Amide substituted imidazoquinolines
OwnerPatrick L. Coleman, Stephen L. Crooks +4inventors
InventorsPatrick L. Coleman, Stephen L. Crooks, George W. Griesgraber, Kyle J. Lindstrom, Bryon A. Merrill, Michael J. Rice
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Abstract
Imidazoquinoline and tetrahydroimidazoquinoline 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.
Claims4
-23. (canceled)
A pharmaceutical composition comprising a therapeutically effective amount of a compound of the formula (Ib):
- wherein
- R1 is —C2-4 alkyl-NR3—CO—R4 wherein R4 is heterocyclyl which may be unsubstituted or substituted by one or more substituents selected from the group consisting of:
- -alkyl;
- -alkenyl;
- -alkynyl,
- -(alkyl)0-1-aryl;
- -(alkyl)0-1-(substituted aryl);
- -(alkyl)0-1-heterocyclyl;
- -(alkyl)0-1-(substituted heterocycyl);
- -(alkyl)0-1-heteroaryl;
- -(alkyl)0-1-(substituted heteroaryl);
- —O-alkyl;
- —O-(alkyl)0-1-aryl;
- —O-(alkyl)0-1-(substituted aryl);
- —O-(alkyl)0-1-heterocyclyl;
- —O-(alkyl)0-1-(substituted heterocyclyl);
- —O-(alkyl)0-1-heteroaryl;
- —O-(alkyl)0-1-(substituted heteroaryl);
- —CO-aryl;
- —CO-(substituted aryl);
- —CO-heteroaryl;
- —CO-(substituted heteroaryl);
- —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-heterocyclyl;
- —S(O)0-2-(alkyl)0-1-(substituted heterocyclyl);
- —S(O)0-2-(alkyl)0-1-heteroaryl;
- —S(O)0-2-(alkyl)0-1-(substituted heteroaryl);
- —P(O)(OR3)2;
- —NR3—CO—O-alkyl;
- —N3;
- -halogen;
- —NO2;
- —CN;
- -haloalkyl;
- —O-haloalkyl;
- —CO-haloalkyl;
- —OH;
- —SH;
- or R4 is
- wherein R5 is an aryl, (substituted aryl), heteroaryl, (substituted heteroaryl), heterocyclyl or (substituted heterocyclyl) group;
- R2 is selected from the group consisting of:
- -hydrogen;
- -alkyl;
- -alkenyl;
- -aryl;
- -(substituted aryl);
- -heteroaryl;
- -(substituted heteroaryl);
- -heterocyclyl;
- -(substituted heterocyclyl);
- -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—C1-10alkyl;
- —CO—O—C1-10alkyl;
- —N3;
- -aryl;
- -(substituted aryl);
- -heteroaryl;
- -(substituted heteroaryl);
- -heterocyclyl;
- -(substituted heterocyclyl);
- —CO-aryl;
- and
- —CO-heteroaryl;
- each R3 is independently selected form the group consisting of hydrogen;
- C1-10alkyl-heteroaryl;
- C1-10alkyl-(substituted heteroaryl);
- C1-10alkyl-aryl;
- C1-10alkyl-(substituted aryl) and C1-10alkyl;
- n is 0 to 4;
- and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.
The pharmaceutical compound of claim 1 wherein
- R4 is heterocyclyl.
The pharmaceutical compound of claim 1 wherein
- R4 is substituted heterocyclyl.
Dependencies are inferred from the claim text.