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- Nachgewiesen in: USPTO Patent Applications
- Sprachen: English
- Document Number: 20160200686
- Publication Date: July 14, 2016
- Appl. No: 14/911000
- Application Filed: August 08, 2014
- Claim: 1. A compound of formula (I) [chemical expression included] wherein n represents 0, 1, 2, 3, or 4; D represents ═N— or ═C(R5)—; E represents ═N— or ═C(R4A)—; R9 represents (C1-C4)alkyl or halogen; R1 represents (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, cyano or halogen; R2 and R3 represent independently of each other hydrogen or methyl; or R2 and R3 form, together with the carbon atom to which they are attached, a mono-cyclic (C3-C5)cycloalkyl ring; R4 and R4A represent independently of each other hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, cyano, nitro or halogen; R5 represents hydrogen or halogen; R6 represents hydrogen or methyl; R7 represents hydrogen, (C1-C4)alkyl or hydroxy-(C1-C4)alkyl; R8 represents a mono- or bi-cyclic (C3-C8)cycloalkyl group, which group is unsubstituted or mono- or disubstituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy, hydroxy-(C1-C4)alkyl, halogen, —COR10, or phenyl which is unsubstituted or mono- or di-substituted with (C1-C4)alkyl, (C1-C4)fluoroalkyl, halogen, or —COOR11; a mono- or bi-cyclic heterocyclyl group, which group is unsubstituted; mono-substituted at a nitrogen-atom with (C1-C4)alkyl, (C1-C4)fluoroalkyl, (C1-C4)alkyl-carbonyl, (C1-C4)alkyl-sulfonyl, phenyl-(C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl or —COOR11; mono- or di-substituted at a carbon-atom with fluoro or oxo; or mono-, di-, tri-, tetra- or penta-substituted with methyl; a mono-cyclic (C5-C6)cycloalkenyl group; a partially saturated bi-cyclic aryl group or a partially saturated bi-cyclic heteroaryl group, which groups are independently unsubstituted or mono- or disubstituted, wherein the substituents are independently selected from (C1-C4)alkoxy or hydroxy; a phenyl-group which group is unsubstituted or mono-substituted with (C1-C4)alkoxy; a mono-cyclic heteroaryl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl, unsubstituted mono-cyclic heteroaryl, benzyl or phenyl, wherein the phenyl is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkoxy or halogen; a (C4-C6)alkyl group; or a (C1-C4)alkyl group which is mono-substituted with a substituent selected from X; mono-substituted with a substituent selected from Y; di-substituted with one substituent selected from X and one substituent selected from Y; or di-substituted with one mono-cyclic heterocyclyl group and one substituent selected from Y; wherein X represents (C1-C4)alkoxy, (C1-C4)fluoroalkyl, cyano, hydroxy, dimethylamino, —COOR11 or —CONH2; Y represents a mono-cyclic (C3-C6)cycloalkyl group, which group is unsubstituted or mono-substituted with hydroxy or phenyl; a mono-cyclic heterocyclyl group, which group is unsubstituted or mono-substituted at a nitrogen-atom with (C1-C4)alkyl, (C1-C4)alkyl-carbonyl or —COOR11; a partially saturated bi-cyclic aryl group or a partially saturated bi-cyclic heteroaryl group; an aryl-group which group is unsubstituted or mono-, di- or tri-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C3)alkoxy-(C1-C2)alkyl, mono-cyclic heterocyclyl-(C1-C2)alkyl, mono-cyclic heteroaryl-(C1-C2)alkyl, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, cyano, halogen, —COOR11 or bis-[(C1-C2)alkyl]-amino-(C1-C2)alkyl; or a benzo[d][1,3]dioxolyl group; or a heteroaryl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, (C1-C4)fluoroalkoxy-(C1-C2)alkyl, halogen, mono-cyclic heterocyclyl or phenyl which is unsubstituted or mono-substituted with (C1-C4)alkoxy; or R7 and R8 form, together with the nitrogen atom to which they are attached, a mono- or bi-cyclic heterocyclyl group, which group is unsubstituted; or mono-substituted at a nitrogen-atom with (C1-C4)alkyl, (C1-C4)alkyl-carbonyl or —COOR11; R10 represents hydroxy, (C1-C4)alkoxy or amino; and R11 represents (C1-C4)alkyl; or a salt of the compound.
- Claim: 2. The compound according to claim 1, wherein R1 represents (C1-C4)alkoxy or (C1-C4)fluoroalkyl; or a salt of the compound.
- Claim: 3. The compound according to claim 1, wherein R2 represents hydrogen; or a salt of the compound.
- Claim: 4. The compound according to claim 1, wherein R8 represents a mono- or bi-cyclic (C3-C8)cycloalkyl group, which group is unsubstituted or mono- or disubstituted, wherein the substituents are independently selected from (C1-C4)alkyl, hydroxy, hydroxy-(C1-C4)alkyl, fluoro, or —CONH2; or a salt of the compound.
- Claim: 5. The compound according to claim 1, that is also a compound of formula (II), [chemical expression included] wherein n represents 0, 1, or 2; R9 represents (C1-C4)alkyl or halogen; R1 represents (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, or halogen; R3 represents hydrogen or methyl; R4 represents hydrogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, cyano or halogen; R8 represents a mono- or bi-cyclic (C3-C8)cycloalkyl group, which group is unsubstituted or mono- or disubstituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, hydroxy, hydroxy-(C1-C4)alkyl, fluoro or —COR10, wherein the mono- or bi-cyclic (C3-C8)cycloalkyl group is selected from cyclopentyl, cyclohexyl, bicyclo[2.2.1]heptyl or bicyclo[2.2.2]octyl; a mono- or bi-cyclic heterocyclyl group, which group is unsubstituted; mono-substituted at a nitrogen-atom with (C1-C4)alkyl, (C1-C4)fluoroalkyl, phenyl-(C1-C4)alkyl or mono-cyclic (C3-C6)cycloalkyl; or mono- or di-substituted at a carbon-atom with fluoro; wherein the mono- or bi-cyclic heterocyclyl group is selected from pyrrolidinyl, piperidinyl or 1-azabicyclo[2.2.2]octyl; a partially saturated bi-cyclic aryl group, which group is unsubstituted or mono- or disubstituted with (C1-C4)alkoxy; a mono-cyclic heteroaryl-group which group is mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl or phenyl; wherein the mono-cyclic heteroaryl group is selected from isoxazolyl or pyrazolyl; or a (C1-C4)alkyl group which is mono-substituted with a substituent selected from Y; di-substituted with one substituent selected from X and one substituent selected from Y; or di-substituted with one morpholinyl and one substituent selected from Y; wherein X represents (C1-C4)alkoxy, hydroxy or —CONH2; Y represents a phenyl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C3)alkoxy-(C1-C2)alkyl, mono-cyclic heterocyclyl-(C1-C2)alkyl, mono-cyclic heteroaryl-(C1-C2)alkyl, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, cyano, halogen, or bis-[(C1-C2)alkyl]-amino-(C1-C2)alkyl; or a heteroaryl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, (C1-C4)fluoroalkoxy-(C1-C2)alkyl, halogen, mono-cyclic heterocyclyl or phenyl which is unsubstituted or mono-substituted with (C1-C4)alkoxy; and R10 represents (C1-C4)alkoxy or amino; or a salt of the compound.
- Claim: 6. The compound according to claim 5, wherein R4 represents hydrogen or halogen; or a salt of the compound.
- Claim: 7. The compound according to claim 5, wherein R8 represents a mono- or bi-cyclic (C3-C8)cycloalkyl group, which group is unsubstituted or mono- or disubstituted, wherein the substituents are independently selected from (C1-C4)alkyl, hydroxy, hydroxy-(C1-C4)alkyl, fluoro, or —CONH2; or a salt of the compound.
- Claim: 8. The compound according to claim 5, wherein R8 represents a (C1-C4)alkyl group which is mono-substituted with a substituent selected from Y; di-substituted with one substituent selected from X and one substituent selected from Y; or di-substituted with one morpholinyl and one substituent selected from Y; wherein X represents (C1-C4)alkoxy, hydroxy or —CONH2; and Y represents a phenyl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C3)alkoxy-(C1-C2)alkyl, mono-cyclic heterocyclyl-(C1-C2)alkyl, mono-cyclic heteroaryl-(C1-C2)alkyl, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, cyano, halogen, or bis-[(C1-C2)alkyl]-amino-(C1-C2)alkyl; or a heteroaryl-group which group is unsubstituted or mono- or di-substituted, wherein the substituents are independently selected from (C1-C4)alkyl, mono-cyclic (C3-C6)cycloalkyl, (C1-C4)alkoxy, (C1-C4)fluoroalkyl, (C1-C4)fluoroalkoxy, (C1-C4)fluoroalkoxy-(C1-C2)alkyl, halogen, mono-cyclic heterocyclyl or phenyl which is unsubstituted or mono-substituted with (C1-C4)alkoxy; or a salt of the compound.
- Claim: 9. The compound according to claim 1, that is also a compound of formula (V), [chemical expression included] wherein n represents 0, 1 or 2; R9 represents methyl or fluoro; R1 represents methyl, ethyl, methoxy, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1-difluoroethyl, chloro or bromo; R3 represents hydrogen or methyl; R4 represents hydrogen, methyl, methoxy, trifluoromethyl, cyano, fluoro, chloro or bromo; and R8 represents 4-hydroxy-cyclohexyl, 4-hydroxy-4-methyl-cyclohexyl, 4-hydroxymethyl-cyclohexyl, 4-(2-hydroxyethyl)-cyclohexyl, bicyclo[2.2.1]hept-2-yl or 4-hydroxy-bicyclo[2.2.2]oct-1-yl; or a salt of the compound.
- Claim: 10. The compound according to claim 1, wherein the compound is: 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-cyclopentylurea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(cyclopent-3-en-1-yl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4,4-difluorocyclohexyl)urea; (R)-1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-cyclohexylurea; (1R*,2S*)-2-(3-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxamide; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1R,2S)-2-hydroxycyclopentyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1 S*,2S*)-2-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(bicyclo[2.2.1]heptan-2-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1,2,3,4-tetrahydronaphthalen-1-yl)urea; (1R*,2S*)-Ethyl 2-(3-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxylate; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)urea; (R)-1-(2-((1H-1,2,4-Triazol-1-yl)methyl)benzyl)-3-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1S*,2S*)-2-(hydroxymethyl)cyclohexyl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1 S*,2R*)-2-(hydroxymethyl)cyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromophenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(6-chloro-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-hydroxycyclohexyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-(isopropoxymethyl)benzyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-(morpholinomethyl)benzyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-methoxy-3-phenylpropan-2-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4-(hydroxymethyl)cyclohexyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-cyclopentylurea; 1-(2-(4-Bromophenyl)-1-(5-chloro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(trans-4-Hydroxycyclohexyl)-3-(2-(4-methoxyphenyl)-1-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)ethyl)urea; 1-(trans-4-Hydroxycyclohexyl)-3-((R)-2-(4-methoxyphenyl)-1-(5-methyl-1H-benzo[d]imidazol-2-yl)ethyl)urea; 1-(trans-4-Hydroxycyclohexyl)-3-((R)-1-(5-methoxy-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)urea; 1-((R)-1-(5-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2,2,6,6-tetramethylpiperidin-4-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(quinuclidin-3-yl)urea; (R)-1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-cyclohexylpiperidin-4-yl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(cyclopentylmethyl)urea; tert-butyl 3-(3-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)pyrrolidine-1-carboxylate; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-phenethylpiperidin-4-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4-(2-hydroxyethyl)cyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1R,2R)-2-hydroxycyclopentyl)urea; (R)-tert-butyl 3-(3-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)pyrrolidine-1-carboxylate; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-chlorophenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((R)-piperidin-3-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((S)-piperidin-3-yl)urea; 1-((R)-2-(4-Bromophenyl)-1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(trans-4-Hydroxycyclohexyl)-3-((R)-2-(4-methoxyphenyl)-1-(5-nitro-1H-benzo[d]imidazol-2-yl)ethyl)urea; 1-((R)-1-(6-Cyano-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(6-cyano-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2,2,6,6-tetramethylpiperidin-4-yl)urea; 1-((R)-1-(6-Cyano-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(quinuclidin-3-yl)urea; (1R*,2R*)-ethyl 2-(3-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxylate; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((3S*,4R*)-3-fluoropiperidin-4-yl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((3S*,4S*)-3-fluoropiperidin-4-yl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(3-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1R*,3S*)-3-hydroxycyclopentyl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1 S*,3S*)-3-hydroxycyclopentyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-((R)-1-(5-Bromo-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(2,2-difluoroethyl)piperidin-4-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(-1-(2,2-difluoroethyl)piperidin-3-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-3-fluorophenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-2-fluorophenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(cis-4-hydroxy-4-methylcyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(p-tolyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(6-Chloro-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(3-fluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; (R)-1-(2-(4-Bromophenyl)-1-(6-chloro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; (R)-1-(2-(4-Bromophenyl)-1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; (R)-1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-phenylpropyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((S)-1-methoxy-3-phenylpropan-2-yl)urea; (S)-2-(3-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)-3-phenylpropanamide; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((S)-1-hydroxy-3-phenylpropan-2-yl)urea; 1-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-morpholino-1-phenylethyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-morpholino-2-phenylethyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((2-(((1,1,1-trifluoropropan-2-yl)oxy)methyl)pyridin-3-yl)methyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((3-(2,2,2-trifluoroethoxy)pyrazin-2-yl)methyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(isochroman-4-yl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2-(2,2,2-trifluoroethoxy)benzyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromophenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-((R)-2-(4-Bromophenyl)-1-(6-methyl-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-2-(4-Bromophenyl)-1-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; trans-Methyl 4-(3-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxylate; trans-4-(3-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxylic acid; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(3-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; Methyl 3-(3-((R)-1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)cyclohexanecarboxylate; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-3-fluorophenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-3-fluorophenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,3-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,6-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,6-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(2-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,5-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,6-difluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,5-difluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2, 5-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,3-difluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,3-difluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-2-fluorophenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-bromo-2-fluorophenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxy-4-methylcyclohexyl)urea; 1-((R)-1-(5-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(5-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(4-(trifluoromethyl)phenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-phenylpropyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((R)-2-hydroxy-2-phenylethyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((1-(4-methoxyphenyl)-1H-pyrazol-5-yl)methyl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2,3,5,6-tetrafluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; (R)-1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea; 1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(3-fluoro-4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(6-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(3-fluoro-4-methoxyphenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((S)-1-(3-methoxyphenyl)ethyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((S)-1-(2-methoxyphenyl)ethyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(imidazo[2,1-b]thiazol-6-yl)ethyl)urea; (S)-2-(3-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)ureido)-2-phenylacetamide; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-hydroxy-1-phenylpropyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(5,6-dimethoxy-2,3-dihydro-1H-inden-1-yl)urea; 1-(1-(5-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(5-Fluoro-1H-benzo[d]imidazol-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-((R)-1-(1H-Benzo[d]imidazol-2-yl)-2-(4-(fluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(2-(2,6-difluoro-4-methoxyphenyl)-1-(5-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(2-(2,6-difluoro-4-methoxyphenyl)-1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(2-(4-ethylphenyl)-1-(5-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-(difluoromethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(2-(2,3-difluoro-4-methoxyphenyl)-1-(5-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-(1,1-difluoroethyl)phenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)propyl)-3-(trans-4-hydroxycyclohexyl)urea; or 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxy-2-methylphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; or a salt of the compound.
- Claim: 11. The compound according to claim 1, wherein the compound is: (S)-1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(2,2,6,6-tetramethylpiperidin-4-yl)urea; 1-(2-(4-bromo-3-fluorophenyl)-1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)-3-(4-hydroxybicyclo[2.2.2]octan-1-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(5-methylisoxazol-3-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(5-methylthiazol-2-yl)urea; 1-(1-(1H-Benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-(4-chlorophenyl)-1-methyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-cyclopropyl-1-phenyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(4-methoxyphenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(4-isopropylphenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(3-methyl-1-phenyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(pyridin-4-yl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(4-fluorophenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(pyridin-2-yl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-phenyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(tert-butyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-benzyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1,3-dimethyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-ethyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-methyl-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(3-methoxyphenyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(p-tolyl)-1H-pyrazol-5-yl)urea; 1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(1-(2-methoxyphenyl)-1H-pyrazol-5-yl)urea; 1-(2-(1H-benzo[d]imidazol-2-yl)-1-(4-methoxyphenyl)propan-2-yl)-3-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)urea; (R)-1-(1-(1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-((4-(1,1-difluoroethyl)oxazol-2-yl)methyl)urea; 1-(1-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(1-(5,6-dibromo-1H-benzo[d]imidazol-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; 1-(trans-4-hydroxycyclohexyl)-3-(2-(4-methoxyphenyl)-1-(7H-purin-8-yl)ethyl)urea; 1-(1-(3H-imidazo[4,5-b]pyridin-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; or 1-(1-(3H-imidazo[4,5-c]pyridin-2-yl)-2-(4-methoxyphenyl)ethyl)-3-(trans-4-hydroxycyclohexyl)urea; or a salt of the compound.
- Claim: 12. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound is formulated as a medicament.
- Claim: 13. A pharmaceutical composition comprising, as active principle, a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.
- Claim: 14. A method of treating or preventing a disease comprising administering to a subject in need thereof a compound according to claim 1, wherein the disease is selected from an inflammatory disease, an obstructive airway disease, an allergic condition, an HIV-mediated retroviral infection, a cardiovascular disorder, neuroinflammation, a neurological disorder, pain, a prion-mediated disease or an amyloid-mediated disorder.
- Claim: 15. A method of treating or preventing a disease comprising administering to a subject in need thereof a composition according to claim 13, wherein the disease is selected from an inflammatory disease, an obstructive airway disease, an allergic condition, an HIV-mediated retroviral infection, a cardiovascular disorder, neuroinflammation, a neurological disorder, pain, a prion-mediated disease or an amyloid-mediated disorder.
- Claim: 16. A method of modulating an immune response comprising administering to a subject in need thereof the compound according to claim 1.
- Claim: 17. A method of modulating an immune response comprising administering to a subject in need thereof the composition according to claim 13.
- Current International Class: 07; 07; 07; 07; 07; 07; 07
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