Inhibition and dispersion of bacterial biofilms with imidazole-triazole derivatives
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-403/06
A61K-031/4192
출원번호
US-0011532
(2011-01-21)
등록번호
US-8367713
(2013-02-05)
발명자
/ 주소
Melander, Christian
Rogers, Steven A.
Huigens, III, Robert W.
Reed, Catherine S.
출원인 / 주소
North Carolina State University
인용정보
피인용 횟수 :
4인용 특허 :
11
초록
Disclosure is provided for imidazole-triazole derivative compounds such as those given in Formulas (I)-(VI) that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.
대표청구항▼
1. A compound of Formula (IV)(a): wherein: R1a and R1b are each H;R2, R3, R5 and are each independently H or alkyl;each occurrence of Rx, Ry, Ru, Rv, Rz and Rw is present or absent (depending upon chain saturation), and are each independently H or alkyl;R6 is independently selected from the group c
1. A compound of Formula (IV)(a): wherein: R1a and R1b are each H;R2, R3, R5 and are each independently H or alkyl;each occurrence of Rx, Ry, Ru, Rv, Rz and Rw is present or absent (depending upon chain saturation), and are each independently H or alkyl;R6 is independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide;n=0 to 10;m=0 to 10; andp=0 to 20or a pharmaceutically acceptable salt or prodrug thereof. 2. The compound of claim 1, wherein R6 is H. 3. The compound of claim 1, wherein R6 is aryl. 4. The compound of claim 1, wherein p=0 and R6 is substituted aryl or heteroaryl. 5. The compound of claim 1, wherein R6 is a group: wherein: X, Y and Z are each independently selected from the group consisting of: H, methyl, Br and Cl. 6. The compound of claim 1, wherein R6 is a group: wherein: R20, R21, R22, R23 and R24 are each independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide. 7. The compound of claim 6, wherein said compound has the formula: or a pharmaceutically acceptable salt or prodrug thereof. 8. A compound of Formula (V)(a): wherein: R1a and R1b are each H;R2, R3, R5 and are each independently H or alkyl;each occurrence of Rx, Ry, Ru, Rv, Rz and Rw is present or absent (depending upon chain saturation), and are each independently H or alkyl;R6 is independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide;n=0 to 10;m=0 to 10; andp=0 to 20or a pharmaceutically acceptable salt or prodrug thereof. 9. The compound of claim 8, wherein R6 is aryl. 10. The compound of claim 8, wherein R6 is H. 11. The compound of claim 10, wherein said compound has the formula: or a pharmaceutically acceptable salt or prodrug thereof. 12. A composition comprising the compound of claim 1 and a biocide. 13. A composition comprising the compound of claim 1 in a pharmaceutically acceptable carrier. 14. A composition comprising: a compound of Formula (IV)(a): wherein: R1a and R1b are each H;R2, R3, R5 and are each independently H or alkyl;each occurrence of Rx, Ry, Ru, Rv, Rz and Rw is present or absent (depending upon chain saturation), and are each independently H or alkyl;R6 is independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide;n=0 to 10;m=0 to 10; andp=0 to 20covalently coupled to a substrate. 15. A biofilm removing or inhibiting coating composition, comprising: (a) a film-forming resin;(b) a solvent that disperses said resin;(c) an effective amount of the compound of claim 1, wherein said effective amount of said compound removes or inhibits the growth of a biofilm thereon; and(d) optionally, at least one pigment. 16. A biofilm removing or inhibiting coating composition, comprising: (a) a film-forming resin;(b) a solvent that disperses said resin;(c) an effective amount of:a compound of Formula (IV)(a): wherein: R1a and R1b are each H;R2, R3, R5 and are each independently H or alkyl;each occurrence of Rx, Ry, Ru, Rv, Rz and Rw is present or absent (depending upon chain saturation), and are each independently H or alkyl;R6 is independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide;n=0 to 10;m=0 to 10; andp=0 to 20 wherein said effective amount of said compound removes or inhibits the growth of a biofilm thereon; and (d) optionally, at least one pigment, wherein said compound is covalently coupled to said resin. 17. The coating composition of claim 15, wherein said resin comprises a polymeric material. 18. A substrate coated with the coating composition of claim 15. 19. The compound of claim 1, wherein n=1 to 6. 20. The compound of claim 1, wherein n=1 to 6 and m=1 to 3. 21. The compound of claim 1, wherein n=1 to 6, m=1 to 3, p=0, and R6 is a substituted aryl. 22. The compound of claim 1, wherein n=1 to 6, m=1 to 3, p=0, and R6 is an aryl substituted with an alkyl having from 1 to 10 carbon atoms. 23. The compound of claim 1, wherein n=1 to 6, m=1 to 3, p=0, and R6 is a group: wherein: R20, R21, R22, R23 and R24 are each independently selected from the group consisting of: H, hydroxy, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclo, aryl, heteroaryl, alkoxy, amino, amide, thiol, sulfone, sulfoxide, oxo, oxy, nitro, carbonyl, carboxy, amino acid sidechain, amino acid and peptide. 24. The compound of claim 23, wherein R20, R21, R23 and R24 are each H, and wherein R22 is an alkyl having from 1 to 20 carbon atoms. 25. The compound of claim 23, wherein R20, R21, R23 and R24 are each H, and wherein R22 is an alkyl having from 1 to 10 carbon atoms. 26. The compound of claim 23, wherein R20, R21, R23 and R24 are each H, and wherein R22 is an alkyl having from 4 to 7 carbon atoms. 27. The compound of claim 6, wherein said compound has the formula: or a pharmaceutically acceptable salt thereof.
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