# US 12,180,168 B1 · 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid as an antimicrobial compound

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,180,168 B1
- Document ID: US12180168B1
- Status: Granted
- Kind: B1
- Application number: 18/402,564
- Filed: 2024-01-02
- Granted: 2024-12-31
- Earliest claimed: 2024-01-02
- 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/US12180168B1

## CPC

- C07D 233/76: with substituted hydrocarbon radicals attached to the third ring carbon atom
- A61K 31/4166: having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound having the formula I:

### Claim 2 (depends on 1)

The 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 1, wherein the compound has a melting point of about 173° C. to about 175° C.

### Claim 3 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 4 (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 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 1.

### Claim 5 (depends on 4)

The method of treating the microbial infection of claim 4, wherein the microbial infection is caused by one or more bacteria or fungi.

### Claim 6 (depends on 5)

The method of treating the microbial infection of claim 5, wherein the microbial infection is caused by a gram-positive bacteria, one or more gram-negative bacteria, a fungus, or a combination thereof.

### Claim 7 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the gram-positive bacteria is Staphylococcus aureus.

### Claim 8 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the one or more gram-negative bacteria are Pseudomonas aeruginosa, Escherichia coli, or a combination thereof.

### Claim 9 (depends on 5)

The method of treating the microbial infection of claim 5, wherein the fungus is Candida albicans.

### Claim 10 (depends on 1)

A method of making the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 1, the method comprising:
adding 5,5-bis(4-nitrophenyl) imidazolidine-2,4-dione to 3-bromopropionic acid and anhydrous potassium carbonate in DMF to obtain a reaction mixture;
stirring the reaction mixture;
diluting the reaction mixture to form a precipitate;
filtering, washing, and drying the formed precipitate;
recrystallizing the filtered, washed, and dried precipitate from ethanol; and
obtaining the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound.

### Claim 11 (depends on 10)

The method of making the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 10, wherein the reaction mixture is stirred at room temperature for about 12 hours.

### Claim 12 (depends on 10)

The method of making the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 10, wherein the reaction mixture is diluted with ice water.

### Claim 13 (depends on 10)

The method of making the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 10, wherein the 5,5-bis(4-nitrophenyl) imidazolidine-2,4-dione, 3-bromopropionic acid, and anhydrous potassium carbonate are added in about a 1:1:1 molar ratio.

### Claim 14 (depends on 10)

The method of making 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 10, wherein the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound is obtained in a yield of about 90%.

### Claim 15 (depends on 10)

The method of making the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound of claim 10, wherein the 3-[4,4-bis(4-nitrophenyl)-2,5-dioxoimidazolidin-1-yl]propanoic acid compound is obtained as a white powder.