# US 11,897,850 B1 · N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide as an antimicrobial compound

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- Number: US 11,897,850 B1
- Document ID: US11897850B1
- Status: Granted
- Kind: B1
- Application number: 18/484,734
- Filed: 2023-10-11
- Granted: 2024-02-13
- Earliest claimed: 2023-10-11
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Mai Mostafa Khalaf Ali; Hany Mohamed Abd El-Lateef Ahmed; Antar Ahmed Abdelhamid Ahmed; Amer A. Amer
- Web page: https://patentgrep.com/patent/US11897850B1

## CPC

- C07D 271/113: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound, its synthesis, and its use as an antimicrobial agent.

## Claims

### Claim 1

A N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound having the formula I:

### Claim 2 (depends on 1)

The N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 1, wherein the compound is obtained as crystals.

### Claim 3 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide 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 of the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide 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 one or more gram positive bacteria, one or more gram negative bacteria, one or more fungi, or a combination thereof.

### Claim 7 (depends on 6)

The method of treating the microbial infection of claim 6, wherein the one or more gram positive bacteria are Bacillus cereus, Staphylococcus aureus, or a combination thereof.

### 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 6)

The method of treating the microbial infection of claim 6, wherein the one or more fungi are Aspergillus flavus, Chrysosporium keratinophilum, or a combination thereof.

### Claim 10 (depends on 1)

A method of making the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 1, the method comprising:
adding carbonyldiimidazole (CDI) to a solution of 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetic acid and acetonitrile to obtain a first reaction mixture;
stirring the first reaction mixture;
adding N′-hydroxy-4-methoxybenzene-1-carboximidamide to the first reaction mixture to obtain a second reaction mixture;
stirring the second reaction mixture;
filtering a formed precipitate and recrystallizing using acetonitrile; and
obtaining the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound.

### Claim 11 (depends on 10)

The method of making the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 10, wherein the stirring the first reaction mixture lasts for at least about 30 minutes.

### Claim 12 (depends on 11)

The method of making the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 11, wherein the stirring the second reaction mixture lasts for at least about 6 hours.

### Claim 13 (depends on 11)

The method of making the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 11, wherein the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide is obtained in a yield of about 73%.

### Claim 14 (depends on 11)

The method of making the N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide compound of claim 11, wherein the 2-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-ylthio)acetic acid, CDI, and N′-hydroxy-4-methoxybenzene-1-carboximidamide are added in a 2:2.4:2 molar ratio.