Compositions and methods for targeted delivery of immune response modifiers

An immunomodulatory composition comprising:

• an IRM moiety coupled to a targeting moiety, wherein the IRM moiety is a compound of the formula:
• wherein:
• R1 is a linker group;
• 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(R5)2;
• —CO—N(R5)2;
• —CS—N(R5)2;
• —SO2—N(R5)2;
• —NR5—CO—C1-10 alkyl;
• —NR5—CS—C1-10 alkyl;
• —NR5—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 each independently:
• -hydrogen;
• -halogen;
• -alkyl;
• -alkenyl;
• —O-alkyl;
• —S-alkyl;
• and
• —N(R5)2;
• or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
• -halogen;
• -alkyl;
• -alkenyl;
• —O-alkyl;
• —S-alkyl;
• and
• —N(R5)2;
• or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of,
• -halogen;
• -alkyl;
• -alkenyl;
• —O-alkyl;
• —S-alkyl;
• and
• —N(R5)2;
• and
• each R5 is independently hydrogen or C1-10 alkyl.