Tricyclic derivative compound, method for preparing same, and pharmaceutical composition comprising same

1. A tricyclic compound represented by the following formula 1, an optical isomer thereof, a racemate thereof or a pharmaceutically acceptable salt thereof:

wherein

L is —CH 2 — or —C(═O)—;

R 1 is H, a halogen atom, or C 1 -C 3 alkoxy;

R 2 and R 3 are each independently H or C 1 -C 3 alkyl, or R 2 and R 3 are linked to each other to form a ring;

ring A is phenyl or a heteroaryl, selected from the group consisting of pyridine, pyrazine, pyrimidine, pyridazine, thiophene, thiazole, thiadiazole, oxazole, oxadiazole, indole, indazole, cyclopentapyridine, dihydrocyclopentapyridine, furopyridine, dihydrofuropyridine, oxazolopyridine, benzoxazole and benzoisoxazole.

wherein the phenyl and the heteroaryl are each independently unsubstituted, or one or more H atoms thereof are each independently substituted with a substituent selected from the group consisting of a halogen atom, —CN, —CF 3 , —C 1 -C 3 alkyl, —C 1 -C 3 alkoxy, —CH 2 —OR 4 , —C(═O)—R 4 , —C(═O)—OR 4 , —S(═O) 2 —R 4 , —NH—C(═O)—R 4 , —NO 2 , —NR 4 R 5 and —C(═O)—NR 6 R 7 ;

R 4 , R 5 and R 6 are each independently H or C 1 -C 3 alkyl; and

R 7 is C 1 -C 3 alkyl or C 3 -C 7 cycloalkyl.

2. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 1 , wherein R 2 and R 3 are each independently H or C 1 -C 3 alkyl.

3. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 2 , wherein ring A is substituted with one or more substituents.

4. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 1 , wherein R 2 and R 3 are linked to each other to form a ring.

5. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 1 , wherein the compound is any one of the following compounds:

1) 8-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

2) 8-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-10-methoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

3) 10-ethoxy-8-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

4) 10-ethoxy-8-({[4-(pyrimidin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

5) 10-ethoxy-8-{[4-(pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

6) 10-ethoxy-8-{[4-(5-fluoropyrimidin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

7) 10-ethoxy-8-{[4-(5-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

8) 10-ethoxy-8-{[4-(6-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

9) 10-ethoxy-8-{[4-(3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

10) 8-{[4-(5-chloro-3-fluoropyridin-2-yl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

11) 10-ethoxy-8-{[4-(6-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

12) 8-({4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}methyl)-10-ethoxy-1,2,3,4-tretrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

13) 8-{[4-(5-chloropyridin-2-yl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

14) 8-{[4-(6-chloropyridin-2-yl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

15) 8-{[4-(3-chloropyridin-2-yl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

16) 8-{[4-(5-bromopyridin-2-yl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

17) 10-ethoxy-8-{[4-(3-methylpyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

18) 6-{4-{(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperzin-1-yl})-N-methylnicotinamide;

19) 6-{4-{(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-ethylnicotinamide;

20) N-cyclopropyl-6-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinamide;

21) 8-{[4-(4-chlorophenyl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

22) 8-{[4-(4-bromophenyl)piperazin-1-yl]methyl}-10-ethoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

23) 4-{4-[(1-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

24) 3-fluoro-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

25) 3-chloro-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

26) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-3-methylbenzonitrile;

27) 10-ethoxy-8-{[4-(4-fluoro-2-methylphenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

28) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-3,5-difluorobenzonitrile;

29) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-2-fluorobenzonitrile;

30) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-ethylbenzamide;

31) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-2-fluoro-N-methylbenzamide;

32) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-ethyl-2-fluorobenzamide;

33) 3-chloro-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-ethylbenzamide;

34) 3-chloro-N-cyclopropyl-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

35) 3-chloro-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-methylbenzamide;

36) 4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N,3-dimethylbenzamide;

37) 4-{4-[(1-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-N-ethyl-3-methylbenzamide;

38) N-cyclopropyl-4-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-3-methylbenzamide;

39) 10-methoxy-8-{[4-(pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

40) 10-methoxy-8-{[4-(3-methylpyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

41) 8-{[4-(5-fluoropyridin-2-yl)piperazin-1-yl]methyl}-10-methoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

42) 4-{4-[(1-methoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

43) 8-{[4-(4-fluoro-2-methylphenyl)piperazin-1-yl]methyl}-10-methoxy-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

44) 4-{4-[(10-methoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-3-methylbenzonitrile;

45) 3-fluoro-4-{4-[(10-methoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

46) 3,5-difluoro-4-{4-[(10-methoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

47) 2-fluoro-4-{4-[(10-methoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

48) 8-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

49) 8-{[4-(4-fluoro-2-methylphenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

50) 3-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

51) 3-chloro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

52) 3-bromo-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

53) 3-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

55) 8-({4-[4-(diethylamino)-2-fluorophenyl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-(6H)-one;

56) 3-acetyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

57) 4-fluoro-2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

58) 3,5-difluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

59) 8-{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

60) 2-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

61) 2-chloro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

62) 4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-2-(trifluoromethyl)benzonitrile;

63) 2-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

64) N-ethyl-3-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

65) N-cyclopropyl-3-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

66) 3-fluoro-N-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

67) N-ethyl-3-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

68) N-(3-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}phenyl)propionamide;

69) N-cyclopropyl-3-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

70) 3-chloro-N-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

71) 3-chloro-N-ethyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

72) 3-chloro-N-cyclopropyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

73) 3-bromo-N-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

74) 3-bromo-N-ethyl-4-{(4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

75) 3-bromo-N-cyclopropyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

76) 2-fluoro-N-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

77) N-ethyl-2-fluoro-4-{(4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

78) N-cyclopropyl-2-fluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

79) N-ethyl-2-fluoro-N-methyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

80) 2-chloro-N-methyl-4-{(4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

81) 2-chloro-N-ethyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

82) 2-chloro-N-cyclopropyl-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

83) ethyl 2-chloro-5-(4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzoate;

84) N-ethyl-3,5-difluoro-4-{(4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

85) N-cyclopropyl-3,5-difluoro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzamide;

86) 8-{[4-(pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

87) 8-({(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

88) 8-({4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

89) 6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

90) 8-{[4-(3-methylpyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

91) 8-{[4-(5-fluoro-3-methylpyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

92) 8-{[4-(pyrazin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

93) 8-{[4-(6-chloropyridazin-3-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

94) 8-{[4-(3,5-dichloropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

95) N-methyl-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl})nicotinamide;

96) N-ethyl-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinamide;

97) N-cyclopropyl-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinamide;

98) 8-{[4-(thiazol-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

99) ethyl-2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiazole-4-carboxylate;

100) N-ethyl-2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiazole-4-carboxamide;

101) 2-fluoro-4-{8-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-3,8-diazabicyclo[3,2,1]octan-3-yl}benzonitrile;

102) 6-{8-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-3,8-diazabicyclo[3,2,1]octan-3-yl}nicotinonitrile;

103) 2-fluoro-4-{(1S,4S)-5-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}benzonitrile;

104) 6-{(1S,4S)-5-[(oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}nicotinonitrile;

105) 10-ethoxy-8-{[4-(5-fluoropyrimidin-2-yl)-2-methylpiperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

106) 10-ethoxy-8-{[4-(5-fluoropyridin-2-yl)-2-methylpiperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

107) 3-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

108) (R)-3-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

109) (S)-3-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

110) (R)-3-fluoro-4-{2-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

111) 2-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

112) (R)-2-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

113) (S)-2-fluoro-4-{3-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

114) (R)-2-fluoro-4-{2-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

115) 8-({(4-[4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,2]naphthyridin-5(6H)-one;

116) 6-{4-[(10-ethoxy-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

117) 8-({(4-[2-chloro-4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

118) 8-({(4-[3-chloro-4-(trifluoromethyl)phenyl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

119) 8-{[4-(3-fluoro-4-nitrophenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

120) 8-{[4-(5-chloropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

121) 8-({4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

122) 8-({4-[5-(methylsulfonyl)pyridin-2-yl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

123) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}picolinonitrile;

124) 2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}isonicotinonitrile;

125) 2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

126) 6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}picolinonitrile;

127) 8-{[4-(4-methoxypyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

128) 8-({4-[5-(methoxymethyl)-pyridin-2-yl]piperazin-1-yl}methyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

129) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}pyrazine-2-carbonitrile;

130) 8-{[4-(6-methylpyridazin-3-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

131) 8-{[4-(6-methoxypyridazin-3-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

132) 6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}pyridazine-3-carbonitrile;

133) 5-chloro-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

134) 6-chloro-4-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

135) 4-chloro-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

136) 5-chloro-2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}isonicotinonitrile;

137) 4-methoxy-6-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}nicotinonitrile;

138) 8-{[4-(5-bromo-4-methoxypyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

139) 2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiazole-4-carbonitrile;

140) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiophene-2-carbonitrile;

141) ethyl-2-{4-[((5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiazole-5-carboxylate;

142) 2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiazole-5-carbonitrile;

143) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-1,3,4-thiadiazole-2-carbonitrile;

144) 2-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}oxazole-4-carbonitrile;

145) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-1,2,4-thiadiazole-3-carbonitrile;

146) 5-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-1,3,4-oxadiazole-2-carbonitrile;

147) 8-{[4-(5-chlorobenzo[d]oxazol-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

148) 8-{[4-(2-methylbenzo[d]oxazol-6-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

149) 8-{[4-(3-methylbenzo[d]isoxazol-5-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

150) 8-{[4-(1H-indol-6-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

151) 8-{[4-(1H-indazol-5-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

152) 8-{[4-(1H-indazol-6-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

153) 8-{[4-(benzo[d]isoxazol-5-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

154) 8-{[4-(oxazolo[4,5-b]pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

155) 8-{[4-(oxazolo[5,4-b]pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

156) 8-{[4-(2,3-dihydrofuro[2,3-b]pyridin-6-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

157) 1-{4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carbonitrile;

158) 8-{[3-(pyrazin-2-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

159) 6-{3-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl)nicotinonitrile;

160) 8-{[3-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

161) 3-fluoro-4-{(1 S,4S)-5-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}benzonitrile;

162) 8-{[(1 S,4S)-5-(2-fluoro-4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]methyl) 1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

163) 8-{[(1 S,4S)-5-(6-chloropyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]methyl}-10-fluoro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

164) 10-fluoro-8-{[(1 S,4S)-5-(pyridazin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

165) (S)-2-fluoro-4-{2-methyl-4-[(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}benzonitrile;

166) 10-fluoro-8-{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

167) 10-fluoro-8-{[4-(pyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

168) 10-fluoro-8-{[4-(3-methylpyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

169) 10-fluoro-8-{[4-(5-fluoropyridin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

170) 6-{4-[(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl]methyl}piperazin-1-yl)nicotinonitrile;

171) 2-{4-[(10-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl]methyl}piperazin-1-yl)thiazole-5-carbonitrile;

172) 10-fluoro-8-{[4-(4-fluorphenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

173) 2-fluoro-4-{[4-(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl]methyl}piperazin-1-yl)benzonitrile;

174) 4-{[4-(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl]methyl}piperazin-1-yl)-2-(trifluoromethyl)benzonitrile;

175) 10-fluoro-8-{[4-(4-fluoro-2-methylphenyl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

176) 3-fluoro-4-{4-[(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl]methyl}piperazin-1-yl)benzonitrile;

177) 6-f (1 S,4S)-5-[(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl}nicotinonitrile;

178) 10-fluoro-8-{[4-(pyrazin-2-yl)piperazin-1-yl]methyl}-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

179) 8-{[4-(5-chloropyridin-2-yl)piperazin-1-yl]methyl}-10-fluoro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

180) 5-{4-[(1-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}picolinonitrile;

181) 8-{[4-(6-chloropyridazin-3-yl)piperazin-1-yl]methyl})-10-fluoro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5(6H)-one;

182) 6-{4-[(10-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}pyridazine-3-carbonitrile;

183) 5-{4-[(10-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}thiophene-2-carbonitrile;

184) 6-{8-[(10-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]-3,8-diazabicyclo[3,2,1]octan-3-yl}nicotinonitrile;

185) 4-{4-[(10-fluoro-5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-yl)methyl]piperazin-1-yl}-3-methoxybenzonitrile;

186) 5-[4-(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-carbonyl)piperazin-1-yl]thiophene-2-carbonitrile;

187) 6-[4-(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-carbonyl)piperazin-1-yl]nicotinonitrile;

188) 2-[4-(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-carbonyl)piperazin-1-yl]thiazole-4-carbonitrile; and

189) 2-[4-(5-oxo-1,2,3,4,5,6-hexahydrobenzo[h][1,6]naphthyridin-8-carbonyl)piperazin-1-yl]thiazole-5-carbonitrile.

6. A method for preparing a tricyclic compound represented by the following formula 1a, an optical isomer thereof, a racemate thereof or a pharmaceutically acceptable salt thereof, the method comprising the steps of:

(1) preparing an acid chloride using a reagent that converts a nicotinic acid compound of formula 2 to the acid chloride, and subjecting the acid chloride to an amidation reaction with an aniline of formula 3, or subjecting the nicotinic acid compound of formula 2 to a coupling reaction with the aniline of formula 3, thereby preparing a compound of formula 4;

(2) introducing a protection group into the compound of formula 4, prepared in step (1), thereby preparing an N-protected compound of formula 5;

(3) cyclizing the compound of formula 5, prepared in step (2), in the presence of a metal catalyst, thereby preparing a compound of formula 6;

(4) subjecting the compound of formula 6, prepared in step (3), to a ring-reducing reaction with hydrogen in the presence of a palladium catalyst, thereby preparing a compound of formula 7;

(5) reducing the compound of formula 7, prepared in step (4), with a reducing agent, thereby preparing a compound of formula 8;

(6) subjecting the compound of formula 8, prepared in step (5), to halogenation and an amination reaction with an amine compound, thereby preparing a compound of formula 9; and

(7) removing the protection group from the compound of formula 9, prepared in step (6), by a deprotection reaction, thereby preparing a compound of formula 1a

wherein

X is a halogen atom;

Y is He, C 1 -C 3 alkoxy or a halogen atom;

Alk is a C 1 -C 10 straight or branched chain alkyl;

pro is a protection group selected from the group consisting of an aryl group, a benzyl group, a benzyloxymethyl group, a para-methoxybenzyl group and a methoxymethyl group; and

B is

wherein ring A, R 2 and R 3 are as defined in claim 1 .

7. A method for preparing a tricyclic compound represented by the following formula 1a, an optical isomer thereof, a racemate thereof or a pharmaceutically acceptable salt thereof, the method comprising the steps of:

(1) removing a protection group from a compound of formula 8 by a deprotection reaction, thereby preparing a compound of formula 10; and

(2) subjecting the compound of formula 10, prepared in step (1), to halogenation and an amination reaction with an amine compound, thereby preparing a compound of formula 1a

wherein

Y is H, C 1 -C 3 alkoxy or a halogen atom;

pro is a protection group selected from the group consisting of an aryl group, a benzyl group, a benzyloxymethyl group, a para-methoxybenzyl group and a methoxymethyl group; and

B is

wherein ring A, R 2 and R 3 are as defined in claim 1 .

8. A method for preparing a tricyclic compound represented by the following formula 1b, an optical isomer thereof, a racemate thereof or a pharmaceutically acceptable salt thereof, the method comprising the steps of:

(1) removing a protection group from a compound of formula 7 by a deprotection reaction, thereby preparing a compound of formula 11;

(2) adding an aqueous solution of potassium hydroxide or sodium hydroxide slowly dropwise to the compound of formula 11, prepared in step (1), thereby preparing a compound of formula 12, which is a hydrolyzed carboxylic acid; and

(3) subjecting the compound of formula 12, prepared in step (2), to a coupling reaction with an amine compound, thereby preparing a compound of formula 1b

wherein

Y is H, C 1 -C 3 alkoxy or a halogen atom;

Alk is a C 1 -C 10 straight or branched chain alkyl;

pro is a protection group selected from the group consisting of an aryl group, a benzyl group, a benzyloxymethyl group, a para-methoxybenzyl group and a methoxymethyl group; and

B is

wherein ring A, R 2 and R 3 are as defined in claim 1 .

9. A pharmaceutical composition, comprising a tricyclic compound according to claim 1 , an optical isomer thereof, the racemate thereof or a pharmaceutically acceptable salt thereof; and

a pharmaceutically acceptable carrier.

10. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 1 , wherein

L is —CH 2 — or —C(═O)—;

R 1 is H, a halogen atom or C 1 -C 3 alkoxy;

R 2 and R 3 are each independently H or C 1 -C 3 alkyl, or R 2 and R 3 are linked to each other to form a ring;

ring A phenyl or a heteroaryl selected from the group consisting of pyridine, pyrazine, pyrimidine, pyridazine, thiophene, thiazole, thiadiazole, oxazole, oxadiazole, indole, indazole, cyclopentapyridine, dihydrocyclopentapyridine, furopyridine, dihydrofuropyridine, oxazolopyridine, benzoxazole, and benzoisoxazole,

wherein one or more H atoms of the phenyl is substituted with a substituent selected from the group consisting of a halogen atom, —CN, —CF 3 , —C 1 -C 3 alkyl, —C 1 -C 3 alkoxy, —C(═O)—R 4 , —C(═O)—OR 4 , —S(═O) 2 —R 4 , —NH—C(═O)—R 4 , —NO 2 , —NR 4 R 5 and —C(═O)—NR 6 R 7 , and the heteroaryl is unsubstituted, or one or more H atoms of the heteroaryl is substituted with a substituent selected from the group consisting of a halogen atoms, —CN, —CF 3 , —C 1 -C 3 alkyl, —C 1 -C 3 alkoxy, —CH 2 —OR 4 , —C(═O)—OR 4 , —S(═O) 2 —R 4 , —NO 2 , —NR 4 R 5 and —C(═O)—NR 6 R 7

R 4 is C 1 -C 3 alkyl;

R 5 is H or C 1 -C 3 alkyl;

R 6 is H or C 1 -C 3 alkyl; and

R 7 is C 1 -C 3 alkyl or C 3 -C 7 cycloalkyl.

11. The tricyclic compound, the optical isomer thereof, the racemate thereof or the pharmaceutically acceptable salt according to claim 10 , wherein

L is —CH 2 — or —C(═O)—;

R 1 is H or a halogen atom or C 1 -C 3 alkoxy;

R 2 and R 3 are each independently H or C 1 -C 3 alkyl, or R 2 and R 3 are linked to each other to form a ring;

ring A is the phenyl or the heteroaryl selected from the group consisting of pyridine, pyrazine, pyrimidine, pyridazine, thiophene, thiazole, thiadiazole, indole, indazole, cyclopentapyridine, dihydrocyclopentapyridine, dihydrofuropyridine, oxazolopyridine, benzoxazole, and benzoisoxazole,

wherein one or more H atoms of the phenyl is substituted with a substituent selected from the group consisting or a halogen atom, —CN, —CF 3 , —C 1 -C 3 alkyl, —C 1 -C 3 alkoxy, —C(═O)—R 4 , —C(═O)—OR 4 , —NH—C(═O)—R 4 , —NO 2 , —NR 4 R 5 and —C(═O)—NR 6 R 7 , and the heteroaryl is unsubstituted, or one or more H atoms of the heteroaryl is substituted with a substituent selected from the group consisting of a halogen atom, —CN, —CF 3 , —C 1 -C 3 alkyl, —C 1 -C 3 alkoxy, —CH 2 —OR 4 , —C(═O)—OR 4 , —S(═O) 2 —R 4 and —C(═O)—NR 6 R 7

R 4 is C 1 -C 3 alkyl;

R 5 is H or C 1 -C 3 alkyl;

R 6 is H or C 1 -C 3 alkyl; and

R 7 is C 1 -C 3 alkyl or C 3 -C 7 cycloalkyl.