Amido ether substituted imidazoquinolines

A compound selected from the group consisting of:

• N-{2-[2-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}benzamide;
• N-{2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethyl}benzamide;
• and
• N(2-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethyl)-N-methylcyclohexanecarboxamide;
• 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—CR3—Z—R6-alkyl;
• —R4—CR3—Z—R6-alkenyl;
• —R4—CR3—Z—R6-aryl;
• —R4—CR3—Z—R6-heteroaryl;
• —R4—CR3—Z—R6-heterocyclyl;
• —R4—CR3—Z—H;
• —R4—NR7—CR3—R6-alkyl;
• —R4—NR7—CR3—R6-alkenyl;
• —R4—NR7—CR3—R6-aryl;
• —R4—NR7—CR3—R6-heteroaryl;
• —R4—NR7—CR3—R6-heterocyclyl;
• and
• —R4—NR7—CR3—R8;
• Z is —N5—, —O—, or —S—;
• 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;
• R3 is ═O or ═S;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 is a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is alkyl and R7 is C1-10 alkyl, R4 and R7 can join together to form a piperidine ring;
• R8 is H or C1-10 alkyl;
• Y is —O— or —S(O)0-2—;
• n is 0;
• 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—CR3—Z—R6-alkyl;
• —R4—CR3—Z—R6-alkenyl;
• —R4—CR3—Z—R6-aryl;
• —R4—CR3—Z—R6-heteroaryl;
• —R4—CR3—Z—R6-heterocyclyl;
• —R4—CR3—Z—H;
• —R4—NR7—CR3—R6-alkyl;
• —R4—NR7—CR3—R6-alkenyl;
• —R4—NR7—CR3—R6-aryl;
• —R4—NR7—CR3—R6-heteroaryl;
• —R4—NR7—CR3—R4-heterocyclyl;
• and
• —R4—NR7—CR3—R8;
• Z is —NR5—, —O—, or —S—;
• 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;
• R3 is ═O or ═S;
• R4 is independently alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 is a bond, or is alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is alkyl and R7 is C1-10 alkyl, R4 and R7 can join together to form a piperidine ring;
• R8 is H or C1-10 alkyl;
• Y is independently —O— or —S(O)0-2—;
• n is 0;
• 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 —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• R1 is selected from the group consisting of:
• —R4—CR3—Q—R6-alkyl;
• —R4—CR3—Q—R6-alkenyl;
• —R4—CR3—Q—R6-heteroaryl;
• —R4—CR3—Q—R6-heterocyclyl;
• —R4—CR3—Q—H;
• —R4—NR5—CR3—R6-alkyl;
• —R4—NR5—CR3—R6-alkenyl;
• —R4—NR7—CR3—R6-aryl;
• —R4—NR7—CR3—R6-heteroaryl;
• —R4—NR7—CR3—R6-heterocyclyl;
• and
• —R4—NR7—CR3—R8;
• Q is —NR5— or —O—;
• R3 is ═O or ═S;
• R4 is alkyl or alkenyl, which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R6 a bond, alkyl, or alkenyl, which may be interrupted by one or more —O— groups;
• R7 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is alkyl and R7 is C1-10 alkyl, R4 and R7 can join together to form a piperidine ring;
• R8 is H or C1-10 alkyl;
• n is 0;
• 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 compound of the formula (V):

• wherein:
• X is —CHR5—, —CHR5-alkyl-, or —CHR5-alkenyl-;
• 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;
• R4 is alkyl or alkenyl which may be interrupted by one or more —O— groups;
• each R5 is independently H or C1-10 alkyl;
• R7 is H, C1-10 alkyl, or arylalkyl;
• or when R4 is alkyl and R7 is C1-10 alkyl, R4 and R7 can join together to form a piperidine ring;
• Y is —O— or —S(O)0-2—;
• n is 0;
• 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 selected from the group consisting of:

• 1-[2-(2-aminoethoxy)ethyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine;
• 1-[2-(2-aminoethoxy)ethyl]-2-ethyl-1H-imidazo[4,5-c]quinolin-4-amine;
• 1-[2-(2-aminoethoxy)ethyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine;
• and pharmaceutically acceptable salts thereof.