US2009247508A1PendingUtilityA1
Benzoimidazole Compounds
Est. expirySep 30, 2023(expired)· nominal 20-yr term from priority
A61P 37/08A61P 35/02A61P 37/04C07K 16/00C07K 2318/10C07K 2317/50C07D 401/12A61P 29/00C04B 35/632C07D 401/04C07D 235/18C07D 403/12C07D 401/14C07K 2317/53
67
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Claims
Abstract
Benzoimidazole compounds, compositions, and methods of using them in leukocyte recruitment inhibition, in modulating H4 receptor, and in treating conditions such as inflammation, H4 receptor-mediated conditions, and related conditions.
Claims
exact text as granted — not AI-modified1 . A method for modulating an H 4 receptor, comprising exposing an H 4 receptor to at least one chemical entity selected from compounds of formula (II), enantiomers, diastereomers, and racemates thereof, pharmaceutically acceptable salts, amides and esters thereof,
wherein
X is N;
Y is O, NR 12 , or CR 12 R 13 ;
Z is CR 14 ;
n is 1;
each of R 1-4 is, independently from other substituent assignments, H, C 1-4 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 3-6 cycloalkyl, —C 1-4 alkoxy, —C 1-4 alkylamino, —C 1-4 alkylthio, —C 1-4 alkylsulfonyl, —OC 3-6 cycloalkyl, —OCH 2 Ph, cyano, —CF 3 , F, Cl, Br, I, nitro, —OCF 3 , —SCF 3 , —OR c , —SR c , —S(O)R c , —SO 2 R c , —C(O)R c , phenyl, benzyl, phenethyl, —C(O)NR a R b , —C(O)OR c , —NR a R b , —CH 2 NR a R b or —CH 2 OR c ; wherein each of R a , R b and R c is, independently from other substituent assignments, selected from H, C 1-4 alkyl, C 3-6 cycloalkyl, phenyl, (C 3-6 cycloalkyl)C 1-2 alkyl-, benzyl and phenethyl, or R a and R b taken together with the nitrogen to which they are attached, form a 4-7 membered heterocyclic ring HetCyc1, wherein said ring HetCyc1 has 0 or 1 additional heteroatoms selected from O, S, >NH and >NC 1-6 alkyl, and wherein any phenyl, phenethyl, benzyl, alkyl or cycloalkyl moiety in any of said R 1-4 , R a , R b , R c , and said ring HetCyc1 is optionally, and independently from other substituent assignments, substituted with 1, 2 or 3 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
each of R 5-7 is, independently from other substituent assignments, H, C 1-6 alkyl, F, Cl, Br, I, CF 3 , —OCF 3 , —OR c , —SR c , —S(O)R c , —SO 2 R c , C 1-4 alkoxy, cyano, nitro, —C(O)NR a R b , —C(O)phenyl, —C(O)C 1-6 alkyl, —S(O)C 1-4 alkyl, or —SO 2 C 1-4 alkyl; or, R 7 and R 6 for a compound of formula (II) taken together with the carbon atoms to which they are attached form a cyclic structure Cyc2 selected from aryl, heteroaryl, 5- or 6-membered carbocycle, and 5- or 6-membered heterocycle with 1 or 2 heteroatoms, wherein said cyclic structure Cyc2 is, independently from other substituent assignments, substituted with 0, 1, or 2 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
R 8 is H, C 1-6 alkyl, C 1-4 alkoxy, or OH;
each of R 9 and R 10 is, independently from other substituent assignments, H or C 1-6 alkyl, or R 9 and R 10 taken together form a 5-6 membered cyclic structure Cyc3, wherein said cyclic structure Cyc3 is a 5- or 6-membered carbocycle or a 5- or 6-membered heterocycle with 1 or 2 heteroatoms, and wherein said cyclic structure Cyc3 is, independently from other substituent assignments, substituted with 0, 1, or 2 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
R 11 is H, C 1-4 alkyl;
each of R 12 and R 13 is, independently from other substituent assignments, H or C 1-4 alkyl; or, when Y is CR 12 R 13 , R 12 and R 13 taken together with the carbon member to which they are attached form an optionally substituted cyclic structure Cyc4, wherein said cyclic structure Cyc4 is a 3- to 6-membered carbocycle or a 3- to 6-membered heterocycle with 0 or 1 additional heteroatoms, or CR 12 R 13 is C═O;
R 14 is H, C 1-4 alkyl, OH, or C 1-4 alkoxy;
provided that:
when Y is O or NR 12 , then R 3 is not OH or C 1-4 alkoxy; and
neither R 1 nor R 4 is C(O)NH 2 .
2 . A method as in claim 1 , wherein Y is CR 12 R 13 .
3 . A method as in claim 1 , wherein Y is CH 2 .
4 . A method as in claim 1 , wherein Z is CH.
5 . A method as in claim 1 , wherein R 1 is selected from the group consisting of H, methyl, ethyl, isopropyl, cyclopropyl, F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and CH 2 OMe.
6 . A method as in claim 1 , wherein R 1 is H, methyl, F, or Cl.
7 . A method as in claim 1 , wherein R 2 is selected from the group consisting of H, methyl, ethyl, isopropyl, t-butyl, cyclopropyl, CF 3 , OCF 3 , F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and benzoyl.
8 . A method as in claim 1 , wherein R 2 is H, F, Cl, methyl, CF 3 , OCF 3 , or t-butyl.
9 . A method as in claim 1 , wherein R 3 is selected from the group consisting of H, methyl, ethyl, isopropyl, t-butyl, cyclopropyl, CF 3 , OCF 3 , F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and benzoyl.
10 . A method as in claim 1 , wherein R 3 is H, F, Cl, methyl, CF 3 , OCF 3 , or t-butyl.
11 . A method as in claim 1 , wherein R 4 is selected from the group consisting of H, methyl, ethyl, isopropyl, cyclopropyl, R, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and CH 2 OMe.
12 . A method as in claim 1 , wherein R 4 is H, methyl, F, or Cl.
13 . A method as in claim 1 , wherein one or two of R 1-4 are not H.
14 . A method as in claim 1 , wherein R 5 is H, F, Cl, methyl, or ethyl.
15 . A method as in claim 1 , wherein R 5 is F, Cl, or methyl.
16 . A method as in claim 1 , wherein R 6 is H, F, Cl, or methyl.
17 . A method as in claim 1 , wherein R 7 is H, F, Cl, or methyl.
18 . A method as in claim 1 , wherein R 8 is H, methyl, or OH.
19 . A method as in claim 1 , wherein R 8 is H.
20 . A method as in claim 1 , wherein R 9 and R 10 are, independently, selected from the group consisting of: H, methyl, ethyl, propyl, and isopropyl.
21 . A method as in claim 1 , wherein each of R 9 and R 10 is, independently, H or methyl.
22 . A method as in claim 1 , wherein R 11 is H, methyl, or ethyl.
23 . A method as in claim 1 , wherein R 11 is methyl.
24 . A method for modulating an H 4 receptor, comprising exposing an H 4 receptor to at least one compound selected from:
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-6-chloro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-tert-butyl-1H-benzoimidazole;
5-tert-Butyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4,6-Dimethyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Chloro-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
6-Chloro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-tert-Butyl-2-[2-(4-piperidin-4-yl-butoxy)-pyridin-4-yl]-1H-benzoimidazole;
4,6-Dimethyl-2-[2-(4-piperidin-4-yl-butoxy)-pyridin-4-yl]-1H-benzoimidazole;
2-{2-[4-(1-Ethyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4,6-Dimethyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Methyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
6-Chloro-4-methyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
6-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
5-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-6-fluoro-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-tert-Butyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
5-Chloro-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-6-fluoro-1H-benzoimidazole;
5-tert-Butyl-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-chloro-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-6-fluoro-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-1H-benzoimidazole;
{4-(4,6-Dimethyl-1H-benzoimidazol-2-yl)-6-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-3-yl}-methanol;
and pharmaceutically acceptable salts of said compounds.
25 . A method for inhibiting leukocyte recruitment in a subject, comprising administering to the subject a pharmaceutical composition comprising a therapeutically effective amount of at least one chemical entity selected from compounds of formula (II), enantiomers, diastereomers, and racemates thereof, pharmaceutically acceptable salts, amides and esters thereof,
wherein
X is N;
Y is O, NR 12 or CR 12 R 13 ;
Z is CR 14 ;
n is 1;
each of R 1-4 is, independently from other substituent assignments, H, C 1-4 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, C 3-6 cycloalkyl, —C 1-4 alkoxy, —C 1-4 alkylamino, —C 1-4 alkylthio, —C 1-4 alkylsulfonyl, —OC 3-6 cycloalkyl, —OCH 2 Ph, cyano, —CF 3 , F, Cl, Br, I, nitro, —OCF 3 , —SCF 3 , —OR c , —SR c , —S(O)R c , —SO 2 R c , —C(O)R c , phenyl, benzyl, phenethyl, —C(O)NR a R b , —C(O)OR c , —NR a R b , —CH 2 NR a R b or —CH 2 OR c ; wherein each of R a , R b and R c is, independently from other substituent assignments, selected from H, C 1-4 alkyl, C 3-6 cycloalkyl, phenyl, (C 3-6 cycloalkyl)C 1-2 alkyl-, benzyl and phenethyl, or R a and R b taken together with the nitrogen to which they are attached, form a 4-7 membered heterocyclic ring HetCyc1, wherein said ring HetCyc1 has 0 or 1 additional heteroatoms selected from O, S, >NH and >NC 1-6 alkyl, and wherein any phenyl, phenethyl, benzyl, alkyl or cycloalkyl moiety in any of said R 1-4 , R a , R b , R c , and said ring HetCyc1 is optionally, and independently from other substituent assignments, substituted with 1, 2 or 3 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
each of R 5-7 is, independently from other substituent assignments, H, C 1-6 alkyl, F, Cl, Br, I, CF 3 , —OCF 3 , —OR c , —SR c , —S(O)R c , —SO 2 R c , C 1-4 alkoxy, cyano, nitro, —C(O)NR a R b , —C(O)phenyl, —C(O)C 1-6 alkyl, —S(O)C 1-4 alkyl, or —SO 2 C 1-4 alkyl; or, R 7 and R 6 for a compound of formula (II) taken together with the carbon atoms to which they are attached form a cyclic structure Cyc2 selected from aryl, heteroaryl, 5- or 6-membered carbocycle, and 5- or 6-membered heterocycle with 1 or 2 heteroatoms, wherein said cyclic structure Cyc2 is, independently from other substituent assignments, substituted with 0, 1, or 2 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
R 8 is H, C 1-6 alkyl, C 1-4 alkoxy, or OH;
each of R 9 and R 10 is, independently from other substituent assignments, H or C 1-6 alkyl, or R 9 and R 10 taken together form a 5-6 membered cyclic structure Cyc3, wherein said cyclic structure Cyc3 is a 5- or 6-membered carbocycle or a 5- or 6-membered heterocycle with 1 or 2 heteroatoms, and wherein said cyclic structure Cyc3 is, independently from other substituent assignments, substituted with 0, 1, or 2 substituents selected from C 1-3 alkyl, halo, hydroxy, amino, and C 1-3 alkoxy;
R 11 is H, C 1-4 alkyl;
each of R 12 and R 13 is, independently from other substituent assignments, H or C 1-4 alkyl; or, when Y is CR 12 R 13 , R 12 and R 13 taken together with the carbon member to which they are attached form an optionally substituted cyclic structure Cyc4, wherein said cyclic structure Cyc4 is a 3- to 6-membered carbocycle or a 3- to 6-membered heterocycle with 0 or 1 additional heteroatoms, or CR 12 R 13 is C═O;
R 14 is H, C 1-4 alkyl, OH, or C 1-4 alkoxy;
provided that:
when Y is O or NR 12 , then R 8 is not OH or C 1-4 alkoxy; and
neither R 1 nor R 4 is C(O)NH 2 .
26 . A method as in claim 25 , wherein Y is CR 12 R 13 .
27 . A method as in claim 25 , wherein Y is CH 2 .
28 . A method as in claim 25 , wherein Z is CH.
29 . A method as in claim 25 , wherein R 1 is selected from the group consisting of H, methyl, ethyl, isopropyl, cyclopropyl, F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and CH 2 OMe.
30 . A method as in claim 25 , wherein R 1 is H, methyl, F, or Cl.
31 . A method as in claim 25 , wherein R 2 is selected from the group consisting of H, methyl, ethyl, isopropyl, t-butyl, cyclopropyl, CF 3 , OCF 3 , F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and benzoyl.
32 . A method as in claim 25 , wherein R 2 is H, F, Cl, methyl, CF 3 , OCF 3 , or t-butyl.
33 . A method as in claim 25 , wherein R 3 is selected from the group consisting of H, methyl, ethyl, isopropyl, t-butyl, cyclopropyl, CF 3 , OCF 3 , F, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and benzoyl.
34 . A method as in claim 25 , wherein R 3 is H, F, Cl, methyl, CF 3 , OCF 3 , or t-butyl.
35 . A method as in claim 25 , wherein R 4 is selected from the group consisting of H, methyl, ethyl, isopropyl, cyclopropyl, R, Cl, Br, cyano, phenyl, carboxymethyl, dimethylcarboxamido, and CH 2 OMe.
36 . A method as in claim 25 , wherein R 4 is H, methyl, F, or Cl.
37 . A method as in claim 25 , wherein one or two of R 1-4 are not H.
38 . A method as in claim 25 , wherein R 5 is H, F, Cl, methyl, or ethyl.
39 . A method as in claim 25 , wherein R 5 is F, Cl, or methyl.
40 . A method as in claim 25 , wherein R 6 is H, F, Cl, or methyl.
41 . A method as in claim 25 , wherein R 7 is H, F, Cl, or methyl.
42 . A method as in claim 25 , wherein R 8 is H, methyl, or OH.
43 . A method as in claim 25 , wherein R 8 is H.
44 . A method as in claim 25 , wherein R 9 and R 10 are, independently, selected from the group consisting of: H, methyl, ethyl, propyl, and isopropyl.
45 . A method as in claim 25 , wherein each of R 9 and R 10 is, independently, H or methyl.
46 . A method as in claim 25 , wherein R 11 is H, methyl, or ethyl.
47 . A method as in claim 25 , wherein R 11 is methyl.
48 . A method for inhibiting leukocyte recruitment in a subject, comprising administering to the subject a pharmaceutical composition comprising a therapeutically effective amount of at least one compound selected from:
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-6-chloro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-4-methyl-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-tert-butyl-1H-benzoimidazole;
5-tert-Butyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4,6-Dimethyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Chloro-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
6-Chloro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-4-methyl-2-{2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-tert-Butyl-2-[2-(4-piperidin-4-yl-butoxy)-pyridin-4-yl]-1H-benzoimidazole;
4,6-Dimethyl-2-[2-(4-piperidin-4-yl-butoxy)-pyridin-4-yl]-1H-benzoimidazole;
2-{2-[4-(1-Ethyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4,6-Dimethyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4-Methyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
6-Chloro-4-methyl-2-{3-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,5-dimethyl-1H-benzoimidazole;
4-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
6-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
5-Chloro-2-{3-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-methyl-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-6-fluoro-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-tert-Butyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{5-methyl-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4,6-dimethyl-1H-benzoimidazole;
5-Chloro-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
5-Chloro-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-6-fluoro-1H-benzoimidazole;
5-tert-Butyl-2-{5-chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-4-chloro-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-6-fluoro-1H-benzoimidazole;
2-{5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-4-yl}-5-chloro-1H-benzoimidazole;
{4-(4,6-Dimethyl-1H-benzoimidazol-2-yl)-6-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridin-3-yl}-methanol;
and pharmaceutically acceptable salts of said compounds.Join the waitlist — get patent alerts
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