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US 2003/0158192 A1Published application
Urea substituted imidazoquinoline ethers
Assignee3M Innovative Properties Company
InventorsStephen L. Crooks, George W. Griesgraber, Philip D. Heppner, Bryon A. Merrill
Life of this patent
Estimating the term…
Abstract
Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain ether and urea functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.
Claims23
A compound of the Formula (I):
- 56
- wherein:
- X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
- R1 is selected from the group consisting of:
- —R4—NR8—CR3—NR8-Z-R6-alkyl;
- —R4—NR8—CR3—NR5-Z-R6-alkenyl;
- —R4—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—NR8—CR3—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;
- 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;
- each R3 is ═O or ═S;
- each R4 is independently 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 R7 can join with R5 to form a ring;
- R8 is H, C1-10 alkyl, or arylalkyl;
- or R4 and R8 can join together to form a ring;
- R9 is C1-10 alkyl which can join together with R8 to form a ring;
- each Y is independently —O— or —S(O)0-2—;
- Z is a bond, —C—, or —SO2—;
- n is 0 to 4;
- 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.
52 more elements
A compound selected from the group consisting of:
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N′-phenylurea;
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N′-phenylurea;
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)morpholine-4-carboxamide;
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-1 μl-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methylmorpholine-4-carboxamide;
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methyl-N′-phenylurea;
- and
- N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methyl-N′-phenylurea;
- or a pharmaceutically acceptable salt thereof.
5 more elements
A compound of the formula (II)
- 57
- 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—CR3—NR5-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—NR9—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;
- each R3 is ═O or ═S;
- each R4 is independently 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 R7 can join with R5 to form a ring;
- R8 is H, C1-10 alkyl, or arylalkyl;
- or R4 and R8 can join together to form a ring;
- R9 is C1-10 alkyl which can join together with R8 to form a ring;
- each Y is independently —O— or —S(O)0-2—;
- Z is a bond, —CO—, or —SO2—;
- n is 0 to 4;
- 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.
52 more elements
A compound of the formula (III):
- 58
- 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—CR3—NR5-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-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;
- each R3 is ═O or ═S;
- each R4 is independently 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 R7 can join with R5 to form a ring;
- R8 is H, C1-10 alkyl, arylalkyl;
- or R4 and R8 can join to form a ring;
- R9 is C1-10 alkyl which can join together with R8 to form a ring;
- each Y is independently —or —S(O)0-2—;
- Z is a bond, —CO—, or —SO2—;
- n is 0 to 4;
- 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.
52 more elements
A compound of the formula (IV):
- 59
- wherein:
- X is —CHR5—, —CHR5-alkylene-, or —CHR5-alkenylene-;
- R1 is selected from the group consisting of:
- —R4—NR8—CR3—NR5-Z-R6-alkyl;
- —R4—NR8CR3—NR5-Z-R6-alkyl;
- —R4—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—NR8—CR3—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;
- each Y is independently —O— or —S(O)0-2—;
- Z is a bond, —CO, or —SO2—;
- each R4 is independently 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 R7 can join with R5 to form a ring;
- R8 is H, C1-10 alkyl, or arylalkyl;
- or R4 and R8 can join to form a ring;
- R9 is C1-10 alkyl which can join together with R8 to form a ring;
- n is 0 to 4;
- 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.
26 more elements
Dependencies are inferred from the claim text.