Thiazole tethered organoselenides as 5-lipoxygenase inhibitors

Patent metadata

Field	Value
Publication number	US-11999708-B1
Application number	US-202418590133-A
Country	US
Kind code	B1
Filing date	Feb 28, 2024
Priority date	Feb 28, 2024
Publication date	Jun 4, 2024
Grant date	Jun 4, 2024

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).

First claim

We 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.

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

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

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

5. 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.

6. 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.

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

8. 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 .

9. 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.

10. 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 .

11. 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 .

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

13. 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.

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.

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

16. 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 .

17. 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.

Assignees

• Univ King Faisal

Inventors

• Shaaban Saad
• Ba-Ghazal Hussein
• Mohamed Mohamed Alaa
• Ashmawy Abeer M

Classifications

• A61K31/427

  not condensed and containing further heterocyclic rings · CPC title

• C07D277/34 Primary

  Oxygen atoms · CPC title