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US 2014/0371204 A1Published application
4-(Benzoimidazol-2-yl)-thiazole Compounds and Related Aza Derivatives
AssigneeActelion Pharmaceuticals Ltd.
InventorsEva Caroff, Marcel Keller, Thierry Kimmerlin, Emmanuel Meyer
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4′, R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.
Claims17
A compound of Formula (I)
- wherein
- X represents CH, or N;
- ring A represents a benzene, pyridine, or pyrimidine ring;
- (R1)n represents one or two optional substituents each independently selected from (C1-4)alkyl;
- (C1-4)alkoxy;
- (C1-3)fluoroalkyl;
- (C1-3)fluoroalkoxy;
- halogen;
- cyano;
- (C3-6)cycloalkyl optionally mono-substituted with hydroxy;
- (C1-3)alkoxy-(C1-4)alkyl;
- (C1-3)alkoxy-(C2-4)alkoxy;
- hydroxy-(C1-4)alkyl;
- hydroxy-(C2-4)alkoxy;
- hydroxy;
- (C1-4)alkyl-sulfonyl;
- phenyl;
- 5-membered heteroaryl optionally substituted with (C1-4)alkyl;
- —CO—(C1-4)alkyl;
- —CO—(C1-4)alkoxy;
- —(CH2)q—NR6R7, wherein R6 and R7 independently represent hydrogen or (C1-4)alkyl, and q represents the integer 0, 1, or 2;
- or -L-heterocyclyl, wherein -L- represents —O— or —(CH2)r— wherein r represents the integer 0, 1, or 2, and the heterocyclyl independently is a 4- to 7-membered mono-cyclic saturated ring containing one or two heteroatoms independently selected from nitrogen or oxygen, wherein said heterocyclyl is optionally substituted with one substituent independently selected from (C1-4)alkyl, (C1-4)alkoxy, or oxo;
- R2 represents hydrogen, (C1-4)alkyl, (C1-3)fluoroalkyl;
- (C1-3)alkoxy-(C2-4)alkyl;
- or hydroxy-(C2-4)alkyl;
- R3 represents hydrogen, (C1-4)alkyl, (C1-4)alkoxy;
- (C1-3)fluoroalkyl;
- halogen;
- (C3-6)cycloalkyl, wherein optionally one ring carbon atom may be replaced by oxygen;
- (C1-3)alkoxy-(C1-4)alkyl;
- hydroxy-(C1-4)alkyl;
- —(C1-3)alkylene-COOH;
- —(C1-3)alkylene-NR8R9 wherein R8 and R9 independently represent (C1-3)alkyl;
- or 5- or 6-membered monocyclic heteroaryl or phenyl, wherein said 5- or 6-membered monocyclic heteroaryl or phenyl independently is unsubstituted, mono-, or di-substituted wherein the substituents are independently selected from (C1-4)alkyl;
- (C1-4)alkoxy;
- (C1-3)fluoroalkyl;
- (C1-3)fluoroalkoxy;
- halogen;
- or cyano;
- R4 and R4′ independently represent hydrogen, (C1-4)alkyl, (C1-3)alkoxy-(C1-4)alkyl;
- R12R13N—(CH2)—, wherein R12 and R13 independently represent (C1-3)alkyl;
- or R4 and R4′ together form a bridge —(CH2)m—, wherein m represents the integer 1 or 2;
- p represents the integer 1, or 2;
- and
- R5 represents aryl or 5- to 10-membered heteroaryl, wherein said aryl or heteroaryl independently is unsubstituted, or mono-, di-, or tri-substituted, wherein the substituents are independently selected from (C1-4)alkyl;
- (C1-4)alkoxy;
- (C1-3)fluoroalkyl;
- (C1-3)fluoroalkoxy;
- halogen;
- cyano;
- (C1-3)alkoxy-(C1-4)alkyl;
- (C1-3)alkoxy-(C2-4)alkoxy;
- hydroxy;
- —CO—(C1-4)alkoxy;
- hydroxy-(C1-4)alkyl;
- —(C1-3)alkylene-NR10R11 wherein R10 and R11 independently represent (C1-3)alkyl;
- phenyl;
- 5-membered heteroaryl;
- or and heterocyclyl, wherein the heterocyclyl is a 5- to 7-membered mono-cyclic saturated ring containing one or two nitrogen atoms, wherein said heterocyclyl is optionally substituted on a nitrogen having a free valency with (C1-4)alkyl;
- or R5 represents 9- or 10-membered partially aromatic bicyclic heterocyclyl;
- wherein said heterocyclyl is a phenyl or 5- or 6-membered heteroaryl ring which is fused to a 5- or 6-membered saturated or partially unsaturated non-aromatic ring containing one or two heteroatoms independently selected from oxygen, sulphur or nitrogen;
- wherein said heterocyclyl is unsubstituted, or mono-, di- or tri-substituted, wherein the substituents are independently selected from (C1-4)alkyl, (C1-4)alkoxy, halogen or oxo;
- or a salt thereof.
60 more elements
Dependencies are inferred from the claim text.