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Claims for Patent: 4,078,071

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Claims for Patent: 4,078,071

Title: Derivatives of substituted N-alkyl imidazoles
Abstract:Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl or one of the above substituted in the phenyl ring with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 8 with the proviso that n is not 1 when R.sup.1 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
Inventor(s): Walker; Keith A. M. (Palo Alto, CA)
Assignee: Syntex (U.S.A.) Inc. (Palo Alto, CA)
Application Number:05/758,094
Patent Claims: 1. A compound of the formula ##STR16## wherein R.sup.1 is phenethyl, phenylpropyl or styryl and R.sup.2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain alkenyl, wherein the phenyl rings of R.sup.1 and R.sup.2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower akyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from one to three; and the antimicrobial acid addition salts therof.

2. The compound of claim 1 wherein n is 1.

3. The compound of claim 1 wherein R.sup.1 is halo-substituted phenethyl or styryl.

4. The compound of claim 3 wherein R.sup.1 has a 4-halo substituent.

5. The compound of claim 3 wherein, when R.sup.1 has more than one halo substituent, all such substituents are the same halo.

6. The compound of claim 3 wherein the halo substituent on R.sup.1 is chloro.

7. The compound of claim 3 wherein R.sup.2 is substituted or unsubstituted phenyl or benzyl.

8. The compound of claim 7 wherein R.sup.2 is halo-substituted phenyl or benzyl.

9. The compound of claim 8 wherein R.sup.2 is phenyl having at least one ortho-halo substituent.

10. The compound of claim 9 wherein, when R.sup.2 has more than one halo substituent, all such substituents are the same halo.

11. The compound of claim 8 wherein the halo substituent on R.sup.2 is chloro.

12. The compound of claim 9 wherein X is sulfur.

13. The compound of claim 8 wherein R.sup.2 is halo-substituted benzyl.

14. The compound of claim 13 wherein R.sup.2 is chloro-substituted benzyl.

15. The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

16. The compound of claim 8 which is 1-[2-(2,5-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

17. The compound of claim 8 which is 1-[2-(2,4-dichlorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

18. The compound of claim 8 which is 1-[2-(2-chorophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

19. The compound of claim 8 which is 1-[2-(2,3-dichlorophenylthio)-4-(4-chorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

20. The compound of claim 8 which is 1-[2-(2-bromophenylthio)-4-(4-chlorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

21. The compound of claim 8 which is 1-[2-(2,6-dibromophenylthio)-4-(4-chorophenyl)butyl]imidazole and the antimicrobial acid addition salts thereof.

22. The compound of claim 8 which is 1-[2-(2,4,6-trichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.

23. The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.

24. The compound of claim 8 which is 1-[2-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)but-3-enyl] imidazole and the antimicrobial acid addition salts thereof.

25. The compound of claim 8 which is 1-[3-(2,6-dichlorophenylthio)-5-(4-chlorophenyl)pentyl] imidazole and the antimicrobial acid addition salts thereof.

26. The compound of claim 8 which is 1-[2-(2,5-dichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.

27. The compound of claim 8 which is 1-[2-(2,4,5-trichlorophenylthio)-4-(4-fluorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.

28. The compound of claim 8 which is 1-[2-(2,4,5-trichlorophenylthio)-4-(4-chlorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.

29. A composition useful for inhibiting the growth of fungi, bacteria or portozoa which comprises an effective amount of a compound of the formula ##STR17## wherein R.sup.1 is phenethyl, phenylpropyl or styryl and R.sup.2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl, wherein the phenyl rings of R.sup.1 and R.sup.2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur, n is an integer of from 1 to 3; or an anti-microbial acid addition salt thereof; in admixture with a suitable carrier.

30. The composition of claim 29 suitable for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.

31. The composition of claim 30 for topical administration wherein the compound of Formula I is present as between about 0.1 and 10.0 weight percent of the composition.

32. A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing, or subject to attack by, fungi, bacteria or protozoa an effective amount of a compound of the formula ##STR18## wherein R.sup.1 is phenyl, phenylpropyl or styryl and R.sup.2 is phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl wherein the phenyl rings of R.sup.1 and R.sup.2 may independently be unsubstituted or substituted with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is a integer of from 1 to 3; or an antimicrobial acid addition salt thereof, or a composition containing same as an active ingredient.

33. The method of claim 32 wherein the compound of Formula I is administered topically.

34. The method of claim 32 wherein the compound of Formula I is administered orally or parenterally.

35. The compound 1-[3-(2,6-dichlorophenylthio)-4-(4-chlorophenyl)butyl] imidazole and the antimicrobial acid addition salts thereof.
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