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US 6,573,273 B1Granted
Urea substituted imidazoquinolines
Assignee3M Innovative Properties Company
InventorsStephen L. Crooks, George W. Griesgraber, Kyle J. Lindstrom, Bryon A. Merrill, Michael J. Rice
Life of this patent
Estimating the term…
Abstract
Imidazoquinoline and tetrahydroimidazoquinoline compounds that contain urea, thiourea, acylurea, or sulfonylurea 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.
Claims18
A compound of the formula (I):
- wherein
- bonds represented by dashed lines are present or absent;
- R1 is —C2-6 alkyl-NR3—CY—NR5—R4 wherein
- Y is ═O or ═S;
- R4 is hydrogen, alkyl, aryl, or substituted aryl;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -substituted aryl;
- -heteroaryl;
- -substituted heteroaryl;
- -alkyl-O-aryl;
- -alkyl-O-alkyl;
- -alkyl-O-alkenyl;
- and
- -alkyl or alkenyl substituted by one of more substituents selected from the group consisting of:
- —OH;
- -halogen;
- —N(R3)2;
- —CO—N(R3)2;
- —CO—C1-10 alkyl;
- —CO—O—C1-10 alkyl;
- —N3;
- -aryl;
- -substituted aryl;
- -heterocyclyl;
- -substituted heterocyclyl;
- —CO-aryl;
- —CO-(substituted aryl);
- —CO-heteroaryl;
- and
- —CO-(substituted heteroaryl);
- each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
- R5 is selected from the group consisting of hydrogen and C1-10 alkyl, or R4 and R5 can combine to form a 3 to 7 membered heterocyclic or substituted heterocyclic 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 triflutoromethyl, or a pharmaceutically acceptable salt thereof.
34 more elements
A compound selected from the group consisting of:
- N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-phenylurea;
- N-[4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-phenylurea;
- N-{8-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]octyl}-N′-phenylurea;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-phenylurea;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-phenylthiourea;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N-butylurea;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]morpholine-4-carboxamide;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-propylthiourea;
- N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-cyclohexylurea;
- N-[8-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)octyl]-N′-phenylurea;
- N-[4-(4-amino-2-hexyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-phenylurea;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-propylthiourea;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-cyclohexylthiourea;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-cyclohexylurea;
- N-[4-(4-amino-2-pentyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N′-phenylurea;
- N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-N′-phenylurea;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}-N′-phenylurea;
- N-3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}-N′-butylurea
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide;
- N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N′-phenylurea;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide;
- N-{3-[4-amino-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide;
- N-[3-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]morpholine-4-carboxamide;
- N-{3-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]propyl}morpholine-4-carboxamide;
- N-{3-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl}-N′-phenylurea;
- N-[4-(4-amino-2-methyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]morpholine-4-carboxamide;
- N-{4-[4-amino-2-(3-phenoxypropyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}morpholine-4-carboxamide;
- and
- N-[4-(4-amino-2-pentyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]morpholine-4-carboxamide;
- or a pharmaceutically acceptable salt thereof.
27 more elements
A pharmaceutical composition comprising a therapeutically effective amount of a compound of the formula Ia:
- wherein
- bonds represented by dashed lines are present or absent;
- R1 is -alkyl-NR3—CO—O—R4;
- R4 is alkyl, aryl, or substituted aryl;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -substituted aryl;
- -heteroaryl;
- -substituted heteroaryl;
- -alkyl-O-aryl;
- -alkyl-O-alkyl;
- -alkyl-O-alkenyl;
- and
- -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- -halogen;
- —N(R3)2;
- —CO—N(R3)2;
- —CO—C1-10 alkyl;
- —CO—O—C1-10 alkyl;
- —N3;
- -aryl;
- -substituted aryl;
- -heteroaryl;
- -substituted heterocyclyl;
- —CO-aryl;
- —CO-(substituted aryl);
- —CO-heteroaryl;
- and
- —CO-(substituted heteroaryl);
- each R3 is independently selected from the group consisting of hydrogen and C1-10 alkyl;
- n is 0 to 4 and each R present is independently selected from the groups consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl;
- or a pharmaceutically acceptable salt therefore in combination with a pharmaceutically acceptable carrier.
33 more elements
Dependencies are inferred from the claim text.