# US 12,006,293 B1 · Bis diselenide-based schiff bases as deubiquitination signaling pathway modulators

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- Number: US 12,006,293 B1
- Document ID: US12006293B1
- Status: Granted
- Kind: B1
- Application number: 18/545,056
- Filed: 2023-12-19
- Granted: 2024-06-11
- Earliest claimed: 2023-12-19
- Assignees: King Faisal University
- Applicants: King Faisal University
- Inventors: Saad Shaaban; Amr Negm
- Web page: https://patentgrep.com/patent/US12006293B1

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A61K 31/4155: non condensed and containing further heterocyclic rings
- A61K 31/4375: the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- C07D 213/65: attached in position 3 or 5
- C07D 401/14: containing three or more hetero 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

Diselenide organo compounds, their synthesis, and their use as deubiquitination signaling pathway modulators and anti-cancer agents.

## Claims

### Claim 1

A diselenide organo compound having the formula:
wherein Ar is selected from the group consisting of a pyrazole, a pyridine, and an indole, and wherein said Ar is optionally substituted with a chlorine, a hydroxy, or a pyridine.

### Claim 2 (depends on 1)

The diselenide organo compound of claim 1, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 3)

The pharmaceutically acceptable composition of claim 3, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 5 (depends on 1)

A method of inhibiting Ubiquitin-specific proteases in a subject comprising administering to a subject in need thereof a therapeutically effective amount of the diselenide organo compound of claim 1.

### Claim 6 (depends on 5)

The method of inhibiting Ubiquitin-specific proteases in a patient of claim 5, wherein the Ubiquitin-specific proteases are selected from the group consisting of USP7 and USP9X.

### Claim 7 (depends on 5)

The method of inhibiting Ubiquitin-specific proteases of claim 5, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 8 (depends on 1)

A method of restoring p53 function in a subject, the method comprising administering to a subject in need thereof a therapeutically effective amount of the diselenide organo compound of claim 1.

### Claim 9 (depends on 8)

The method of restoring p53 function of claim 8, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 10 (depends on 1)

A method of inducing cancer death in a subject, the method comprising administering to a subject in need thereof a therapeutically effective amount of the diselenide organo compound of claim 1.

### Claim 11 (depends on 10)

The method of inducting cancer death of claim 10, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 12 (depends on 1)

A method of treating cancer in a subject, the method comprising administering to a subject in need thereof a therapeutically effective amount of the diselenide organo compound of claim 1.

### Claim 13 (depends on 12)

The method of treating cancer of claim 12, wherein the diselenide organo compound is selected from the group consisting of:

### Claim 14 (depends on 1)

A method of making the diselenide organo compound of claim 1, the method comprising:
adding an aldehyde to a bis diselenide Schiff base in ethanol to obtain a reaction mixture;
adding a catalyst to the reaction mixture;
refluxing the reaction mixture;
cooling the reaction mixture to obtain a formed precipitate;
filtering and recrystallizing the formed precipitate from ethanol; and
obtaining the diselenide organo compound.

### Claim 15 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein the aldehyde is 4-chloro-1H-pyrazole-3-carboxaldehyde and the diselenide organo compound is diselenide bis (4-chloro-1H-pyrazole-3-carboxaldehyde).

### Claim 16 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein the aldehyde is 3-hydroxypyridine-2-carboxaldehyde and the diselenide organo compound is diselenide bis (3-hydroxypyridine-2-carboxaldehyde).

### Claim 17 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein the aldehyde is 2-pyridin-3-yl-1H-indole-3-carboxaldehyde and the diselenide organo compound is diselenide bis (2-pyridin-3-yl-1H-indole-3-carboxaldehyde).

### Claim 18 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein the catalyst is acetic acid.

### Claim 19 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein about 1 equivalent of the aldehyde is added to about −0.5 equivalents of the diselenide Schiff base.

### Claim 20 (depends on 14)

The method of making the diselenide organo compounds of claim 14, wherein the reaction mixture is refluxed for at least 6 hours.