Urea substituted imidazopyridines
View Patent ↗Imidazopyridine compounds that contain urea or thiourea 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.
1. A compound of the formula (I):
wherein
X is C 1-10 alkylene;
Y is —CO—;
Z is —NR 6 —;
R 1 is C 1-10 alkyl wherein alkyl is straight chain alkyl, branched chain alkyl, or cycloalkyl;
R 2 is selected from the group consisting of:
C 1-4 alkyl,
ethoxymethyl, and
methoxyethyl;
R 3 and R 4 are methyl;
R 5 is hydrogen; and
R 6 is hydrogen;
or a pharmaceutically acceptable salt thereof.
2. The compound or salt of claim 1 wherein R 1 is cyclohexyl, and R 2 is ethoxymethyl.
3. The compound or salt of claim 1 wherein R 1 is C 1-6 alkyl.
4. The compound or salt of claim 1 wherein R 1 is C 1-4 alkyl.
5. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 1 in combination with a pharmaceutically acceptable carrier.
6. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 2 in combination with a pharmaceutically acceptable carrier.
7. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 3 in combination with a pharmaceutically acceptable carrier.
8. A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 4 in combination with a pharmaceutically acceptable carrier.
9. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
10. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
11. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 1 to the animal.
12. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 2 to the animal.
13. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 2 to the animal.
14. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 2 to the animal.
15. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 3 to the animal.
16. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 3 to the animal.
17. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 3 to the animal.
18. A method of inducing cytokine biosynthesis in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 4 to the animal.
19. A method of treating a viral disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 4 to the animal.
20. A method of treating a neoplastic disease in an animal comprising administering a therapeutically effective amount of a compound or salt of claim 4 to the animal.