Urea substituted imidazoquinoline ethers

A compound selected from the group consisting of:

• N-{2-[2-(4-amino-2-methyl-1H imidazo[4, 5-c]quinolin-1-yl) ethoxy]ethyl}-N′-cyclohexyl urea;
• N-{2-[2-(4-amino-2-ethyl-1H-imidazo[4, 5-c]quinolin-1-yl) ethoxy]ethyl}-N′-phenylurea;
• N-{2-[2-(4-amino-2-ethyl-1H imidazo[4, 5-c]quinolin-1-yl) ethoxy]ethyl}-N′-cyclohexyl urea;
• N-{2-[2-(4-amino-2-methyl-1H-imidazo[4, 5-c]quinolin-1-yl) ethoxy]ethyl}-N′-phenylurea;
• and
• N-{2-[2-(4-amino-2-ethyl-1H-imidazo[4, 5-c]quinolin-1-yl) ethoxy] ethyl} morpholine-4-carboxamide;
• N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N′-phenylurea;
• N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy} ethyl)-N′-cyclohexylurea;
• N-(2-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)morpholine-4-carboxamide;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• R1 is selected from the group consisting of:
• R4—NR8CR3—NR5-Z-R6-alkyl;
• R4-NR8—CR3—NR5-Z-R6-alkenyl;
• R4—NR8—CR3—NR5-Z-R6-aryl;
• R4—N8—CR3—NR5-Z-R6—heteroaryl;
• R4—NR8—CR3—NR5-Z-R6-heterocyclyl;
• R4—NR8—CR3—NR5R7;
• R4—NR8—CR3NR9-Z-R6-alkyl;
• R4NR8—CR3—NR9-Z-R6-alkenyl;
• R4—NR8—CR3—NR9-Z-R6-aryl;
• R4—NR8—CR3—NR9-Z-R6-heteroaryl;
• and
• R4—NR8—CR3—NR9-Z-R6-heterocyclyl;
• R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-alkenyl;
• -alkyl-Y-aryl;
• and
• -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
• OH;
• -halogen;
• N(R5)2;
• CO—N(R5)2;
• CO—C1-10 alkyl;
• CO—O—C1-10 alkyl;
• N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• CO-aryl;
• and
• CO-heteroaryl;
• R3 is ═O or ═S;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H or C1-10 alkyl which may be interrupted by a hetero atom, or when R7 is C1-10 alkyl which may be interrupted by a hetero atom and R5 is C1-10 alkyl, R7 can join wit R5 to form a morpholine ring;
• R8 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is C1-10 alkyl and R8 is C1-10 alkyl, R4 and R8 can join together to form a piperidine ring;
• R9 is C1-10 alkyl;
• Y is —O— or —S(O)0-2—;
• Z is a bond, —CO—, or —SO2—;
• n is 0;
• and
• each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, hydroxy, halogen, and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (III):

• wherein:
• X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• R1 is selected from the group consisting of:
• R4—NR8—CR3—NR5-Z—R6-alkyl;
• R4—NR8—CR3—NR5-Z-R6-alkenyl;
• R4-NR8—CR3NR5—-Z—R6-aryl;
• R4—NR8—CR3—NR5-Z—R6-heteroaryl;
• R4—NR8—CR3—NR5-Z-R6-heterocyclyl;
• R4—NR8—CR3—NR5R7;
• R4—NR8—CR3—NR9-Z-R6-alkyl;
• R4—NR8—CR3—NR9-Z-R6-alkenyl;
• R4—NR8—CR3—NR9-Z-R6aryl;
• R4—NR8—CR3—NR9-Z-R6-heteroaryl;
• and
• R4—NR8—CR3—NR9-Z-R6-heterocyclyl;
• R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-alkenyl;
• -alkyl-Y-aryl;
• and
• -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
• —OH;
• -halogen;
• —N(R5)2;
• —CO—N(R5)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R3 is ═O or ═S;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 is a bond, or is alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H or C1-10 alkyl which may be interrupted by a hetero atom, or when R7 is C1-10 alkyl which may be interrupted by a hetero atom and R5 is C1-10 alkyl, R7 can join with R5 to form a morpholine ring;
• R8 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is C1-10 alkyl and R8 is C1-10 alkyl, R4 and R8, can join together to form a piperidine ring;
• R9 is C1-10 alkyl;
• Y is —O— or —S(O)0-2—;
• Z is a bond, —CO—, or —SO2—;
• n is 0;
• and
• each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (IV):

• wherein:
• X is —CHR5—, —CHR5-alkylene-, or —CHR5-alkenylene-;
• R1 is selected from the group consisting of:
• R4—NR8—CR3NR5-Z-R6-alkyl;
• R4—NR8CR3—NR5-Z-R6-alkyl;
• R—NR8—CR3—NR5-Z-R6-aryl;
• R4—NR8—CR3—NR5-Z-R6-heteroaryl;
• R4—NR8—CR3—NR5-Z-R6-heterocyclyl;
• —R4——NR8—CR3—NR5R7;
• R4—NR8CR3—NR9-Z-R6-alkyl;
• R4—NR8—CR3—NR9-Z-R6-alkenyl;
• R4—NR8—CR3—NR9-Z-R6-aryl;
• R4—NR8—CR3—NR9-Z-R6-heteroaryl;
• and
• R4—NR8—CR3—NR9-Z-R6-heterocyclyl;
• Z is a bond, —CO—, or —SO2—;
• R3 is ═O or ═S;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 is a bond, or is alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H or C1-10 alkyl which may be interrupted by a hetero atom, or when R7 is C1-10 alkyl which may be interrupted by a hetero atom and R5 is C1-10 alkyl, R7 can join wit R5, to form a morpholine ring;
• R8 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is C1-10 alkyl and R8 is C1-10 alkyl, R4 and R8 can join together to form a piperidine ring;
• R9 is C1-10 alkyl;
• n is 0;
• and
• each R present is independently selected from the group consisting of C1-10 alkyl,
• C1-10 alkoxy, halogen and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.