# US 11,993,575 B1 · Ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate as an antimicrobial compound

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- Number: US 11,993,575 B1
- Document ID: US11993575B1
- Status: Granted
- Kind: B1
- Application number: 18/400,944
- Filed: 2023-12-29
- Granted: 2024-05-28
- Earliest claimed: 2023-12-29
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Mohamed Gouda; Antar Ahmed Abdelhamid Ahmed
- Web page: https://patentgrep.com/patent/US11993575B1

## CPC

- C07D 233/80: with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- A61K 31/4166: having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

A ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

Ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound having the formula I:

### Claim 2 (depends on 1)

The ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 1, wherein the compound has a melting point of about 200° C.

### Claim 3 (depends on 1)

The ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 1, wherein the compound is a white powder.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A method of treating a microbial infection in a patient comprising administering to a patient in need thereof a therapeutically effective amount ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 1.

### Claim 6 (depends on 5)

The method of treating the microbial infection of claim 5, wherein the microbial infection is caused by one or more bacteria or fungi.

### Claim 7 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the microbial infection is caused by a gram positive bacteria, one or more gram negative bacteria, a fungus, or a combination thereof.

### Claim 8 (depends on 7)

The method of treating the microbial infection of claim 7, wherein the gram positive bacteria is Staphylococcus aureus.

### Claim 9 (depends on 7)

The method of treating the microbial infection of claim 7, wherein the one or more gram negative bacteria are Pseudomonas aeruginosa, Escherichia coli, or a combination thereof.

### Claim 10 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the fungus is Candida albicans.

### Claim 11 (depends on 1)

A method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 1, the method comprising:
mixing 5,5-bis(4-bromophenyl)imidazolidine-2,4-dione, ethyl bromoacetate, and anhydrous potassium carbonate in DMF to obtain a solution;
stirring the solution at room temperature;
diluting the solution with ice water to obtain a resulting precipitate;
filtering, washing and drying the precipitate;
purifying the precipitate by crystallization; and
obtaining the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound.

### Claim 12 (depends on 11)

The method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the solution is stirred for at least about 9 hours.

### Claim 13 (depends on 11)

The method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the precipitate is washed with water.

### Claim 14 (depends on 11)

The method of making ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound is obtained as a white powder.

### Claim 15 (depends on 11)

The method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the 5,5-bis(4-bromophenyl)imidazolidine-2,4-dione, ethyl bromoacetate, and anhydrous potassium carbonate can be added in about a 1:1:1 molar ratio.

### Claim 16 (depends on 11)

The method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound is obtained in a yield of about 92%.

### Claim 17 (depends on 11)

The method of making the ethyl [4,4-bis(4-bromophenyl)-2,5-dioxoimidazolidin-1-yl]acetate compound of claim 11, wherein the precipitate is recrystallized from aqueous ethanol.