IP Library Granted Patent US 9,723,837
Granted Patent B2
US 9,723,837 · App. 14/465,423 · Granted Aug 8, 2017

Imidazole derivatives useful for controlling microbial growth

Inventors: Christian Melander (Raleigh, NC); Zhaoming Su (Jupiter, FL); Lingling Peng (San Diego, CA)
Assignee: North Carolina State University
A01N43/50A01N25/08A61K31/4168A61K45/06C07D233/88
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Quick Facts
Patent No.
US 9,723,837
App. No.
14/465,423
Granted
Aug 8, 2017
Kind
B2
Abstract

Disclosure is provided for 1,4,5-substituted amino imidazole compounds useful to control microbial growth, compositions including these compounds, devices including these compounds, and methods of using the same.

Claims (44)

1. A method of reducing microbial growth on a substrate comprising the step of contacting a compound of Formula (I)(a)(i):

wherein:

R 2 is —(CH 2 ) a R 5 , wherein a is 0, and R 5 is:

wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is alkyl or alkenyl, and the others are H;

R 3 is —(CH 2 ) b R 6 , wherein b is 0, and R 6 is phenyl; and

R 4 is unsubstituted C 1 -C 5 alkyl,

or a pharmaceutically acceptable salt or prodrug thereof,

to said substrate in an amount effective to reduce said microbial growth.

2. The method of claim 1 , wherein said microbial growth is Gram-positive bacterial growth.

3. The method of claim 2 , wherein said bacterial growth is Staphylococcus aureus.

4. The method of claim 2 , wherein said bacterial growth is methicillin-resistant Staphylococcus aureus (MRSA).

5. The method of claim 1 , wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is C 1 -C 15 alkyl, and the others are H,

or a pharmaceutically acceptable salt or prodrug thereof.

6. The method of claim 1 , wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is a C 1 , C 3 , C 5 , C 7 , C 9 or C 11 alkyl, and the others are H,

or a pharmaceutically acceptable salt or prodrug thereof.

7. The method of claim 1 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

8. The method of claim 1 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

9. The method of claim 1 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

10. A method for treating a bacterial infection in a subject in need thereof, comprising administering to said subject a compound of Formula (I)(a)(i):

wherein:

R 2 is —(CH 2 ) a R 5 , wherein a is 0, and R 5 is:

wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is alkyl or alkenyl, and the others are H;

R 3 is —(CH 2 ) b R 6 , wherein b is 0, and R 6 is phenyl; and

R 4 is unsubstituted C 1 -C 5 alkyl,

or a pharmaceutically acceptable salt or prodrug thereof,

in an amount effective to reduce a bacterial component of said infection.

11. The method of claim 10 , wherein said bacterial component is Gram-positive bacteria.

12. The method of claim 10 , wherein said bacterial component is Staphylococcus aureus.

13. The method of claim 10 , wherein bacterial component is methicillin-resistant Staphylococcus aureus (MRSA).

14. The method of claim 10 , wherein a biocide is administered to said subject in combination with said compound.

15. The method of claim 14 , wherein the compound is administered to said subject in an amount effective to enhance the effects of the biocide.

16. The method of claim 10 , wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is C 1 -C 15 alkyl, and the others are H,

or a pharmaceutically acceptable salt or prodrug thereof.

17. The method of claim 10 , wherein one of D 1 , D 2 , D 3 , D 4 or D 5 is a C 1 , C 3 , C 5 , C 7 , C 9 or C 11 alkyl, and the others are H,

or a pharmaceutically acceptable salt or prodrug thereof.

18. The method of claim 10 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

19. The method of claim 10 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

20. The method of claim 10 , wherein said compound is:

or a pharmaceutically acceptable salt thereof.

Assignments (1)
CONFIRMATORY LICENSE Recorded Nov 18, 2019
From: NORTH CAROLINA STATE UNIVERSITY RALEIGH
To: THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 051044/0627 →
Continuity (3)
Continuation 13737161 · Jan 9, 2013
Provisional Application 61584553 · Jan 9, 2012
Related Publication 20140364474A1 · Dec 11, 2014