Naphthoquinone containing gold carbene complexes and methods of uses thereof

Patent metadata

Field	Value
Publication number	US-11332483-B2
Application number	US-201816625023-A
Country	US
Kind code	B2
Filing date	Jun 29, 2018
Priority date	Jun 30, 2017
Publication date	May 17, 2022
Grant date	May 17, 2022

Abstract

The present disclosure relates gold carbene naphthoquinone compounds and salts thereof. In some aspects, these compounds can be used to treat cancer including cancers which are resistant to one or more other chemotherapeutic agents such as cisplatin or platinum chemotherapeutic agents. Also provided herein are pharmaceutical compositions comprising the gold carbene naphthoquinone compounds.

First claim

What is claimed is:

1. A compound of the formula:

wherein:
M 1 is an Au or Ag ion;
R 1 , R 2 , R 3 , and R 4 are each independently alkyl (C≤12) , aryl (C≤18) , or a substituted version of any of these groups;
R 5 and R 6 are each independently hydrogen, or alkyl (C≤12) , or a substituted version thereof;
m and n are each independently 1, 2, 3, or 4;
X 1 is Cl − , Br − , I − , PF 6 − , BF 4 − , OTf − , SbF 6 − , AgCl 2 − , ClO 4 − , NO 3 − , or H 3 CC(O)O—.

2. The compound of claim 1 further defined as:

wherein:
M 1 is an Au or Ag ion;
R 1 , R 2 , R 3 , and R 4 are each independently aryl (C≤18) , or a substituted version of any of these groups;
X 1 is Cl − , Br − , I − , PF 6 − , BF 4 − , OTf − , SbF 6 − , AgCl 2 − , ClO 4 − , NO 3 − , or H 3 CC(O)O—.

3. The compound of claim 1 , wherein R 1 is aryl (C≤18) or substituted aryl (C≤18) .

4. The compound of claim 1 , wherein R 2 is aryl (C≤18) or substituted aryl (C≤18) .

5. The compound of claim 1 , wherein R 3 is aryl (C≤18) or substituted aryl (C≤18) .

6. The compound of claim 1 , wherein R 4 is aryl (C≤18) or substituted aryl (C≤18) .

7. The compound of claim 1 , wherein M 1 is an Au ion.

8. The compound of claim 1 , wherein M 1 is an Ag ion.

9. The compound of claim 1 , wherein X 1 − is Cl − or AgCl 2 − .

10. The compound of claim 1 , wherein the compound is further defined as:

11. A pharmaceutical composition comprising:
(A) a compound of claim 1 ; and
(B) an excipient.

Assignees

• Univ Texas
• Georgia Southern Univ
• Univ Wright State

Inventors

• Arambula Jonathan
• Arumugam Kuppuswamy
• Sessler Jonathan L
• Bielawski Christopher

Classifications

• C07F1/00 Primary

  Compounds containing elements of Groups 1 or 11 of the Periodic Table · CPC title

• A61P35/00

  Antineoplastic agents · CPC title