# US 11,993,579 B1 · 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1h-imidazol-2-yl)pyridin-4-ol as an anti-microbial compound

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

- Number: US 11,993,579 B1
- Document ID: US11993579B1
- Status: Granted
- Kind: B1
- Application number: 18/367,889
- Filed: 2023-09-13
- Granted: 2024-05-28
- Earliest claimed: 2023-09-13
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Antar Ahmed Abdelhamid Ahmed; Adel A. Marzouk
- Web page: https://patentgrep.com/patent/US11993579B1

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61P 31/04: Antibacterial agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound, its synthesis, and its use as an anti-microbial agent.

## Claims

### Claim 1

A 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound having the formula I:

### Claim 2 (depends on 1)

The 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 1, wherein the compound is obtained as crystals.

### Claim 3 (depends on 1)

The 3-(4,5-Diphenyl-2-(pyridin-3-yl)-1H-imidazol-1-yl)-N,N-dimethylpropan-1-amine compound of claim 1, having a melting point of about 137° C. to about 139° C.

### Claim 4 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol 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 of the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol 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 one or more Gram-negative bacterial strains selected from the group consisting of Escherichia coli and Pseudomonas aeruginosa; one or more Gram-positive bacterial strains that is Staphylococcus aureus; Candida albicans; or any combination thereof.

### Claim 8 (depends on 6)

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

### Claim 9 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the microbial infection is caused by Escherichia coli or Pseudomonas aeruginosa.

### Claim 10 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the microbial infection is caused by Staphylococcus aureus.

### Claim 11 (depends on 1)

A method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 1, the method comprising:
adding benzil, N, N-dimethyl-3-aminopropane, ammonium acetate, and 4-hydroxypyridine-3-carbaldehyde to piperidinium hydrogen sulfate in an oil bath to obtain a reaction mixture;
heating the reaction mixture with stirring until reaction completion to obtain a crude product;
purifying the crude product by recrystallization using absolute ethyl alcohol; and
obtaining the 3-(1(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound.

### Claim 12 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein the oil bath is at a temperature of about 30° C.

### Claim 13 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein heating is at a temperature of about 100° C.

### Claim 14 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein after reaction completion the reaction mixture is washed with water.

### Claim 15 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein the benzil, the 4-hydroxypyridine-3-carbaldehyde, and the ammonium acetate are added in an about 1:1:1 molar ratio.

### Claim 16 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein the benzil, the 4-hydroxypyridine-3-carbaldehyde, the ammonium acetate, and the N,N-dimethyl-3-aminopropane are added in an about 1:1:1:0.5 molar ratio.

### Claim 17 (depends on 11)

The method of making the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound of claim 11, wherein the 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-4-ol compound is obtained in an about 90% yield.