# US 9,517,994 B2 · Antibacterial agents: phloroglucinol derivatives

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- Number: US 9,517,994 B2
- Document ID: US9517994B2
- Status: Granted
- Kind: B2
- Application number: 14/370,395
- Filed: 2013-01-07
- Published: 2015-01-08
- Granted: 2016-12-13
- Earliest claimed: 2012-01-05
- Assignees: Rutgers, The State University of New Jersey
- Applicants: Rutgers, the State University of New Jersey
- Inventors: Richard H. Ebright; Juan Shen
- Web page: https://patentgrep.com/patent/US9517994B2

## CPC

- C07C 49/84: 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
- A61P 31/04: Antibacterial agents
- A61P 31/06: for tuberculosis
- C07C 49/825: all hydroxy groups bound to the ring
- C07C 49/83: polycyclic
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention provides a compound of formula I: or a salt thereof, wherein R1-R3 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.

## Claims

### Claim 1

A compound of formula I:
wherein:
R1 is H, Cl, Br, I, (C1-C6)alkyl, optionally substituted by halogen, or (C1-C6)alkoxy, optionally substituted by halogen;
R2 is H, halogen, trifluoromethyl, (C2-C6)alkyl, optionally substituted by halogen, or (C1-C6)alkoxy, optionally substituted by halogen; and
R3 is H, halogen, trifluoromethyl, (C2-C6)alkyl, optionally substituted by halogen, or (C2-C6)alkoxy, optionally substituted by halogen;
provided that at least one of R1, R2, or R3 is not H;
or a salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, which is
or a salt thereof.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 3)

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

### Claim 8 (depends on 2)

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

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 2)

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.

### Claim 11 (depends on 2)

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.

### Claim 12 (depends on 2)

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.

### Claim 13

A compound of formula I:
wherein:
R1 is H, Cl, Br, I, (C1-C6)alkyl, optionally substituted by halogen, or (C1-C6)alkoxy, optionally substituted by halogen;
R2 is H, Cl, Br, I, trifluoromehtyl, (C2-C6)alkyl, optionally substituted by halogen, or (C1-C6)alkoxy, optionally substituted by halogen;
R3 is H, halogen, trifluoromethyl, (C2-C6)alkyl, optionally substituted by halogen, or (C2-C6)alkoxy, optionally substituted by halogen;
provided that at least one of R1, R2, or R3 is not H;
or a salt thereof.

### Claim 14 (depends on 13)

The compound of claim 13, provided that at least one of R1 or R3 is H.