Guanidine substituted imidazo[4,5-c] ring compounds

1. A compound of the Formula (I):

wherein:

R 3 and R 4 are taken together to form a fused benzene ring, a fused pyridine ring, a fused cyclohexene ring, or a fused tetrahydropyridine ring; wherein the fused benzene ring, fused pyridine ring, fused cyclohexene ring, or fused tetrahydropyridine ring is either unsubstituted or substituted by one or more R groups;

R is selected from the group consisting of halogen, hydroxyl, alkyl, alkoxy, haloalkyl, —C(O)—O-alkyl, —C(O)—OCH 2 Ph, —C(O)—O-aryl, amino, alkylamino, and dialkylamino, aryl, arylalkylenyl, aryloxyalkylenyl, arylalkyleneoxy, aryloxy, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkyenyl, heteroarylalkyleneoxy, and heteroaryloxy, wherein the alkyl, aryl, arylalkylenyl, aryloxyalkylenyl, arylalkyleneoxy, aryloxy, heteroaryl, heteroarylalkylenyl, heteroaryloxyalkyenyl, heteroarylalkyleneoxy, and heteroaryloxy groups can be unsubstituted or substituted by one or more substituents independently selected from the group consisting of alkyl, alkoxy, halogen, haloalkyl, hydroxyl, hydroxyalkylenyl, alkoxyalkylenyl, arylalkyleneoxy, nitrile, amino, alkylamino, and dialkylamino;

R 1 is selected from the group consisting of —W—X—N(R 5 )—C(═NH)—NH 2 , —W—Z—N(R 5 )—C(═NH)—NH 2 , and

W is selected from the group consisting of a covalent bond, —O—, and —NH—;

X is selected from the group consisting of alkylene, alkenylene, and alkynylene, wherein any of the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by one or more —O— groups;

Z is selected from the group consisting of

—X-arylene-X—,

—X-heteroarylene-X—,

—X-arylene-, and

—X-heteroarylene-;

R 2 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, —O-alkyl, hydroxyalkylenyl, alkoxyalkylenyl, alkylaminoalkylenyl, hydroxyl, —CH 2 —NH—O-alkyl, and —CH 2 NHC(O)-alkyl;

R 5 is selected from the group consisting of hydrogen, alkyl, arylalkylenyl, alkoxyalkylenyl, aryloxyalkylenyl, benzyloxyalkylenyl, aryl-(CH 2 ) 2-6 —O-alkylenyl, and cycloalkylalkylenyl, wherein any of the alkyl, arylalkylenyl, alkoxyalkylenyl, aryloxyalkylenyl, benzyloxyalkylenyl, aryl-(CH 2 ) 2-6 —O-alkylenyl, and cycloalkylalkylenyl groups can be either unsubstituted or substituted with one or more substituents independently selected from the group consisting of halogen, hydroxyl, alkoxy, alkyl, haloalkyl, and nitrile;

Q is selected from the group consisting of a bond, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 —O—CH 2 —, and —OCH 2 —;

or a pharmaceutically acceptable salt thereof.

2. The compound or salt of claim 1 , wherein R 3 and R 4 are taken together to form a fused benzene ring, a fused pyridine ring, or a fused cyclohexene ring, and wherein the fused benzene ring, fused pyridine ring, or fused cyclohexene ring is either unsubstituted or substituted by one and only one R group.

3. The compound or salt of claim 1 , wherein R 1 is selected from the group consisting of —W—X—N(H)—C(═NH)—NH 2 , and —W—Z—N(H)—C(═NH)—NH 2 .

4. The compound or salt of claim 1 , wherein W is a covalent bond or —O—.

5. The compound or salt of claim 1 , wherein X is alkylene optionally interrupted by one or more —O— groups.

6. The compound or salt of claim 5 , wherein X is selected from the group consisting of —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 C(CH 3 ) 2 —, —CH 2 C(CH 3 ) 2 CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —O—CH 2 CH 2 —, —(CH 2 ) 2-4 —(OCH 2 CH 2 -) 1-5 , and —(CH 2 ) 2-6 —(OCH 2 CH 2 -) 1-4 .

7. The compound or salt of claim 1 , wherein Z is —C 1-5 alkylene-arylene-C 1-5 alkylene- or —C 1-5 alkylene-heteroarylene-C 1-5 alkylene-.

8. The compound or salt of claim 6 , wherein Z is —CH 2 -phenylene-CH 2 —.

9. The compound or salt of claim 1 , wherein R 2 is selected from the group consisting hydrogen, alkyl, alkoxyalkylenyl, alkylaminoalkylenyl, and hydroxyalkylenyl.

10. The compound or salt of claim 9 , wherein R 2 is selected from the group consisting of hydrogen, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH 2 CH 2 OCH 3 , —CH 2 NHCH 3 , —CH 2 NHCH 2 CH 3 , —CH 2 CH 2 NHCH 3 , —CH 2 OH, and —CH 2 CH 2 OH.

11. The compound or salt of claim 10 , wherein R 2 is selected from the group consisting of hydrogen, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , and —CH 2 CH 2 OCH 3 .

12. A compound of the Formula XIII:

wherein:

R 1B is selected from the group consisting of —X B —N(R 5B )—C(═NH)—NH 2 , —Z B —N(R 5B )—C(═NH)—NH 2 , and

X B is selected from the group consisting of alkylene, alkenylene, and alkynylene, wherein any of the alkylene, alkenylene, and alkynylene groups can be optionally interrupted by one or more —O— groups;

Z B is selected from the group consisting of

—X B -arylene-X B —,

—X B -heteroarylene-X B —,

—X B -arylene-, and

—X B -heteroarylene-;

R 2B is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, —O-alkyl, hydroxyalkylenyl, alkoxyalkylenyl, alkylaminoalkylenyl, hydroxyl, —CH 2 —NH—O-alkyl, and —CH 2 NHC(O)-alkyl;

R 5B is selected from the group consisting of hydrogen, alkyl, arylalkylenyl, alkoxyalkylenyl, aryloxyalkylenyl, benzyloxyalkylenyl, aryl-(CH 2 ) 2-6 —O-alkylenyl,and cycloalkylalkylenyl, wherein any of the alkyl, arylalkylenyl, alkoxyalkylenyl, aryloxyalkylenyl, benzyloxyalkylenyl, aryl-(CH 2 ) 2-6 —O-alkylenyl, and cycloalkylalkylenyl groups can be either unsubstituted or substituted with one or more substituents independently selected from the group consisting of halogen, hydroxyl, alkoxy, alkyl, haloalkyl, and nitrile;

Q B is selected from the group consisting of a bond, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 —O—CH 2 —, and —OCH 2 —;

or a pharmaceutically acceptable salt thereof.

13. The compound or salt of claim 12 , wherein R 1B is selected from the group consisting of —X B —N(H)—C(═NH)—NH 2 , and —Z B —N(H)—C(═NH)—NH 2 .

14. The compound or salt of claim 12 , wherein

X B is alkylene optionally interrupted by one or more —O— groups; and

Z B is —C 1-5 alkylene-arylene-C 1-5 alkylene- or —C 1-5 alkylene-heteroarylene-C 1-5 alkylene-.

15. The compound or salt of claim 12 , wherein Z B is —CH 2 -phenylene-CH 2 —.

16. The compound or salt of claim 12 , wherein X B is selected from the group consisting of —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 C(CH 3 ) 2 —, —CH 2 C(CH 3 ) 2 CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —O—CH 2 CH 2 —, —(CH 2 ) 2-4 —(OCH 2 CH 2 -) 1-5 , and —(CH 2 ) 2-6 —(OCH 2 CH 2 -) 1-4 .

17. The compound or salt of claim 12 , wherein R 2B is selected from the group consisting of hydrogen, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , and —CH 2 CH 2 OCH 3 .

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

19. A method of inducing biosynthesis of IFN-alpha in an animal comprising administering an effective amount of a compound or salt of claim 17 to the animal.

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