Anti-cancer azole compounds

Patent metadata

Field	Value
Publication number	US-10918624-B2
Application number	US-201916429642-A
Country	US
Kind code	B2
Filing date	Jun 3, 2019
Priority date	Jun 3, 2019
Publication date	Feb 16, 2021
Grant date	Feb 16, 2021

Abstract

Compounds comprising azole moieties are disclosed. The disclosed compounds are shown to have anticancer activity. Also disclosed are pharmaceutical composition of the compounds and method of their use in the treatment of cancer.

First claim

The invention claimed is:

1. A compound having the chemical structure of formula I:

wherein the azole is selected from the group consisting of:

wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of a hydrogen, NR 12 R 13 , OR 12 , SR 12 , SeR 12 , an optionally substituted alkyl, an optionally substituted alkylene, an optionally substituted cycloalkyl, an optionally substituted aryl, and an optionally substituted arylalkyl; and R 12 and R 13 are independently hydrogen, an optionally substituted alkyl, an optionally cycloalkyl, an optionally substituted heterocyclyl, an optionally substituted aryl, and an optionally substituted arylalkyl; or R 2 and R 3 , R 7 and R 8 , or R 9 and R 10 are linked together forming an optionally substituted ring selected from the group consisting of a five membered ring, a six membered ring, a seven membered ring, or an eight membered ring.

2. A pharmaceutical composition comprising the compound of claim 1 , and a pharmaceutically acceptable carrier and/or excipient.

3. The pharmaceutical composition of claim 2 , which comprises 0.1-400 μM of the compound relative to the total volume of the composition.

4. The pharmaceutical composition of claim 2 , wherein the pharmaceutically acceptable carrier and/or excipient is at least one selected from the group consisting of a buffer, an inorganic salt, a fatty acid, a vegetable oil, a synthetic fatty ester, a surfactant, and a polymer.

5. The pharmaceutical composition of claim 2 , further comprising at least one chemotherapeutic agent.

6. A method of treating a cancer, comprising:
administering to a subject in need of treatment for the cancer a sufficient amount of the pharmaceutical composition of claim 2 ,
wherein the amount is sufficient to reduce the cancer, inhibit the progression of the cancer, reduce the severity of one or more symptoms of the cancer, or ameliorate one or more symptoms of the cancer.

7. The method of claim 6 , wherein the cancer is at least one selected from the group consisting of ovarian cancer, cervical cancer, testicular cancer, colon cancer, rectal cancer, bladder cancer, breast cancer, non-small cell lung cancer, esophageal cancer, endometrial cancer, head and neck cancer, and osteogenic sarcoma.

8. The method of claim 6 , wherein the subject is a mammal.

Assignees

• Univ Imam Abdulrahman Bin Faisal

Inventors

• Bozkurt Ayhan
• Khan Firdos Alam
• Anil Seyda Tugba Gunday

Classifications

• A61K31/41

  having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole · CPC title

• A61K31/4178 Primary

  not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K31/4196 Primary

  1,2,4-Triazoles · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title