Patent ID: 11944622
Assignee: ANNAPURNA BIO, INC.
Field: Pharmaceuticals (Chemistry)
Classification: CPC A  C  Y | IPC A  C

Claim 0:
1. A method for treating a subject having fibrosis, wherein the fibrosis is associated with an organ or tissue selected from the group consisting of lung, liver, heart, mediastinum, bone marrow, retroperitoneum, skin, intestine, joint, and a reproductive organ, or a combination thereof, comprising administering to the subject an effective amount of a compound selected from:, 2

N-(1-(2,6-dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)methanesulfonamide,

 

3 

N-(1-(2,6-dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- phenylmethanesulfonamide, 

 

4 

1-cyclopropyl-N-(1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)methanesulfonamide, 

 

5 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)benzenesulfonamide, 

 

22 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)cyclopropanesulfonamide, 

 

23 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyridine-2-sulfonamide, 

 

24 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyridine-3-sulfonamide, 

 

25 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyridine-4-sulfonamide, 

 

26 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyridin-3- yl)methanesulfonamide, 

 

27 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyridin-2- yl)methanesulfonamide, 

 

28 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyrimidin-2- yl)methanesulfonamide, 

 

29 

2-cyclopropyl-N-(1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)ethanesulfonamide, 

 

30 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)oxetane-3-sulfonamide, 

 

31 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)cyclobutanesulfonamide, 

 

32 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-N- methylmethanesulfonamide, 

 

33 

cis-N-(1-(2,6-dimethoxyphenyl)- 2-(6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-3- hydroxycyclobutane-1- sulfonamide, 

 

34 

trans-N-(1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-3- hydroxycyclobutane-1- sulfonamide, 

 

35 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyrimidin-5- yl)methanesulfonamide, 

 

36 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)tetrahydro-2H-pyran-4- sulfonamide, 

 

37 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)morpholine-4-sulfonamide, 

 

38 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (piperidin-4- yl)methanesulfonamide, 

 

39 

trans-N-(1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)- 4-hydroxycyclohexane-1- sulfonamide, 

 

40 

cis-N-(1-(2,6-dimethoxyphenyl)- 2-(6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-4- hydroxycyclohexane-1- sulfonamide, 

 

41 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyrimidine-2-sulfonamide, 

 

42 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-4- hydroxypiperidine-1- sulfonamide, 

 

60 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-3- hydroxy-3-methylbutane-1- sulfonamide, 

 

61 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(1- hydroxycyclopropyl)methanesul- fonamide, 

 

64 

N-(5-chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)methanesulfonamide, 

 

69

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyrazin-2- yl)methanesulfonamide, 

 

70

N-(1-(2,6-Dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-2- hydroxy-2-methylpropane-1- sulfonamide,

 

71

(S)-N-(1-(2,6-Dimethoxyphenyl)- 2-(6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(1- methyl-2-oxopiperidin-4- yl)methanesulfonamide,

 

72 

(R)-N-(1-(2,6-dimethoxyphenyl)- 2-(6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(1- methyl-2-oxopiperidin-4- yl)methanesulfonamide, 

 

73 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyrrolidine-1-sulfonamide, 

 

74 

N-(1-(2,6-Dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)piperazine-1-sulfonamide, 

 

75 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)piperidine-1-sulfonamide, 

 

76 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)- N′,N′-dimethylsulfamide, 

 

77 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-N′- methyl-N′-cyclopropylsulfamide, 

 

78 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(5- fluoropyridin-2- yl)methanesulfonamide, 

 

79 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (5-fluoropyrimidin-2- yl)methanesulfonamide, 

 

80 

N-(1-(2,6-dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(5- methylpyrimidin-2- yl)methanesulfonamide, 

 

81 

trans-N-(1-(2,6- Dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- ((1r,3r)-3-hydroxy-3- methylcyclobutyl)methanesul- fonamide, 

 

82 

N-(1-(2,6-Dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)but-2- yne-1-sulfonamide, 

 

83 

N-(1-(2,6-Dimethoxyphenyl)-2- (6-ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (5-methylpyridin-2- yl)methanesulfonamide, 

 

94 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(3- fluoropyridin-2- yl)methanesulfonamide, 

 

95 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyridin-2- yl)methanesulfonamide, 

 

96 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (5-fluoropyridin-2- yl)methanesulfonamide, 

 

97 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)cyclopropanesulfonamide, 

 

98 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)morpholine-4-sulfonamide, 

 

99 

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-5- fluoropyridine-2-sulfonamide, 

 

100

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (2-fluoro-4- methylphenyl)methanesul- fonamide, 

 

101

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-5- methylpyridine-2-sulfonamide,

 

102

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyridine-2-sulfonamide,

 

103

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-4- (fluoromethyl)benzenesulfon- amide, 

 

104

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)pyridine-3-sulfonamide, 

 

105

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(5- fluoropyrimidin-2-yl)methanesul- fonamide, 

 

106

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-4- (difluoromethyl)benzenesulfon- amide, 

 

107

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(3- fluoro-4-methylphenyl)methane- sulfonamide, 

 

108

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(4- fluorophenyl)methanesulfonamide, 

 

109

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- (pyrimidin-2- yl)methanesulfonamide, 

 

110

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)but- 2-yne-1-sulfonamide, 

 

111

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6- yl)tetrahydro-2H-pyran-4- sulfonamide, 

 

112

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-N′- methyl-N′-cyclopropylsulfamide, 

 

113

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(1- hydroxycyclopropyl)methanesul- fonamide, 

 

114

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(5- methylpyridin-2- yl)methanesulfonamide, 

 

115

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1- ((1r,3r)-3-hydroxy-3- methylcyclobutyl)methanesulfon- amide, 

 

116

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-4- hydroxypiperidine-1-sulfonamide, 

 

142

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(5- methylpyrimidin-2- yl)methanesulfonamide,

 

and

 

143

N-(5-Chloro-1-(2,6- dimethoxyphenyl)-2-(6- ethoxypyridin-2-yl)-1H- imidazo[4,5-b]pyrazin-6-yl)-1-(3- fluorophenyl)methanesulfonamide,

or a pharmaceutically acceptable salt thereof.