CA2628131A1 - Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods - Google Patents

Hydroxy and alkoxy substituted 1h-imidazoquinolines and methods Download PDF

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CA2628131A1
CA2628131A1 CA002628131A CA2628131A CA2628131A1 CA 2628131 A1 CA2628131 A1 CA 2628131A1 CA 002628131 A CA002628131 A CA 002628131A CA 2628131 A CA2628131 A CA 2628131A CA 2628131 A1 CA2628131 A1 CA 2628131A1
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alkylenyl
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Tushar A. Kshirsagar
Philip D. Heppner
Scott E. Langer
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3M Innovative Properties Co
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Coley Pharmaceutical Group, Inc.
Tushar A. Kshirsagar
Philip D. Heppner
Scott E. Langer
3M Innovative Properties Company
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Abstract

1H-Imidazo[4,5-c]quinolin-4-amines with a hydroxy, alkoxy, hydroxyalkoxy, or alkoxyalkoxy substituent at the 2-position, pharmaceutical compositions containing these compounds, methods of making the compounds, intermediates, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

Claims (45)

1. A compound of the Formula I:

wherein:
R2 is selected from the group consisting of hydrogen, C1-4 alkyl, hydroxyC2-4 alkylenyl, and C1-4 alkoxyC2-4 alkylenyl;
R is selected from the group consisting of:
halogen, hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, and -N(R9)2, n is an integer from 0 to 4;
R1 is selected from the group consisting of:
hydrogen, -CH(R11)-Ar, -CH(R11)-Ar'-R4, -CH(R11)-Ar'-Y-R4, -CH(R11)-Ar'-CH(R11)-Y-R4, -CH(R11)-Ar'-R5, -CH(R11)-Ar'-CH(R11)-R5, -X1-Het, and -X1-N(R8)-Q-R4;
Ar is selected from the group consisting of aryl and heteroaryl each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Het is heterocyclyl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, hydroxyalkyleneoxyalkylenyl, amino, alkylamino, dialkylamino, and oxo;
X1 is C1-6 alkylene that is optionally interrupted by one or more -O- groups;
R11 is selected from the group consisting of hydrogen and C1-3 alkylene;
R3 is selected from the group consisting of:
-Z-R4, -Z-X-R4, -Z-X-Y-R4, -Z-X-Y-X-Y-R4, and -Z-X-R5;
m is 0 or 1; with the proviso that when m is 1, then n is 0 or 1;
X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more -O- groups;
Y is selected from the group consisting of:
-O-, -S(O)0-2-, -S(O)2-N(R8)-, -C(R6)-, -C(R6)-O-, -O-C(R6)-, -O-C(O)-O-, -N(R8)-Q-, -C(R6)-N(R8)-, -O-C(R6)-N(R8)-, -C(R6)-N(OR9)-, -O-N(R8)-Q-, -O-N=C(R4)-, -C(=N-O-R8)-, -CH(-N(-O-R8)-Q-R4)-, Z is a bond or -O-;
R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl; alkoxy; hydroxyalkyl; haloalkyl;
haloalkoxy; halogen;
nitro; hydroxy; mercapto; cyano; aryl; aryloxy; arylalkyleneoxy; heteroaryl;

heteroaryloxy; heteroarylalkyleneoxy; heterocyclyl; amino; alkylamino;
dialkylamino;
(dialkylamino)alkyleneoxy; and, in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;
R5 is selected from the group consisting of:

R6 is selected from the group consisting of =O and =S;
R7 is C2-7 alkylene;
R8 is selected from the group consisting of hydrogen, C1-10 alkyl, C2-10 alkenyl, hydroxy-C1-10 alkylenyl, C1-10 alkoxy-C1-10 alkylenyl, aryl-C1-10 alkylenyl, and heteroaryl-C1-10 alkylenyl;

R9 is selected from the group consisting of hydrogen and alkyl;
R10 is C3-8 alkylene;

A is selected from the group consisting of -CH2-, -O-, -C(O)-, -S(O)0-2-, and -N(-Q-R4)-;
A' is selected from the group consisting of -O-, -S(O)0-2-, -N(-Q-R4)-, and -CH2-;
Q is selected from the group consisting of a bond, -C(R6)-, -C(R6)-C(R6)-, -S(O)2-, -C(R6)-N(R8)-W-, -S(O)2-N(R8)-, -C(R6)-O-, -C(R6)-S-, and -C(R6)-N(OR9)-;
V is selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
W is selected from the group consisting of a bond, -C(O)-, and -S(O)2-; and a and b are independently integers from 1 to 6 with the proviso that a + b is <= 7;
or a pharmaceutically acceptable salt thereof.
2. A compound of the Formula II:

wherein:
G1 is selected from the group consisting of:
-C(O)-R', .alpha.-aminoacyl, .alpha.-aminoacyl-.alpha.-aminoacyl, -C(O)-O-R', -C(O)-N(R")R', -C(=NY')-R', -CH(OH)-C(O)-OY', -CH(OC1-4 alkyl)Y0, -CH2Y1, and -CH(CH3)Y1;

R' and R" are independently selected from the group consisting of C1-10 alkyl, C3-7 cycloalkyl, phenyl, and benzyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of halogen, hydroxy, nitro, cyano, carboxy, C1-6 alkyl, C1-4 alkoxy, aryl, heteroaryl, aryl-C1-4 alkylenyl, heteroaryl-C1-4 alkylenyl, halo-C1-4 alkylenyl, halo-C1-4 alkoxy, -O-C(O)-CH3, -C(O)-O-CH3, -C(O)-NH2, -O-CH2-C(O)-NH2, -NH2, and -S(O)2-NH2, with the proviso that R" can also be hydrogen;

.alpha.-aminoacyl is an .alpha.-aminoacyl group derived from an amino acid selected from the group consisting of racemic, D-, and L-amino acids;

Y' is selected from the group consisting of hydrogen, C1-6 alkyl, and benzyl;
Y0 is selected from the group consisting of C1-6 alkyl, carboxy-C1-6 alkylenyl, amino-C1-4 alkylenyl, mono-N-C1-6 alkylamino-C1-4 alkylenyl, and di-N, N-C1-6 alkylamino-C1-4 alkylenyl;

Y1 is selected from the group consisting of mono-N-C1-6 alkylamino, di-N, N-C1-6 alkylamino, morpholin-4-yl, piperidin-1-yl, pyrrolidin-1-yl, and 4-C1-4 alkylpiperazin-1-yl;
R2 is selected from the group consisting of hydrogen, C1-4 alkyl, hydroxyC2-4 alkylenyl, and C1-4 alkoxyC2-4 alkylenyl;
R is selected from the group consisting of:
halogen, hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, and -N(R9)2;
n is an integer from 0 to 4;
R1 is selected from the group consisting of:
hydrogen, -CH(R11)-Ar, -CH(R11)-Ar'-R4, -CH(R11)-Ar'-Y-R4, -CH(R11)-Ar'-CH(R11)-Y-R4, -CH(R11)-Ar'-R5, -CH(R11)-Ar'-CH(R11)-R5, -X1-Het, and -X1-N(R8)-Q-R4;
Ar is selected from the group consisting of aryl and heteroaryl each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Het is heterocyclyl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, hydroxyalkyleneoxyalkylenyl, amino, alkylamino, dialkylamino, and oxo;
X1 is C1-6 alkylene that is optionally interrupted by one or more -O- groups;
R11 is selected from the group consisting of hydrogen and C1-3 alkylene;
R3 is selected from the group consisting of:
-Z-R4, -Z-X-R4, -Z-X-Y-R4, -Z-X-Y-X-Y-R4, and -Z-X-R5;
m is 0 or 1; with the proviso that when m is 1, then n is 0 or 1;
X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more -O- groups;
Y is selected from the group consisting of:
-O-, -S(O)0-2-, -S(O)2-N(R8)-, -C(R6)-, -C(R6)-O-, -O-C(R6)-, -O-C(O)-O-, -N(R8)-Q-, -C(R6)-N(R8)-, -O-C(R6)-N(R8)-, -C(R6)-N(OR9)-, -O-N(R8)-Q-, -O-N=C(R4)-, -C(=N-O-R8)-, -CH(-N(-O-R8)-Q-R4)-, Z is a bond or -O-;

R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl; alkoxy; hydroxyalkyl; haloalkyl;
haloalkoxy; halogen;
nitro; hydroxy; mercapto; cyano; aryl; aryloxy; arylalkyleneoxy; heteroaryl;
heteroaryloxy; heteroarylalkyleneoxy; heterocyclyl; amino; alkylamino;
dialkylamino;
(dialkylamino)alkyleneoxy; and, in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;
R5 is selected from the group consisting of:

R6 is selected from the group consisting of =O and =S;
R7 is C2-7 alkylene;
R8 is selected from the group consisting of hydrogen, C1-10 alkyl, C2-10 alkenyl, hydroxy-C1-10 alkylenyl, C1-10 alkoxy-C1-10 alkylenyl, aryl-C1-10 alkylenyl, and heteroaryl-C1-10 alkylenyl;
R9 is selected from the group consisting of hydrogen and alkyl;
R10 is C3-8 alkylene;

A is selected from the group consisting of -CH2-, -O-, -C(O)-, -S(O)0-2-, and -N(-Q-R4)-;
A' is selected from the group consisting of -O-, -S(O)0-2-, -N(-Q-R4)-, and -CH2-;
Q is selected from the group consisting of a bond, -C(R6)-, -C(R6)-C(R6)-, -S(O)2-, -C(R6)-N(R8)-W-, -S(O)2-N(R8)-, -C(R6)-O-, -C(R6)-S-, and -C(R6)-N(OR9)-;
V is selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;

W is selected from the group consisting of a bond, -C(O)-, and -S(O)2-; and a and b are independently integers from 1 to 6 with the proviso that a + b is <= 7;
or a pharmaceutically acceptable salt thereof.
3. The compound or salt of claim 1 or claim 2 wherein R2 is hydrogen.
4. The compound or salt of claim 1 or claim 2 wherein R2 is ethyl or propyl, and R1 is hydrogen.
5. A compound or salt of the Formula III:

wherein:
G2 is selected from the group consisting of:
-X2-C(O)-R', .alpha.-aminoacyl, .alpha.-aminoacyl-.alpha.-aminoacyl, -X2-C(O)-O-R', -C(O)-N(R")R', and -S(O)2-R';
X2 is selected from the group consisting of a bond; -CH2-O-; -CH(CH3)-O-;
-C(CH3)2-O-; and, in the case of -X2-C(O)-O-R', -CH2-NH-;
R' and R" are independently selected from the group consisting of C1-10 alkyl, C3-7 cycloalkyl, phenyl, and benzyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of halogen, hydroxy, nitro, cyano, carboxy, C1-6 alkyl, C1-4 alkoxy, aryl, heteroaryl, aryl-C1-4 alkylenyl, heteroaryl-C1-4 alkylenyl, halo-C1-4 alkylenyl, halo-C1-4 alkoxy, -O-C(O)-CH3, -C(O)-O-CH3, -C(O)-NH2, -O-CH2-C(O)-NH2, -NH2, and -S(O)2-NH2, with the proviso that R" can also be hydrogen;
.alpha.-aminoacyl is an .alpha.-aminoacyl group derived from an amino acid selected from the group consisting of racemic, D-, and L-amino acids;
R is selected from the group consisting of:
halogen, hydroxy, alkyl, alkenyl, haloalkyl, alkoxy, alkylthio, and -N(R9)2, n is an integer from 0 to 4;
R1 is selected from the group consisting of:
hydrogen, -CH(R11)-Ar, -CH(R11)-Ar'-R4, -CH(R11)-Ar'-Y-R4, -CH(R11)-Ar'-CH(R11)-Y-R4, -CH(R11)-Ar'-R5, -CH(R11)-Ar'-CH(R11)-R5, -X1-Het, and -X1-N(R8)-Q-R4;
Ar is selected from the group consisting of aryl and heteroaryl each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, amino, alkylamino, and dialkylamino;
Het is heterocyclyl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, cyano, hydroxyalkyleneoxyalkylenyl, amino, alkylamino, dialkylamino, and oxo;

X1 is C1-6 alkylene that is optionally interrupted by one or more -O- groups;
R11 is selected from the group consisting of hydrogen and C1-3 alkylene;
R3 is selected from the group consisting of:
-Z-R4, -Z-X-R4, -Z-X-Y-R4, -Z-X-Y-X-Y-R4, and -Z-X-R5;
m is 0 or 1; with the proviso that when m is 1, then n is 0 or 1;
X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted or terminated by arylene, heteroarylene or heterocyclylene and optionally interrupted by one or more -O- groups;
Y is selected from the group consisting of:
-O-, -S(O)0-2-, -S(O)2-N(R8)-, -C(R6)-, -C(R6)-O-, -O-C(R6)-, -O-C(O)-O-, -N(R8)-Q-, -C(R6)-N(R8)-, -O-C(R6)-N(R8)-, -C(R6)-N(OR9)-, -O-N(R8)-Q-, -O-N=C(R4)-, -C(=N-O-R8)-, -CH(-N(-O-R8)-Q-R4)-, Z is a bond or -O-;

R4 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl; alkoxy; hydroxyalkyl; haloalkyl;
haloalkoxy; halogen;
nitro; hydroxy; mercapto; cyano; aryl; aryloxy; arylalkyleneoxy; heteroaryl;
heteroaryloxy; heteroarylalkyleneoxy; heterocyclyl; amino; alkylamino;
dialkylamino;
(dialkylamino)alkyleneoxy; and, in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;

R5 is selected from the group consisting of:

R6 is selected from the group consisting of =O and =S;
R7 is C2-7 alkylene;

R8 is selected from the group consisting of hydrogen, C1-10 alkyl, C2-10 alkenyl, hydroxy-C1-10 alkylenyl, C1-10 alkoxy-C1-10 alkylenyl, aryl-C1-10 alkylenyl, and heteroaryl-C1-10 alkylenyl;

R9 is selected from the group consisting of hydrogen and alkyl;
R10 is C3-8 alkylene;

A is selected from the group consisting of -CH2-, -O-, -C(O)-, -S(O)0-2-, and -N(-Q-R4)-;
A' is selected from the group consisting of -O-, -S(O)0-2-, -N(-Q-R4)-, and -CH2-;
Q is selected from the group consisting of a bond, -C(R6)-, -C(R6)-C(R6)-, -S(O)2-, -C(R6)-N(R8)-W-, -S(O)2-N(R8)-, -C(R6)-O-, -C(R6)-S-, and -C(R6)-N(OR9)-;
V is selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;

W is selected from the group consisting of a bond, -C(O)-, and -S(O)2-; and a and b are independently integers from 1 to 6 with the proviso that a + b is <= 7;
or a pharmaceutically acceptable salt thereof.
6. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is -CH(R11)-Ar.
7. The compound or salt of claim 6 wherein R1 is selected from the group consisting of benzyl, 1-phenylethyl, and pyridinylmethyl, each of which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, haloalkyl, haloalkoxy, and halogen.
8. The compound or salt of claim 7 wherein R1 is selected from the group consisting of benzyl, 4-methoxybenzyl, 1-phenylethyl, and pyridin-3-ylmethyl.
9. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is -CH(R11)-Ar'-CH(R11)-Y-R4.
10. The compound or salt of claim 9 wherein:
each R11 is hydrogen;
Ar' is phenylene;
Y in -CH(R11)-Ar'-CH(R11)-Y-R4 is -NHQ-wherein Q is selected from the group consisting of -C(O)-, -S(O)2-, -C(R6)-N(R8)-, -S(O)2-N(R8)-, -C(O)-O-, and -C(O)-S-; and R4 in -CH(R11)-Ar'-CH(R11)-Y-R4 is selected from the group consisting of alkyl, aryl, heteroaryl, and arylalkylenyl wherein alkyl, aryl, and heteroaryl are each unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, and halogen.
11. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is -CH(R11)-Ar'-CH(R11)-R5.
12. The compound or salt of claim 11 wherein:
each R11 is hydrogen;
Ar' is phenylene; and R5 in -CH(R11)-Ar'-CH(R11)-R5 is wherein A is selected from the group consisting of -CH2-, -O-, and -N(alkyl)-, and a and b are each independently 1, 2, or 3.
13. The compound or salt of claim 12 wherein a and b are each 2.
14. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is -X1-N(R8)-Q-R4.
15. The compound or salt of claim 14 wherein:
X1 is C1-4 alkylene;
R8 in -X1-N(R8)-Q-R4 is hydrogen;

Q in -X1-N(R8)-Q-R4 is selected from the group consisting of -C(O)-, -S(O)2-, -C(R6)-N(R8)-, and -S(O)2-N(R8)-; and R4 in -X1-N(R8)-Q-R4 is selected from the group consisting of alkyl, aryl, heteroaryl, heterocyclyl, and arylalkylenyl wherein alkyl, aryl, and heteroaryl are each unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, and halogen.
16. The compound or salt of claim 14 wherein:
X1 is C1-4 alkylene;
R8 in -X1-N(R8)-Q-R4 is C1-10 alkyl or hydroxy-C1-10 alkylenyl;
Q in-X1-N(R8)-Q-R4 is a bond; and R4 in -X1-N(R8)-Q-R4 is selected from the group consisting of alkyl, aryl, arylalkylenyl, and heteroarylalkylenyl wherein alkyl is optionally substituted by one or more substituents independently selected from the group consisting of alkoxy and hydroxy.
17. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is -X1-Het.
18. The compound or salt of claim 17 wherein Het is selected from the group consisting of piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, azepanyl, and dihydroisoquinolin-(1H)-yl each of which is optionally substituted by one or more substituents independently selected from the group consisting of alkyl and hydroxy.
19. The compound or salt of any one of claims 1, 2, 3, and 5 wherein R1 is tetrahydropyranylmethyl.
20. The compound or salt of claim 19 wherein R1 is tetrahydro-2H-pyran-4-ylmethyl.
21. The compound or salt of any one of claims 1 through 20 wherein n is 0, and R3 is pyridin-3-yl, 3-hydroxyphenyl, 4-hydroxymethylphenyl, or benzyloxy.
22. The compound or salt of any one of claims 1 through 21 wherein n is 0, and R3 is at the 7-position.
23. The compound or salt of any one of claims 1 through 20 wherein m is 0, and R is hydroxy.
24. The compound or salt of any one of claims 1 through 20 wherein m and n are both 0.
25. A compound selected from the group consisting of 4-amino-1-benzyl-1H-imidazo[4,5-c]quinolin-2-ol, 4-amino-1-(1-phenylethyl)-1H-imidazo[4,5-c]quinolin-2-ol, 4-amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]quinolin-2-ol, and 4-amino-1-(pyridin-3-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol, or a pharmaceutically acceptable salt thereof.
26. The compound 4-amino-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-ol or a pharmaceutically acceptable salt thereof.
27. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier.
28. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in inducing cytokine biosynthesis in an animal.
29. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in selectively inducing the biosynthesis of IFN-.alpha. in an animal.
30. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in treating a viral disease in an animal.
31. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in treating a viral disease in an animal and selectively inducing the biosynthesis of IFN-.alpha. in the animal.
32. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in treating a neoplastic disease in an animal.
33. A pharmaceutical composition comprising a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 and a pharmaceutically acceptable carrier for use in treating a neoplastic disease in an animal and selectively inducing the biosynthesis of IFN-.alpha. in the animal.
34. Use of an effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for inducing cytokine biosynthesis in an animal.
35. Use of an effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for inducing cytokine biosynthesis in an animal.
36. Use of an effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for selectively inducing the biosynthesis of IFN-.alpha. in an animal.
37. Use of an effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for selectively inducing the biosynthesis of IFN-.alpha. in an animal.
38. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for treating a viral disease in an animal.
39. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for treating a viral disease in an animal.
40. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for treating a viral disease in an animal and selectively inducing the biosynthesis of IFN-.alpha.
in the animal.
41. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for treating a viral disease in an animal and selectively inducing the biosynthesis of IFN-.alpha. in the animal.
42. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for treating a neoplastic disease in an animal.
43. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for treating a neoplastic disease in an animal.
44. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 in the manufacture of a medicament for treating a neoplastic disease in an animal and selectively inducing the biosynthesis of IFN-.alpha. in the animal.
45. Use of a therapeutically effective amount of the compound or salt as defined in any one of claims 1 to 26 or the pharmaceutical composition of claim 27 for treating a neoplastic disease in an animal and selectively inducing the biosynthesis of IFN-.alpha. in the animal.
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