Beta-cyclodextrin derivatives as antibacterial agents

• US 20060199785A1
• Filed: 01/27/2006
• Published: 09/07/2006
• Est. Priority Date: 01/28/2005
• Status: Active Grant

• Current Assignee: Pinnacle Pharmaceuticals, Inc.
• Original Assignee: Pinnacle Pharmaceuticals, Inc.
• Inventors: Fahmi, Noureddine, Hecht, Sidney, Schmidtmann, Frank Werner
• Granted Patent: US 7,737,132 B2
• Time in Patent Office: Days
• 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 compound having the formula

2. The compound according to claim 1, wherein _n is from about 1 to about 10.

3. The compound 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.

4. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

5. A method for inhibiting the growth of a bacterium, comprising contacting the bacterium with a compound having the formula

6. The method according to claim 5, wherein _n is from about 1 to about 10, and wherein _m is from about 1 to about 10.

7. The method according to claim 5, 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.

8. The method according to claim 5, wherein the bacterium is in a mammal.

9. The method according to claim 7, wherein the mammal is a human.

10. A method for treating a bacterial infection, comprising administering to a mammal with a bacterial infection a compound having the formula

11. The method according to claim 10, wherein _n is from about 1 to about 10, and wherein _m is from about 1 to about 10.

12. The method according to claim 10, 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.

13. The method according to claim 10, wherein the mammal is a human.

14. A method for preventing a bacterial infection, comprising administering to a mammal susceptible to a bacterial infection a compound having the formula

15. The method according to claim 14, wherein _n is from about 1 to about 10, and wherein _m is from about 1 to about 10.

16. The method according to claim 14, 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.

17. The method according to claim 14, wherein the mammal is a human.

18. A method for potentiating the activity of 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

19. The method according to claim 18, wherein _n is from about 1 to about 10, and wherein _m is from about 1 to about 10.

20. The method according to claim 18, 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.

21. The method according to claim 18, wherein the bacterium is in a mammal.

22. The method according to claim 21, wherein the mammal is a human.