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US 6,720,422 B2Granted
Amide 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 amide 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.
Claims2
A compound of the formula (IV):
- wherein:
- X is alkylene or alkenylene;
- 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 CH1-10 alkyl, or when R5 is C1-10 alkyl and X is alkylene or alkenylene, R5 can join with X to form a ring that contains one nitrogen atom;
- each R6 is independently H or C1-10 alkyl;
- or a pharmaceutically acceptable salt thereof.
42 more elements
A compound of the formula (V):
- wherein:
- X is alkylene or alkenylene;
- 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 when R5 is C1-10 alkyl and X is alkylene or alkenylene, R5 can join with X to form a ring that contains one nitrogen atom;
- each R6 is independently H or C1-10 alkyl;
- or a pharmaceutically acceptable salt thereof.
42 more elements
Dependencies are inferred from the claim text.