Sulfonamido ether substituted imidazoquinolines

A compound selected from the group consisting of:

• N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)methanesulfonamide;
• N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)methanesulfonamide;
• N-(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methylmethanesulfonamide;
• N-(2-{2-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methylmethanesulfonamide;
• 2-butyl-1-{2-[2-(1,1-dioxidoisothiazolidin-2-yl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinolin-4-amine;
• and
• N-[10-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-4,7-dioxadecyl]-5-dimethylaminonaphthalene-1-sulfonamide;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (II)

• wherein:
• X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• R1 is selected from the group consisting of:
• —R4—NR3—SO2—R6-alkyl;
• —R4—NR3—SO2—R6-alkenyl;
• —R4—NR3—SO2—R6-aryl;
• —R4—NR3—SO2—R6-heteroaryl;
• —R4—NR3—SO2—R6-heterocyclyl;
• —R4—NR3—SO2—R7;
• —R4—NR3—SO2—NR5—R6-alkyl;
• —R4—NR3—SO2—NR5—R6-alkenyl;
• —R4—NR3—SO2—NR5—R6-aryl;
• —R4—NR3—SO2—NR5—R6-heteroaryl;
• —R4—NR3—SO2—NR5—R6-heterocyclyl;
• and
• —R4—NR3—SO2—NH2;
• R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-alkenyl;
• -alkyl-Y-aryl;
• 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;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• Y is —O— or —S(O)0-2—;
• R3 is H, C1-10 alkyl, or arylalkyl;
• each R4 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• or when R3 is C1-10 alkyl R3 and R4 can join together to form a piperidine cyclic or ring;
• each R5 is independently H, C1-10 alkyl, or C2-10 alkenyl;
• R6 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is C1-10 alkyl;
• or when R3 is C1-10 alkyl R3 and R7 can join together to form a 5-membered 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, hydroxy, halogen, and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (III):

• wherein
• X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• R1 is selected from the group consisting of:
• —R4—NR3—SO2—R6-alkyl;
• —R4—NR3—SO2—R6-alkenyl;
• —R4—NR3—SO2—R6-aryl;
• —R4—NR3—SO2—R6-heteroaryl;
• —R4—NR3—SO2—R6-heterocyclyl;
• —R4—NR3—SO2—R7;
• —R4—NR3—SO2—NR5—R6-alkyl;
• —R4—NR3—SO2—NR5—R6-alkenyl;
• —R4—NR3—SO2—NR5—R6-aryl;
• —R4—NR3—SO2—NR5—R6-heteroaryl;
• —R4—NR3—SO2—NR5—R6-heterocyclyl;
• and
• —R4—NR3—SO2—NH2;
• R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-alkenyl;
• -alkyl-Y-aryl;
• 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;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• Y is —O— or —S(O)0-2—;
• R3 is H, C1-10 alkyl, or arylalkyl;
• each R4 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• or when R3 is C1-10 alkyl R4 and R3 can join to form a piperidine ring;
• each R5 is independently H, C1-10 alkyl, or C2-10 alkenyl;
• R6 is a bond, or is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is C1-10 alkyl;
• or when R3 is C1-10 alkyl R3 and R7 can join together to form a 5-membered 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, hydroxy, halogen and trifluoromethyl;
• or a pharmaceutically acceptable salt thereof.