# US 12,758,574 B2 · Antibiotics

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- Number: US 12,758,574 B2
- Document ID: US12758574B2
- Status: Granted
- Kind: B2
- Application number: 17/909,197
- Filed: 2021-02-24
- Published: 2023-03-23
- Granted: 2026-10-13
- Earliest claimed: 2020-03-06
- Assignees: Aston University
- Applicants: Aston University
- Inventors: Jonathan Cox; Nicolas Barry; James Harrison; Victoria Nolan; Anaïs Pitto-Barry; Joan Soldevila-Barreda
- Web page: https://patentgrep.com/patent/US12758574B2

## CPC

- A61K 31/7135: Compounds containing heavy metals
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 9/12: Aerosols; Foams {(A61K9/0043, A61K9/0056, A61K9/006, A61K9/0073 take precedence; spray-films A61K9/7015)}
- A61K 9/20: Pills, tablets, {discs, rods (A61K9/0004, A61K9/0007, A61K9/0056, A61K9/0065 take precedence; for reconstitution of a drink A61K9/0095)}
- A61P 31/04: Antibacterial 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

The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt; wherein L is a substituted or non-substituted aromatic ligand; Z is a halogen or coordinating ligand; M is a group 8 or group 9 transition metal selected from; Fe, Ru, Os, Co, Rh and Os; A and B are independently selected from a substituted or non-substituted indole or pyridine, may be the same or different and coordinate to the transition metal M through the nitrogen atom of the indole or pyridine. The compounds have been shown to have use against antibiotic-resistant bacteria. A further aspect of the invention is directed towards treating or preventing bacterial infections.

## Claims

### Claim 1

A method of treating or prophylaxis of a bacterial infection caused by a bacterium comprising administering to a subject an effective amount of a compound or pharmaceutically acceptable salt of a compound of Formula I:
wherein L is a substituted or non-substituted aromatic ligand; Z is a halogen or coordinating ligand; M is a group 8 or group 9 transition metal selected from; Fe, Ru, Os, Co, Rh or Ir; A and B are independently selected from a substituted or non-substituted indole or pyridine, may be the same or different and coordinate to the transition metal M through the nitrogen atom of the indole or pyridine.

### Claim 2 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein one of A or B is a substituted or non-substituted indole; and
the second of B or A is a substituted or non-substituted pyridine.

### Claim 3 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein L comprises 1 or 2 aromatic rings.

### Claim 4 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein L is a substituted or non-substituted cyclopentadienyl ring or a substituted or non-substituted benzene.

### Claim 5 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein L is substituted by one or more side groups comprising a sugar, hydroxyl, halogen, carboxylate, triazole, amide or a C1 to C4 straight or branched chain alkyl group.

### Claim 6 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein L is selected from para-cymene, pentamethylcyclopentadienyl, hexamethyl benzene, biphenyl or cyclopentadienyl.

### Claim 7 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein the compound of Formula I is selected from FKB3, FKB10 or FKB11:

### Claim 8 (depends on 1)

The method of treating or prophylaxis of claim 1 wherein the bacterial infection is caused by a Mycobacterium, a Gram-positive bacterium or a Gram-negative bacterium.

### Claim 9 (depends on 1)

The method of treating or prophylaxis of claim 1 wherein the bacterium is antibiotic resistant.

### Claim 10 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein the bacterium produces a β-lactamase or carbapenumase.

### Claim 11 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein the bacterium is from the genus Mycobacterium, Escherichia, Salmonella, Clostridium, Streptococcus, Staphylococcus, Pseudomonas, Klebsiella, Acinetobacter or Enterobacter.

### Claim 12 (depends on 1)

The method of treating or prophylaxis of claim 1, wherein the bacterium is Mycobacterium absessus, or Escherichia coli, Pseudomonas aeruginosa, or Klebsiella pneumonia.

### Claim 13

A compound of Formula I
or a pharmaceutically acceptable salt; wherein L is a substituted or non-substituted aromatic ligand; Z is a halogen or coordinating ligand; M is a group 8 or group 9 transition metal selected from; Fe, Ru, Os, Co, Rh or Ir; A and B are independently selected from a substituted or non-substituted indole or pyridine, may be the same or different and coordinate to the transition metal M through the nitrogen atom of the indole or pyridine; in combination with a pharmaceutically acceptable carrier.

### Claim 14 (depends on 13)

The compound or pharmaceutically acceptable salt of claim 13, selected from FKB3, FKB10 or FKB11

### Claim 15 (depends on 13)

The compound or pharmaceutically acceptable salt of claim 13 in the form of an oral tablet, an oral suspension and solution, an injectable formulation, eye drops, a topical lotion, a topical cream or an aerosol.

### Claim 16 (depends on 13)

A method of killing or inhibiting the growth of a bacterium comprising contacting the bacterium with an effective amount of the compound or pharmaceutically acceptable salt of claim 13.

### Claim 17 (depends on 2)

The method of treating or prophylaxis of claim 2, wherein one of A or B is a non-substituted indole; and the second of B or A is a non-substituted pyridine.