# US 11,999,708 B1 · Thiazole tethered organoselenides as 5-lipoxygenase inhibitors

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- Number: US 11,999,708 B1
- Document ID: US11999708B1
- Status: Granted
- Kind: B1
- Application number: 18/590,133
- Filed: 2024-02-28
- Granted: 2024-06-04
- Earliest claimed: 2024-02-28
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Saad Shaaban; Hussein Ba-Ghazal; Mohamed Alaa Mohamed; Abeer M. Ashmawy
- Web page: https://patentgrep.com/patent/US11999708B1

## CPC

- C07D 277/34: Oxygen atoms
- A61K 31/427: not condensed and containing further heterocyclic rings
- 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)

## Abstract

Thiazole tethered organoselenide compounds, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The thiazole tethered organoselenide compounds are identified as being capable of inhibiting 5-lipoxygenase (5-LO).

## Claims

### Claim 1

A compound having the formula I:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof, wherein:
R is selected from the group consisting of
methyl, ethyl, butyl, pentyl, and hexyl; and
each X is the same or different and is H or COOMe.

### Claim 2 (depends on 1)

The compound of claim 1, wherein each X is H.

### Claim 3 (depends on 1)

The compound of claim 1, wherein each X is COOMe.

### Claim 4 (depends on 1)

The compound of claim 1, wherein:
R is methyl, ethyl, butyl, pentyl, and hexyl; and
X is H or COOMe.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof;
wherein X is H or COOMe.

### Claim 7 (depends on 1)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 1)

A method of inhibiting 5-lipoxygenase (5-LO) activity in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.

### Claim 9 (depends on 8)

The method of inhibiting 5-lipoxygenase (5-LO) activity in a patient of claim 8, wherein administration of the compound to the patient treats asthma, a respiratory viral infection, or a combination thereof in the patient.

### Claim 10 (depends on 1)

A method of treating asthma in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.

### Claim 11 (depends on 1)

A method of treating a respiratory viral infection in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 1.

### Claim 12 (depends on 11)

The method of treating a respiratory viral infection in a patient of claim 11, wherein the respiratory viral infection is caused by COVID-19.

### Claim 13 (depends on 12)

The method of treating a respiratory viral infection in a patient of claim 12, wherein the administration of the compound reduces patient mortality rate, prevents COVID-19 progression, or prevents COVID-19 severity.

### Claim 14

A compound selected from the group consisting of:
or a pharmaceutically acceptable salt, ester, stereoisomer, or solvate thereof;
wherein X is H or COOMe.

### Claim 15 (depends on 14)

A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of claim 14 and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 14)

A method of inhibiting 5-lipoxygenase (5-LO) activity in a patient, comprising administering to a patient in need thereof a therapeutically effective amount of the compound of claim 14.

### Claim 17 (depends on 16)

The method of inhibiting 5-lipoxygenase (5-LO) activity in a patient of claim 16, wherein administration of the compound to the patient treats asthma, a respiratory viral infection, or a combination thereof in the patient.