Aryl ether substituted imidazoquinolines

A compound of the formula (II)

• wherein X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R10 is selected from the group consisting of:
• —H;
• -alkyl;
• -alkenyl;
• and
• -aryl;
• 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(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• n is 0 to 4;
• each Y is independently —O— or —S(O)0-2—;
• each R3 is independently H or C1-10 alkyl;
• 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 —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• and
• R4-aryl;
• —R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-aryl;
• -alkyl-Y-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;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently H or C1-10 alkyl;
• each Y is independently —O— or —S(O)0-2—;
• 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 (IV):

• wherein:
• X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R10 is selected from the group consisting of:
• —H;
• -alkyl;
• -alkenyl;
• and
• -aryl;
• R2 is selected from the group consisting of:
• -hydrogen;
• -alkyl;
• -alkenyl;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• -alkyl-Y-alkyl;
• -alkyl-Y-aryl;
• -alkyl-Y-alkonyl;
• 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;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• each R3 is independently H or C1-10 alkyl;
• each Y is independently —O— or —S(O)0-2—;
• 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 (V):

• wherein X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• —R4-aryl;
• and
• —(CH2)1-10—C≡C—R10;
• 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(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently H or C1-10 alkyl;
• R10 is selected from the group consisting of H, alkyl, alkenyl and aryl;
• each Y is independently —O— or —S(O)0-2—;
• 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 (VI):

• wherein X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• —R4-aryl;
• and
• —(CH2)1-10—C≡C—R10;
• 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(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently 14 or C1-10 alkyl;
• R10 is selected from the group consisting of H, alkyl, alkenyl and aryl;
• each Y is independently —O— or —S(O)0-2—;
• 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 (VII):

• wherein:
• X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• —R4-aryl;
• and
• —(CH2)1-10—C≡C—R10;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently H or C1-10 alkyl;
• R10 is selected from the group consisting of H, alkyl, alkenyl and aryl;
• 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 (VIII):

• wherein:
• X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• —R4-aryl;
• and
• —CH2)1-10—C≡C—R10;
• 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(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —CO—O—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently H or C1-10 alkyl;
• R10 is selected from the group consisting of H, alkyl, alkenyl and aryl;,
• each Y is independently —O— or —S(O)0-2—;
• n is 0 to 4;
• each R present is independently selected from the group consisting of C1-10 alkyl, C1-10 alkoxy, hydroxy, halogen and trifluoromethyl;
• and
• R7 is tert-butyl or benzyl;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula (IX)

• wherein:
• X is —CHR3—, —CHR3-alkyl-, or —CHR3-alkenyl-;
• R1 is selected from the group consisting of:
• -aryl;
• -alkenyl;
• R4-aryl;
• and
• —(CH2)1-10—C≡CH;
• 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(R3)2;
• —CO—N(R3)2;
• —CO—C1-10 alkyl;
• —CO—C1-10 alkyl;
• —N3;
• -aryl;
• -heteroaryl;
• -heterocyclyl;
• —CO-aryl;
• and
• —CO-heteroaryl;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R3 is independently H or C1-10 alkyl;
• each Y is independently —O— or —S(O)0-2—;
• 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.