Antibacterial agents: phloroglucinol derivatives

Patent metadata

Field	Value
Publication number	US-9517994-B2
Application number	US-201314370395-A
Country	US
Kind code	B2
Filing date	Jan 7, 2013
Priority date	Jan 5, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

The invention provides a compound of formula I:

or a salt thereof, wherein R 1 -R 3 have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful as antibacterial agents.

First claim

What is claimed is:

1. A compound of formula I:

wherein:
R 1 is H, Cl, Br, I, (C 1 -C 6 )alkyl, optionally substituted by halogen, or (C 1 -C 6 )alkoxy, optionally substituted by halogen;
R 2 is H, halogen, trifluoromethyl, (C 2 -C 6 )alkyl, optionally substituted by halogen, or (C 1 -C 6 )alkoxy, optionally substituted by halogen; and
R 3 is H, halogen, trifluoromethyl, (C 2 -C 6 )alkyl, optionally substituted by halogen, or (C 2 -C 6 )alkoxy, optionally substituted by halogen;
provided that at least one of R 1 , R 2 , or R 3 is not H;
or a salt thereof.

2. The compound of claim 1 , which is

or a salt thereof.

3. A composition comprising a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable vehicle.

4. A method for inhibiting a bacterial RNA polymerase comprising contacting the bacterial RNA polymerase with a compound of formula I as described in claim 1 , or a salt thereof.

5. A method for inhibiting the growth of a bacterium comprising contacting the bacterium with a compound of formula I as described in claim 1 , or a salt thereof.

6. A method for treating a bacterial infection selected from Mycobacterium tuberculosis, Staphylococcus aureus MSSA and MRSA, Enterococcus faecalis, Enterococcus faecium, Bacillus anthracis, Escherichia coli, Haemophilus influenzae, Moraxella catarrhalis, Francisella tularensis or Burkholderia mallei in a mammal comprising administering to the mammal an effective amount of a compound of formula I as described in claim 1 , or a pharmaceutically acceptable salt thereof.

7. The composition of claim 3 , in the form of a disinfectant, sterilant, antispoilant, or antiseptic.

8. A composition comprising a compound of formula I as described in claim 2 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable vehicle.

9. The composition of claim 8 , in the form of a disinfectant, sterilant, antispoilant, or antiseptic.

10. A method for treating a bacterial infection selected from Mycobacterium tuberculosis, Staphylococcus aureus MSSA and MRSA, Enterococcus faecalis, Entercoccus faecium, Bacillus anthracis, Escherichia coli, Haemophilus infuenzae, Moraxella catarrhalis, Francisella tularensis or Burkholderia mallei in a mammal comprising administering to the mammal an effective amount of a compound of formula I as described in claim 2 , or a pharmaceutically acceptable salt thereof.

11. A method for inhibiting a bacterial RNA polymerase comprising contacting the bacterial RNA polymerase with a compound of formula I as described in claim 2 , or a salt thereof.

12. A method for inhibiting the growth of a bacterium comprising contacting the bacterium with a compound of formula I as described in claim 2 , or a salt thereof.

13. A compound of formula I:

wherein:
R 1 is H, Cl, Br, I, (C 1 -C 6 )alkyl, optionally substituted by halogen, or (C 1 -C 6 )alkoxy, optionally substituted by halogen;
R 2 is H, Cl, Br, I, trifluoromehtyl, (C 2 -C 6 )alkyl, optionally substituted by halogen, or (C 1 -C 6 )alkoxy, optionally substituted by halogen;
R 3 is H, halogen, trifluoromethyl, (C 2 -C 6 )alkyl, optionally substituted by halogen, or (C 2 -C 6 )alkoxy, optionally substituted by halogen;
provided that at least one of R 1 , R 2 , or R 3 is not H;
or a salt thereof.

14. The compound of claim 13 , provided that at least one of R 1 or R 3 is H.

Assignees

• Univ Rutgers

Inventors

• Ebright Richard H
• Shen Juan

Classifications

• A61P31/04

  Antibacterial agents · CPC title

• C07C49/83

  polycyclic · CPC title

• A61P31/06

  for tuberculosis · CPC title

• C07C49/84 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07C49/825

  all hydroxy groups bound to the ring · CPC title