CA2536136A1 - Aryloxy and arylalkyleneoxy substituted imidazoquinolines - Google Patents

Aryloxy and arylalkyleneoxy substituted imidazoquinolines Download PDF

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Publication number
CA2536136A1
CA2536136A1 CA002536136A CA2536136A CA2536136A1 CA 2536136 A1 CA2536136 A1 CA 2536136A1 CA 002536136 A CA002536136 A CA 002536136A CA 2536136 A CA2536136 A CA 2536136A CA 2536136 A1 CA2536136 A1 CA 2536136A1
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group
alkyl
independently selected
alkylene
compound
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CA002536136A
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CA2536136C (en
Inventor
Kyle J. Lindstrom
Hugues Martin
Bryon A. Merrill
Michael J. Rice
Joshua R. Wurst
Chad A. Haraldson
Tushar Kshirsagar
Philip D. Heppner
Shri Niwas
George W. Griesgraber
Matthew R. Radmer
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3M Innovative Properties Co
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Kyle J. Lindstrom
Hugues Martin
Bryon A. Merrill
Michael J. Rice
Joshua R. Wurst
Chad A. Haraldson
Tushar Kshirsagar
Philip D. Heppner
Shri Niwas
George W. Griesgraber
Matthew R. Radmer
3M Innovative Properties Company
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Abstract

Imidazoquinoline compounds with an aryloxy or arylalkyleneoxy or hydroxy substituent at the 6, 7, 8, or 9-position, pharmaceutical compositions containing the compounds, intermediates, and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

Claims (54)

1. A compound of the formula (I):
wherein:
R3 is selected from the group consisting of -Z-Ar, -Z-Ar'-Y-R4, -Z-Ar'-X-Y-R4, -Z-Ar'-R5, and -Z-Ar'-X-R5 Z is selected from the group consisting of a bond, alkylene, alkenylene, and alkynylene wherein alkylene, alkenylene, and alkynylene are optionally interrupted with -O-;
Ar is selected from the group consisting of aryl and heteroaryl both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, vitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;

X is selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alk~mylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
Y is selected from the group consisting of _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)-, 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:
each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
R8 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
R9 is selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;
A is selected from the group consisting of -O-, -C(O)-, -S(O)0-2-, -CH2-, and -N(R4)-;
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)-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;
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
R' and R" are independently selected from the group consisting of hydrogen and non-interfering substitutents; and n is 0 or 1;

or a pharmaceutically acceptable salt thereof.
2. The compound or salt of claim 1 wherein n is 0.
3. The compound or salt of claim 1 or claim 2 wherein R3 is selected from the group consisting of -Z-Ar, -Z-Ar'-X-Y-R4, and -Z-Ar'-Y-R4.
4. The compound or salt of claim 3 wherein R3 is Z-Ar.
5. The compound or salt of claim 3 wherein R3 is -Z-Ar'-X-Y-R4, or Z-Ar'-Y-R4 wherein Y is -S(O)2-, N(R8)-S(O)2-, -C(R6)-, or -C(R6)-O-; X is C1-alkylene; and R4 is alkyl or phenyl.
6. The compound or salt of claim 4 wherein Ar is phenyl or heteroaryl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, nitro, cyano, carboxy, halogen, hydroxyalkyl, amino, alkylamino, dialkylamino, trifluoromethyl, trifluoromethoxy, and thienyl.
7. The compound or salt of claim 6 wherein heteroaryl is selected from the group consisting of benzothiazolyl, furanyl, imidazolyl, indolyl, isoxazolyl, oxadiazolyl, pyrazinyl, pyridinyl, pyrrolyl, thiazolyl, and thienyl.
8. The compound or salt of any one of claims 1 through 7 wherein Z is a bond, alkylene, or alkylene interrupted by -O-.
9. The compound or salt of claim 8 wherein Z is C1-3 alkylene.
10. The compound or salt of claim 8 wherein Z is a bond.
11. The compound or salt of any one of claims 1 through 10 wherein R' is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, -X-Y-X-Y-R4, and -X-R5.
12. The compound or salt of any one of claims 1 through 10 wherein R" is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, and -X-R5.
13. The compound or salt of claim 11 wherein R' is selected from the group consisting of alkyl, arylalkylenyl, aryloxyalkylenyl, hydroxyalkyl, dihydroxyalkyl, alkylsulfonylalkylenyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X-Y-R4, and -X-R5; wherein X is alkylene, Y is N(R8)-C(O)-, -N(R8)-S(O)2-, N(R8)-C(R6)-N(R8)-, or ; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino;
and R5 is
14. The compound or salt of claim 12 wherein R" is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and -X-N(R8)-C(R6)-N(R8)-R4 wherein X
is C1-4 alkylene, and R4 is C1-4 alkyl.
15. A compound of the formula (II):

wherein:
R3 is selected from the group consisting of:
-Z-Ar, -Z-Ar'-Y-R4, -Z-Ar'-X-Y-R4, -Z-Ar'-R5, and -Z-Ar'-X-R5;
Z is selected from the group consisting of a bond, alkylene, alkenylene, and alkynylene wherein alkylene, alkenylene, and alkynylene are optionally interrupted with -O-;
Ar is selected from the group consisting of aryl and heteroaryl both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
n is 0 or 1;
R1 is selected from the group consisting of:

-R4, -X-R4, -X-Y-R4, -X-Y-X-Y-R4, and -X-R5;
R2 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, and -X-R5;
each X is independently selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
each Y is independently selected from the group consisting of:
-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)-, each R4 is independently 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;
each R5 is independently selected from the group consisting of:
each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
each R8 is independently selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
each R9 is independently selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;
each A is independently selected from the group consisting of -O-, -C(O)-, -S(O)0-2-, -CH2-, and -N(R4)-;

each Q is independently selected from the group consisting of a bond, -C(R6)-, -C(R6)-C(R)-, -S(O)2-, -C(R6)-N(R8)-W-, -S(O)2-N(R8)-, -C(R6)-O-, and -C(R6)-N(OR9)-;
each V is independently selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
each W is independently 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.
16. The compound or salt of claim 15 wherein n is 0.
17. The compound or salt of claim 15 or claim 16 wherein R3 is Z-Ar'-Y-R4 or -Z-Ar'-X-Y-R4.
18. The compound or salt of claim 17 wherein X is C1-2 alkylene; Y is -NH-S(O)a-, -S(O)a-, -C(O)-, or-C(O)O-; and R4 is C1-4 alkyl or phenyl.
19. The compound or salt of any one of claims 15 through 18 wherein Z is a bond, alkylene, or alkylene interrupted by -O-.
20. The compound or salt of claim 19 wherein Z is Cl-3 alkylene.
21. The compound or salt of claim 19 wherein Z is a bond.
22. The compound or salt of any one of claims 15 through 21 wherein R1 is selected from the group consisting of alkyl, arylalkylenyl, aryloxyalkylenyl, hydroxyalkyl, dihydroxyalkyl, alkylsulfonylalkylenyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X-Y-R4, and -X-R5;
wherein X is alkylene, Y is N(R8)-C(O)-, -N(R8)-S(O)2-, N(R8)-C(R6)-N(R8)-, or ; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino;
and R5 is
23. The compound or salt of claim 22 wherein R1 is selected from the group consisting of 2-hydroxy-2-methylpropyl, 2-methylpropyl, propyl, 2,3-dihydroxypropyl, 4-[(methylsulfonyl)amino]butyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 4-(1,1-dioxidoisothiazolidin-2-yl)butyl, tetrahydro-2H pyran-4-ylmethyl, and (2,2-dimethyl-1,3-dioxolan-4-yl)methyl.
24. The compound or salt of any one of claims 15 through 23 wherein R2 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and -X-N(R8)-C(R6)-N(R8)-R4 wherein X is C1-4 alkylene, and R4 is C1-4 alkyl.
25. The compound or salt of claim 24 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, ethoxymethyl, methoxymethyl, 2-methoxyethyl, and methylaminocarbonylaminomethyl.
26. The compound or salt of claim 25 wherein R2 is selected from the group consisting of ethyl, propyl, 2-methoxyethyl, ethoxymethyl, and methoxymethyl.
27. A compound of the formula (III):

wherein:
R3-1 is -Z-Ar;
Z is selected from the group consisting of a bond, alkylene, alkenylene, and alkynylene wherein alkylene, alkenylene, and alkynylene are optionally interrupted with Ar is selected from the group consisting of aryl and heteroaryl both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
n is 0 or 1;
R1 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, -X-Y-X-Y-R4, and -X-R5;
R2 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, and -X-R5;

each X is independently selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
each Y is independently selected from the group consisting of:
-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)-, each R4 is independently 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;
each R5 is independently selected from the group consisting of each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
each R8 is independently selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
each R9 is independently selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;
each A is independently selected from the group consisting of -O-, -C(O)-, -S(O)0-2-, -CH2-, and -N(R4)-;
each Q is independently 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-, and -C(R6)-N(OR9)-;
each V is independently selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
each W is independently 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.
28. The compound or salt of claim 27 wherein n is 0.
29. The compound or salt of claim 27 or 28 wherein Ar is phenyl or heteroaryl which is unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, nitro, cyano, carboxy, halogen, hydroxyalkyl, amino, alkylamino, dialkylamino, trifluoromethyl, trifluoromethoxy, and thienyl.
30. The compound or salt of claim 29 wherein heteroaryl is selected from the group consisting of benzothiazolyl, furanyl, imidazolyl, indolyl, isoxazolyl, oxadiazolyl, pyrazinyl, pyridinyl, pyrrolyl, thiazolyl, and thienyl.
31. The compound or salt of any one of claims 27 through 30 wherein Z is a bond, alkylene, or alkylene interrupted by -O-.
32. The compound or salt of claim 31 wherein Z is C1-3 alkylene.
33. The compound or salt of claim 31 wherein Z is a bond.
34. The compound or salt of any one of claims 27 through 33 wherein R1 is selected from the group consisting of alkyl, arylalkylenyl, aryloxyalkylenyl, hydroxyalkyl, dihydroxyalkyl, alkylsulfonylalkylenyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X-Y-R4, and -X-R5;
wherein X is alkylene, Y is N(R8)-C(O)-, -N(R8)-S(O)2-, N(R8)-C(R6)-N(R8)-, or ; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino;
and R5 is
35. The compound or salt of claim 34 wherein R1 is selected from the group consisting of 2-hydroxy-2-methylpropyl, 2-methylpropyl, propyl, 2,3-dihydroxypropyl, 4-[(methylsulfonyl)amino]butyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 4-(1,1-dioxidoisothiazolidin-2-yl)butyl, tetrahydro-2H pyran-4-ylmethyl, and (2,2-dimethyl-1,3-dioxolan-4-yl)methyl.
36. The compound or salt of any one of claims 27 through 35 wherein R2 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and -X-N(R8)-C(R6)-N(R8)-R4 wherein X is C1-4 alkylene, and R4 is C1-4 alkyl.
37. The compound or salt of claim 36 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, ethoxymethyl, methoxymethyl, 2-methoxyethyl, and methylaminocarbonylaminomethyl.
38. The compound or salt of claim 37 wherein R2 is selected from the group consisting of ethyl, propyl, 2-methoxyethyl, ethoxymethyl, and methoxymethyl.
39. A compound of the formula (VII):
wherein:
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
n is 0 or 1;
R1-1 is selected from the group consisting of:
-R4-1, -X'-R4-1, -X'-Y'-R4, -X'-Y'-X-Y-R4, and -X~-R5;
R2 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, and -X-R5;
each X is independently selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
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 by an arylene, heteroarylene or heterocyclylene group;
each Y is independently selected from the group consisting of:
-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)- Y' is selected from the group consisting of:
-s(O)2-N(R8)-, -C(R6)-, -C(R6)-O-, -O-C(O)-O-, -N(R8)-Q-, -C(R6)-NR(R8)-, -O-C(R6)-N(R8)-, -C(R6)-N(OR9)-, each R4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alk3myl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyallcylenyl, 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;
R4-1 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, 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, vitro, hydroxy, mercapto, cyano, aryl, heteroaryl, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;
each R5 is independently selected from the group consisting of:
each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
each R8 is independently selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
each R9 is independently selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;
each A is independently selected from the group consisting of -O-, -C(O)-, -S(O)0-2, -CH2-, and -N(R4)-;
each Q is independently 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-, and -C(R6)-N(OR9)-each V is independently selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
each W is independently 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; with the proviso that when R1-1 is hydrogen or 2-methylpropyl, R2 is other than hydrogen, and with the further proviso that when R1-1 is 2-methylpropenyl or 2-hydroxy-2-methylpropyl, R2 is other than methyl, ethoxymethyl, and hydroxymethyl.
40. The compound or salt of claim 39 wherein R1-1 is selected from the group consisting of alkyl, arylalkylenyl, hydroxyalkyl, dihydroxyalkyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X'-Y'-R4, and -X'-R5; wherein X' is alkylene; Y' is N(R8)-Q-, and Q is selected from the group consisting of -C(R6)-, -S(O)2-, and -C(R6)-N(R8)-W-; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino; and R5 is
41. The compound or salt of claim 40 wherein R1-1 is selected from the group consisting of 2-hydroxy-2-methylpropyl, 2-methylpropyl, propyl, 2,3-dihydroxypropyl, 4-[(methylsulfonyl)amino]butyl, 2-methyl-2-[(methylsulfonyl)amino]propyl, 2-[(cyclohexylcarbonyl)amino]-2-methylpropyl, 4-(1,1-dioxidoisothiazolidin-2-yl)butyl, tetrahydro-2H pyran-4-ylmethyl, and (2,2-dimethyl-1,3-dioxolan-4-yl)methyl.
42. The compound or salt of any one of claims 39 through 41 wherein n is 0.
43. The compound or salt of any one of claims 39 through 42 wherein R2 is selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and -X-N(R8)-C(R6)-N(R8)-R4 wherein X is C1-4 alkylene, and R4 is C1-4 alkyl.
44. The compound or salt of claim 43 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, ethoxymethyl, methoxymethyl, 2-methoxyethyl, and methylaminocarbonylaminomethyl.
45. The compound or salt of claim 44 wherein R2 is selected from the group consisting of ethyl, propyl, ethoxymethyl, 2-methoxyethyl, and methoxymethyl.
46. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of any one of claims 1 through 45 in combination with a pharmaceutically acceptable carrier.
47. A method of inducing cytokine biosynthesis in an animal comprising administering an effective amount of a compound or salt of any one of claims 1 through 45 to the animal.
48. A method of treating a viral disease in an animal in need thereof comprising administering a therapeutically effective amount of a compound or salt of any one of claims 1 through 45 to the animal.
49. A method of treating a neoplastic disease in an animal in need thereof comprising administering a therapeutically effective amount of a compound or salt of any one of claims 1 through 45 to the animal.
50. A compound of the formula (IX):

wherein:
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;
n is 0 or 1;
R1-1 is selected from the group consisting of:
-R4-1, -X'-R4, _X'-Y'-R4, and -X'-Y'-X-Y-R4, and -X'-R5;
R2 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, and -X-R5;
each X is independently selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
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 by an arylene, heteroarylene or heterocyclylene group;
each Y is independently selected from the group consisting of:
-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)-, Y' is selected from the group consisting of:
-S(O)2-N(R8)-, -C(R6)-, -C(R6)-O-, -N(R8)-Q-, -C(R6)-N(R8)-, -O-C(R6)-N(R8)-, -C(R6)-N(OR9)-, each R4 is independently 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;
R4-1 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, 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, vitro, hydroxy, mercapto, cyano, aryl, heteroaryl, heterocyclyl, amino, alkylamino, dialkylamino, (dialkylamino)alkyleneoxy, and in the case of alkyl, alkenyl, alkynyl, and heterocyclyl, oxo;
each R5 is independently selected from the group consisting of:

each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
each R8 is independently selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
each R9 is independently selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;
each A is independently selected from the group consisting of -O-, -C(O)-, -S(O)0-2-, -CH2-, and -N(R4)-;
each Q is independently 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-, and -C(R6)-N(OR9)-;
each V is independently selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
each W is independently 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
51. The compound or salt of claim 50 wherein R1-1 is selected from the group consisting of alkyl, arylalkylenyl, hydroxyalkyl, dihydroxyalkyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X'-Y'-R4, and -X'-R5; wherein X' is alkylene; Y' is N(R8)-Q-; and Q is selected from the group consisting of-C(R6)-, -S(O)2-, and -C(R6)-N(R8)-W-; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino; and R5 is
52. A compound of the formula (XI):

wherein:
R3 is selected from the group consisting of:
-Z-Ar, -Z-Ar'-Y-R4, -Z-Ar'-X-Y-R4, -Z-Ar'-R5, and -Z-Ar'-X-R5;
Z is selected from the group consisting of a bond, alkylene, alkenylene, and alkynylene wherein alkylene, alkenylene, and alkynylene are optionally interrupted with -O-;
Ar is selected from the group consisting of aryl and heteroaryl both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, methylenedioxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
Ar' is selected from the group consisting of arylene and heteroarylene both of which can be unsubstituted or can be substituted by one or more substituents independently selected from the group consisting of alkyl, alkenyl, alkoxy, haloalkyl, haloalkoxy, halogen, nitro, hydroxy, hydroxyalkyl, mercapto, cyano, carboxy, formyl, aryl, aryloxy, arylalkyleneoxy, heteroaryl, heteroaryloxy, heteroarylalkyleneoxy, heterocyclyl, heterocyclylalkylenyl, amino, alkylamino, and dialkylamino;
R is selected from the group consisting of alkyl, alkoxy, hydroxy, halogen, and trifluoromethyl;

n is 0 or 1;
R1 is selected from the group consisting of:
-R4, -X-R4, -X-Y-R4, -X-Y-X-Y-R4, and -X-R5;
R2 is selected from the group consisting of:
-X-R4, -X-Y-R4, and -X-R5, each X is independently selected from the group consisting of alkylene, alkenylene, alkynylene, arylene, heteroarylene, and heterocyclylene wherein the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by arylene, heteroarylene or heterocyclylene or by one or more -O- groups;
each Y is independently selected from the group consisting of:
-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)-, each R4 is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, arylalkylenyl, aryloxyalkylenyl, alkylarylenyl, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkylenyl, alkylheteroarylenyl, and heterocyclyl wherein the alkyl, alkenyl, alkenyl, 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;
each R5 is independently selected from the group consisting of:

each R6 is independently selected from the group consisting of =O and =S;
each R7 is independently C2-7 alkylene;
each R8 is independently selected from the group consisting of hydrogen, alkyl, alkoxyalkylenyl, and arylalkylenyl;
each R9 is independently selected from the group consisting of hydrogen and alkyl;
each R10 is independently C3-8 alkylene;

each A is independently selected from the group consisting of -O-, -C(O)-, -S(O)0-2-, -CH2-, and -N(R4)-;
each Q is independently 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-, and -C(R6)-N(OR9)-;
each V is independently selected from the group consisting of -C(R6)-, -O-C(R6)-, -N(R8)-C(R6)-, and -S(O)2-;
each W is independently 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.
53. The compound or salt of claim 52 wherein R3 is benzyl.
54. The compound or salt of claim 52 or claim 53 wherein R1 is selected from the group consisting of alkyl, arylalkylenyl, aryloxyalkylenyl, hydroxyalkyl, alkylsulfonylalkylenyl, heterocyclylalkylenyl wherein heterocyclyl is optionally substituted by one or more alkyl groups, -X-Y-R4, and -X-R5; wherein X is alkylene, Y is N(R8)-C(O)-, -N(R8)-S(O)2-, N(R8)-C(O)-N(R8)-, or ; R4 is alkyl, aryl, arylalkylenyl, or heteroaryl, each of which is optionally substituted by one or more substituents selected from the group consisting of alkyl, alkoxy, halogen, or dialkylamino;
and R5 is
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