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Claims for Patent: 4,689,338

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Claims for Patent: 4,689,338

Title: 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
Abstract:1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described.
Inventor(s): Gerster; John F. (Woodbury, MN)
Assignee: Riker Laboratories, Inc. (St. Paul, MN)
Application Number:06/798,385
Patent Claims: 1. A compound of the formula ##STR26## wherein R.sub.1 is selected from the group consisting of alkyl of one to about ten carbon atoms, hydroxylalkyl of one to about six carbon atoms, acyloxyalkyl wherein the acyloxy moiety is alkanoyloxy of two to about four carbon atoms or benzoyloxy, and the alkyl moiety contains one to about six carbon atoms, benzyl, (phenyl)ethyl and phenyl, said benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms and halogen, with the proviso that if said benzene ring is substituted by two of said moieties, then said moieties together contain no more than 6 carbon atoms; R.sub.2 is selected from the group consisting of hydrogen, alkyl of one to about eight carbon atoms, benzyl, (phenyl)ethyl and phenyl, the benzyl, (phenyl)ethyl or phenyl substituent being optionally substituted on the benzene ring by one or two moieties independently selected from the group consisting of alkyl of one to about four carbon atoms, alkoxy of one to about four carbon atoms and halogen, with the proviso that when the benzene ring is substituted by two of said moieties, then the moieties together contain no more than 6 carbon atoms; and each R is independently selected from the group consisting of alkoxy of one to about four carbon atoms, halogen and alkyl of one to about four carbon atoms, and n is an integer from 1 to 2, with the proviso that if n is 2, then said R groups together contain no more than 6 carbon atoms; or a pharmaceutically acceptable acid addition salt thereof.

2. A compound according to claim 1 wherein R.sub.2 is hydrogen.

3. A compound according to claim 2 wherein R is hydrogen.

4. A compound according to claim 1, wherein R.sub.1 is alkyl, benzyl, cyclohexylmethyl or hydroxyalkyl.

5. A compound according to claim 1, wherein R.sub.1 is alkyl of one to about eight carbon atoms.

6. A compound according to claim 1, wherein R.sub.1 is alkyl of about four to about six carbon atoms.

7. The compound 1-methyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

8. The compound 1,2,8-trimethyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

9. The compound 1-(2-hydroxyethyl)-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

10. The compound 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

11. The compound 1,8-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

12. The compound 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

13. The compound 1-(2,3-dihydroxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

14. The compound 1-cyclohexylmethyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

15. The compound 1-benzyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

16. The compound 1-benzyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

17. The compound 1-n-hexyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

18. The compound 1-n-hexyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine according to claim 1.

19. An antiviral pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier, said compound being present in an amount sufficient to exert antiviral activity.

20. A method for treating a mammal infected with a virus comprising administering a compound according to claim 1 to said mammal in an amount effective to reduce severity of or prevent the infection.

21. A method treating a mammal infected with Type I or Type II Herpes simplex virus comprising administering a compound according to claim 1 to said mammal in an amount sufficient to inhibit development of lesions caused by said virus.

22. A method according to claim 21, wherein said compound is administered topically to a lesion caused by said virus.
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