| abstract |
Imidazo [4,5-c] quinolin-4-amines and tetrahydroimidazo [4,5-c] quinolin-4-amines of formula (1), wherein: the bonds represented by the dotted lines are present or absent; X is -CHR5-, -CHR5-alkyl-, or -CHR5-alkenyl-; R1 is selected from the group consisting of R4-NR8-CR3-NR5-Z-R6-alkyl, R4-NR8-CR3-NR5-Z-R6-alkenyl, R4-NR8-CR3-NR5-Z-R6-aryl , R4-NR8-CR3-NR5-Z-R6-heteroaryl, R4-NR8-CR3-NR5-Z-R6-heterocyclyl, R4-NR8-CR3-NR5R7, R4-NR8-CR3-NR9-Z-R6-alkyl , R4-NR8-CR3-NR9-Z-R6-alkenyl, R4-NR8-CR3-NR9-Z-R6-aryl, R4-NR8-CR3-NR9-Z-R6-heteroaryl, and R4-NR8-CR3- NR9-Z-R6-heterocyclyl; 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 with 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; each R3 is = O or = S; each R4 is independently alkyl or alkenyl, which may be interrupted with 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 with one or more -O- groups; R7 is H or C1-10 alkyl, which can be interrupted with a heteroatom or R7 can be linked with R5 to form a ring; R8 is H, C1-10 alkyl or arylalkyl; or R4 and R8 can join to form a ring; R9 is C1-10 alkyl which may be linked with R8 to form a ring; each Y is independently -O- or -S (O) 0-2-; Z is a bond, -CO- or -SO2-; 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 or trifluoromethyl; or pharmaceutically acceptable salts thereof. These compounds are useful as modifiers of the immune response. Such compounds can induce the biosynthesis of several cytokines and are useful in the treatment of a variety of disorders that include viral diseases and neoplastic diseases. Also disclosed are: pharmaceutical compositions comprising them, the use of said compounds in the preparation of medicaments, and intermediates useful in the synthesis of said compounds. |