US 2009/0156613 A1Published application

Bicyclic heteroaryl-substituted imidazoles as modulators of the histamine H4 receptor

AssigneeJanssen Pharmaceutica NV

InventorsDavid E. Kindrachuk, Jennifer D. Venable

Life of this patent

Estimating the term…

Abstract

Bicyclic heteroaryl-substituted imidazole compounds are described, which are useful as H4 receptor modulators. Such compounds may be used in pharmaceutical compositions and methods for the modulation of histamine H4 receptor activity and for the treatment of disease states, disorders, and conditions mediated by H4 receptor activity, such as allergy, asthma, autoimmune diseases, and pruritis.

Claims24

Dependent claims

A chemical entity selected from the group consisting of compounds of Formula (I), pharmaceutically acceptable salts of compounds of Formula (I), pharmaceutically acceptable prodrugs of compounds of Formula (I), and pharmaceutically active metabolites of compounds of Formula (I):

wherein
R1 is:
a) an imidazol-2-yl ring, substituted with one or two Ra substituents;
where each Ra substitutent is independently C1-4alkyl, CF3, or a phenyl ring unsubstituted or substituted with one or two substituents independently selected from methyl, halo, and CF3;
b) a benzimidazol-2-yl ring, unsubstituted or substituted with one or two Rb substituents;
where each Rb substituent is independently C1-4alkyl, C2-4alkenyl, C2-4alkynyl, phenyl, —CF3, —OCF3, —CN, halo, —NO2, —OC1-4alkyl, —SC1-4alkyl, —S(O)C1-4alkyl, —SO2C1-4alkyl, —C(O)C1-4alkyl, —C(O)phenyl, —C(O)NRcRd, —CO2C1-4alkyl, —CO2H, —C(O)NRcRd, or —NRcRd;
where Rc and Rd are each independently H or C1-4alkyl;
or two Rb substituents on adjacent carbon atoms taken together form —O(CH2)1-2O—;
or
c) a ring system selected from the group consisting of:
each ring system unsubstituted or substituted with C1-4alkyl, CF3, or halo;
A is N or CRe;
where R3 is H, methyl, or halo;
each R2 substituent is independently H, methyl, or halo;
X is —(CH2)2—, —C(Rf)═C(R9)—, or —N═CH—,
where Rf is H, methyl, halo, or —CH2N(CH3)2;
and R9 is H or methyl;
m is 1 or 2;
n is 1 or 2;
Z is N or CH;
and
R3 is H or C1-4alkyl.

19 more elements

An chemical entity selected from the group consisting of:

5-Fluoro-4-methyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
2-{4-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-4,6-dimethyl-1H-benzoimidazole;
2-{4-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-5fluoro-4-methyl-1H-benzoimidazole;
2-{4-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole-5-carboxylic acid methyl ester;
5-Fluoro-2-{4-fluoro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-4-methyl-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-56-yl}-1H-benzoimidazole;
2-{4-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{4-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-4,6-dimethyl-1H-benzoimidazole;
5-Chloro-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
4-Methyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazol;
5-Fluoro-4-methyl-2-{1-[3-(4-methyl-piperazin-1-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
2-{2,3-Dimethyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-4,6-dimethyl-1H-benzoimidazole;
2-{2,3-Dimethyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
4-Chloro-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
2-{1-[4-(1-Methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-5-trifluoromethyl-1H-benzoimidazole;
6-{1-[4-(1-Methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazole;
(2-{1-[4-(1-Methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazol-5-yl)-1H-methanone;
2-{1-[4-(1-Methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-naphtho[2,3-d]imidazole;
6-Chloro-4-methyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
4-Methyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
5-tert-Butyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
4,6-Dimethyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-6-yl}-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-6-yl}-1H-benzoimidazole;
4-Methyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-6-yl}-1H-benzoimidazole;
5-tert-Butyl-2-{3-chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
6-Chloro-2-{3-chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-4-methyl-1H-benzoimidazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-5-trifluoromethyl-1H-benzoimidazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yI)-butyl]-1H-indol-4-yl}-5,6-difluoro-1H-benzoimidazole;
5-Fluoro-4-methyl-2-[1-(3-piperazin-1-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-tert-Butyl-2-[3-chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-Fluoro-4-methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4-Chloro-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4,6-Dimethyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-6-yl]-1H-benzoimidazole;
5-Fluoro-4-methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-6-yl]-1H-benzoimidazole;
[5-(5-tert-Butyl-1H-benzoimidazol-2-yl)-1-(4-piperidin-4-yl-butyl)-1H-indol-3-ylmethyl]-dimethyl-amine;
5-Fluoro-4-methyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-4-methyl-3′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,3′H-[2,5′]bibenzoimidazolyl;
4-Methyl-1′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
4-Methyl-3′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H ,3′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-4-methyl-1′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-4-methyl-3′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,3′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-4-methyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1H-benzoimidazole;
2-{6-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-4,6-difluoro-1H-benzoimidazole;
2-[6-Chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-5-fluoro-4-methyl-1H-benzoimidazole;
2-{6-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-5-fluoro-4-methyl-1H-benzoimidazole;
5-Fluoro-4,4′-dimethyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
5,4′-Trimethyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
4,4′-Dimethyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Chloro-4,4′-dimethyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
6-Fluoro-4,4′-dimethyl-1′-[3-(1-methyl-piperidin-4-yl)-propyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
4,5-Dimethyl-2-[1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indol-5-yl]-1H-benzoimidazole;
4,6-Dimethyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
5-Chloro-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
6-Fluoro-4-methyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
2-Methyl-7-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-6H-imidazo[4′,5′:3,4]benzo[2,1-d]thiazole;
4,6-Dimethyl-2-{4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
4,5-Dimethyl-2-[1-(3-piperazin-1-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-tert-Butyl-2-[1-(3-piperazin-1-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-Chloro-2-[1-(3-piperazin-1-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-Chloro-2-{1-[3-(4-methyl-piperazin-1-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
4-Methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
5,6-Difluoro-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
5-Chloro-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
5-Fluoro-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
4,6-Difluoro-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
2-{1-[4-(1-Methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-naphtho[1,2-d]imidazole;
(2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-3H-benzoimidazol-4-yl)-phenyl-methanone;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-4,5-dimethyl-1H-benzoimidazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-4,5-dimethyl-1H-benzoimidazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-4,5-difluoro-1H-benzoimidazole;
6-[1-(4-Piperidin-4-yl-butyl)-1H-indol-4-yl]-5H-[1 ,3]dioxolo[4′,5′:4,5]-benzo[1,2-d]imidazole;
Phenyl-{2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazol-5-yl}-methanone;
4,5-Dimethyl-2-{1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-1H-benzoimidazole;
1-[3-(4-Methyl-piperazin-1-yl)-propyl]-5-[5-methyl-4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-1H-indole;
5-[4-(4-Chloro-phenyl)-5-methyl-1H-imidazol-2-yl]-1-[3-(4-methyl-piperazin-1-yl)-propyl]-1H-indole;
4-Methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-5-(4-methyl-5-propyl-1H-imidazol-2-yl)-1H-benzoimidazole;
4-Methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-5-[4-methyl-5-(4-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-1H-benzoimidazole;
5-[5-(3,5-Dichloro-phenyl)-4-methyl-1H-imidazol-2-yl]-4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-benzoimidazole;
4-Methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-5-(5-phenyl-4-trifluoromethyl-1H-imidazol-2-yl)-1H-benzoimidazole;
5-[5-(4-Chloro-phenyl)-4-p-tolyl-1H-imidazol-2-yl]-4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-benzoimidazole;
{5-(5-Fluoro-4-methyl-1H-benzoimidazol-2-yl)-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-3-ylmethyl}-dimethyl-amine;
2-[3-Chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-5-fluoro-4-methyl-1-benzoimidazole;
2-{3-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-l H-indol-5-yl}-5-fluoro-4-benzoimidazole;
2-[2,3-Dimethyl-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-4,6-dimethyl-1H-benzoimidazole;
2-[2,3-Dimethyl-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-5-fluoro-4-methyl-1H-benzoimidazole;
5-Fluoro-4-methyl-2-[1-(3-piperidin-4-yl-propyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-1H-benzoimidazole;
5-tert-Butyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1H-benzoimidazole;
5-Fluoro-4-methyl-2-[1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indol-5-yl]-1H-benzoimidazole;
5-Chloro-2-[1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indol-5-yl]-1H-benzoimidazole;
4-Methyl-2-[1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indol-5-yl]-1H-benzoimidazole;
5-Fluoro-4-methyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
5-Chloro-2-{l -[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
4-Methyl-2-{1-[3-(1-methyl-piperidin-4-yl)-propyl]-2,3-dihydro-1H-indol-5-yl}-1H-benzoimidazole;
2-[6-Chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-4,6-difluoro-1H-benzoimidazole;
2-[6-Chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-4,5-dimethyl-1H-benzoimidazole;
5-Chloro-2-[6-chloro-1-(3-piperidin-4-yl-propyl)-1H-indol-5-yl]-1H-benzoimidazole;
5-Chloro-2-{6-chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-1H-benzoimidazole;
2-{6-Chloro-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-indol-5-yl}-4,5-dimethyl-1H-benzoimidazole;
6-Chloro-4-methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
5-tert-Butyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
6,7-Dimethyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4-Methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-6-yl]-1H-benzoimidazole;
6-Chloro-4-methyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-6-yl]-1H-benzoimidazole;
5-tert-Butyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-6-yl]-1H-benzoimidazole;
4,5-Difluoro-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4,4′-Dimethyl-1′-(3-piperidin-4-yl-propyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
6-Fluoro-4,4′-dimethyl-1′-(3-piperidin-4-yl-propyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Chloro-4,4′-dimethyl-1′-(3-piperidin-4-yl-propyl)-1H ,1′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-4,4′-dimethyl-1′-(3-piperidin-4-yl-propyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4,6-Difluoro-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
4-Methyl-1′-(4-piperidin-4-yl-butyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
4,5-Dimethyl-1′-(4-piperidin-4-yl-butyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-1′-(4-piperidin-4-yl-butyl)-1H,1′H-[2,4′]bibenzoimidazolyl;
5-Fluoro-1′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
4,5-Dimethyl-1′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,1′H-[2,5′]bibenzoimidazolyl;
4-Methyl-3′-(4-piperidin-4-yl-butyl)-1H,3′H-[2,5′]bibenzoimidazolyl;
4,5-Dimethyl-3′-(4-piperidin-4-yl-butyl)-1H,3′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-3′-(4-piperidin-4-yl-butyl)-1H,3′H-[2,5′]bibenzoimidazolyl;
4,5-Dimethyl-3′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,3′H-[2,5′]bibenzoimidazolyl;
5-Fluoro-3′-[4-(1-methyl-piperidin-4-yl)-butyl]-1H,3′H[2,5′]bibenzoimidazolyl;
2-[1-(4-Piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-naphtho[2,3-d]imidazole;
2-[1-(4-Piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-naphtho[1,2-d]imidazole;
{2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazol-5-yl}-phenyl-methanone;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-5-trifluoromethyl-1H-benzoimidazole;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-5,6-difluoro-1H-benzoimidazole;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-4,5-difluoro-1H-benzoimidazole;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-5-fluoro-4-methyl-1H-benzoimidazole;
7-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-2-methyl-8H-imidazo[4′,5′:3,4]benzo[1,2-d]thiazole;
2-[3-Chloro-1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-3H-benzoimidazole-5-carboxylic acid methyl ester;
7-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-2-methyl-8H-imidazo[4′,5′:3,4]benzo[1,2-d]thiazole;
2-{3-Chloro-1-[4-(1-methyl-piperidin-4-yl)-butyl]-1H-indol-4-yl}-3H-benzoimidazole-5-carboxylic acid methyl ester;
4,5,4′-Trimethyl-1′-(3-piperidin-4-yl-propyl)-1H,1′H-[2,5′]bibenzoimidazolyl;
4,6-Dimethyl-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
6-Chloro-2-[1-(4-piperidin-4-yl-butyl)-1H-indol-4-yl]-1H-benzoimidazole;
2-[1-(4-Piperidin-4-yl-butyl)-1H-indol-4-yl]-6-trifluoromethyl-1H-benzoimidazole;
4-Methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-5-[4-methyl-5-(4-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-1H-benzoimidazole;
5-[5-(4-Methoxy-phenyl)-4-methyl-1H-imidazol-2-yl]-4-methyl-1-[3-(1-methyl-piperidin-4-yl)-propyl]-1H-benzoimidazole;
and pharmaceutically acceptable salts, prodrugs, and active metabolites thereof.

141 more elements

A pharmaceutical composition comprising an effective amount of at least one chemical entity selected from compounds of Formula (I), pharmaceutically acceptable salts of compounds of Formula (I), pharmaceutically acceptable prodrugs of compounds. of Formula (I), and pharmaceutically active metabolites of compounds of Formula (I).

Dependencies are inferred from the claim text.

Facts

Application: 12/316,835Filed 16 Dec 2008
Priority: 18 Dec 2007
Published: 18 Jun 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 491/056
Ortho-condensed systems: with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Family

Application61/014,572Us provisional application · filed 18 Dec 2007
US 8,084,466 B2Related patent
US 2009/0156613 A1This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

Facts

Application

12/316,835Filed 16 Dec 2008

Priority

18 Dec 2007

Published

18 Jun 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
C07D 403/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 491/056
Ortho-condensed systems: with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring