# US 11,077,109 B2 · Compounds having antibacterial activity and methods of use

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- Number: US 11,077,109 B2
- Document ID: US11077109B2
- Status: Granted
- Kind: B2
- Application number: 16/052,212
- Filed: 2018-08-01
- Published: 2019-07-04
- Granted: 2021-08-03
- Earliest claimed: 2017-08-01
- Assignees: The Trustees of Princeton University
- Applicants: The Trustees of Princeton University
- Inventors: Zemer Gitai; James Martin; Hsin-Jung Li; Max Wilson; Hahn Kim
- Web page: https://patentgrep.com/patent/US11077109B2

## CPC

- A61K 31/517: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 31/04: Antibacterial agents
- A61P 35/00: Antineoplastic agents
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

In one aspect, methods of treating bacterial infections are described herein employing compounds having more than one target for antibacterial activity. Additionally pharmaceutical compositions comprising such compounds are also described.

## Claims

### Claim 1

A method of treating a bacterial infection comprising:
administering to a patient in need thereof a therapeutically effective amount of a compound of Formula (I) and/or salt thereof:
wherein R1-R4 are independently selected from the group consisting of hydrogen, alkyl, alkenyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amide, and sulfonamide, wherein the alkyl, alkenyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amide and sulfonamide are optionally substituted with one or more substituents selected from the group consisting of (C1-C10)-alkyl, cycloalkyl, alkoxy, halo, and hydroxy; and wherein X and Z are independently selected from the group consisting of C, N and O; and wherein Y is selected from the group consisting of OH and NR9R10, wherein R9 and R10 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl, and wherein R9 and R10 may optionally form a ring structure; and n is an integer from 0 to 5.

### Claim 2 (depends on 1)

The method of claim 1, wherein bacteria of the infection are gram negative.

### Claim 3 (depends on 1)

The method of claim 1, wherein bacteria of the infection are gram positive.

### Claim 4 (depends on 1)

The method of claim 1, wherein the bacterial infection is resistant to one or more antibiotic compounds differing from the compound of Formula 1.

### Claim 5 (depends on 1)

The method of claim 1, wherein the compound of Formula (I) is administered at a concentration of 0.1 μg/ml to 100 μg/ml.

### Claim 6 (depends on 1)

The method of claim 1, wherein the compound of Formula (I) exhibits more than one target for antibacterial activity.

### Claim 7 (depends on 6)

The method of claim 6, wherein the compound of Formula (I) targets bacterial folate metabolism.

### Claim 8 (depends on 7)

The method of claim 7, wherein the compound of Formula (I) targets membrane polarization and/or membrane permeability.

### Claim 9 (depends on 1)

The method of claim 1, wherein R1 is selected from the group consisting of cycloalkyl and heterocycloalkyl and R2 is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl.

### Claim 10 (depends on 1)

The method of claim 1, wherein the bacterial infection comprises A. baumanii.

### Claim 11 (depends on 1)

The method of claim 1, wherein the compound of Formula (I) and/or salt thereof is:

### Claim 12 (depends on 11)

The method of claim 11, wherein the compound of Formula (I) and/or salt thereof is:

### Claim 13 (depends on 12)

The method of claim 12, wherein the compound of Formula (I) and/or salt thereof is administered at a concentration of 0.1 μg/ml to 100 μg/ml.

### Claim 14 (depends on 12)

The method of claim 12, wherein the compound of Formula (I) and/or salt thereof targets bacterial folate metabolism.