Back to results
US 2003/0195209 A1Published application
Urea substituted imidazopyridines
Assignee3M Innovative Properties Company
InventorsJoseph F. Dellaria, Chad A. Haraldson, Kyle J. Lindstrom, Bryon A. Merrill
Life of this patent
Estimating the term…
Abstract
Imidazopyridine compounds that contain urea or thiourea 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.
Claims30
A compound of the formula (I):
- 72
- wherein
- X is alkylene or alkenylene;
- Y is —CO— or —CS—;
- Z is —NR6—;
- —NR6—CO—;
- —NR6—SO2—;
- or —NR7—;
- R1 is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of:
- -alkyl;
- -alkenyl;
- -aryl;
- -heteroaryl;
- -heterocyclyl;
- -substituted cycloalkyl;
- -substituted aryl;
- -substituted heteroaryl;
- substituted heterocyclyl;
- —O-alkyl;
- —O-(alkyl)0-1-aryl;
- —O-(alkyl)0-1-substituted aryl;
- —O-(alkyl)0-1-heteroaryl;
- —O-(alkyl)0-1-substituted heteroaryl;
- —O-(alkyl)0-1-heterocyclyl;
- —O-(alkyl)0-1-substituted heterocyclyl;
- —COOH;
- —CO—O-alkyl;
- -CO-alkyl;
- —S(O)0-2-alkyl;
- —S(O)0-2-(alkyl)0-1-aryl;
- —S(O)0-2-(alkyl)0-1-substituted aryl;
- —S(O)0-2-(alkyl)0-1-heteroaryl;
- —S(O)0-2-(alkyl)0-1-substituted heteroaryl;
- —S(O)0-2-(alkyl)0-1-heterocyclyl;
- —S(O)0-2-(alkyl)0-1-substituted heterocyclyl;
- -(alkyl)0-1-N(R6)2;
- -(alkyl)0-1-NR6—CO—O-alkyl;
- -(alkyl)0-1-NR6—CO-alkyl;
- -(alkyl)0-1-NR6—CO-aryl;
- -(alkyl)0-1-NR6—CO-substituted aryl;
- -(alkyl)0-1-NR6—CO-heteroaryl;
- -(alkyl)0-1-NR6—CO-substituted heteroaryl;
- —P(O)(Oalkyl)2;
- —N3;
- -halogen;
- -haloalkyl;
- -haloalkoxy;
- —CO-haloalkyl;
- —CO-haloalkoxy;
- —NO2;
- —CN;
- —OH;
- —SH;
- and in the case of alkyl, alkenyl, and heterocyclyl, oxo;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -substituted aryl;
- -heteroaryl;
- -substituted heteroaryl;
- -alkyl-O-alkyl;
- -alkyl-S-alkyl;
- -alkyl-O-aryl;
- -alkyl-S-aryl:
- -alkyl-O— alkenyl;
- -alkyl-S— alkenyl;
- and
- -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
- —OH;
- -halogen;
- —N(R6)2;
- —CO—N(R6)2;
- —CS—N(R6)2;
- —SO2—N(R6)2;
- —NR6—CO—C1-10 alkyl;
- —NR6—CS—C1-10 alkyl;
- —NR6—SO2—C1-10 alkyl;
- —CO—C1-10 alkyl;
- —CO—O—C1-10 alkyl;
- —N3;
- -aryl;
- -substituted aryl;
- -heteroaryl;
- -substituted heteroaryl;
- -heterocyclyl;
- -substituted heterocyclyl;
- —CO-aryl;
- —CO-(substituted aryl);
- —CO-heteroaryl;
- and
- —CO-(substituted heteroaryl);
- R3 and R4 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthio;
- R5 is H or C1-10 alkyl, or R5 can join with X to form a ring that contains one or two hetero atoms;
- each R6 is independently H or C1-10 alkyl;
- R7 is H or C1-10 alkyl which may be interrupted by a heteroatom or when R1 is alkyl, R7 and R1 can join to form a ring;
- or a pharmaceutically acceptable salt thereof.
95 more elements
A compound selected from the group consisting of:
- N-[4-(4-Amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N′-phenylurea;
- N-[4-(4-Amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N′-phenylthiourea;
- N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}morpholin-4-ylcarboxamide;
- N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]morpholin-4-ylcarboxamide;
- 2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(morpholin-4-ylcarbonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;
- N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]morpholin-4-ylcarboxamide;
- N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}morpholin-4-ylcarboxamide;
- N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1,1-dimethylethyl}-N′-phenylurea
- N-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]-1, 1-dimethylethyl}morpholin-4-ylcarboxamide;
- and
- N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]morpholin-4-ylcarboxamide;
- or a pharmaceutically acceptable salt thereof.
9 more elements
A compound of the formula (III):
- 73
- wherein:
- Q is NO2 or NH2;
- X is alkylene or alkenylene;
- R3 and R4 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, halogen, alkoxy, amino, alkylamino, dialkylamino and alkylthio;
- and
- R5 is H or C1-10 alkyl, or R5 and X can join to form a ring that contains one or two hetero atoms;
- or a pharmaceutically acceptable salt thereof.
5 more elements
Dependencies are inferred from the claim text.