# US 11,998,532 B1 · Substituted 1,3,4-oxadiazole derivatives as anti-tubercular agents

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- Number: US 11,998,532 B1
- Document ID: US11998532B1
- Status: Granted
- Kind: B1
- Application number: 18/385,809
- Filed: 2023-10-31
- Granted: 2024-06-04
- Earliest claimed: 2023-10-31
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Katharigatta N. Venugopala; Pran Kishore Deb; Melendran Pillay; Rashmi Venugopala
- Web page: https://patentgrep.com/patent/US11998532B1

## CPC

- A61K 31/4245: Oxadiazoles
- A61P 31/06: for tuberculosis
- 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

Compounds for treating tuberculosis and, particularly, anti-tubercular compounds that are substituted 1,3,4-oxadiazole derivatives and their use as anti-tubercular agents are provided.

## Claims

### Claim 1

A method of treating tuberculosis in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of a compound having the formula I:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R, R1, and R2 may be the same or different and are independently selected from the group consisting of hydrogen, halogen, nitro, and methyl.

### Claim 2 (depends on 1)

The method of claim 1, wherein R and R2 are hydrogen and R1 is chlorine, fluorine, or bromine.

### Claim 3 (depends on 1)

The method of claim 1, wherein R2 is hydrogen, R is bromine or nitro, and R1 is methyl.

### Claim 4 (depends on 1)

The method of claim 1, wherein R, R1, and R2 are all be hydrogen.

### Claim 5 (depends on 1)

The method of claim 1, wherein R2 is hydrogen, R1 is bromine, and R is methyl.

### Claim 6 (depends on 1)

The method of claim 1, wherein R1 and R2 are hydrogen and R is fluorine.

### Claim 7 (depends on 1)

The method of claim 1, wherein R2 is chlorine and either R or R1 is hydrogen and the other of R and R1 is chlorine.

### Claim 8 (depends on 1)

The method of claim 1, wherein the compound is selected from the group consisting of:
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole (7a);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole (7b);
2-(3-Bromo-4-methylphenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole (7c);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole (7d);
2-(4-Bromophenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1Hpyrazol-4-yl)-1,3,4-oxadiazole (7e);
2-(4-Bromo-3-methylphenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole (7f);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3-fluorophenyl)-1,3,4-oxadiazole (7g);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3,5-dichlorophenyl)-1,3,4-oxadiazole (7h);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazole (7i);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-methyl-3-nitrophenyl)-1,3,4-oxadiazole (7j);
and a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.

### Claim 9 (depends on 1)

The method of claim 1, wherein the tuberculosis comprises multiple drug resistant (MDR) strains of Mycobacterium tuberculosis.

### Claim 10 (depends on 1)

The method of claim 1, wherein the tuberculosis comprises H37Rv strains of Mycobacterium tuberculosis.

### Claim 11

A method of treating tuberculosis in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of a compound having the formula I:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R, R1, and R2 may be the same or different and are independently selected from the group consisting of hydrogen, chlorine, fluorine, bromine, nitro, and methyl.

### Claim 12 (depends on 10)

The method of claim 10, wherein the tuberculosis comprises multiple drug resistant (MDR) strains of Mycobacterium tuberculosis.

### Claim 13 (depends on 10)

The method of claim 10, wherein the tuberculosis comprises H37Rv strains of Mycobacterium tuberculosis.

### Claim 14

A method of treating tuberculosis in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of a compound selected from the group consisting of:
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole (7a);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-fluorophenyl)-1,3,4-oxadiazole (7b);
2-(3-Bromo-4-methylphenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole (7c);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole (7d);
2-(4-Bromophenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1Hpyrazol-4-yl)-1,3,4-oxadiazole (7e);
2-(4-Bromo-3-methylphenyl)-5-(1-(5-chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-1,3,4-oxadiazole (7f);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3-fluorophenyl)-1,3,4-oxadiazole (7g);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3,5-dichlorophenyl)-1,3,4-oxadiazole (7h);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(3,4-dichlorophenyl)-1,3,4-oxadiazole (7i);
2-(1-(5-Chloro-2-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl)-5-(4-methyl-3-nitrophenyl)-1,3,4-oxadiazole (7j);
and a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.

### Claim 15 (depends on 13)

The method of claim 13, wherein the tuberculosis comprises multiple drug resistant (MDR) strains of Mycobacterium tuberculosis.

### Claim 16 (depends on 13)

The method of claim 13, wherein the tuberculosis comprises H37Rv strains of Mycobacterium tuberculosis.