N-1 BRANCHED IMIDAZOQUINOLINES, CONJUGATES THEREOF, AND METHODS
Imidazoquinoline compounds, salts thereof, conjugates thereof, pharmaceutical compositions containing the compounds and conjugates, and methods of use of such compounds as immune response modifiers, for inducing cytokine biosynthesis in humans and animals.
1 . A compound of Formula (I), or a salt thereof:
wherein:
n is an integer of 0 or 1;
R is selected from the group consisting of halogen, hydroxy, alkyl, alkoxy, and —C(O)—O-alkyl;
R1 is —C1-3alkylene-O—C1-3alkyl;
R 2 is a C 2-18 alkylene group or C 2-18 alkenylene group, optionally interrupted by one or more non-peroxidic —O— atoms; and
X is NH 2 .
2 . (canceled)
3 . (canceled)
4 . The compound or salt of claim 1 , wherein R is selected from the group consisting of halogen, hydroxy, —C 1-7 alkyl, and —C 1-7 alkoxy.
5 . The compound or salt of claim 1 , wherein n is 0.
6 . The compound or salt of claim 1 , wherein R 2 is a C 2-18 alkylene group optionally interrupted by one or more non-peroxidic —O-atoms.
7 . The compound or salt of claim 1 that is of Formula (II):
wherein:
R 2 is a C 2-18 alkylene group or C 2-18 alkenylene group, optionally interrupted by one or more non-peroxidic —O— atoms; and
X is NH 2 .
8 . (canceled)
9 . An IRM-containing conjugate of Formula (V-A):
wherein:
n is an integer of 0 or 1;
R is selected from the group consisting of halogen, hydroxy, alkyl, alkoxy, and —C(O)—O-alkyl;
R1 is —C1-3alkylene-O—C1-3alkyl;
R 2 is a C 2-18 alkylene group or C 2-18 alkenylene group, optionally interrupted by one or more non-peroxidic —O— atoms;
Y is N or NH;
Linker is a heterobifunctional crosslinking group;
m=0 or 1;
Z is a polymeric moiety or second active moiety; and
the Y-Linker m -Z portion of the conjugate, with or without a linker, optionally includes a labile bond.
10 . The IRM-containing conjugate of claim 6 that is of Formula (V-B):
wherein:
R 2 is a C 2-18 alkylene group or C 2-18 alkenylene group, optionally interrupted by one or more non-peroxidic —O— atoms;
Y is N or NH;
Linker is a heterobifunctional crosslinking group;
m=0 or 1;
Z is a polymeric moiety or second active moiety; and
the Y-Linker m -Z portion of the conjugate, with or without a linker, optionally includes a labile bond.
11 . The conjugate of claim 10 , wherein Z is a polymeric moiety.
12 . The conjugate of claim 10 , wherein Z is a second active moiety (SAM).
13 . A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.
14 . A pharmaceutical composition comprising the IRM-containing conjugate of claim 9 and a pharmaceutically acceptable carrier.
15 . (canceled)