Sulfonamido substituted imidazopyridines

• US 6,696,465 B2
• Filed: 12/17/2002
• Issued: 02/24/2004
• Est. Priority Date: 12/08/2000
• Status: Expired due to Fees

• Current Assignee: Coley Pharmaceutical Group, Inc. (Pfizer Inc.)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Haraldson, Chad A., Merrill, Byron A., Lindstrom, Kyle J., Heppner, Philip D., Dellaria, Joseph F.
• Primary Examiner(s): AULAKH, CHARANJIT
• Application Number:
  US10/322,262
• Publication Number:
  US 20040019076A1
• Time in Patent Office: 434 Days
• Field of Search: 514/303, 546/118
• US Class Current: 514/303
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

Imidazopyridine compounds that contain sulfonamide functionality at the 1-position are useful as immune response modifiers. The compounds and compositions of the invention can induce the biosynthesis of various cytokines and are useful in the treatment of a variety of conditions including viral diseases and neoplastic diseases.

Claims

1. A compound of the formula (I):

wherein

X is ethylene, propylene, or butylene;

Y is —

SO₂—

;

Z is a bond or —

NR₆—

;

R₁ is aryl, heteroaryl, C_1-10 alkyl, or C_2-10 alkenyl, each of which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of;

-alkyl;

-aryl;

-substituted aryl;

—

O-alkyl;

—

COOH;

—

S(O)_0-2-alkyl;

-(alkyl)_0-1—

NR₆—

CO-aryl;

-halogen;

-haloalkyl;

-haloalkoxy;

—

NO₂;

—

CN; and

in the case of alkyl and alkenyl, oxo;

R₂ is selected from the group consisting of;

-hydrogen;

—

C_1-10 alkyl; and

—

C_1-10 alkyl-O—

C_1-10 alkyl;

R₃ and R₄ are independently selected from the group consisting of hydrogen, and methyl;

R₅ is H or C_1-10 alkyl, or R₅ can join with X to form a ring;

or when R₁ is C_1-10 alkyl, R₅ and R₁ can join to form a ring;

each R₆ is independently H or C_1-10 alkyl;

or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 in combination with a pharmaceutically acceptable carrier.

17. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 1 to the animal.

18. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 1 to the animal.

19. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 1 to the animal.

2. A compound selected from the group consisting of:

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]ethanesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]propane-2-sulfonamide;

N′

-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]butane-1-sulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]thiophene-2-sulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-1-phenylmethanesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-fluorobenzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-3-cyanobenzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-methoxybenzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]naphthalene-1-sulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]quinoline-8-sulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(trifluoromethyl)benzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-1,1′

-biphenyl-4-sulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(methylsulfonyl)benzenesulfonamide;

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-(trifluoromethoxy)benzenesulfonamide; and

N-[4-(4-amino-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzenesulfonamide;

or a pharmaceutically acceptable salt thereof.

10. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 2 in combination with a pharmaceutically acceptable carrier.

20. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 2 to the animal.

21. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 2 to the animal.

22. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 2 to the animal.

3. A compound selected from the group consisting of:

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}ethanesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}propane-2-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}butane-1-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}thiophene-2-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-phenylmethanesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-fluorobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2,4-difluorobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-1-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}quinoline-8-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(methylsulfonyl)benzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl]buty1}-4-(trifluoromethoxy)benzenesulfonamide; and

N-[4-(4-amino-2-ethoxymethyl-6-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzenesulfonamide;

or a pharmaceutically acceptable salt thereof.

11. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 3 in combination with a pharmaceutically acceptable carrier.

23. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 3 to the animal.

24. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 3 to the animal.

25. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 3 to the animal.

4. A compound selected from the group consisting of:

2-(ethoxymethyl)-1-{2-[1-(ethylsulfonyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;

2-(ethoxymethyl)-1-{2-[1-(isopropylsulfonyl)piperidin-4-yl]ethyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;

4-{2-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]ethyl}-N,N-dimethylpiperidine-1-sulfonamide;

1-{2-[1-(butylsulfonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;

2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(2-naphthylsulfonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;

2-(ethoxymethyl)-6,7-dimethyl-1-{2-[1-(quinolin-8-ylsulfonyl)piperidin-4-yl]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine;

2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine;

1-[4-(1,1-dioxidoisothiazolidin-2-yl)butyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine;

1-{2-[1-(1,1′

-biphenyl-4-ylsulfonyl)piperidin-4-yl]ethyl}-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;

2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-{[4-(methylsulfonyl)phenyl]sulfonyl}piperidin-4-yl)ethyl]-1H-imidazo[4,5-c]pyridin-4-amine; and

1-(2-{1-[4-(4-dimethylaminophenylazo)benzenesulfonyl]piperidin-4-yl}ethyl)-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine;

or a pharmaceutically acceptable salt thereof.

12. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 4 in combination with a pharmaceutically acceptable carrier.

26. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 4 to the animal.

27. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 4 to the animal.

28. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 4 to the animal.

5. A compound selected from the group consisting of:

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]ethanesulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]propane-2-sulfonamide;

N′

-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-N,N-dimethylsulfamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]butane-1-sulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]thiophene-2-sulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-fluorobenzenesulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzenesulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]naphthalene-1-sulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]naphthalene-2-sulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-1,1′

-biphenyl-4-sulfonamide; and

N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-4-(trifluoromethoxy)benzenesulfonamide;

or a pharmaceutically acceptable salt thereof.

13. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 5 in combination with a pharmaceutically acceptable carrier.

29. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 5 to the animal.

30. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 5 to the animal.

31. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 5 to the animal.

6. A compound selected from the group consisting of:

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}ethanesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}propane-2-sulfonamide;

N′

-[4-(4-amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-N,N-dimethylsulfamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}butane-1-sulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}benzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}thiophene-2-sulfonamide;

(E)-N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2-phenylethenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-fluorobenzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-cyanobenzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-3-cyanobenzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-methoxybenzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-2,4-difluorobenzenesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}naphthalene-1-sulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}naphthalene-2-sulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(trifluoromethyl)benzenesulfonamide;

N-[3-(4-amino-2-ethoxymethyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-1,1′

-biphenyl-4-sulfonamide; and

N-{3-[4-amino-2-(ethoxymethyl)-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl]propyl}-4-(methylsulfonyl)benzenesulfonamide;

or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 6 in combination with a pharmaceutically acceptable carrier.

32. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 6 to the animal.

33. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 6 to the animal.

34. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 6 to the animal.

7. A compound selected from the group consisting of:

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]ethanesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]propane-2-sulfonamide;

N′

-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-N,N-dimethylsulfamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]butane-1-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]benzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]thiophene-2-sulfonamide;

(E)-N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylethenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-fluorobenzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2,4-difluorobenzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-1-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-2-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethyl)benzenesulfonamide;

N-[2-(4-Amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-C-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1,1′

-biphenyl-4-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(methylsulfonyl)benzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethoxy)benzenesulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1-methyl-1H-imidazole-4-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-3,5-dimethylisoxazole-4-sulfonamide;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-5-chlorothiophene-2-sulfonamide;

4-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}sulfonyl)benzoic acid;

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-1-(2-nitrophenyl)methanesulfonamide; and

N-{[5-({[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]amino}sulfonyl)thien-2-yl]methyl}benzamide;

or a pharmaceutically acceptable salt thereof.

15. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 7 in combination with a pharmaceutically acceptable carrier.

35. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 7 to the animal.

36. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 7 to the animal.

37. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 7 to the animal.

8. A compound selected from the group consisting of:

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}ethanesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}propane-2-sulfonamide;

N′

-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-N,N-dimethylsulfamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}butane-1-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}benzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}thiophene-2-sulfonamide;

(E)-N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2-phenylethenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-fluorobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-cyanobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3-cyanobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-methoxybenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-2,4-difluorobenzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-1-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}naphthalene-2-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(trifluoromethyl)benzenesulfonamide;

N-[4-(4-amino-2-ethoxymethyl-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-C-(7,7-dimethyl-2-oxobicyclo[2.21]hept-1-yl)methanesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-biphenyl-4-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-4-(methylsulfonyl)benzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-(trifluoromethoxy)benzenesulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-1-methyl-1H-imidazole-4-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-3,5-dimethylisoxazole-4-sulfonamide;

N-{4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}-5-chlorothiophene-2-sulfonamide; and

N-({5-[({4-[4-amino-2-(ethoxymethyl)-7-methyl-1H-imidazo[4,5-c]pyridin-1-yl]butyl}amino)sulfonyl]thien-2-yl}methyl)benzamide;

or a pharmaceutically acceptable salt thereof.

16. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 8 in combination with a pharmaceutically acceptable carrier.

38. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound of claim 8 to the animal.

39. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound of claim 8 to the animal.

40. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound of claim 8 to the animal.