Amide substituted imidazoquinolines

A compound selected from the group consisting of:

• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-ethoxy-1-naphthamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-cyanobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-cyanobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-naphthamide;
• N2-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-naphthamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-4-(1-pyrrolyl)benzamide;
• N1-{4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl}-1-naphthamide;
• N2-{4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl}-2-naphthamide;
• N1-{4-(4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl}-1-naphthamide;
• N2-{4-(4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl}-2-naphthamide;
• N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-naphthamide;
• N2-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-naphthamide;
• N1-[4-(4-Amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-naphthamide;
• and
• N2-[4-(4-Amino-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-naphthamide.

A pharmaceutical composition comprising a therapeutically effective amount of a compound of the formula (Ib):

• wherein
• R1 is -alkyl-NR3—CO—R4 or -alkenyl-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 heterocyclyl);
• -(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;
• oxo;
• -halogen;
• —NO2;
• —CN;
• -haloalkyl;
• —O-haloalkyl;
• —CO-haloalkyl;
• —OH;
• and
• —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—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -(substituted aryl);
• -heteroaryl;
• -(substituted heteroaryl);
• -heterocyclyl;
• -(substituted heterocyclyl);
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen;
• C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• n is 0 to 4;
• and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

A compound of the formula (Ic):

• wherein
• R1 is -alkyl-NR3—CO—R4 or -alkenyl-NR3—CO—R4 wherein R4 is aryl, heteroaryl, heterocyclyl, alkyl or alkenyl, each of 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-heteroaryl;
• -(alkyl)0-1-(substituted heteroaryl);
• -(alkyl)0-1-heterocyclyl;
• -(alkyl)0-1-(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);
• —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-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);
• —NR6—CO—O-alkyl;
• —P(O)(OR3)2;
• —N3;
• -halogen;
• —NO2;
• —CN;
• -haloalkyl;
• —O-haloalkyl;
• —CO-haloalkyl;
• —OH;
• —SH;
• and in the case of alkyl, alkenyl, or heterocyclyl, oxo;
• 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(R6)2;
• —CO—N(R6)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -(substituted aryl);
• -heteroaryl;
• -(substituted heteroaryl);
• -heterocyclyl;
• -(substituted heterocyclyl);
• —CO-aryl;
• and
• —CO-heteroaryl;
• R3 is selected from the group consisting of C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• each R6 is independently selected from the group consisting of hydrogen;
• C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• n is 0 to 4;
• and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, wherein the substituent(s) of the substituted aryl, heteroaryl, and heterocyclyl groups are independently selected from the group consisting of alkyl, alkoxy, alkylthio, hydroxy, halogen, haloalkyl, haloalkylcarbonyl, haloalkoxy, nitro, alkylcarbonyl, alkenylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocycloalkyl, nitrile, alkoxycarbonyl, alkanoyloxy, alkanoylthio, and, in the case of a heterocyclyl group, oxo;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (Id):

• wherein
• R1 is -alkyl-NR3—CO—R4 or -alkenyl-NR3—CO—R4 wherein R4 is aryl or heteroaryl 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-heteroaryl;
• -(alkyl)0-1-(substituted heteroaryl);
• -(alkyl)0-1-heterocyclyl;
• -(alkyl)0-1-(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);
• —CO-aryl;
• —CO-(substituted aryl);
• —CO-heteroaryl;
• —CO-(substituted heteroaryl);
• —CO—O-alkyl;
• —COOH;
• —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);
• —NR3—CO—O-alkyl;
• —P(O)(OR3)2;
• —N3;
• -halogen;
• —NO2;
• —CN;
• -haloalkyl;
• —O-haloalkyl;
• —CO-haloalkyl;
• —OH;
• and
• —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—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -(substituted aryl);
• -heteroaryl;
• -(substituted heteroaryl);
• -heterocyclyl;
• -(substituted heterocyclyl);
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen;
• C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• n is 0 to 4;
• and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof,
• with the proviso that R4 is not an unsubstituted benzene ring, and that when R4 is a substituted benzene ring the substituents are selected from the group consisting of alkyl, alkoxy, alkylthio, hydroxy, haloalkyl, haloalkylcarbonyl, haloalkoxy, alkylcarbonyl, alkenylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocycloalkyl, nitrile, alkoxycarbonyl, alkanoyloxy, alkanoylthio, and —(C1-10alkyl)—NR3—(C1-10alkyl)—R5, wherein R5 is an aryl, (substituted aryl), heteroaryl, (substituted heteroaryl), heterocyclyl or (substituted heterocyclyl) group.

A compound of the formula (Ie):

• wherein
• R1 is -alkyl-NR3—CO—R4 or -alkenyl-NR3—CO—R4 wherein R4 is an alkyl or alkenyl group that is substituted by one or more substituents selected from the group consisting of:
• -alkynyl;
• -(substituted aryl) wherein the substituent(s) is selected from the group consisting of alkyl, alkoxy, alkylthio, hydroxy, haloalkyl, haloalkylcarbonyl, haloalkoxy, alkylcarbonyl, alkenylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocycloalkyl, nitrile, alkoxycarbonyl, alkanoyloxy, and alkanoylthio;
• -heteroaryl;
• -(substituted heteroaryl);
• —O-alkyl;
• —O-(alkyl)0-1-(substituted aryl) wherein the substituent(s) is selected from the group consisting of alkyl, alkoxy, alkylthio, hydroxy, haloalkyl, haloalkylcarbonyl, haloalkoxy, alkylcarbonyl, alkenylcarbonyl, arylcarbonyl, heteroarylcarbonyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocycloalkyl, nitrile, alkoxycarbonyl, alkanoyloxy, and alkanoylthio;
• —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-heteroaryl;
• —S(O)0-2-(alkyl)0-1-(substituted heteroaryl);
• —NR3—CO—O-alkyl;
• —P(O)(OR3)2;
• —N3;
• oxo;
• —NO2;
• —CN;
• —O-haloalkyl;
• —CO-haloalkyl;
• —OH;
• and
• —SH;
• 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—C1-10 alkyl;
• —N3;
• -aryl;
• -(substituted aryl);
• -heteroaryl;
• -(substituted heteroaryl);
• -heterocyclyl;
• -(substituted heterocyclyl);
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen;
• C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• n is 0 to 4;
• and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof.

A pharmaceutical composition comprising a therapeutically effective amount of a compound selected from the group consisting of:

• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide;
• N1-[4-(4-Amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide;
• N1-[4-(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide;
• N1-[4-(4-Amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide;
• N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]benzamide;
• N1-[5-(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide;
• N1-[5-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]benzamide;
• N1-[3-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzamide;
• N1-[2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]benzamide;
• N1-[3-(4-Amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]benzamide;
• N1-[6-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)hexyl]benzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-phenylpropanamide;
• N1-[2-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-3-phenylpropanamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-phenoxyacetamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-ethylhexanamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-phenoxypropanamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-chlorobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3,4-dichlorobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2,6-dichlorobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-fluorobenzamnide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-chlorobenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-methoxybenzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-(trifluoromethyl)benzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-phenylacetamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-(E)-3-phenyl-2-propenamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-cyclopentylpropanamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-cyclopentanecarboxamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-cyclohexanecarboxamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-methylbenzamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-cyclopentanecarboxamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-cyclohexanecarboxamide,
• N1-{4-[4-Amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}benzamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-phenylacetamide;
• N1-[4-(4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide;
• N1-[4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide;
• N1-[4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2,2,2trifluoroacetamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2,2,2-trifluoroacetamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-(trans)-2-phenylcyclopropane-1-carboxamide;
• and
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-(trans)-2-phenylcyclopropane-1-carboxamide
• in combination with a pharmaceutically acceptable carrier.

A compound selected from the group consisting of:

• N6-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-6-quinolinecarboxamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-3-quinolinecarboxamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2,6-dimethoxynicotinamide;
• N8-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-8-quinolinecarboxamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]nicotinamide;
• N4-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]isonicotinamide;
• N4-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-quinolinecarboxamide;
• N4-[4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-phenyl-4-quinolinecarboxamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-(pentylsulfanyl)nicotinamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-6-cyanonicotinamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-6-chloronicotinamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-6-(2,2,2-trifluoroethoxy)nicotinamide;
• N2-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-quinolinecarboxamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-1-isoquinolinecarboxamide;
• N2-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-5-butyl-2-pyridinecarboxamide;
• N3-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-3-indolecarboxamide;
• N2-{4-[4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-quinolinecarboxamide;
• N3-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-6-(1-pyrrolyl)nicotinamide;
• N5-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-5-indolecarboxamide;
• N3-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-5-(2-phenyl-1-ethynyl)nicotinamide;
• N3-[4-(4-Amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]nicotinamide;
• N2-[4-(4-Amino-2-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-quinolinecarboxamide;
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-chloronicotinamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-(2-thienyl)acetamide;
• N1-[4-(4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-(3thienyl)acetamide;
• N2-{4-[4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-pyridinecarboxamide;
• N3-{4-[4-Amino-2-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-nicotinamide;
• N4-{4-[4-Amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-1-yl]butyl}isonicotinamide;
• N3-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-3-furamide;
• N3-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}nicotinamide;
• N2-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-furamide;
• N2-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-thiophenecarboxamide;
• and
• N2-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-nitro-2-furamide.

A compound selected from the group consisting of:

• N1-[4-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(2-oxoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(2-oxoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide;
• N1-[2-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-5-(2-iminoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide;
• N1-[2-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-5-(2-oxoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide;
• and
• N1-[2-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-5-(2-oxoperhydrothieno[3,4-d]imidazol-4-yl)pentanamide.

A compounds selected from the group consisting of:

• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-(morpholinomethyl)benzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-{[(4-pyridylmethyl)amino]methyl}benzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-{[(2-methoxyphenethyl)amino]methyl}benzamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-({methyl[2-(2-pyridyl)ethyl]amino}methyl)benzamide;
• N1-{4-[4-Amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]butyl}-2-oxo-2-phenylacetamide;
• N1-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-[(2-tetrahydro-1H-1-pyrrolyl-1H-benzo[d]imidazol-1-yl)methyl]benzamide;
• and
• N3-[4-(4-Amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-6-morpholinonicotinamide.

A compound selected from the group consisting of:

• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-methoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-bromobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(5-bromo-2-hydroxybenzyl)-acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-butoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2-chlorobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2-chloro-5-nitrobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(5-chloro-2-nitrobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-2-[(4-chlorophenyl)sulfanyl]benzylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(3,5-dichlorobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(3,4-difluorobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2,5-dimethoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2,3-dimethoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2,4-dimethylbenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-[(5-ethyl-2-furyl)methyl]acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2-furylmethyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(3-furylmethyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(3-phenylpropyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-octylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(1-naphthylmethyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-[(2-methoxy-1naphthylmethyl]acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-nitrobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2-nitrobenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-pyridylmethyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2-methylbenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(2,3,4-trimethoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(3,4,5-trimethoxybenzyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-cyclopentylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-(4-fluorophenyl)acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-isopropylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-[4-(trifluoromethyl)phenyl]acetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-cyclohexylmethylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-benzylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-methylacetamide;
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-ethylacetamide;
• and
• N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N1-benzyl-2,2,2-trifluoroacetamide.

A pharmaceutical composition comprising a therapeutically effective amount of a compound of the formula (Ia):

• wherein
• R1 is -alkyl-NR3—CO—R4 or -alkenyl-NR3—CO—R4 wherein R4 is aryl, heteroaryl, alkyl or alkenyl, each of which may be unsubstituted or substituted by one or more substituents selected from the group consisting of:
• -heterocyclyl;
• -(substituted heterocyclyl);
• -(alkyl)0-1heterocyclyl;
• -(alkyl)0-1(substituted heterocyclyl);
• —O-(alkyl)0-1heterocyclyl;
• —O-(alkyl)0-1(substituted heterocyclyl);
• —S(O)0-2-(alkyl)0-1heterocyclyl;
• and
• —S(O)0-2-(alkyl)0-1(substituted heterocyclyl);
• 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—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -(substituted aryl);
• -heteroaryl;
• -(substituted heteroaryl);
• -heterocyclyl;
• -(substituted heterocyclyl);
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently selected from the group consisting of hydrogen;
• C1-10 alkyl-heteroaryl;
• C1-10 alkyl-(substituted heteroaryl);
• C1-10 alkyl-aryl;
• C1-10 alkyl-(substituted aryl) and C1-10 alkyl;
• n is 0to 4;
• and each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, halogen and trifluoromethyl, or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.