β-cyclodextrin derivatives as antibacterial agents

• US 7,737,132 B2
• Filed: 01/27/2006
• Issued: 06/15/2010
• Est. Priority Date: 01/28/2005
• Status: Expired due to Fees

• Current Assignee: Pinnacle Pharmaceuticals, Inc.
• Original Assignee: Pinnacle Pharmaceuticals, Inc.
• Inventors: Fahmi, Noureddine, Hecht, Sidney, Schmidtmann, Frank Werner
• Primary Examiner(s): Jiang; Shaojia Anna
• Assistant Examiner(s): Krishnan; Ganapathy
• Application Number:
  US11/342,339
• Publication Number:
  US 20060199785A1
• Time in Patent Office: 1,600 Days
• Field of Search: 514/58, 536/46
• US Class Current: 514/58
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C08B 37/0009 alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
• CPC Class Codes: C08B 37/0012 Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof

Abstract

The invention provides a new class of antibiotics to which pathogenic bacteria have not been exposed, and thus should not have developed resistance. This new class of antibiotics are derivatives of β-cyclodextrin (β-CD), which is a cyclic molecule comprising seven D-glucose units.

Claims

1. A method for potentiating the activity of an antibiotic to inhibit the growth of a bacterium which is resistant to said antibiotic, comprising contacting the bacterium with said antibiotic and a compound having the formula

2. The method according to claim 1, wherein for each of R₂, R₃ and R₆ any one or more of the carbon atoms may be optionally replaced by S, N or O.

3. The method according to claim 1, wherein the bacterium is in a mammal.

4. The method according to claim 3, wherein the mammal is a human.

5. The method according to claim 1, wherein the compound has the formula

6. The method according to claim 1, wherein the compound is

7. The method according to claim 1, wherein the compound is

8. The method according to claim 1, wherein the compound is

9. The method according to claim 1, wherein the antibiotic is Methicillin, Penicillin, Vancomycin, Chloramphenicol, Norfloxacin or Tobramycin.

10. The method according to claim 9, wherein the antibiotic is Methicillin.

11. The method according to claim 9, wherein the antibiotic is Penicillin.

12. The method according to claim 9, wherein the antibiotic is Vancomycin.

13. The method according to claim 9, wherein the antibiotic is Chloramphenicol.

14. The method according to claim 9, wherein the antibiotic is Norfloxacin.

15. The method according to claim 9, wherein the antibiotic is Tobramycin.

16. The method according to claim 5, wherein the antibiotic is Methicillin, Penicillin, Vancomycin, Chloramphenicol, Norfloxacin or Tobramycin.

17. The method according to claim 16, wherein the antibiotic is Methicillin.

18. The method according to claim 16, wherein the antibiotic is Penicillin.

19. The method according to claim 16, wherein the antibiotic is Vancomycin.

20. The method according to claim 16, wherein the antibiotic is Chloramphenicol.

21. The method according to claim 16, wherein the antibiotic is Norfloxacin.

22. The method according to claim 16, wherein the antibiotic is Tobramycin.

23. The method according to claim 6, wherein the antibiotic is Methicillin, Penicillin, Vancomycin, Chloramphenicol, Norfloxacin or Tobramycin.

24. The method according to claim 23, wherein the antibiotic is Methicillin.

25. The method according to claim 23, wherein the antibiotic is Penicillin.

26. The method according to claim 23, wherein the antibiotic is Vancomycin.

27. The method according to claim 23, wherein the antibiotic is Chloramphenicol.

28. The method according to claim 23, wherein the antibiotic is Norfloxacin.

29. The method according to claim 23, wherein the antibiotic is Tobramycin.

30. The method according to claim 7, wherein the antibiotic is Methicillin, Penicillin, Vancomycin, Chloramphenicol, Norfloxacin or Tobramycin.

31. The method according to claim 30, wherein the antibiotic is Methicillin.

32. The method according to claim 30, wherein the antibiotic is Penicillin.

33. The method according to claim 30, wherein the antibiotic is Vancomycin.

34. The method according to claim 30, wherein the antibiotic is Chloramphenicol.

35. The method according to claim 30, wherein the antibiotic is Norfloxacin.

36. The method according to claim 30, wherein the antibiotic is Tobramycin.

37. The method according to claim 8, wherein the antibiotic is Methicillin, Penicillin, Vancomycin, Chloramphenicol, Norfloxacin or Tobramycin.

38. The method according to claim 37, wherein the antibiotic is Methicillin.

39. The method according to claim 37, wherein the antibiotic is Penicillin.

40. The method according to claim 37, wherein the antibiotic is Vancomycin.

41. The method according to claim 37, wherein the antibiotic is Chloramphenicol.

42. The method according to claim 37, wherein the antibiotic is Norfloxacin.

43. The method according to claim 37, wherein the antibiotic is Tobramycin.

44. The method according to claim 1, wherein R² and R³ are OH.