Benzimidazole derivatives as adenosine receptor antagonists
The invention relates to benzimidazole derivatives of the general formula I, and the use of the compounds of the present invention for the treatment and/or prevention of hyperproliferative or infectious diseases and disorders in mammals, especially humans, and pharmaceutical compositions containing such compound.
1. A compound of formula I,
wherein
Q, Y are CH,
R 1 is Br or one of the following structures:
which is unsubstituted or mono-, di- or trisubstituted with R 4 ,
R 2 is one of the following structures:
which is unsubstituted or mono-, di- or trisubstituted with R 5
R 3 is OCH 3 ,
R 4 is H, R 5 , ═S, ═NR 5 , ═O, OH, COOH, Hal, NH 2 , SO 2 CH 3 , SO 2 NH 2 , CN, CONH 2 , NHCOCH 3 , NHCONH 2 , NO 2 , or linear or branched alkyl having 1-10 C atoms which is unsubstituted or mono-, di- or trisubstituted by R 5 and in which 1-4 C atoms may be replaced, independently of one another, by O, S, SO, SO 2 , NH, NCH 3 , —OCO—, —NHCONH—, —NHCO—, —COO—, —CONH—, —NCH 3 CO—, —CONCH 3 —, —C≡C— groups and/or —CH═CH— groups, and/or, in addition, 1-10 H atoms may be replaced by F and/or CI, or mono-or bicyclic cyclic alkyl having 3-7 C atoms which is unsubstituted or mono-, di- or trisubstituted by R 5 and in which 1-4 C atoms may be replaced, independently of one another, by O, S, SO, SO 2 , NH, NCH 3 , —OCO—, —NHCONH—, —NHCO—, —COO—, —CONH—, —NCH 3 CO—, —CONCH 3 —, —C≡C— groups and/or by —CH═CH— groups and/or, in addition, 1-10 H atoms may be replaced by F and/or CI, or mono- or bicyclic heteroaryl, heterocyclyl, aryl or cyclic alkylaryl, containing 3 to 14 carbon atoms and 0-4 heteroatoms, independently selected from N, O and S, which is unsubstituted or mono-, di- or trisubstituted by R 5 ,
R 5 , R 6 are independently of one another selected from the group consisting of H, ═S, ═NH, ═O, OH, COOH, Hal, NH 2 , SO 2 CH 3 , SO 2 NH 2 , CN, CONH 2 , NHCOCH 3 , NHCONH 2 , NO 2 and linear or branched alkyl having 1-10 C atoms in which 1-4 C atoms may be replaced, independently of one another, by O, S, SO, SO 2 , NH, NCH 3 , —OCO—, —NHCONH—, —NHCO—, —COO—, —CONH—, —NCH 3 CO—, —CONCH 3 —, —C≡C— groups and/or —CH═CH— groups, and/or, in addition, 1-10 H atoms may be replaced by F and/or CI,
Hal is F, C, Br, or I,
or physiologically acceptable salts, solvates, prodrugs or stereoisomers thereof, including mixtures thereof in all ratios.
2. The compound according to claim 1 , wherein R 1 is
3. Compound according to claim 1 , wherein R 1 is Br or one of the following structures:
which is unsubstituted or mono-, di- or trisubstituted with R 5
and physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios.
4. A compound selected from the group consisting of:
No.
IUPAC-Name
2
4-Fluoro-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-yl)-
benzamide,
3
2-Bromo-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-yl)-
isonicotinamide,
4
2-Bromo-N-(4-bromo-7-methoxy-1H-benzoimidazol-2-yl)-
isonicotinamide,
5
6-Bromo-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-yl)-
nicotinamide,
6
6-Bromo-N-(4-bromo-7-methoxy-1H-benzoimidazol-2-yl)-
nicotinamide,
7
N-(7-Methoxy-4-phenyl-1H-benzoimidazol-2-yl)-2-morpholin-4-yl-
isonicotinamide,
8
N-(7-Methoxy-4-phenyl-1H-benzoimidazol-2-yl)-6-morpholin-4-yl-
nicotinamide,
9
N′-(7-Methoxy-4-phenyl-1H-benzoimidazol-2-yl)-N,N-dimethyl-
formamidine,
10
4-Chloromethyl-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-yl)-
benzamide,
11
4-Ethylaminomethyl-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-
yl)-benzamide,
12
4-Hydroxy-4-methyl-piperidine-1-carboxylic acid (7-methoxy-4-
phenyl-1H-benzoimidazol-2-yl)-amide,
13
4-Aminomethyl-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-yl)-
benzamide,
15
4-Imidazol-1-ylmethyl-N-(7-methoxy-4-phenyl-1H-benzoimidazol-2-
yl)-benzamide,
16
4-Hydroxy-4-methyl-piperidine-1-carboxylic acid (4-cyclohexyl-7-
methoxy-1H-benzoimidazol-2-yl)-amide,
17
N-(4-Cyclohexyl-7-methoxy-1H-benzoimidazol-2-yl)-2-morpholin-4-
yl-isonicotinamide,
21
4-hydroxy-N-(7-methoxy-4-morpholino-1H-benzimidazol-2-yl)-4-
methyl-piperidine-1-carboxamide,
22
4-Hydroxy-4-methyl-piperidine-1-carboxylic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
23
N-(7-Methoxy-4-morpholin-4-yl-1H-benzoimidazol-2-yl)-2-
morpholin-4-yl-isonicotinamide,
24
4-Hydroxy-4-methyl-piperidine-1-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
26
N-[7-Methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-
2-morpholin-4-yl-isonicotinamide,
28
4-Methyl-piperidine-1-carboxylic acid (7-methoxy-4-phenyl-1H-
benzoimidazol-2-yl)-amide,
29
N-[7-Methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-6-
morpholin-4-yl-nicotinamide,
30
2-(3-Hydroxy-3-methyl-pyrrolidin-1-yl)-N-[7-methoxy-4-(1-methyl-
1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-isonicotinamide,
31
3-Hydroxy-3-methyl-pyrrolidine-1-carboxylic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
32
4-Hydroxy-4-trifluoromethyl-piperidine-1-carboxylic acid [7-
methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-
amide,
33
2-Oxa-7-aza-spiro[3.5]nonane-7-carboxylic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
34
4-Difluoromethyl-4-hydroxy-piperidine-1-carboxylic acid [7-
methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-
amide,
35
4-Hydroxymethyl-4-methyl-piperidine-1-carboxylic acid [7-methoxy-
4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
36
4-Fluoromethyl-4-hydroxy-piperidine-1-carboxylic acid [7-methoxy-
4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
37
4-Methoxy-piperidine-1-carboxylic acid [7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
38
3-Oxa-9-aza-spiro[5.5]undecane-9-carboxylic acid [7-methoxy-4-
(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
39
4-Methyl-piperidine-1-carboxylic acid [7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
40
4-Hydroxy-piperidine-1-carboxylic acid [7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
41
4-Benzyl-4-hydroxy-piperidine-1-carboxylic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
42
N-[4-methoxy-7-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-
c]pyridin-2-yl]-2-(morpholin-4-yl)pyridine-4-carboxamide,
43
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-oxa-6-azaspiro[3.4]octane-6-carboxamide,
44
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-oxo-1-oxa-3,8-diazaspiro[4.5]decane-8-carboxamide,
45
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide,
46
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]morpholine-4-carboxamide,
47
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-3-oxo-2,8-diazaspiro[4.5]decane-8-carboxamide,
48
4-[(dimethylamino)methyl]-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-
yl)-1H-1,3-benzodiazol-2-yl]benzamide,
49
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-(methoxymethyl)benzamide,
50
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxamide,
51
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-oxo-1,8-diazaspiro[4.5]decane-8-carboxamide,
52
4-(2-hydroxyethyl)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]-1,2,3,6-tetrahydropyridine-1-carboxamide,
53
3-butyl-4-hydroxy-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]piperidine-1-carboxamide,
54
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-phenoxypiperidine-1-carboxamide,
55
4-hydroxy-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-4-(pyridin-3-yl)piperidine-1-carboxamide,
56
4-hydroxy-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-3-(2-methylpropyl)piperidine-1-carboxamide,
57
N-[4-(2,6-dimethylpyridin-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-2-(morpholin-4-yl)pyridine-4-carboxamide,
58
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-oxopiperidine-1-carboxamide,
60
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxamide,
62
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-methyl-5-oxo-1,4,9-triazaspiro[5.5]undecane-9-carboxamide,
63
4-fluoro-N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-
yl]benzamide,
64
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-6-oxaspiro[2.5]octane-1-carboxamide,
65
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-{3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy}pyrazine-2-
carboxamide,
66
(chloromethyl)({2-[(1-{[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]carbamoyl}-4-methylpiperidin-4-
yl)oxy]ethyl})dimethylazanium hydrochloride,
67
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-7-oxa-2-azaspiro[4.5]decane-2-carboxamide,
68
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-8-oxa-2-azaspiro[4.5]decane-2-carboxamide,
69
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-oxa-7-azaspiro[4.4]nonane-7-carboxamide,
70
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-3-oxabicyclo[3.1.0]hexane-6-carboxamide,
71
4-[(1H-imidazol-1-yl)methyl]-N-[7-methoxy-4-(1-methyl-1H-pyrazol-
4-yl)-1H-1,3-benzodiazol-2-yl]benzamide,
72
(1S,2S)-2-bromo-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]cyclopropane-1-carboxamide,
73
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-(2-methoxyethoxy)pyrazine-2-carboxamide,
74
4-hydroxy-N-[7-methoxy-4-(pyridin-4-yl)-1H-1,3-benzodiazol-2-yl]-
4-methylpiperidine-1-carboxamide,
75
4-benzyl-4-hydroxy-N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-
benzodiazol-2-yl]piperidine-1-carboxamide,
76
4-[(1H-imidazol-1-yl)methyl]-N-[7-methoxy-4-(morpholin-4-yl)-1H-
1,3-benzodiazol-2-yl]benzamide,
77
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-1-
benzofuran-5-carboxamide,
78
4-hydroxy-N-{7-methoxy-4-[1-(oxan-2-yl)-1H-pyrazol-4-yl]-1H-1,3-
benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
79
4-hydroxy-N-[7-methoxy-4-(1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
80
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-benzofuran-5-carboxamide,
81
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-(morpholin-4-yl)pyrazine-2-carboxamide,
82
4-hydroxy-N-[4-methoxy-7-(1-methyl-1H-pyrazol-4-yl)-3H-
imidazo[4,5-c]pyridin-2-yl]-4-methylpiperidine-1-carboxamide,
83
4-benzyl-4-hydroxy-N-[4-methoxy-7-(1-methyl-1H-pyrazol-4-yl)-3H-
imidazo[4,5-c]pyridin-2-yl]piperidine-1-carboxamide,
84
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1,2-oxazole-3-carboxamide,
85
N-[7-methoxy-4-(pyridin-4-yl)-1H-1,3-benzodiazol-2-yl]-2-oxa-6-
azaspiro[3.4]octane-6-carboxamide,
86
1-(1-chloro-3-hydroxypropan-2-yl)-N-[7-methoxy-4-(morpholin-4-
yl)-1H-1,3-benzodiazol-2-yl]-1H-pyrazole-4-carboxamide,
87
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-6-(morpholin-4-yl)pyridazine-3-carboxamide,
88
4-[(dimethylamino)methyl]-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
89
4-[(dimethylamino)methyl]-N-[7-methoxy-4-(pyridin-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
90
4-[(dimethylamino)methyl]-N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
91
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-6-(morpholin-
4-yl)pyridazine-3-carboxamide,
92
4-hydroxy-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-4-(prop-2-yn-1-yl)piperidine-1-carboxamide,
93
N4-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-N1,N1-dimethylbenzene-1,4-dicarboxamide,
94
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-(trifluoromethoxy)benzamide,
95
2-bromo-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]pyridine-4-carboxamide,
96
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-methyl-1,3-oxazole-4-carboxamide,
97
4-[(1H-imidazol-1-yl)methyl]-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
98
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1,3-benzoxazole-5-carboxamide,
99
3-amino-4-hydroxy-N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
100
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-[(2-oxopyrrolidin-1-yl)methyl]benzamide,
101
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2,3-dihydro-1-benzofuran-5-carboxamide,
102
4-hydroxy-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-4-
(prop-2-yn-1-yl)piperidine-1-carboxamide,
103
4-benzyl-4-hydroxy-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-
benzodiazol-2-yl]piperidine-1-carboxamide,
104
2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-N-[7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-yl]pyridine-4-
carboxamide,
105
2-(4-hydroxy-4-methylpiperidin-1-yl)-N-[7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-1,3-benzodiazol-2-yl]pyridine-4-carboxamide,
106
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-{2-oxa-7-azaspiro[4.4]nonan-7-yl}pyridine-4-carboxamide,
107
2-[(3R)-3-hydroxy-3-methylpyrrolidin-1-yl]-N-[7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-yl]pyridine-4-
carboxamide,
108
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2,3-dihydro-
1-benzofuran-5-carboxamide,
109
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-3-(methoxymethyl)pyrrolidine-1-carboxamide,
110
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-oxa-7-
azaspiro[4.4]nonane-7-carboxamide,
111
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-8-oxa-2-
azaspiro[4.5]decane-2-carboxamide,
112
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-hexahydro-
1H-furo[3,4-c]pyrrole-5-carboxamide,
113
(5R)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-7-oxa-2-azaspiro[4.5]decane-2-carboxamide,
114
(5S)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-7-oxa-2-azaspiro[4.5]decane-2-carboxamide,
115
(5S)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-2-oxa-7-azaspiro[4.4]nonane-7-carboxamide,
116
(5R)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-2-oxa-7-azaspiro[4.4]nonane-7-carboxamide,
117
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-3-
(methoxymethyl)pyrrolidine-1-carboxamide,
118
2-(4-hydroxy-4-methylpiperidin-1-yl)-N-[7-methoxy-4-(oxan-4-yl)-
1H-1,3-benzodiazol-2-yl]pyridine-4-carboxamide,
119
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-{2-oxa-7-
azaspiro[4.4]nonan-7-yl}pyridine-4-carboxamide,
120
2-(4-fluorophenoxy)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-
1H-1,3-benzodiazol-2-yl]-2-methylpropanamide,
121
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-hexahydro-1H-furo[3,4-c]pyrrole-5-carboxamide,
122
2-(3-hydroxy-3-methylpyrrolidin-1-yl)-N-[7-methoxy-4-(oxan-4-yl)-
1H-1,3-benzodiazol-2-yl]pyridine-4-carboxamide,
123
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-2-oxa-7-
azaspiro[4.4]nonane-7-carboxamide,
124
1-{[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]carbamoyl}piperidine-4-carboxylic acid,
125
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-8-oxa-2-
azaspiro[4.5]decane-2-carboxamide,
126
N1-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]piperidine-1,4-dicarboxamide,
127
4-(diethylamino)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]benzamide,
128
4-hydroxy-N-{7-methoxy-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]-1H-
1,3-benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
129
N-[7-methoxy-4-(pyridin-4-yl)-1H-1,3-benzodiazol-2-yl]-8-oxa-2-
azaspiro[4.5]decane-2-carboxamide,
130
2-(1-{[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-
yl]carbamoyl}piperidin-4-yl)acetic acid,
131
4-hydroxy-N-[7-methoxy-4-(2-methylphenyl)-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
132
2-(1-{[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-
2-yl]carbamoyl}piperidin-4-yl)acetic acid,
133
N4-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
134
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-3-(2-methoxyethyl)pyrrolidine-1-carboxamide,
135
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-(morpholin-4-yl)pyridine-2-carboxamide,
136
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-pyrazole-4-carboxamide,
137
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-3-(2-
methoxyethyl)pyrrolidine-1-carboxamide,
138
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-4-[(2-
oxopyrrolidin-1-yl)methyl]benzamide,
139
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-5-(morpholin-
4-yl)pyridine-2-carboxamide,
140
(3R)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-3-(2-methoxyethyl)pyrrolidine-1-carboxamide,
141
(3S)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-3-(2-methoxyethyl)pyrrolidine-1-carboxamide,
142
2-[(3R)-3-hydroxy-3-methylpyrrolidin-1-yl]-N-[7-methoxy-4-(oxan-4-
yl)-1H-1,3-benzodiazol-2-yl]acetamide,
143
2-[(3S)-3-hydroxy-3-methylpyrrolidin-1-yl]-N-[7-methoxy-4-(oxan-4-
yl)-1H-1,3-benzodiazol-2-yl]acetamide,
144
N-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-4-
hydroxy-4-methylpiperidine-1-carboxamide,
145
tert-butyl 4-(4-{2-[(4-hydroxy-4-methylpiperidine-1-carbonyl)amino]-
4-methoxy-1H-1,3-benzodiazol-7-yl}-1H-pyrazol-1-yl)piperidine-1-
carboxylate,
146
4-{[2-amino-7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-1-yl]methyl}benzoic acid,
147
(3S)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-3-(methoxymethyl)pyrrolidine-1-carboxamide,
148
(3R)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-3-(methoxymethyl)pyrrolidine-1-carboxamide,
149
(5S)-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-oxa-7-
azaspiro[4.4]nonane-7-carboxamide,
150
(5R)-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-oxa-7-
azaspiro[4.4]nonane-7-carboxamide,
151
4-hydroxy-N-{7-methoxy-4-[1-(3-methylbutyl)-1H-pyrazol-4-yl]-1H-
1,3-benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
152
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-[(morpholin-4-yl)methyl]benzamide,
153
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-[(5R)-2-
oxa-7-azaspiro[4.4]nonan-7-yl]pyridine-4-carboxamide,
154
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-[(5S)-2-
oxa-7-azaspiro[4.4]nonan-7-yl]pyridine-4-carboxamide,
155
N-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-hydroxy-4-methylpiperidine-1-carboxamide,
156
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-methyl-1H-1,2,3-triazole-4-carboxamide,
157
4-hydroxy-N-{4-methoxy-7-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-
1,3-benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
158
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-(2-methoxyethoxy)pyridine-2-carboxamide,
159
2-(1-{[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-
2-yl]carbamoyl}piperidin-3-yl)acetic acid,
160
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-methyl-1H-pyrazole-4-carboxamide,
161
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
162
N5-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-N2,N2-dimethylpyridine-2,5-dicarboxamide,
163
4-hydroxy-N-[4-methoxy-1-methyl-7-(1-methyl-1H-pyrazol-4-yl)-1H-
1,3-benzodiazol-2-yl]-4-methylpiperidine-1-carboxamide,
164
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-(2-methoxyethyl)-1H-1,2,3-triazole-4-carboxamide,
165
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-methyl-1,3-thiazole-5-carboxamide,
167
1-(2-Hydroxy-ethyl)-1H-pyrazole-4-carboxylic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
168
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-[(4-methylpiperazin-1-yl)methyl]benzamide,
169
1-Methyl-1H-pyrazole-4-carboxylic acid [7-methoxy-4-(1-methyl-
1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
170
5-Methyl-isoxazole-4-carboxylic acid [7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
171
5-Cyclopropyl-isoxazole-4-carboxylic acid [7-methoxy-4-(1-methyl-
1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
172
1-Cyano-cyclopropanecarboxylic acid [7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
173
Thiazole-5-carboxylic acid [7-methoxy-4-(1-methyl-1H-pyrazol-4-
yl)-1H-benzoimidazol-2-yl]-amide,
174
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid [7-
methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-
amide,
175
4-(4-Methyl-piperazin-1-yl)-but-2-ynoic acid [7-methoxy-4-(1-
methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
179
(S)-3-Methanesulfonyl-pyrrolidine-1-carboxylic acid [7-methoxy-4-
(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
180
(S)-3-Fluoro-pyrrolidine-1-carboxylic acid [7-methoxy-4-(1-methyl-
1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
181
(S)-3-Cyano-pyrrolidine-1-carboxylic acid [7-methoxy-4-(1-methyl-
1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-amide,
182
(R)-3-Dimethylaminomethyl-pyrrolidine-1-carboxylic acid [7-
methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-benzoimidazol-2-yl]-
amide,
183
5-Methyl-isoxazole-4-carboxylic acid (7-methoxy-4-morpholin-4-yl-
1H-benzoimidazol-2-yl)-amide,
184
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-1,2,3-triazole-4-carboxamide,
185
1-Methyl-1H-[1,2,3]triazole-4-carboxyylic acid (7-methoxy-4-
morpholin-4-yl-1H-benzoimidazol-2-yl)-amide,
186
Pyridine-2,5-dicarboxylic acid 2-dimethylamide 5-{[7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide},
187
1-(2-Methoxy-ethyl)-1H-pyrazole-4-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
188
N-[7-Methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-4-
morpholin-4-ylmethyl-benzamide,
189
N-[7-Methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-4-
(4-methyl-piperazin-1-ylmethyl)-benzamide,
190
1-Methyl-1H-pyrazole-4-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
191
5-Methyl-isoxazole-4-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
192
5-Cyclopropyl-isoxazole-4-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
193
1-(2-Methoxy-ethyl)-1H-[1,2,3]triazole-4-carboylic acid [7-
methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
194
1-Methyl-1H-[1,2,3]triazole-4-carboylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
195
1-Cyano-cyclopropanecarboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
196
Thiazole-5-carboxylic acid [7-methoxy-4-(tetrahydro-pyran-4-yl)-
1H-benzoimidazol-2-yl]-amide,
197
2-Methyl-oxazole-5-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
198
2-Methyl-thiazole-5-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
199
Imidazo[1,2-a]pyridine-3-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
200
5-Amino-2H-[1,2,4]triazole-3-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
201
(S)-3-Methanesulfonyl-pyrrolidine-1-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
202
(S)-3-Fluoro-pyrrolidine-1-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
203
(S)-3-Cyano-pyrrolidine-1-carboxylic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
204
(R)-3-Dimethylaminomethyl-pyrrolidine-1-carboxylic acid [7-
methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
205
Pyrazolo[1,5-a]pyridine-3-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
206
1H-[1,2,4]Triazole-3-carboxylic acid [7-methoxy-4-(tetrahydro-
pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
207
5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid [7-
methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
208
2,3-Dimethyl-3H-imidazole-4-sulfonic acid [7-methoxy-4-
(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-amide,
209
1-[7-Methoxy-4-(tetrahydro-pyran-4-yl)-1H-benzoimidazol-2-yl]-3-
thiazol-2-ylmethyl-urea,
210
N-[7-methoxy-4-(morpholin-4-yl)-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-1,2,3-triazole-4-carboxamide,
211
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-1,2,3-triazole-4-carboxamide,
212
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-1-methyl-1H-
1,2,3-triazole-4-carboxamide,
213
1-cyano-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]cyclopropane-1-carboxamide,
214
N5-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-N2,N2-
dimethylpyridine-2,5-dicarboxamide,
215
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-2-methyl-1,3-oxazole-5-carboxamide,
216
N-[4-(azepan-1-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-4-hydroxy-
4-methylpiperidine-1-carboxamide,
217
N-[4-(3-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-4-
hydroxy-4-methylpiperidine-1-carboxamide,
218
N-[4-(2-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-4-
hydroxy-4-methylpiperidine-1-carboxamide,
219
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1,3-thiazole-5-carboxamide,
220
(3R)-3-methanesulfonyl-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-
yl)-1H-1,3-benzodiazol-2-yl]pyrrolidine-1-carboxamide,
221
(3S)-3-fluoro-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]pyrrolidine-1-carboxamide,
222
4-hydroxy-N-[7-methoxy-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-
yl)-1H-1,3-benzodiazol-2-yl]-4-methylpiperidine-1-carboxamide,
223
(3S)-3-(aminomethyl)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-
1H-1,3-benzodiazol-2-yl]pyrrolidine-1-carboxamide,
224
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-1-methyl-1H-
pyrazole-4-carboxamide,
225
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
226
1-cyano-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-
yl]cyclopropane-1-carboxamide,
227
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-methyl-1,3-
thiazole-5-carboxamide,
228
3-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-1-[(1,3-
thiazol-2-yl)methyl]urea,
229
N-{7-[1-(difluoromethyl)-1H-pyrazol-4-yl]-4-methoxy-1H-1,3-
benzodiazol-2-yl}-4-hydroxy-4-methylpiperidine-1-carboxamide,
230
4-hydroxy-N-(4-methoxy-7-{1-[2-(2-methoxyethoxy)ethyl]-1H-
pyrazol-4-yl}-1H-1,3-benzodiazol-2-yl)-4-methylpiperidine-1-
carboxamide,
231
4-hydroxy-N-{4-methoxy-7-[1-(pyridin-2-yl)-1H-pyrazol-4-yl]-1H-
1,3-benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
232
N-[7-methoxy-4-(1-propylcyclopropyl)-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-pyrazole-4-carboxamide,
233
N-[4-(hexan-3-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-methyl-
1H-pyrazole-4-carboxamide,
234
N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-2-methyl-1,3-
oxazole-5-carboxamide,
235
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-4-[(4-methylpiperazin-1-yl)methyl]benzamide,
236
4-hydroxy-N-{4-methoxy-7-[3-(2-methoxyethoxy)phenyl]-1H-1,3-
benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
237
4-hydroxy-N-(4-methoxy-7-{1-[(pyridin-3-yl)methyl]-1H-pyrazol-4-
yl}-1H-1,3-benzodiazol-2-yl)-4-methylpiperidine-1-carboxamide,
238
4-hydroxy-N-{7-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-4-
methoxy-1H-1,3-benzodiazol-2-yl}-4-methylpiperidine-1-
carboxamide,
239
N-[4-(3-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-pyrazole-4-carboxamide,
240
N4-[4-(3-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
241
4-hydroxy-N-{4-methoxy-7-[1-(oxolan-3-yl)-1H-pyrazol-4-yl]-1H-
1,3-benzodiazol-2-yl}-4-methylpiperidine-1-carboxamide,
242
N4-[4-(2-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
243
N-[4-(2-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-pyrazole-4-carboxamide,
244
N-[4-methoxy-1-methyl-7-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-
benzodiazol-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,
245
tert-butyl 3-(4-{2-[(4-hydroxy-4-methylpiperidine-1-carbonyl)amino]-
4-methoxy-1H-1,3-benzodiazol-7-yl}-1H-pyrazol-1-yl)azetidine-1-
carboxylate,
246
N-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-5-oxopyrrolidine-3-carboxamide,
247
3-[7-methoxy-4-(1-methyl-1H-pyrazol-4-yl)-1H-1,3-benzodiazol-2-
yl]-1-[(1,3-thiazol-2-yl)methyl]urea,
248
4-(2,5-dioxopyrrolidin-1-yl)-N-[7-methoxy-4-(1-methyl-1H-pyrazol-
4-yl)-1H-1,3-benzodiazol-2-yl]benzamide,
249
1-[(3R,4S)-4-fluoropyrrolidin-3-yl]-3-[7-methoxy-4-(1-methyl-1H-
pyrazol-4-yl)-1H-1,3-benzodiazol-2-yl]urea,
250
4-(2,5-dioxopyrrolidin-1-yl)-N-[7-methoxy-4-(oxan-4-yl)-1H-1,3-
benzodiazol-2-yl]benzamide,
251
tert-butyl (3S,4R)-3-fluoro-4-({[7-methoxy-4-(1-methyl-1H-pyrazol-
4-yl)-1H-1,3-benzodiazol-2-yl]carbamoyl}amino)pyrrolidine-1-
carboxylate,
252
N4-[7-methoxy-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-1,3-
benzodiazol-2-yl]-N1,N1-dimethylbenzene-1,4-dicarboxamide,
253
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1H-imidazole-4-
carboxamide,
254
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1-methyl-1H-
imidazole-5-carboxamide,
255
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-2-methyl-1H-
imidazole-4-carboxamide,
256
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1,3-thiazole-5-
carboxamide,
257
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-2-methyl-1,3-
thiazole-5-carboxamide,
258
2-amino-N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1,3-
thiazole-5-carboxamide,
259
N4-[7-methoxy-4-(pyridin-3-yl)-1H-1,3-benzodiazol-2-yl]-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
260
N-[7-methoxy-4-(pyridin-3-yl)-1H-1,3-benzodiazol-2-yl]-1-methyl-
1H-pyrazole-4-carboxamide,
261
N4-[4-(2,5-dihydrofuran-3-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-
N1,N1-dimethylbenzene-1,4-dicarboxamide,
262
N4-[4-(3,6-dihydro-2H-pyran-4-yl)-5-fluoro-7-methoxy-1H-1,3-
benzodiazol-2-yl]N1,N1-dimethylbenzene-1,4-dicarboxamide,
263
3-{[dimethyl(oxo)-lambda6-sulfanylidene]amino}-N-[7-methoxy-4-
(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]benzamide,
264
N-[4-(3,6-dihydro-2H-pyran-4-yl)-5-fluoro-7-methoxy-1H-1,3-
benzodiazol-2-yl]-1-methyl-1H-pyrazole-4-carboxamide,
265
N-[7-(3-fluorophenyl)-4-methoxy-1H-1,3-benzodiazol-2-yl]-1H-
imidazole-4-carboxamide,
266
N-[4-methoxy-7-(pyridin-4-yl)-1H-1,3-benzodiazol-2-yl]-1H-
imidazole-4-carboxamide,
267
N-{4-methoxy-7-[3-(2-methoxyethoxy)phenyl]-1H-1,3-benzodiazol-
2-yl}-1H-imidazole-4-carboxamide,
268
N-[4-methoxy-7-(pyridin-3-yl)-1H-1,3-benzodiazol-2-yl]-1H-
imidazole-4-carboxamide,
269
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1,3-dimethyl-1H-
pyrazole-4-carboxamide,
270
4-hydroxy-N-(7-methoxy-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-1,3-
benzodiazol-2-yl)-4-methylpiperidine-1-carboxamide,
271
4-hydroxy-N-[4-(1H-indazol-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
272
4-hydroxy-N-[4-(1H-indol-6-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
273
4-hydroxy-N-[7-methoxy-4-(1-methyl-1H-indazol-5-yl)-1H-1,3-
benzodiazol-2-yl]-4-methylpiperidine-1-carboxamide,
274
4-hydroxy-N-[7-methoxy-4-(3-methyl-1H-indazol-5-yl)-1H-1,3-
benzodiazol-2-yl]-4-methylpiperidine-1-carboxamide,
275
4-hydroxy-N-(4-{imidazo[1,2-a]pyridin-7-yl}-7-methoxy-1H-1,3-
benzodiazol-2-yl)-4-methylpiperidine-1-carboxamide,
277
N4-[5-fluoro-7-methoxy-4-(oxan-4-yl)-1H-1,3-benzodiazol-2-yl]-
N1,N1-dimethylbenzene-1,4-dicarboxamide,
278
N-(7-methoxy-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-1,3-benzodiazol-
2-yl)-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
279
N-[4-(1H-indazol-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
280
N-[4-(1H-indo1-6-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
281
N-[7-methoxy-4-(1-methyl-1H-indazol-5-yl)-1H-1,3-benzodiazol-2-
yl]-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
282
N-[7-methoxy-4-(3-methyl-1H-indazol-5-yl)-1H-1,3-benzodiazol-2-
yl]-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
283
N-[4-(2,3-dihydro-1H-indo1-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
284
N2-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-N5,N5-
dimethylpyridine-2,5-dicarboxamide,
285
4-(2,5-dioxopyrrolidin-1-yl)-N-(7-methoxy-4-phenyl-1H-1,3-
benzodiazol-2-yl)benzamide,
286
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)imidazo[1,2-
a]pyridine-3-carboxamide,
287
4,4-difluoro-N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-
yl)pipendine-1-carboxamide,
288
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)imidazo[1,2-
b]pyridazine-3-carboxamide,
289
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)imidazo[1,2-
a]pyrimidine-3-carboxamide,
290
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-2-(pyridin-4-yl)-
1H-imidazole-4-carboxamide,
291
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-5H,6H,7H,8H-
imidazo[1,2-a]pyridine-3-carboxamide,
292
N-[4-(2,3-dihydro-1H-indo1-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-hydroxy-4-methylpiperidine-1-carboxamide,
293
N1-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-2-yl)-N4-
propylbenzene-1,4-dicarboxamide,
294
N-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-2-yl)-4-(4-
methylpiperazine-1-carbonyl)benzamide,
295
N4-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-2-yl)-N1-(2-
methoxyethyl)-N1-methylbenzene-1,4-dicarboxamide,
296
N1-[2-(dimethylamino)ethyl]-N4-(4-methoxy-7-phenyl-1H-1,3-
benzodiazol-2-yl)-N1-methylbenzene-1,4-dicarboxamide,
297
N4-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-2-yl)-N1-methyl-N1-
propylbenzene-1,4-dicarboxamide,
298
N-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-2-yl)-4-(morpholine-4-
carbonyl)benzamide,
299
N-[4-methoxy-7-(2-methylpyridin-4-yl)-1H-1,3-benzodiazol-2-yl]-
1H-imidazole-4-carboxamide,
300
N-(5-cyano-7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1-
methyl-1H-pyrazole-4-carboxamide,
301
N-(4-{imidazo[1,2-a]pyridin-7-yl}-7-methoxy-1H-1,3-benzodiazol-2-
yl)-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide,
302
N-[4-(1H-indo1-5-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
303
4-hydroxy-N-[4-(1H-indo1-5-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
304
N-[4-(1H-indo1-7-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
305
4-hydroxy-N-[4-(1H-indo1-7-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-methylpiperidine-1-carboxamide,
306
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1-methyl-1H-
pyrazole-4-carboxamide,
307
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-1-(2-
methoxyethyl)-1H-pyrazole-4-carboxamide,
308
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-2-methyl-1,3-
oxazole-5-carboxamide,
309
N4-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
310
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-8-oxa-2-
azaspiro[4.5]decane-2-carboxamide,
311
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-4-[(2-
oxopyrrolidin-1-yl)methyl]benzamide,
312
N1-(2-hydroxyethyl)-N4-(4-methoxy-7-phenyl-1H-1,3-benzodiazol-
2-yl)benzene-1,4-dicarboxamide,
313
N4-[7-methoxy-4-(1,4-oxazepan-4-yl)-1H-1,3-benzodiazol-2-yl]-
N1,N1-dimethylbenzene-1,4-dicarboxamide,
314
N-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]cyclopropanecarboxamide,
315
N-[7-methoxy-4-(pyridin-3-yl)-1H-1,3-benzodiazol-2-
yl]cyclopropanecarboxamide,
316
N4-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-N1,N1-
dimethylbenzene-1,4-dicarboxamide,
317
4-(2,5-dioxopyrrolidin-1-yl)-N-[4-(4-fluorophenyl)-7-methoxy-1H-
1,3-benzodiazol-2-yl]benzamide,
318
N-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-
methyl-1H-pyrazole-4-carboxamide,
319
N4-[4-(2,6-dimethoxypyridin-3-yl)-7-methoxy-1H-1,3-benzodiazol-
2-yl]-N1,N1-dimethylbenzene-1,4-dicarboxamide,
320
N-[4-(2,6-dimethoxypyridin-3-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]cyclopropanecarboxamide,
321
N-[7-methoxy-4-(pyridin-3-yl)-1H-1,3-benzodiazol-2-yl]-2-methyl-
1,3-oxazole-5-carboxamide,
322
N-[4-(2,5-dihydrofuran-3-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-2-
methyl-1,3-oxazole-5-carboxamide,
323
N-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-2-
methyl-1,3-oxazole-5-carboxamide,
324
N4-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-
2-yl]-N1,N1-dimethylbenzene-1,4-dicarboxamide,
325
N-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-1-methyl-1H-pyrazole-4-carboxamide,
326
(4-{2-[(4-hydroxy-4-methylpiperidine-1-carbonyl)amino]-7-methoxy-
1H-1,3-benzodiazol-4-yl}morpholin-2-yl)methyl carbamate,
327
(1-{2-[(4-hydroxy-4-methylpiperidine-1-carbonyl)amino]-7-methoxy-
1H-1,3-benzodiazol-4-yl}piperidin-3-yl)methyl cyanate,
328
(1-{2-[(4-hydroxy-4-methylpiperidine-1-carbonyl)amino]-7-methoxy-
1H-1,3-benzodiazol-4-yl}piperidin-3-yl)methyl carbamate,
329
N-(7-methoxy-4-phenyl-1H-1,3-benzodiazol-2-yl)-2-oxa-8-
azaspiro[4.5]decane-8-carboxamide,
330
N-[4-(1H-indo1-6-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1H-
imidazole-4-carboxamide,
331
N-[4-(1H-indo1-6-yl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-1-methyl-
1H-pyrazole-4-carboxamide,
332
N-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-8-oxa-2-
azaspiro[4.5]decane-2-carboxamide,
333
N-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-8-oxa-2-azaspiro[4.5]decane-2-carboxamide,
334
N-[4-(3,6-dihydro-2H-pyran-4-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]-4-[(2-oxopyrrolidin-1-yl)methyl]benzamide,
335
N-[4-(4-fluorophenyl)-7-methoxy-1H-1,3-benzodiazol-2-yl]-4-[(2-
oxopyrrolidin-1-yl)methyl]benzamide,
336
N-[4-(1H-indo1-6-yl)-7-methoxy-1H-1,3-benzodiazol-2-
yl]cyclopropanecarboxamide,
and physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios.
5. A process for the preparation of a compound of the formula I, of claim 1 , comprising
a) a compound of the formula II undergoes a nitration reaction, followed by a reduction to give a compound of formula IV, a compound of formula IVI is cyclized to give a compound of formula V, a compound of formula V is reacted in a Suzuki type reaction to formula VI employing the use of catalyst and base, a compound of formula VI is converted to a compound of the formula VII by standard amidation or carbamide formation conditions to give a compound of the formula I
b) a compound of the formula III is reacted with a boronic ester or acid under Suzuki-type reaction conditions to give a compound of the formula VII or reacted with an amine in a nucleophilic substitution reaction under increased temperature to form a compound of the formula VII, a compound of formula VII is reduced to a compound of the formula VII and cyclized to a compound of the formula VI and finally reacted with to compound of the formula I under standard amidation or carbamide formation conditions
c) the base of a compound of the formula I is converted into one of its salts by treatment with an acid, or
d) an acid of a compound of the formula I is converted into one of its salts by treatment with a base.
6. A method of inhibiting adenosine A 2A and/or A 2B receptors in a host in need thereof, comprising administering to said host a compound according to claim 1 or physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios an amount effective to inhibit adenosine A 2A and/or A 2B receptors.
7. A pharmaceutical preparation comprising at least one compound according to claim 1 and/or physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios.
8. The pharmaceutical preparation according to claim 7 comprising further excipients and/or adjuvants.
9. The pharmaceutical preparation comprising at least one compound according to claim 1 and/or physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios, and at least one further medicament active compound.
10. A kit consisting of separate packs of
a) an effective amount of a compound according to claim 1 and/or physiologically acceptable salts, solvates, prodrugs and stereoisomers thereof, including mixtures thereof in all ratios, and
b) an effective amount of a further medicament active compound.