99) N-cyclopropyl-3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-methylbenzamide;

100) 7-(4-aminophenethyl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

101) 2-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-fluorophenol;

102) 7-(2-(4-aminonaphthalen-1-yl)ethyl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

103) N-(3-(2-(4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidin-7-yl)ethyl)-4-methylphenyl)cyclopropanecarboxamide;

104) 7-(5-amino-2-methylphenethyl)-N-(4-(4-ethylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidine-4-amine;

105) 4-(methylthio)thieno[3,2-d]pyrimidine-7-carboxylic acid;

105a) 4-(methylthio)-7-vinylthieno[3,2-d]pyrimidine;

105b) 4-(methylthio)thieno[3,2-d]pyrimidine-7-carbaldehyde;

106) 4-amino-N-(3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

106a) N-(3,5-dimethoxyphenyl)-4-(methylthio)thieno[3,2-d]pyrimidine-7-carboxamide;

106b) N-(3,5-dimethoxyphenyl)-4-(methylsulfinyl)thieno[3,2-d]pyrimidine-7-carboxamide;

107d) (4-chlorothieno[3,2-d]pyrimidin-7-yl)methyl acetate;

107e) (4-chlorothieno[3,2-d]pyrimidin-7-yl)methanol;

107f) 4-chlorothieno[3,2-d]pyrimidine-7-carbaldehyde;

108) 4-(cyclopropylamino)-N-(2,6-difluoro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

108a) 4-chloro-N-(2,6-difluoro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

108b) 4-amino-N-(2,6-difluoro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

109) 4-chloro-N-(2-chloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

110) N-(2-chloro-3,5-dimethoxyphenyl)-4-methoxythieno[3,2-d]pyrimidine-7-carboxamide;

111) 4-amino-N-(2-chloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

112) 4-chloro-N-(6-methoxybenzofuran-4-yl)-3-methyl-3,4-dihydrothieno[3,2-d]pyrimidine-7-carboxamide;

113) 4-amino-N-(6-methoxybenzofuran-4-yl)-3-methyl-3,4-dihydrothieno[3,2-d]pyrimidine-7-carboxamide;

114) N-(6-methoxybenzofuran-4-yl)-3-methyl-4-(phenylamino)-3,4-dihydrothieno[3,2-d]pyrimidine-7-carboxamide;

115) 4-chloro-N-(3-cyano-5-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

116) 4-amino-N-(3-carbamoyl-5-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

117) 4-chloro-N-(6-methoxyquinolin-8-yl)thieno[3,2-d]pyrimidine-7-carboxamide;

118) 4-amino-N-(6-methoxyquinolin-8-yl)thieno[3,2-d]pyrimidine-7-carboxamide;

119) 4-chloro-N-(3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

120) N-(3,5-dimethoxyphenyl)-4-methoxythieno[3,2-d]pyrimidine-7-carboxamide;

121) 4-(2,4-dimethoxybenzylamino)-N-(3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

122) 4-amino-N-(3,4,5-trimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

123) 4-amino-N-(4-chloro-3-fluorophenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

124) 4-amino-N-(6-methylpyridin-3-yl)thieno[3,2-d]pyrimidine-7-carboxamide;

125) 4-amino-N-(3-phenoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

126) 4-amino-N-(2,6-dimethylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

127) 4-amino-N-(2-chloro-6-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

128) 4-amino-N-(benzo[d][1,3]dioxol-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide;

129) 4-amino-N-(5-chloro-2,4-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

130) 4-amino-N-(2-fluorophenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

131) 4-amino-N-(2,3-dichlorophenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

132) 4-amino-N-(4-chloro-3-(trifluoromethyl)phenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

133) 4-amino-N-(2-chloro-4-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

134) 4-amino-N-(5-fluoro-2-methylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

135) 4-amino-N-(2-methyl-5-nitrophenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

137) 4-chloro-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

138) 4-methoxy-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

139) 4-amino-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

140) 4-(2-morpholinoethylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

141) 4-(phenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

142) 4-(4-(4-ethylpiperazin-1-yl)phenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

143) 4-(4-(4-ethylpiperazin-1-yl)-2-methoxyphenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

144) 4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methoxyphenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

145) 4-(4-(4-ethylpiperazin-1-yl)-2-isopropoxyphenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

146) 4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-isopropoxyphenylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

147) 4-(pyridin-2-ylamino)-N-(2,4,6-trichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

148) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-chlorothieno[3,2-d]pyrimidine-7-carboxamide;

148b) N-(4-bromo-3,5-dimethoxyphenyl)-4-chlorothieno[3,2-d]pyrimidine-7-carboxamide;

148c) N-(4-bromo-3,5-dimethoxyphenyl)-4-(methylthio)thieno[3,2-d]pyrimidine-7-carboxamide;

149) 4-amino-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

150) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(2-(dimethylamino)ethylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

151) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(diethylamino)propylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

152) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)-2-methoxyphenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

153) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methoxyphenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

154) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)-2-isopropoxyphenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

155) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)-2-isopropoxyphenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

156) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

157) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(diethylamino)butylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

158) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(diethylamino)pentylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

159) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(4-ethylpiperazin-1-yl)propylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

160) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)butylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

161) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(4-ethylpiperazin-1-yl)pentylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

162) 4-(3-(1H-imidazol-1-yl)propylamino)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

163) 4-(4-(1H-imidazol-1-yl)butylamino)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

164) 4-(5-(1H-imidazol-1-yl)pentylamino)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

165) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

166) 4-chloro-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

167) 4-amino-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

168) 4-(cyclopropylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

169) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(2-(dimethylamino)ethylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

170) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(diethylamino)propylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

171) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(4-ethylpiperazin-1-yl)propylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

172) 4-(4-(1H-imidazol-1-yl)butylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

173) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

175) 4-acetamido-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

176) 4-benzamido-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

177) 4-(cyclopropanecarboxamido)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

178) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-methylpyridine-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

179) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((4-ethylpiperazin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

180) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

181) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(4-ethylpiperazin-1-yl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

182) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(4-ethylpiperazin-1-yl)pyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

183) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

184) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-methylpyridin-3-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

185) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(diethylamino)ethoxy)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

186) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-hydroxyethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

187) 4-(4-(1-benzylpiperidine-4-ylcarbamoyl)phenylamino)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

188) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazine-1-carbonyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

189) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((4-ethylpiperazin-1-yl)methyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

190) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(4-ethylpiperazin-1-yl)-2-oxoethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

191) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(4-ethylpiperazin-1-yl)ethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

192) 4-(7-(4-bromo-2,6-dichloro-3,5-dimethoxyphenylcarbamoyl)thieno[3,2-d]pyrimidin-4-ylamino)benzoic acid;

193) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

194) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

195) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

196) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(diethylamino)ethoxy)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

197) 4-(4-(1-benzylpiperidine-4-ylcarbamoyl)phenylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

198) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazine-1-carbonyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

199) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(4-ethylpiperazin-1-yl)-2-oxoethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

200) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

201) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(4-ethylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

202) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

203) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)benzamido)thieno[3,2-d]pyrimidine-7-carboxamide;

204) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-ethylpiperazin-1-yl)benzamido)thieno[3,2-d]pyrimidine-7-carboxamide;

205) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(methylsulfonamido)thieno[3,2-d]pyrimidine-7-carboxamide;

206) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(methylsulfonamido)thieno[3,2-d]pyrimidine-7-carboxamide;

207) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-hydroxypiperidin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

208) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(2-morpholinoethylamino)pyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

209) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(2-(dimethylamino)ethoxy)pyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

210) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(3-(diethylamino)propylamino)pyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

211) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-(3-(4-ethylpiperazin-1-yl)propylamino)pyrimidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

212) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-methyl-6-(2-morpholinoethylamino)pyrimidin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

213) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-nitrothiazol-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

214) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-methyl-6-(2-morpholinoethylamino)pyrimidin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

215) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(3-(trifluoromethyl)phenyl)ureido)thieno[3,2-d]pyrimidine-7-carboxamide;

216) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-(ethoxycarbonyl)thioureido)thieno[3,2-d]pyrimidine-7-carboxamide;

217) 4-amino-N-(2,6-dichloro-3-hydroxy-5-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

218) 4-amino-N-(2,6-dichloro-3,5-dihydroxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

219) 4-amino-N-(2,6-dichloro-3-(2-(dimethylamino)ethoxy)-5-methoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

220) 4-(2-amino-5-(4-ethylpiperazin-1-yl)-6-fluoro-1H-benzo[d]imidazol-1-yl)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

221) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-methylbenzo[d]thiazol-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

222) 4-(2-amino-1H-benzo[d]imidazol-1-yl)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

223) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(1-(4-methoxybenzyl)-1H-benzo[d]imidazol-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

224) 4-(2-amino-5-(4-ethylpiperazin-1-yl)-6-fluoro-1H-benzo[d]imidazol-1-yl)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

225) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-methylbenzo[d]thiazol-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

226) 4-(2-amino-1H-benzo[d]imidazol-1-yl)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

227) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(1-(4-methoxybenzyl)-1H-benzo[d]imidazol-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

228) 4-(1H-indazol-6-ylamino)-N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

229) 4-(1H-indazol-6-ylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

230) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

231) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

232) ethyl 6-(7-(2,6-dichloro-3,5-dimethoxyphenylcarbamoyl)thieno[3,2-d]pyrimidin-4-ylamino)-1H-indazole-3-carboxylate;

236) 4-amino-N-(2,6-dichloro-3,5-dimethylphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

237) 4-amino-N-(2,6-dichloro-3,5-dimethoxybenzyl)thieno[3,2-d]pyrimidine-7-carboxamide;

239) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(dimethylamino)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

240) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-methoxyphenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

241) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(2-hydroxyethyl)piperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

242) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(piperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

243) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-propionylpiperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

244) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(isopropylcarbamoyl)piperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

245) ethyl 4-(4-(7-(2,6-dichloro-3,5-dimethoxyphenylcarbamoyl)thieno[3,2-d]pyrimidin-4-ylamino)phenyl)piperazine-1-carboxylate;

246) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-morpholinophenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

247) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(morpholinomethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

248) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-methylpiperazin-1-ylamino)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

249) 4-(4-(1H-imidazol-1-yl)phenylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

250) 4-(5-chloropyridin-2-ylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

251) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(piperidin-4-ylamino)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

252) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

253) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(4-(pyridin-2-yl)piperazin-1-yl)phenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

254) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((diethylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

255) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(morpholine-4-carbonyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

256) 4-(5-((1H-imidazol-1-yl)methyl)pyridin-2-ylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

257) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(2-morpholino-2-oxoethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

258) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((4-methylpiperidin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

259) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-(trifluoromethyl)piperidin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

260) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3,5-dimethylmorpholino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

261) 4-(5-((4-acetylpiperazin-1-yl)methyl)pyridin-2-ylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

262) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((4-morpholinopiperidin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

263) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-oxopiperazin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

264) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(3-(diethylamino)propylcarbamoyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

265) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-(diethylamino)propylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

266) (R)—N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-hydroxypyrrolidin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

267) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(3-(4-ethylpiperazin-1-yl)propylcarbamoyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

268) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(4-methylpiperazin-1-ylcarbamoyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

269) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-(4-ethylpiperazin-1-yl)propylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

270) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-methylpyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

271) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((2-(diethylamino)ethoxy)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

272) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((diethylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

273) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(6-((diethylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

274) 4-(5-carbamoylpyridin-2-ylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

275) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((2-methoxyethoxy)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

276) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((3-(diethylamino)propoxy)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

277) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-((2-(piperidin-1-yl)ethoxy)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

278) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(pyridin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

279) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((4-ethylpiperazin-1-yl)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

280) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(morpholinomethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

281) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(3-(diethylamino)propoxy)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

282) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(diethylamino)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

285) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(3-(diethylamino)propoxy)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

286) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(2,3,4-trifluorophenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

287) N-(4-bromo-2,6-dichloro-3,5-dimethoxyphenyl)-4-(3-chloro-4-fluorophenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

288) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(piperidin-1-ylmethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

289) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(2,3,4-trifluorophenylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

290) 4-(3-chloro-4-fluorophenylamino)-N-(2,6-dichloro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

291) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(thiazolidin-3-ylmethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

292) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(2-(diethylamino)-2-oxoethyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

293) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((2-(diethylamino)ethylamino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

294) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-(((2-hydroxyethyl)(methyl)amino)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

295) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(4-((2-(diethylamino)ethoxy)methyl)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

296) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(diethylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

297) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(piperidin-4-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

298) 4-(4-((diethylamino)methyl)pyridin-2-ylamino)-N-(3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide;

299) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(5-(2-(dimethylamino)acetamido)pyridin-2-ylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

300) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(phenethylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

301) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(2-hydroxyethylamino)thieno[3,2-d]pyrimidine-7-carboxamide;

302) ethyl 2-(7-(2,6-dichloro-3,5-dimethoxyphenylcarbamoyl)thieno[3,2-d]pyrimidin-4-ylamino)acetate;

303) 2-(7-(2,6-dichloro-3,5-dimethoxyphenylcarbamoyl)thieno[3,2-d]pyrimidin-4-ylamino)acetic acid; and

304) N-(2,6-dichloro-3,5-dimethoxyphenyl)-4-(2-(phenylamino)ethylamino)thieno[3,2-d]pyrimidine-7-carboxamide, or a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.

3. A method for preparing a compound of formula (1e), which comprises subjecting a compound of formula (1a) to a reaction with a compound of formula (2a):

wherein, W, X, Z and R 3 have the same meanings as defined in claim 1 .

4. A method for preparing a compound of formula (1f), which comprises subjecting a compound of formula (1b) to a reaction with a compound of formula (2b):

wherein, W, X, Z and R 3 have the same meanings as defined in claim 1 ; and Y′ is halogen.

5. A method for preparing a compound of formula (1g), which comprises subjecting a compound of formula (1c) to a reaction with a compound of formula (2c):

wherein, W, X, Z and R 3 have the same meanings as defined in claim 1 ; and Y″ is halogen.

6. A method for preparing a compound of formula (1h), which comprises subjecting a compound of formula (1d) to a reaction with a compound of formula (2d):

wherein, W, X and Y have the same meanings as defined in claim 1 , and R 11 has the same meaning as defined in claim 1 for the substituted amino (NH) groups at Z; and when Z′ is halogen, Z″ is NH 2 , and when Z′ is NH 2 , Z″ is halogen.

7. A pharmaceutical composition comprising the compound of claim 1 as an active ingredient and a pharmaceutically acceptable carrier.