Substituted benzimidazoles and imidazo-[4,5]-pyridines
2-Aryl substituted benzimidazoles and imidazo[4,5]pyridines are disclosed as inhibitors of Cds1 and useful as adjuvants to chemotherapy or radiation therapy in the treatment of cancer.
1. A compound of the formula:
wherein
W is COOH, —(CO)NHR 1 , or —(SO 2 )NHR 1 ;
R 1 is H or C 1-4 alkyl;
Q is CH;
R a and R b are H or halogen;
Y, Y 1 and Y 2 are independently selected from N and C—R c with the proviso that 0, 1 or 2 of Y, Y 1 and Y 2 are N and at least 2 of R c must be hydrogen;
R c are independently selected from the group consisting of —H, —OH, —C 1-6 alkyl, —SCF 3 , halo, —CF 3 and —OCF 3 ;
Z is selected from the group consisting of O, S, SO, SO 2 , SO 2 NR 2 , NR 2 SO 2 , NH, CONR 2 , piperazin-diyl or a covalent bond;
R 2 is H or C 1-4 alkyl;
Ar 1 is selected from the group consisting of:
a) phenyl, optionally mono-, di- or tri-substituted with R p ;
R p is selected from the group consisting of —OH, —C 1-6 alkyl, —OC 1-6 alkyl, —C 3-6 cycloalkyl, —OC 3-6 cycloalkyl, —CN, —NO 2 , —N(R y )R z (wherein R y and R z are independently selected from H or C 1-6 alkyl, or may be taken together with the nitrogen of attachment to form an otherwise aliphatic hydrocarbon ring, said ring having 5 to 7 members, optionally having one carbon replaced with >O, ═N—, >NH or >N(C 1-4 alkyl) and optionally having one or two unsaturated bonds in the ring), —(C═O)N(R y )R z , —(N—R t )COR t (wherein R t is independently H or C 1-6 alkyl), —(N—R t )SO 2 C 1-6 alkyl, —(C═O)C 1-6 alkyl, —(S═(O) n )—C 1-6 alkyl (wherein n is selected from 0, 1 or 2), —SO 2 N(R y )R z , —SCF 3 , halo, —CF 3 , —OCF 3 , —COOH, —C 1-6 alkylCOOH, —COOC 1-6 alkyl and —C 1-6 alkylCOOC 1-6 alkyl;
b) phenyl, attached at two adjacent ring members to a C 3-5 alkyl moiety to form a fused 5 to 7 membered ring, said fused ring optionally having a second unsaturated bond, said fused ring optionally having one or two members replaced with, ═N—, >O, >NH or >N(C 1-4 alkyl) except that no such replacement is permitted where the fused ring is 5 membered and has a second unsaturated bond, and said fused ring optionally having one carbon member replaced with >C═O, the fused rings optionally mono-, di- or tri-substituted with R p ;
c) a monocyclic aromatic hydrocarbon group having six ring carbon atoms, having a carbon atom which is the point of attachment, having one or two carbon atoms replaced by N, and optionally mono- or di-substituted with R p ;
d) a monocyclic aromatic hydrocarbon group having six ring carbon atoms, having a carbon atom which is the point of attachment, having zero, one or two carbon atoms replaced by N, and having attachment at two adjacent carbon ring members to a three membered hydrocarbon moiety to form a fused five membered aromatic ring, which moiety has one carbon atom replaced by >O, >S, >NH or >N(C 1-4 alkyl) and which moiety has up to one additional carbon atom optionally replaced by N, the fused rings optionally mono-, di- or tri-substituted with R p ;
e) a monocyclic aromatic hydrocarbon group having six ring carbon atoms, having a carbon atom which is the point of attachment, having zero, one or two carbon atoms replaced by N, and having attachment at two adjacent carbon ring members to a four membered hydrocarbon moiety to form a fused six membered aromatic ring, which moiety has zero, one or two carbon atoms replaced by N, the fused rings optionally mono-, di- or tri-substituted with R p ;
f) a monocyclic aromatic hydrocarbon group having five ring carbon atoms, having a carbon atom which is the point of attachment, having one carbon atom replaced by >O, >S, >NH or >N(C 1-4 alkyl), having up to one additional carbon atom optionally replaced by N, and optionally mono- or di-substituted with R p ;
g) a monocyclic aromatic hydrocarbon group having five ring carbon atoms, having a carbon atom which is the point of attachment, having one carbon atom replaced by >O, >S, >NH or >N(C 1-4 alkyl), and having attachment at two adjacent carbon ring members to a four membered hydrocarbon moiety to form a fused six membered aromatic ring, which moiety has zero, one or two carbon atoms replaced by N, the fused rings optionally mono-, di- or tri-substituted with R p , provided that when W is —COOH, Z is not O; and
and enantiomers, diastereomers and pharmaceutically acceptable salts, esters or amides thereof.
2. The compound of claim 1 wherein W is COOH, —(CO)NHCH 3 , —(CO)NH 2 , —(SO 2 )NHCH 3 or —(SO 2 )NH 2 .
3. The compound of claim 1 wherein W is COOH, —(CO)NH 2 or —(SO 2 )NH 2 .
4. The compound of claim 1 wherein R a and R b are independently H, Cl or F.
5. The compound of claim 1 wherein Y, Y 1 and Y 2 are C—R c .
6. The compound of claim 1 wherein R c is selected from the group consisting of —H, —OH, —CH 3 , —CH 2 CH 3 , —SCF 3 , —F, —Cl, —Br, I, —CF 3 and —OCF 3 .
7. The compound of claim 1 wherein R c is selected from the group consisting of H, F, Cl, CH 3 , OCH 3 .
8. The compound of claim 1 wherein Z is selected from the group consisting of O, S, SO, SO 2 , SO 2 NH, SO 2 NCH 3 , NHSO 2 , NCH 3 SO 2 , NH, CONH, CONCH 3 , piperazin-1,4-diyl and a covalent bond.
9. The compound of claim 1 wherein Z is selected from the group consisting of O, S, SO, SO 2 , SO 2 NH, NHSO 2 , NH and CONH.
10. The compound of claim 1 wherein Z is selected from the group consisting of O, S, SO, SO 2 and SO 2 NH.
11. The compound of claim 1 wherein Ar 1 , optionally substituted with R p , is selected from the group consisting of:
a) phenyl,
b) tetralin-5,6,7 or 8-yl, chroman-5,6,7 or 8-yl, benzo-1,2-pyran-5,6,7 8-yl, benzo-2,3-pyron-5,6,7 or 8-yl, coumarin-5,6,7 or 8-yl, isocoumarin-5,6,7 or 8-yl, benzo-1,3,2-benzoxazin-5,6,7 or 8-yl, benzo-1,4-dioxan-5,6,7 or 8-yl, 1,2,3,4-tetrahydroquinolin-5,6,7 or 8-yl, 1,2,3,4-tetrahydroquinoxalin-5,6,7 or 8-yl, thiochroman-5,6,7 or 8-yl, 2,3-dihydrobenzo[1,4]dithiin-5,6,7 or 8-yl, 1,2,3,4-tetrahydroisoquinolin-5,6,7 or 8-yl, indene-4,5,6, or 7-yl, 1,2,3,4-tetrahydronapth-5,6,7, or 8 yl, 1,2-dihydroisoindolo-4,5,6, or 7-yl, 2,3-dihydroindene-4,5,6, or 7-yl, benzo-1,3-dioxol-4,5,6 or 7-yl, 2,3-dihydroindol-4,5,6 or 7-yl, 2,3-dihydrobenzofuran-4,5,6 or 7-yl, 2,3-dihydrobenzothiophen-4,5,6 or 7-yl, 2,3-dihydrobenzoimidazol-4,5,6 or 7-yl,
c) pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl,
d) benzoxazol-4,5,6 or 7-yl, benzothiophen-4,5,6 or 7-yl, benzofuran-4,5,6 or 7-yl, indol-4,5,6 or 7-yl, benzthiazol-4,5,6 or 7-yl, benzimidazo-4,5,6 or 7-yl, indazol-4,5,6 or 7-yl, 1H-pyrrolo[2,3-b]pyridin-4,5 or 6-yl, 1H-pyrrolo[3,2-c]pyridin-4,6 or 7-yl, 1H-pyrrolo[2,3-c]pyridin-4,5 or 7-yl, 1H-pyrrolo[3,2-b]pyridin-5,6 or 7-yl, purin-2-yl,
e) isoquinolin-5,6,7 or 8-yl, quinolin-5,6,7 or 8-yl, quinoxalin-5,6,7 or 8-yl, quinazolin-5,6,7 or 8-yl, naphthyridinyl,
f) furanyl, oxazolyl, isoxazolyl, thiophenyl, thiazolyl, isothiazolyl, pyrrolyl, imidazolyl, pyrazolyl, and
g) benzothiophen-2 or 3-yl, benzofuran-2 or 3-yl, indol-2 or 3yl, 1H-pyrrolo[2,3-b]pyridin-2 or 3-yl, 1H-pyrrolo[3,2-c]pyridin-2 or 3-yl, 1H-pyrrolo[2,3-c]pyridin-2 or 3-yl, 1H-pyrrolo[3,2-b]pyridin-2 or 3-yl.
12. The compound of claim 1 wherein Ar 1 , optionally substituted with R p , is selected from the group consisting of:
a) phenyl,
b) coumarin-5,6,7 or 8-yl, benzo-1,4-dioxan-5,6,7 or 8-yl, 1,2,3,4-tetrahydroquinolin-5,6,7 or 8-yl, or 8-yl, 1,2,3,4-tetrahydroisoquinolin-5,6,7 or 8-yl, indene-4,5,6, or 7-yl, 1,2,3,4-tetrahydronapth-5,6,7, or 8 yl, 1,2-dihydroisoindolo-4,5,6, or 7-yl, 2,3-dihydroindene-4,5,6, or 7-yl, benzo-1,3-dioxol-4,5,6 or 7-yl, 2,3-dihydroindol-4,5,6 or 7-yl, 2,3-dihydrobenzofuran-4,5,6 or 7-yl, 2,3-dihydrobenzothiophen-4,5,6 or 7-yl,
c) pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl,
d) benzothiophen-4,5,6 or 7-yl, benzofuran-4,5,6 or 7-yl, indol-4,5,6 or 7-yl,
e) isoquinolin-5,6,7 or 8-yl, quinolin-5,6,7 or 8-yl,
f) furanyl, oxazolyl, isoxazolyl, thiophenyl, thiazolyl, isothiazolyl, pyrrolyl, imidazolyl, pyrazolyl, and
g) benzothiophen-2 or 3-yl, benzofuran-2 or 3-yl, indol-2 or 3-yl.
13. The compound of claim 1 wherein Ar 1 , optionally substituted with R p , is selected from the group consisting of: phenyl, benzo-1,4-dioxan-5,6,7 or 8-yl, indene-4,5,6, or 7-yl, 1,2,3,4-tetrahydronapth-5,6,7, or 8 yl, 2,3-dihydroindene-4, 5,6, or 7-yl, benzo-1,3-dioxol-4,5,6 or 7-yl, 2,3-dihydroindol-4,5,6 or 7-yl, 2,3-dihydrobenzofuran-4,5,6 or 7-yl, 2,3-dihydrobenzothiophen-4,5,6 or 7-yl, pyridinyl, benzothiophen-4,5,6 or 7-yl, benzofuran-4,5,6 or 7-yl, indol-4,5,6 or 7-yl, furanyl, thiophenyl, pyrrolyl, pyrazolyl, and benzothiophen-2 or 3-yl, benzofuran-2 or 3-yl and indol-2 or 3yl.
14. The compound of claim 1 wherein Ar 1 , including the R p substituent, is selected from the group consisting of pyridyl, phenyl, naphthyl, 4-chloro phenyl, 4-methyl-3-chloro phenyl, 4-chloro-3-trifluoromethyl phenyl, 3,4-dichloro phenyl, 3-chloro-4-fluoro phenyl, 2-flouro-5-trifluoromethyl, 4-chloro-3-fluoro phenyl, 3,4-dimethyl phenyl, 2-napthyl, 4-trifluoromethyl phenyl, 4-bromo phenyl, 4-fluoro-3-methyl phenyl, 3-chloro phenyl, tetrahydronapthyl, 5-chloro-2-methyl phenyl, 3-trifluoromethyl phenyl, 4-methoxy phenyl, 4-methyl phenyl, 2-fluoro-3-trifluoromethyl phenyl, 2-chloro-4-methyl phenyl, 4-ethyl phenyl, 4-fluoro phenyl, 3,4-dimethoxy phenyl, 3-(dimethylamino) phenyl, 4-nitro phenyl, 4-cyano phenyl, 2-methoxy-4-methyl phenyl, 4-trifluoromethoxy phenyl, 2-chloro phenyl, 4-morpholino phenyl, 3-chloro phenyl, 2,3-dichloro phenyl, benzo[1,3]dioxolyl, 4-amino phenyl, 4-hydroxy phenyl, 4-bromo-3-hydroxy phenyl, 4-chloro-2-hydroxy phenyl, 4-chloro-3-hydroxy phenyl, 2,4-dichloro phenyl, 4-bromo-3-methoxy phenyl and 4-iodo phenyl.
15. The compound of claim 1 wherein R p is selected from the group consisting of —OH, —CH 3 , —CH 2 CH 3 , —OCH 3 , —OCH 2 CH 3 , —OCH(CH 3 ) 2 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -Ocyclopentyl, -Ocyclohexyl, —CN, —NO 2 , —C(O)NH 2 , —C(O)N(CH 3 ) 2 , —C(O)NH(CH 3 ), —NHCOCH 3 , —NCH 3 COCH 3 , —NHSO 2 CH 3 , —NCH 3 SO 2 CH 3 , —C(O)CH 3 , —SOCH 3 , —SO 2 CH 3 , —SO 2 NH 2 , —SO 2 NHCH 3 , —SO 2 N(CH 3 ) 2 , —SCF 3 —F, —Cl, —Br, I, —CF 3 , —OCF 3 , —COOH, —COOCH 3 , —COOCH 2 CH 3 , —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —N(CH 2 CH 3 ) 2 , —NCH 3 (CH(CH 3 ) 2 ), imidazolidin-1-yl, 2-imidazolin-1-yl, pyrazolidin-1-yl, piperidin-1-yl, 2- or 3-pyrrolin-1-yl, 2-pyrazolinyl, morpholin-4-yl, thiomorpholin-4-yl, piperazin-1-yl, pyrrolidin-1-yl, homopiperidin-1-yl.
16. The compound of claim 1 wherein R p is selected from the group consisting of H, —OH, OCH 3 , OCF 3 , —CH 3 , —CH 2 CH 3 , —CF 3 , —F, —Cl, —Br, —I, —NH 2 , —N(CH 3 ) 2 , morpholin-4-yl, —NO 2 , CN, —C(O)NH 2 , —COOH, —NHSO 2 CH 3 , —SO 2 NH 2 .
17. A compound selected from the group consisting of:
EX
Compound Name
1
2-[4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
2
2-[4-(3-chloro-4-methyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
3
2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
4
2-[4-(3,4-dichloro-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
5
2-[4-(3-chloro-4-fluoro-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
6
2-[4-(2-fluoro-5-trifluoromethyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
7
2-[4-(4-chloro-3-fluoro-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
8
2-[4-(3,4-dimethyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
9
2-[4-(2-naphthyloxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
10
2-[4-(4-trifluoromethyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
11
2-[4-(4-bromo-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
12
2-[4-(4-fluoro-3-methyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
13
2-[4-(3-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
14
2-[4-(5,6,7,8-tetrahydro-naphthalen-2-yloxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
15
2-[4-(5-chloro-2-methyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
16
2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
17
2-[4-(4-methoxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
18
2-[4-(4-methyl-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
19
2-[4-(2-fluoro-3-trifluoromethyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
20
2-[4-(2-chloro-4-methyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
21
2-[4-(4-ethyl-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
22
2-[4-(4-fluoro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
23
2-[4-(3,4-dimethoxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
24
2-[4-(4-carbamoyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
25
2-[4-(3-(N,N-dimethyl)amino-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
26
2-[4-(4-nitro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
27
2-[4-(4-cyano-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
28
3-{4-[4-(5-carbamoyl-1H-benzoimidazol-2-yl)-phenoxy]-phenyl}-
propionic acid
29
2-[4-(3-carboxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
30
2-[4-(3-diethylcarbamoyl-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
31
2-[4-(3-pyridyloxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid
amide
32
2-[3-chloro-4-(3,4-dimethoxy-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
33
2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
34
2-[3-chloro-4-(4-fluoro-3-methyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
35
2-[3-chloro-4-(2-methoxy-4-methyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
36
2-[3-chloro-4-(3-chloro-4-methyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
37
2-(6-p-tolyloxy-pyridin-3-yl)-1H-benzoimidazole-5-carboxylic acid
amide
38
2-[4-(3-chloro-4-fluoro-phenylsulfanyl)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
39
2-[4-(4-ethyl-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
40
2-[4-(3,4-dimethoxy-phenylsulfanyl)-phenyl]-1H-benzoimidazole-
5-carboxylic acid amide
41
2-[4-(4-chloro-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
42
2-[6-(4-chloro-phenylsulfanyl)-pyridin-3-yl]-1H-benzoimidazole-5-
carboxylic acid amide
43
2-[6-(4-methyl-phenylsulfanyl)-pyridin-3-yl]-1H-benzoimidazole-
5-carboxylic acid amide
44
2-[4-(4-trifluoromethoxy-phenylsulfanyl)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
45
2-[4-(4-fluoro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
46
2-[4-phenyl-phenyl]-1H-benzoimidazole-5-carboxylic acid amide
47
2-[4-(2-chloro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
48
2-[4-(4-chloro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
49
2-[4-(2-pyridyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid
amide
50
2-[4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid
51
2-[4-(4-methoxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid
52
2-[4-(4-fluoro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid
53
2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid
54
2-[4-(4-nitro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid
55
2-[4-(4-chloro-phenyl)-phenyl]-1H-benzoimidazole-5-carboxylic
acid
56
2-[4-phenoxy-phenyl]-1H-benzoimidazole-5-carboxylic acid
57
2-(4-phenoxy-phenyl]-1H-benzoimidazole-5-sulfonic acid amide
58
2-[4-(3,4-dichloro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-
5-carboxylic acid amide
59
2-[4-(4-chloro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
60
2-[4-(4-nitro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
61
2-[4-(4-bromo-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
62
2-[4-(4-trifluoromethyl-phenylsulfamoyl)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
63
2-[4-(2-naphthylsulfamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
64
2-[4-(4-methoxy-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
65
2-{4-[(4-chloro-phenyl)-methyl-sulfamoyl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
66
2-[4-(4-morpholino-4-yl-phenylsulfamoyl)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
67
2-[4-(3,4-dichloro-benzenesulfonylamino)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
68
6-chloro-2-[4-(3,4-dichloro-phenoxy)-phenyl]-1H-benzoimidazole-
5-carboxylic acid amide
69
2-[4-(4-methoxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid methylamide
70
2-[4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid methylamide
71
2-[4-(4-chloro-benzenesulfonyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
72
2-[4-(4-chloro-benzenesulfinyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
73
2-[4-(4-chloro-benzenesulfonyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid
74
2-[4-(4-chloro-benzenesulfinyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid
75
2-[4-(3,4-dichloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-
carboxylic acid amide
76
2-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-
carboxylic acid amide
77
2-{4-[4-(4-fluoro-phenyl)-piperazin-1-yl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
78
2-{4-[4-(pyridin-2-yl)-piperazin-1-yl]-phenyl}-1H-benzoimidazole-
5-carboxylic acid amide
79
2-{4-[4-(3-chloro-phenyl)-piperazin-1-yl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
80
2-[4-(4-phenyl-piperazin-1-yl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
81
2-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
82
2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
83
2-{4-[4-(4-nitro-phenyl)-piperazin-1-yl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
84
2-[4-(benzo[1,3]dioxol-5-yloxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
85
2-[4-(4-amino-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
86
2-[4-(4-methanesulfonylamino-phenoxy)-phenyl]-1H-
benzoimidazole-5-carboxylic acid amide
87
2-[4-(4-hydroxy-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
88
2-[4-(4-bromo-3-hydroxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
89
2-[4-(4-chloro-2-hydroxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
90
2-[4-(4-chloro-3-hydroxy-phenoxy)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
91
2-[4-(3-chloro-4-fluoro-phenylsulfanyl)-phenyl]-1H-
benzoimidazole-5-sulfonic acid amide
92
2-[4-(naphthalen-2-yloxy)-phenyl]-1H-benzoimidazole-5-sulfonic
acid amide
93
2-[4-(4-chloro-3-trifluoromethyl-phenoxy)-phenyl]-1H-
benzoimidazole-5-sulfonic acid amide
94
2-[4-(4-chloro-phenoxy)-phenyl]-1H-benzoimidazole-5-sulfonic
acid amide
95
2-[4-(2,4-dichloro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-
5-carboxylic acid amide
96
2-[4-(3-chloro-phenoxy)-3-nitro-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
97
2-[4-(4-iodo-phenoxy)-phenyl]-1H-benzoimidazole-5-carboxylic
acid amide
98
2-(4-phenylcarbamoyl-phenyl)-1H-benzoimidazole-5-carboxylic
acid amide
99
2-[4-(4-chloro-phenylcarbamoyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
100
2-{4-[(4-chloro-phenyl)-methyl-carbamoyl]-phenyl}-1H-
benzoimidazole-5-carboxylic acid amide
106A
2-[4-(4-Methoxy-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide
106B
2-[4-(3-Methoxy-phenylsulfanyl)-phenyl]-1H-benzoimidazole-5-
carboxylic acid amide and
106C
2-[4-(4-Bromo-3-methoxy-phenoxy)-phenyl]-1H-benzoimidazole-
5-carboxylic acid amide.
18. A compound selected from the group consisting of: 2-[6-(4-chloro-phenoxy)-pyridazin-3-yl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[4-(4-chloro-phenylamino)-phenyl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[4-(4-chloro-3-dimethylamino-phenoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[4-(4-chloro-3-methanesulfonylamino-phenoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[4-(4-chloro-3-sulfamoyl-phenoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[3-chloro-4-(4-chloro-phenylsulfamoyl)-phenyl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[6-(4-chloro-phenylsulfamoyl)-pyridin-3-yl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[6-(3,4-dichloro-phenylsulfamoyl)-pyridin-3-yl]-3H-benzoimidazole-5-carboxylic acid amide; 2-[6-(2,4-dichloro-phenylsulfamoyl)-pyridin-3-yl]-3H-benzoimidazole-5-carboxylic acid amide; and 2-[6-(4-chloro-benzenesulfonylamino)-pyridin-3-yl]-3H-benzoimidazole-5-carboxylic acid amide.