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US 2009/0264647 A1Published application
Benzoimidazole compounds
AssigneeJanssen Pharmaceutica NV
InventorsKristen L. Arienti, James G. Breitenbucher, Daniel J. Buzard, James P. Edwards, Michael D. Hack, Alice Lee-Dutra
Life of this patent
Estimating the term…
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.
Claims24
A compound of formula (II):
- wherein
- X is CH;
- Y is O, NR12, or CR12R13;
- Z is CR14;
- n is 1;
- each of R1-4 is, independently from other substituent assignments, H, C1-4alkyl, C2-5alkenyl, C2-5alkynyl, C3-6cycloalkyl, —C1-4alkoxy, —C1-4alkylamino, —C1-4alkylthio, —C1-4alkylsulfonyl, —OC3-6cycloalkyl, —OCH2Ph, cyano, —CF3, F, Cl, Br, I, nitro, —OCF3, —SCF3, —ORc, —SRc, —S(O)Rc, —SO2Rc, —C(O)RcC, phenyl, benzyl, phenethyl, —C(O)NRaRb, —C(O)ORc, —NRaRb, —CH2NRaRb or —CH2ORc;
- 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 HetCycl 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;
- each of R5-7 is, independently from other substituent assignments, H, C1-6alkyl, F, Cl, Br, I, 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, R7 and R6 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 C1-3alkyl, halo, hydroxy, amino, and C1-3alkoxy;
- R8 is H, C1-6alkyl, C1-4alkoxy, or OH;
- each of R9 and R10 is, independently from other substituent assignments, H or C1-6alkyl, or R9 and R10 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;
- R11 is H, C1-4alkyl;
- each of R12 and R13 is, independently from other substituent assignments, H or C1-4alkyl;
- or, when Y is CR12R13, R12 and R13 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 CR12R13 is C═O;
- R14 is H, C1-4alkyl, OH, or C1-4alkoxy;
- an enantiomer, diastereomer, racemate thereof, or a pharmaceutically acceptable salt, amide or ester thereof;
- provided that:
- when Y is O or NR12, then R8 is not OH or C1-4alkoxy;
- and
- neither R1 nor R4 is C(O)NH2.
17 more elements
A compound selected from the group consisting of:
- 6-Fluoro-7-methyl-2-{3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 7-Methyl-2-{3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 6,7-Dimethyl-2-{3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 5-Chloro-7-methyl-2-{3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 5,7-Dimethyl-2-{2-methyl-3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 5-Chloro-7-methyl-2-{2-methyl-3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 6-Fluoro-7-methyl-2-{2-methyl-3-[4-(1-methyl-piperidin-4-yl)-butoxy]-phenyl}-1H-benzoimidazole;
- 6-Fluoro-7-methyl-2-{3-[3-(1-methyl-piperidin-4-yloxy)-propoxy]-phenyl}-1H-benzoimidazole;
- and pharmaceutically acceptable salts of said compounds.
6 more elements
Dependencies are inferred from the claim text.