Chalcone-based chemotherapeutic compound for triple negative breast cancer

Patent metadata

Field	Value
Publication number	US-12428405-B2
Application number	US-202318226638-A
Country	US
Kind code	B2
Filing date	Jul 26, 2023
Priority date	Jun 13, 2019
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

Provided herein are compounds, compositions, and methods useful for the treatment of breast cancer, particularly triple negative breast cancers. In certain aspects, provided herein are compounds of formula (I):or a pharmaceutically acceptable salt or solvate thereof. In certain aspects, provided herein are compositions comprising any of the compounds provided herein. In certain aspects, provided herein are methods for the treatment of cancer in a subject in need thereof comprising administering to the subject an effective amount of any of the compounds or compositions provided herein.

First claim

What is claimed is:

1. A method of treating breast cancer in a subject in need thereof comprising administering an effective amount of a chalcone compound to the subject;
wherein the chalcone compound is of formula I:

or a pharmaceutically acceptable salt or solvate thereof,
wherein
R 1 and R 2 are each independently haloalkyl;
R 4 is independently selected from halo, alkyl, hydroxyl, alkoxyl, amino, alkylamino, thio, alkylthio, sulfonyl, alkylsulfonyl, and heterocyclic group;
R 5 is hydrogen;
R 3 , R 6 , and R 7 is independently selected from hydrogen, halo, alkyl, hydroxyl, alkoxyl amino, alkylamino, thio, alkylthio, sulfonyl, alkylsulfonyl, and heterocyclic group;
or R 3 and R 4 , or R 4 and R 5 , or R 5 and R 6 , or R 6 and R 7 form

wherein R 8 is hydrogen or alkyl, and the rest of R 3 , R 4 , R 5 , R 6 , and R 7 are each independently selected from hydrogen, halo, and alkyl; and.

2. The method of claim 1 , wherein R 1 and R 2 are each independently chloroalkyl.

3. The method of claim 1 , wherein R 1 and R 2 are each chloroethyl.

4. The method of claim 1 , wherein at least one of R 3 , R 6 , and R 7 is selected from halo, alkyl, hydroxyl, alkoxyl, amino, alkylamino, thio, alkylthio, sulfonyl, alkylsulfonyl, and a heterocyclic group; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

5. The method of claim 1 , wherein one of R 3 , R 4 , R 6 , and R 7 is independently selected from chloro, methylsulfonyl, methylthio, methoxy, piperazinyl, pyrrolidyl, morpholinyl, and piperidyl; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

6. The method of claim 1 , wherein one of R 3 , R 6 , and R 7 is chloro; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

7. The method of claim 1 , wherein one of R 3 , R 4 , R 6 , and R 7 is methoxy; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

8. The method of claim 1 , wherein one of R 3 , R 4 , R 6 , and R 7 is methylthio; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

9. The method of claim 1 , wherein one of R 3 , R 4 , R 6 , and R 7 is methylsulfonyl; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

10. The method of claim 1 , wherein one of R 3 , R 4 , R 6 , and R 7 is piperazinyl; and wherein the rest of R 3 , R 6 , and R 7 are each hydrogen.

11. The method of claim 1 , wherein R 3 and R 4 , or R 4 and R 5 , or R 5 and R 6 , or R 6 and R 7 form

wherein R 8 is hydrogen or alkyl; and wherein the rest of R 3 , R 4 , R 5 , R 6 , and R 7 are each independently selected from hydrogen, halo, and alkyl.

12. The method of claim 1 , wherein R 4 and R 5 form

(“methylenedioxy”), and wherein R 3 , R 6 , and R 7 are each hydrogen.

13. The method of claim 1 , wherein the chalcone compound of formula I is of formula:

or a pharmaceutically acceptable salt or solvate thereof.

14. The method of claim 12 , wherein the breast cancer is triple negative breast cancer.

Assignees

• Univ Qatar

Inventors

• Khalil Ashraf
• Al Moustafa Ala-Eddin
• Elkhalifa Dana H
• Alali Feras

Classifications

• C07D413/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07C317/30

  with sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton · CPC title

• C07C225/22

  having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• C07D295/033

  with the ring nitrogen atoms directly attached to carbocyclic rings · CPC title