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US 7,253,200 B2Granted
Imidazole compounds
AssigneeJanssen Pharmaceutica NV
InventorsDaniel J. Buzard, James P. Edwards, David E. Kindrachuk, Jennifer D. Venable
Life of this patent
Estimating the term…
Abstract
Imidazole compounds, compositions, and methods of using them in leukocyte recruitment inhibition, in modulating H4 receptor expression, and in treating conditions such as inflammation, H4 receptor-mediated conditions, and related conditions.
Claims21
A compound of formula (II):
- wherein
- W is, independently from other member and substituent assignments, N;
- X is, independently from other member and substituent assignments, CR9;
- Y is, independently from other member and substituent assignments, O, NR10, or CR10R11;
- Z is, independently from other member and substituent assignments, N or CR12;
- n is, independently from other member and substituent assignments, 0, 1, or 2;
- each of R1-2 is, independently from other member and substituent assignments, —H, —CF3, —C1-6alkyl, —C3-6cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl;
- or, R1 and R2 taken together with the carbon atoms to which they are attached form a cyclic structure Cyc1 selected from 5- or 6-membered carbocycle, and 5- or 6-membered heterocycle with 1 heteroatom, wherein said cyclic structure Cyc1 is, independently from other substituent assignments, substituted with 0, 1, or 2 substituents selected from —C1-3alkyl, halo, hydroxy, amino, and —C1-3alkoxy;
- each of R3-4 and R9 is, independently from other member and substituent assignments, —H, —C1-6alkyl, halo, —CF3, —OCF3, —ORc, —SRc, —S(O)Rc, —SO2Rc, C1-4alkoxy, cyano, nitro, —C(O)NRaRb, —C(O)phenyl, —C(O)C1-6alkyl, —S(O)C1-4alkyl, or —SO2C1-4alkyl;
- or, R3 and R4 taken together with the carbon atoms to which they are attached form a cyclic structure Cyc2 selected from aryl, 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 —C1-3alkyl, halo, hydroxy, amino, and —C1-3alkoxy;
- wherein each of Ra, Rb and Rc is, independently from other substituent assignments, selected from H, C1-4alkyl, C3-6cycloalkyl, phenyl, (C3-6cycloalkyl)C1-2alkyl-, benzyl and phenethyl, or Ra and Rb 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 >NC1-6alkyl, and wherein any phenyl, phenethyl, benzyl, alkyl or cycloalkyl moiety in any of said R1-4, Ra, Rb, Rc, and said ring HetCyc1 is optionally, and independently from other substituent assignments, substituted with 1, 2 or 3 substituents selected from C1-3alkyl, halo, hydroxy, amino, and C1-3alkoxy;
- R5 is, independently from other member and substituent assignments, —H, —C1-6alkyl, —C1-4alkoxy, or hydroxy;
- each of R6 and R7 is, independently from other member and substituent assignments, —H or —C1-6alkyl, or R6 and R7 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 —C1-3alkyl, halo, hydroxy, amino, and —C1-3alkoxy;
- R8 is, independently from other member and substituent assignments, —H or —C1-4alkyl;
- each of R10 and R11 is, independently from other member and substituent assignments, —H or —C1-4alkyl;
- or, when Y is CR10R11, R10 and R11 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 non-aromatic heterocycle with 0 or 1 additional heteroatoms, or CR10R11 is C═O;
- R12 is, independently from other member and substituent assignments, —H, —C1-4alkyl, hydroxy, or —C1-4alkoxy;
- an enantiomer, diastereomer, racemate thereof, or a pharmaceutically acceptable salt, amide or ester thereof;
- with the following provisos:
- when Y is O or NR10, then Z is CR12 and R5 is not hydroxy or —C1-4alkoxy;
- when Z is N, Y is CR10R11;
- when R1 and R2 are both —H, Y is CH2, and R8 is methyl, then R5 is not hydroxy.
19 more elements
A compound selected from:
- 2-[4-(1-Methyl-piperidin-4-yl)-butoxy]-4-(4-phenyl-5-trifluoromethyl-1H-imidazol-2-yl)-pyridine;
- 2-[4-(1-Methyl-piperidin-4-yl)-butoxy]-4-[5-methyl-4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-pyridine;
- 4-[4-(4-Chloro-phenyl)-5-methyl-1H-imidazol-2-yl]-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridine;
- 5-Bromo-4-[4-(4-chloro-phenyl)-5-methyl-1H-imidazol-2-yl]-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-pyridine;
- 3-Chloro-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-4-(4-phenyl-5-trifluoromethyl-1H-imidazol-2-yl)-pyridine;
- 1-Methyl-4-(4-{4-[5-methyl-4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-pyridin-2-yloxy}-butyl)-[1,4]diazepane;
- and
- 5-Bromo-2-[4-(1-methyl-piperidin-4-yl)-butoxy]-4-[5-methyl-4-(3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-pyridine.
5 more elements
Dependencies are inferred from the claim text.