Aldosterone synthase inhibitors
View Patent ↗The invention involves compounds of structural Formula (I) and the pharmaceutically acceptable salts thereof. The compounds of the invention are effective at selectively inhibiting CYP11B2, and are therefore useful for the treatment or prophylaxis of disorders that are associated with elevated aldosterone levels, including, but not limited to, hypertension and heart failure.
1. A compound of the formula Formula I
or a pharmaceutically acceptable salt thereof wherein:
Het is a heteroaromatic ring of the formula:
R 1a , R 1b and R 1c are independently selected from the group consisting of:
H; halogen; —CN; —OR 5 ; —NR 8 R 9 ; —N(R 13 )C(O)R 10 ; —N(R 13 )SO 2 —R 10 ; —C(O)R 10 ; —C(O)N(R 6 )(R 7 ), —C(O)OR 10 ; —SO 2 N(R 6 )(R 7 ) or —S(O) m ,—R 10 ; alkyl optionally substituted one or more times by halogen; cycloalkyl optionally substituted one or more times by halogen, alkyl, or haloalkyl; aryl optionally substituted one or more times by halogen, —OR 5 , alkyl, or haloalkyl or heteroaryl optionally substituted one or more times by halogen, —OR 5 , alkyl or haloalkyl;
R 2 is selected from the group consisting of:
—OR 5 , alkyl; alkyl—R 11 ; cycloalkyl optionally substituted one or more times by alkyl and halogen; and —C 1 -C 2 alkyl-cycloalkyl wherein the cycloalkyl group is optionally substituted one or more times by alkyl and halogen;
R 3 is selected from the group consisting of:
H; halogen; —CN; —NO 2 ; —OR 5a ; —NR 8 R 9 ; —N(R 13 )C(O)R 10 ; —C(O)R 10 —
C(O)N(R 6 )(R 7 ), —C(O)OR 10 or —S(O) m —R 10 ; alkyl optionally substituted one or more times by halogen or —OR 5a ; cycloalkyl optionally substituted one or more times by halogen, —OR 5a , alkyl, or haloalkyl; aryl optionally substituted one or more times by halogen, —OR 5a , alkyl, or haloalkyl or heteroaryl optionally substituted one or more times by halogen, —OR 5a , alkyl or haloalkyl;
R 4 is selected from the group consisting of:
H; halogen; —CN; —NO 2 ; —OR 5b ; —NR 8 R 9 ; —N(R 13 )C(O)R 10 ; —C(O)R 10 —C(O)N(R 6 )(R 7 ), —C(O)OR 10 or —S(O) m —R 10 ; alkyl optionally substituted one or more times by halogen or OR 5b ; cycloalkyl optionally substituted one or more times by halogen, alkyl, or haloalkyl; aryl optionally substituted one or more times by halogen, —OR 5b , alkyl, or haloalkyl or heteroaryl optionally substituted one or more times by halogen, —ORb 5 , alkyl or haloalkyl;
or R 3 and R 4 are joined together to form a 5-7 membered carbocyclic or heterocyclic ring that is fused to the pyridyl ring to which R 3 and R 4 are attached, wherein the ring formed by R 3 and R 4 is optionally substituted with 1 to 3 of R 12 ;
R 5 , R 5a and R 5b are each independently selected from the group consisting of H; alkyl optionally substituted with halogen; or aralkyl wherein the aryl ring is optionally substituted one or more times by halogen, —OR 5c , alkyl or haloalkyl;
R 5c is H or alkyl optionally substituted with halogen;
R 6 and R 7 are each independently selected from the group consisting of:
H, alkyl optionally substituted with halogen; cycloalkyl optionally substituted with alkyl or halogen; aryl optionally substituted one or more times by halogen, —OR 5 , alkyl, or haloalkyl or heteroaryl optionally substituted one or more times by halogen, —OR 5 , alkyl or haloalkyl;
or R 6 and R 7 join together with the nitrogen to which they are attached to form a 3-7 membered saturated heterocyclic ring;
R 8 and R 9 are each independently selected from the group consisting of
H, alkyl or aralkyl wherein the aryl ring is optionally substituted one or more times by halogen, —OR 5 , alkyl or haloalkyl;
R 10 is selected from the group consisting of alkyl optionally substituted one or more time with halogen; cycloalkyl optionally substituted one or more times by halogen, alkyl or haloalkyl; or aryl wherein the aryl ring is optionally substituted one or more times by halogen, —OR 5 , alkyl or haloalkyl
R 11 is selected from the group consisting of haloalkyl or —OR 5 ;
R 12 is independently selected at each occurrence from the group consisting of halogen or alkyl optionally substituted one or more time by halogen;
R 13 is H or alkyl; and
m is 0, 1 or 2.
2. The compound as defined in claim 1 or a pharmaceutically acceptable salt thereof wherein:
R 1a , R 1b or R 1c is selected from the group consisting of —H, —F, —Cl, —Br, —CN, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with —OH or halogen, —OC 1 - 6 alkyl, —N(R 13 )C(O)—C 1 -C 6 alkyl, —C(O)N(H)C 1 -C 6 alkyl, —NH 2 , —NH(C 1 -C 6 alkyl), —N(C 1 - 6 alkyl)( C 1 -C 6 alkyl), —C(O)O—C 1 -C 6 alkyl, —S—C 1 -C 6 alkyl, —S(O)—C 1 -C 6 alkyl, —S(O) 2 —C 1 -C 6 alkyl, —N(R 13 )S(O) 2 —C 1 -C 6 alkyl, or optionally C 1 -C 6 alkyl substituted heteroaryl, wherein the heteroaryl is an isooxazolyl, pyrazolyl, oxazolyl, imidazolyl or pyridyl ring;
R 2 is OH, C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with —OH or halogen, —O—C 1 -C 6 alkyl, cyclopropyl optionally substituted by halogen, —OH or —O—C 1 -C 6 alkyl or —OCH 2 -phenyl, wherein the phenyl ring is optionally substituted by halogen, —OH or —O—C 1 -C 6 alkyl; and
R 3 and R 4 are independently H, halogen —CN, —C 1 -C 6 alkyl substituted optionally substituted with —OH, —O—C 1 -C 6 alkyl, or halogen, —O—C 1 -C 6 alkyl, —C(O)C 1 -C 6 alkyl, —C(O)OH, —C(O)O—C 1 -C 6 alkyl, —S—C 1 -C 6 alkyl, —S(O) —C 1 -C 6 alkyl, —S(O) 2 —C 1 -C 6 alkyl,—NH 2 , —NH(C 1-C 6 alkyl), —N(C 1 -C 6 alkyl)(C 1 -C 6 alkyl), optionally halo substituted phenyl, or optionally C 1 -C 6 alkyl substituted heteroaryl, wherein the heteroaryl is an isooxazolyl, pyrazolyl, oxazolyl, imidazolyl or pyridyl ring or R 3 and R 4 together with the pyridyl ring form:
3. The compound as defined in claim 1 having the structural formula
or a pharmaceutically acceptable salt thereof
wherein:
R 1a , R 1b and R 1c are independently selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, —OR 5 , —SO 2 NR 6 R 7 ,
—C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F, or
—C 3 -C 7 cycloalkyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —CH 3 or —F;
R 2 is selected from the group consisting of:
(a) —C 1 -C 5 alkyl-R 11 , (b) —C 1 -C 4 alkyl; (c) cyclopropyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F or —C 1 -C 2 alkyl-cyclopropyl wherein cyclopropyl is optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F;
R 3 is selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, —OR 5a , —C 1 -C 6 perfluoroalkyl, —C 1 -C 6 alkyl optionally substituted with 1 to 3 of F or optionally substituted with —OH, or —C 3 -C 7 cycloalkyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —CH 3 and —F;
R 4 is selected from the group consisting of:
(a) —H, —F, —Cl, —Br, —CN, —OR 5 b, —NR 8 R 9 ,—CO 2 R 10 or—COR 10 ,
(b) —C 1 -C 6 perfluoroalkyl,
(c) —C 1 -C 7 alkyl optionally substituted with 1 to 6 of —F and optionally substituted with 1 or 2 substituents independently selected from the group consisting of (i) —OR 5 b or (ii) aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F,
(d) —C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —C 1 -C6 alkyl, —CF 3 or F,
(e) aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F or
(f) heteroaryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F;
or R 3 and R 4 are joined together to form a 5-7 membered carbocyclic or heterocyclic ring that is fused to the pyridyl ring to which R 3 and R 4 are attached, wherein the ring formed by R 3 and R 4 is optionally substituted with 1 to 3 of R 12;
R 5 , R 5a and R 5b are each independently selected from the group —consisting of —H or —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F;
R 6 and R 7 are each independently selected from the group consisting of
(a) —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F, (b) —C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 and —F, (c) aryl or (d) heteroaryl,
or R 6 and R 7 join together with the nitrogen to which they are attached to form a 3-7 membered saturated heterocyclic ring;
R 8 and R 9 are each independently selected from the group consisting of
—H, —C 1 -C 6 alkyl, or —CH 2 -phenyl wherein phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —CF 3 ,;
R 10 is selected from the group consisting of
—C1-C6 alkyl optionally substituted with 1 to 3 of —F, or
—C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 and —F; or
—phenyl wherein the phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —CF 3;
R 11 is selected from the group consisting of —CH 2 F, —CHF 2 or —CF 3 ;
R 12 is independently selected at each occurrence from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F.
4. The compound as defined in claim 3 or a pharmaceutically acceptable salt thereof wherein R 1c is —H and R 2 is cyclopropyl optionally substituted with one or two substituents independently selected from the group consisting of —CH 3 or —F.
5. The compound as defined claim 3 or a pharmaceutically acceptable salt thereof wherein (a) R 3 is —H and R 4 is selected from the group consisting of —H, —F, —Cl, —Br, —CN or —C 1 -C 7 alkyl optionally substituted with 1 to 6 of —F or optionally substituted with 1 or 2 of —OR 5b ; or (b+heterocyclic ring that is fused to the pyridyl ring to which R 3 and R 4 are attached wherein the ring formed by R 3 and R 4 is optionally substituted with 1 to 3 of R 12 .
6. The compound as defined in claim 5 or a pharmaceutically acceptable salt thereof wherein R 1c is —H and R 2 is cyclopropyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F.
7. The compound as defined claim 3 or a pharmaceutically acceptable salt thereof wherein
R 4 is
wherein R 5b is —H or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F, and R 4a and R 4b are each independently selected from the group consisting of (a) —C 1 -C 3 alkyl, (b) —C 1 —C 3 alkyl substituted with 1 to 3 of —F or (c) aryl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —F, —Cl or —C 1 —C 3 alkyl optionally substituted with 1 to 3 of —F.
8. The compound as defined in claim 3 or a pharmaceutically acceptable salt thereof wherein:
R 1a , R 1b and R 1c are each independently selected from —H, —F, —CF 3 or —OCH 3 ;
R 2 is selected from (a) —C 1 -C 3 alkyl, (b) —C 1 -C 2 alkyl—R 11 , (c) —(CH 2 ) (1-2) -cyclopropyl wherein cyclopropyl is optionally substituted with —CH 3 or —F, or (d) cyclopropyl optionally substituted with —CH 3 or —F;
R 3 is —H or is joined together with R 4 to form a 5-7 membered carbocyclic or heterocyclic ring that is fused to the pyridyl ring to which R 3 and R 4 are attached selected from the group consisting of
R 4 , when not joined with R 3 , is selected from —H, —F, —CN, —OCH 3 , —COCH 3 , —COOCH 3 , —CF 3,
or
wherein R 5b is —H or —CH 3 , and R 4a and R 4b are each independently selected from the group consisting of —CH 3 or —CF 3 ; and
R 5 and R 5a are each independently selected from the group consisting of —H, —CH 3 and —CF 3 .
9. The compound as defined in claim 1 having the structural formula
or a pharmaceutically acceptable salt thereof wherein
R 1a , R 1b and R 1c are independently selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, —OR 5 , —SO 2 NR 6 R 7 , —C(O)OR 10
—C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F, or —C 3 -C 7 cycloalkyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —CH 3 and —F;
R 2 is selected from the group consisting of:
(a) —C 1 -C 5 alkyl-R 11 , (b) —C 1 -C 4 alkyl; (c) cyclopropyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F or (d) —C 1 -C 2 alkyl-cyclopropyl wherein cyclopropyl is optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F;
R 3 is selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, ——OR 5a , —C 1 -C 6 perfluoroalkyl,
—C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F and optionally substituted with —OH, or
—C 3 -C 7 cycloalkyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —CH 3 or —F;
R 4 is selected from the group consisting of:
(a) —H, —F, —Cl, —Br, —CN, —OR 5b , —NR 8 R 9 , —CO 2 R 10 or —COR 10 ,
(b) —C 1 -C 6 perfluoroalkyl,
(c) —C 1 -C 7 alkyl optionally substituted with 1 to 6 of —F and optionally substituted with 1 or 2 substituents independently selected from the group consisting of (i) —OR 5b or (ii) aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F,
(d) —C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —C 1 -C 6 alkyl, —CF 3 or —F,
(e) aryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F and
(f) heteroaryl optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F;
or R 3 and R 4 are joined together to form a 5-7 membered carbocyclic or heterocyclic ring that is fused to the pyridyl ring to which R 3 and R 4 are attached, wherein the ring formed by R 3 and R 4 is optionally substituted with 1 to 3 of R 12;
R 5 , R 5a and R 5b are each independently selected from the group consisting of —H or —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F;
R 6 and R 7 are each independently selected from the group consisting of
(a) —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F, (b) —C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F, (c) aryl or (d) heteroaryl,
or R 6 and R 7 join together with the nitrogen to which they are attached to form a 3-7 membered saturated heterocyclic ring;
R 8 and R 9 are each independently selected from the group consisting of —H, —C 1 -C 6 alkyl or —CH 2 -phenyl wherein phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —CF 3 ;
R 10 is selected from the group consisting of
—C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F, —C 3 -C 7 cycloalkyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of —CH 3 or —F; or
—phenyl which is optionally substituted with 1 to 3 substituents independently selected from the group consisting of —F, —Cl or —CF 3 ;
R 11 is selected from the group consisting of —CH 2 F, —CHF 2 or —CF 3 ;
R 12 is independently selected at each occurrence from the group consisting of —F, —Cl or —C 1 -C 3 alkyl optionally substituted with 1 to 3 of —F.
10. The compound as defined in claim 9 or a pharmaceutically acceptable salt thereof wherein:
R 1a , R 1b and R 1c are independently selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, —OR 5 , —C(O)OR 10 , or —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F;
R 2 is selected from the group consisting of:
C 1 -C 4 alkyl or cyclopropyl;
R 3 is selected from the group consisting of:
—H, —F, —Cl, —Br, —CN, —OR 5a , —C 1 -C 6 perfluoroalkyl, or —C 1 -C 6 alkyl;
R 4 is selected from the group consisting of:
—H, —F, —Cl —Br, —CN, —OR 5b and —C 1 -C 6 perfluoroalkyl,
R 5 and R 5b are each independently selected from the group consisting of —H and —C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F; and
R 10 is selected from the group consisting of
C 1 -C 6 alkyl optionally substituted with 1 to 3 of —F.
11. The compound of claim 1 selected from the group consisting of:
4 (1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)isoquinoline;
4(1-cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)isoquinoline;
1-cyclopropyl-6-fluoro-2-[5-(2-methoxypropan-2-yl)pyridin-3-yl]-1H-benzimidazole;
4-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)isoquinoline;
4-(1-cyclopropyl-5-fluoro-1H-benzimidazol-2-yl)isoquinoline;
2-[5-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
methyl 5-(1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)pyridine-3-carboxylate;
4-(1-ethyl-5-fluoro-1H-benzimidazol-2-yl)isoquinoline;
1-cyclopropyl-6-fluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-6,7-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
6-fluoro-1 -(1 -methylcyclopropyl)-2-(pyridin-3-yl)-1H-benzimidazole;
2-[5-(1-cyclopropyl-5,7-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
5-fluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
8-(1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)-1 ,6-naphthyridine;
8-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)-1 ,6-naphthyridine;
1-cyclopropyl-6-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5-fluoro-2-(pyridin-3-yl)-1 H-benzimidazole;
2[5-(1 -cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
1-cyclopropyl-5,6-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-4,6-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,7-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
2[5-(1 -cyclopropyl-5-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
8(1-cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)-1 ,6-naphthyridine;
2-[5-(1 -cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
2-[5-(1-cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-1 ,1,1-trifluoropropan-2-ol,
1-cyclopropyl-5,6-difluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,6-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,6-difluoro-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
6-fluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
1 -ethyl-6-fluoro-2-(4-methylpyridin-3-yl)- 1H-benzimidazole;
5,6-di-difluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
5,6-di-difluoro-2-(2-hydroxy-2-propylpyrid in-3-yl)-1-methyl-1H-benzimidazole;
1-cyclopropyl-6-fluoro-2-(5-fluoro4-methylpyridin-3-yl)-1H-benzimidazole;
6,7-difluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
5,7-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
1-cyclopropyl-5,7-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1H-benzimidazole;
5,7-difluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
or a the pharmaceutically acceptable salts thereof.
12. The compound as defined in claim 1 selected from the group consisting of:
1-cyclopropyl-6-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
2-[5-(1-cyclopropyl-6-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
1-cyclopropyl-5,6-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-4,6-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,7-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
2-[5-(1-cyclopropyl-5-fluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
8(1-cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)-1 ,6-naphthyridine;
2-[5-(1 -cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
2-[5-(1-cyclopropyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]-1 ,1,1-trifluoropropan-2-ol;
1-cyclopropyl-5,6-difluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,6-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,6-difluoro-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
6-fluoro-2-(4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
1-ethyl-6-fluoro-2-(4-methylpyridin-3-yl)- 1H-benzimidazole;
5,6-di-difluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
5,6-di-difluoro-2-(2-hydroxy-2-propylpyridin-3-yl)-1-methyl-1H-benzimidazole;
1-cyclopropyl-6-fluoro-2-(5-fluoro4-methylpyridin-3-yl)-1H-benzimidazole;
6,7-difluoro-2-(4-methyl pyridin-3-yl)-1 -methyl-1H-benzimidazole;
5,7-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
1 -cyclopropyl-5,7-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1H-benzimidazole;
5,7-difluoro-2-(4-methylpyridin-3-yl)-1 -methyl-1H-benzimidazole;
or the pharmaceutically acceptable salts thereof.
13. The compound of claim 1 selected from the group consisting of:
1-cyclopropyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole-6-carbonitrile;
1-cyclopropyl-2-(5-methoxypyridin-3-yl)-1H-benzimidazole-6-carbonitrile;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-6-carbonitrile;
6-chloro-1-cyclopropyl-5-fluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
4-(6-chloro-1-cyclopropyl-5-fluoro-1H-benzimidazol-2-yl)isoquinoline;
6-chloro-1-cyclopropyl-5-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
6-chloro-1-cyclopropyl-5-fluoro-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
6-bromo-1-cyclopropyl-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
5,6-difluoro-1-methyl-2-(5-methylpyrid in-3-yl)-1H-benzimidazole;
1-cyclopropyl-5,6-difluoro-2-(4-methoxy-5-methylpyridin-3-yl)-1H-benzimidazole;
6-chloro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
6-chloro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
6-chloro-1-cyclopropyl-2-(pyridin-3-yl)-1H-benzimidazole;
4-(5,7-difluoro-1-methyl-1 H-benzimidazol-2-yl)isoquinoline;
5-(6,7-difluoro-1-methyl-1 H-benzimidazol-2-yl)pyridine-3-carbonitrile;
2-(4,5-dimethylpyridin-3-yl)-6,7-difluoro-1 -methyl-1H-benzimidazole;
4(1-cyclopropyl-6,7-difluoro-1H-benzimidazol-2-yl)isoquinoline;
1-cyclopropyl-2-(4,5-dimethylpyridin-3-yl)-6,7-difluoro-1H-benzimidazole;
1-cyclopropyl-6,7-difluoro-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
6-chloro-5-fluoro-1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
1 -(benzyloxy)-5,6-difluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
or a pharmaceutically acceptable salt thereof.
14. A pharmaceutical composition comprised of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
15. A compound selected from the group consisting of:
6-fluoro-2-(5-methoxl-2-(pyridin-3-yl)-1-methyl-1H-benzimidazole;
6-fluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
6-fluoro-1-(propan-2-yl)-2-(pyridin-3-yl)-1H-benzimidazole;
5-fluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
6-Methoxy-2-(5-methoxypyridin-3-yl)-i-methyl-1H-benzimidazole;
6-fluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
1-ethyl-6-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
6-fluoro-2-(5-fluoropyridin-3-yl)-1-(propan-2-yl)-1H-benzimidazole;
1-cyclopropyl-4-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
1-ethyl-5-fluoro-2-(pyridin-3-yl)-1H-benzimidazole;
4-(1-ethyl-5-fluoro-1H-benzimidazol-2-yl)isoquinoline;
4-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)isoquinoline;
1-ethyl-5,6-difluoro-2-(pyridin-3-yl)-1H-benzimidazole;
8-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)-1,6-naphthyridine; methyl5-(6-fluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carboxylate;
2-[5-(1-ethyl-5,6-difluoro-1H-benzimidazol-2-yl)pyridin-3-yl]propan-2-ol;
6-fluoro-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
6-fluoro-2-(5-isopropoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-Difluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
5,6-Difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
6,7-Difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
5,7-Difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
6-Fluoro-2-(4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
1-Ethyl-6-fluoro-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
5,6-Di-difluoro-2-(4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-Di-difluoro-2-(2-hydroxy-2-propylpyridin-3-yl)-1-methyl-1H-benzimidazole;
6,7-Difluoro-2-(4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5,7-Difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5,7-Difluoro-2-(4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
2-(isoquinolin-4-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(5-cyanopyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(5-bromopyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole-6-carbonitrile;
1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole-6-carbonitrile;
1-methyl-2-(4-methylpyridin-3-yl)-1H-benzimidazole-6-carbonitrile;
1-methyl-2-[5-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole-6-carbonitrile;
2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(3-aminopyridin-4-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-(4-ethyl-5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
2-[5-fluoro-4-(hydroxymethyl)pyridin-3-yl]-1-methyl-1H-benzimidazole-6-carbonitrile;
5-bromo-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
4-(5-bromo-1-methyl-1H-benzimidazol-2-yl)isoquinoline;
5-bromo-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
5-bromo-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
4-(5-bromo-1-methyl-1H-benzimidazol-2-yl)-8-fluoroisoquinoline;
5-bromo-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
5-bromo-1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
5-bromo-2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole;
5-bromo-1-ethyl-2-(pyridin-3-yl)-1H-benzimidazole;
5-bromo-1-(propan-2-yl)-2-(pyridin-3-yl)-1H-benzimidazole;
1-methyl-2-(pyridin-3-yl)-5-(trifluoromethyl)-1H-benzimidazole;
2-(5-methoxypyridin-3-yl)-1-methyl-5-(trifluoromethyl)-1H-benzimidazole;
2-(5-fluoropyridin-3-yl)-1-methyl-5-(trifluoromethyl)-1H-benzimidazole;
1-methyl-5-(trifluoromethyl)-2-[5-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-1-methyl-5-(trifluoromethyl)-1H-benzimidazole;
1-methyl-2-[5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-5-(trifluoromethyl)-1H-benzimidazole;
2-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-1-methyl-5-(trifluoromethyl)-1H-benzimidazole;
6-fluoro-4-[1-methyl-5-(trifluoromethyl)-1H-benzimidazol-2-yl]isoquinoline;
1-methyl-2-(pyridin-4-yl)-5-(trifluoromethyl)-1H-benzimidazole;
6-chloro-5-fluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-5-carbonitrile;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-5-carbonitrile;
2-(5-bromopyridin-3-yl)-1-methyl-1H-benzimidazole-5-carbonitrile;
2-(8-fluoroisoquinolin-4-yl)-1-methyl-1H-benzimidazole-5-carbonitrile;
1-methyl-2- [5-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole-5-carbonitrile;
1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole-5-carbonitrile;
1-methyl-2-[5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-1H-benzimidazole-5-carbonitrile;
2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole-5-carbonitrile;
2-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-1-methyl-1H-benzimidazole-5-carbonitrile;
2-(isoquinolin-4-yl)-1-methyl-1H-benzimidazole-5-carbonitrile;
1-methyl-2-(pyridin-4-yl)-1H-benzimidazole-5-carbonitrile;
5-bromo-6-fluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1-H-benzimidazole;
5-bromo-6-fluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
5-bromo-6-fluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
4-(5-bromo-6-fluoro-1-methyl-1H-benzimidazol-2-yl)isoquinoline;
5-bromo-2-(3-chloropyridin-4-yl)-6-fluoro-1-methyl-1H-benzimidazole;
1-methyl-5-(methyl sulfonyl)-2-(pyridin-3-yl)-1H-benzimidazole;
2-(5-fluoropyridin-3-yl)-1-methyl-5-(methylsulfonyl)-1H-benzimidazole;
2-(5-methoxypyridin-3-yl)-1-methyl-5-(methylsulfonyl)-1H-benzimidazole;
1-ethyl-5-(methylsulfonyl)-2-(pyridin-3-yl)-1H-benzimidazole;
1-ethyl-2-(5-fluoropyridin-3-yl)-5-(methylsulfonyl)-1H-benzimidazole;
4-[1-ethyl-5-(methylsulfonyl)-1H-benzimidazol-2-yl]isoquinoline;
1-ethyl-2-(5-methoxypyridin-3-yl)-5-(methylsulfonyl)-1H-benzimidazole;
1-ethyl-5-(methylsulfonyl)-2-(pyridin-3-yl)-1H-benzimidazole;
5-(methylsulfonyl)-1-(propan-2-yl)-2-(pyridin-3-yl)-1H-benzimidazole;
6-bromo-1-cyclopropyl-2-(pyridin-3-yl)-1H-benzimidazole;
5,6-dichloro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-dichloro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-dichloro-2-(5-methoxy-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-dichloro-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
5,6-dichloro-2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole;
5,6-dichloro-2-(3-chloropyridin-4-yl)-1-methyl-1H-benzimidazole;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazol-5-amine;
2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazol-5-amine;
1-ethyl-2-(pyridin-3-yl)-1H-benzimidazol-5-amine;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazol-5-amine;
1-methyl-5-nitro-2-(pyridin-3-yl)-1H-benzimidazole;
N-[1-methyl-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]acetamide;
methyl 1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-7-carboxylate;
methyl 2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-7-carboxylate;
methyl 1-methyl-2-(pyridin-4-yl)-1H-benzimidazole-7-carboxylate;
methyl 1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-5-carboxylate;
methyl 2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-5-carboxylate;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-5-carboxylic acid;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-7-carboxylic acid;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-7-carboxylic acid;
5,6-difluoro-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-5,6-difluoro-1-methyl-1H-benzimidazole;
5-(5,6-difluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
5,6-difluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
5,6-difluoro-2-(5-fluoropyridin-3-yl)-1-(propan-2-yl)-1H-benzimidazole;
1-ethyl-5,6-difluoro-2-(5-fluoropyridin-3-yl)-1H-benzimidazole;
[3-(5,6-difluoro-1-methyl-1H-benzimidazol-2-yl)-5-fluoropyridin-4-yl]methanol;
6-chloro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
6-chloro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
6-chloro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
6-chloro-2-(5-methoxy-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5-(6-chloro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
6-chloro-2-(5-fluoro-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-6-chloro-1-methyl-1H-benzimidazole;
6-chloro-2-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-1-methyl-1H-benzimidazole;
6-chloro-1-methyl-2-(4-methyl-pyridin-3-yl)-1H-benzimidazole;
6-chloro-1-methyl-2-(5-methyl-pyridin-3-yl)-1H-benzimidazole;
6-chloro-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
6-chloro-2-(3-chloropyridin-4-yl)-1-methyl-1H-benzimidazole;
6-chloro-1-methyl-2-[4-(trifluoro-methyl)pyridin-3-yl]-1H-benzimidazole;
6-chloro-2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole;
6-chloro-1-methyl-2-[5-(trifluoro-methyl)pyridin-3-yl]1H-benzimidazole;
6-chloro-1-methyl-2-[5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-1H-benzimidazole;
4-(5,7-difluoro-1-methyl-1H-benzimidazol-2-yl)isoquinoline;
4-(5,7-difluoro-1-methyl-1H-benzimidazol-2-yl)isoquinoline;
5,7-difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-5,7-difluoro-1-methyl-1H-benzimidazole;
5,7-difluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
5-(5,7-difluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
5,7-difluoro-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
6,7-difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
6,7-difluoro-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-6,7-difluoro-1-methyl-1H-benzimidazole;
5-(6,7-difluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
5-(6,7-difluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
2-(4,5-dimethylpyridin-3-yl)-6,7-difluoro-1-methyl-1H-benzimidazole;
6,7-difluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
6,7-difluoro-1-methyl-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
1 6,7-difluoro-1-methyl-2-(3-methylpyridin-4-yl)-1H-benzimidazole;
6,7-difluoro-1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
2-(3-bromopyridin-4-yl)-6,7-difluoro-1-methyl-1H-benzimidazole;
4-(6,7-difluoro-1-methyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile;
6,7-difluoro-2-(5-methoxy-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
6,7-difluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
6,7-difluoro-1-methyl-2-[5-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
6,7-difluoro-2-(5-fluoro-4-methylpyridin-3-yl)-1-methyl-1H-benzimidazole;
5-fluoro-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
5-fluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
5-fluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
4,6-difluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole;
4,6-difluoro-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzimidazole;
4,6-difluoro-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
2-(3-chloropyridin-4-yl)-4,6-difluoro-1-methyl-1H-benzimidazole;
4,6-difluoro-2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole;
6-bromo-1-methyl-2-(4-methyl-pyridin-3-yl)-1H-benzimidazole;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-5-carboxylic acid;
2-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-1-methyl-1H-benzimidazole-6-carbonitrile;
1-methyl-2-(pyridin-4-yl)-1H-benzimidazole-6-carbonitrile;
2-(3-chloropyridin-4-yl)-1-methyl-1H-benzimidazole-6-carbonitrile;
1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-2-(pyridin-3-yl)-1H-benzimidazole;
2-(5-methoxypyridin-3-yl)-1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazole;
5-(3,5-dimethylisoxazol-4-yl)-6-fluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
5-(3,5-dimethylisoxazol-4-yl)-6-fluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
4-[1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazol-2-yl]isoquinoline;
5-(3,5-dimethylisoxazol-4-yl)-2-(5-methoxy-pyridin-3-yl)-1-methyl-1H-benzimidazole;
6-Chloro-5-fluoro-1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole;
6-chloro-5-fluoro-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
6-chloro-5-fluoro-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
4-(6-chloro-5-fluoro-1-methyl-1H-benzimidazol-2-yl)isoquinoline;
6-chloro-5-fluoro-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
6-chloro-2-(3-chloropyridin-4-yl)-5-fluoro-1-methyl-1H-benzimidazole;
6-chloro-5-fluoro-2-(3-fluoropyridin-4-yl)-1-methyl-1H-benzimidazole;
N, 1-dimethyl-2-(pyridin-3-yl)-1H-benzimidazole-7-carboxamide;
N, 1-dimethyl-2-(pyridin-3-yl)-1H-benzimidazole-5-carboxamide;
2-(5-fluoropyridin-3-yl)-N,1-dimethyl-1H-benz-imidazole-7-carboxamide;
N-[1-methyl-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide;
N-[2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazol-5-yl]methanesulfonamide;
N-[2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazol-5-yl]methanesulfonamide;
N-[1-(propan-2-yl)-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide;
N-[2-(5-fluoropyridin-3-yl)-1-(propan-2-yl)-1H-benzimidazol-5-yl]methanesulfonamide;
N-[1-ethyl-2-(pyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide;
N-[1-ethyl-2-(5-fluoropyridin-3-yl)-1H-benzimidazol-5-yl]methanesulfonamide;
5-Methoxy-1-methyl-2-[5-(1H-pyrazol-4-yl)pyridin-3-yl]-1H-benzimidazole;
2-(5-bromopyridin-3-yl)-5-methoxy-1-methyl-1H-benzimidazole;
5-methoxy-1-methyl-2-(pyridin-4-yl)-1H-benzimidazole;
5-methoxy-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole;
2-(5-fluoropyridin-3-yl)-5-methoxy-1-methyl-1H-benzimidazole;
5-methoxy-2-(5-methoxypyridin-3-yl)-1-methyl-1H-benzimidazole;
4-(5-methoxy-i-methyl-iH-benzimidazol-2-yl)-4 a ,8 a -dihydroisoquinoline;
5-methoxy-1-methyl-2-(4-methylpyridin-3-yl)-1H-benzimidazole;
2-(5-bromo-4-methylpyridin-3-yl)-5-methoxy-1-methyl-1H-benzimidazole;
2-[5-(3,5-dimethylisoxazol-4-yl)pyridin-3-yl]-5-methoxy-1-methyl-1H-benzimidazole;
4-[1-methyl-5-(propan-2-yloxy)-1H-benzimidazol-2-yl]isoquinoline;
5-Bromo-1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-6-carbonitrile;
5-bromo-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benz-imidazole-6-carbonitrile;
5-fluoro-2-[5-fluoro-4-(hydroxymethyl)pyridin-3-yl]-1-methyl-1H-benzimidazole-6-carbonitrile;
or a pharmaceutically acceptable salt thereof.
16. A compound selected from the group consisting of:
1-methyl-5-nitro-2-(pyridin-3-yl)-1H-benzimidazole;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-5-carboxylic acid;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-7-carboxylic acid;
1-methyl-2-(pyridin-3-yl)-1H-benzimidazole-7-carboxylic acid;
1-cyclopropyl-2-(5-fluoropyridin-3-yl)-1H-benzimidazole-5-carboxylic acid;
2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-5-carboxylic acid;
or a pharmaceutically acceptable salt thereof