IP Library › Granted Patent US 12,275,685
Granted Patent B2
US 12,275,685 · App. 17/337,830 · Granted Apr 15, 2025

Oligo-benzamide analogs and their use in cancer treatment

Inventors: Ganesh Raj (Plano, TX); Jung-Mo Ahn (Plano, TX); Ratna K. Vadlamudi (Helotes, TX)
Assignee: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
C07C235/56A61P35/00C07D215/38C07D231/56C07D233/88
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Quick Facts
Patent No.
US 12,275,685
App. No.
17/337,830
Granted
Apr 15, 2025
Kind
B2
Abstract

The present disclosure compounds of the formulae: wherein the variables are defined herein, as well as pharmaceutical compositions thereof. The present disclosure also provides methods for the use of said compounds and/or pharmaceutical compositions, such as in the treatment of cancer.

Claims (91)

1. A compound of the formula:

wherein:

R 1 is halo, —NO 2 , alkyl (C≤12) , substituted alkyl (C≤12) , amido (C≤12) , substituted amido (C≤12) , or —NHC(O)CH(R 1a )NH 2 , wherein:

R 1a is aralkyl (C≤18) , substituted aralkyl (C≤18) , or the side chain of a canonical amino acid;

R 2 , R 3 , and R 4 are each independently alkyl (C≤12) , substituted alkyl (C≤12) , aralkyl (C≤18) , or substituted aralkyl (C≤18) ; and

R 5 is —NHR 5b , wherein:

R 5b is

cycloalkyl (C≤12) , or heteroaryl (C≤12) , or a substituted version of these groups; or

a group of the formula:

wherein:

 L 1 is —C(O)NR L1 —, wherein:

 R L1 is hydrogen, alkyl (C≤12) , or substituted alkyl (C≤12) ;

 R 5b′ is aryl (C≤12) , aralkyl (C≤18) , heteroaryl (C≤12) , heteroaralkyl (C≤18) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt thereof.

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

wherein:

R 1 is halo, —NO 2 , alkyl (C≤12) , substituted alkyl (C≤12) , amido (C≤12) , substituted amido (C≤12) , or —NHC(O)CH(R 1a )NH 2 , wherein:

R 1a is aralkyl (C≤18) , substituted aralkyl (C≤18) , or the side chain of a canonical amino acid;

R 2 , R 3 , and R 4 are each independently alkyl (C≤12) , substituted alkyl (C≤12) , aralkyl (C≤18) , or substituted aralkyl (C≤18) ; and

R 5 is —NHR 5b , wherein:

R 5b is

a group of the formula:

wherein:

 L 1 is —C(O)NR L1 —, wherein:

 R L1 is hydrogen, alkyl (C≤12) , or substituted alkyl (C≤12) ;

 R 5b′ is aryl (C≤12) , aralkyl (C≤18) , heteroaryl (C≤12) , heteroaralkyl (C≤18) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt thereof.

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

wherein:

R 1 is halo, —NO 2 , alkyl (C≤12) , substituted alkyl (C≤12) , amido (C≤12) , substituted amido (C≤12) , or —NHC(O)CH(R 1a )NH 2 , wherein:

R 1a is aralkyl (C≤18) , substituted aralkyl (C≤18) , or the side chain of a canonical amino acid;

R 2 , R 3 , and R 4 are each independently alkyl (C≤12) , substituted alkyl (C≤12) , aralkyl (C≤18) , or substituted aralkyl (C≤18) ; and

R 5 is —NHR 5b , wherein:

R 5b is

a group of the formula:

wherein:

 L 1 is —C(O)NR L1 —, wherein:

 R L1 is hydrogen;

 R 5b′ is aryl (C≤12) , aralkyl (C≤18) , heteroaryl (C≤12) , heteroaralkyl (C≤18) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1 , wherein the compound is further defined as:

wherein:

R 1 is halo, —NO 2 , alkyl (C≤12) , substituted alkyl (C≤12) , amido (C≤12) , substituted amido (C≤12) , or —NHC(O)CH(R 1a )NH 2 , wherein:

R 1a is aralkyl (C≤18) , substituted aralkyl (C≤18) , or the side chain of a canonical amino acid;

R 2 , R 3 , and R 4 are each independently alkyl (C≤12) , substituted alkyl (C≤12) , aralkyl (C≤18) , or substituted aralkyl (C≤18) ; and

R 5 is —NHR 5b , wherein:

R 5b is

a group of the formula:

wherein:

 L 1 is —C(O)NR L1 —, wherein:

 R L1 is hydrogen;

 R 5b′ is aryl (C≤12) , aralkyl (C≤18) , or heteroaryl (C≤12) , or a substituted version of any of these groups;

or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1 , wherein R 2 is aralkyl (C≤18) or substituted aralkyl (C≤18) .

6. The compound according to claim 1 , wherein R 2 is alkyl (C≤12) or substituted alkyl (C≤12) .

7. The compound according to claim 1 , wherein R 2 is 1-hydroxyethyl.

8. The compound according to claim 1 , wherein R 4 is alkyl (C≤12) or substituted alkyl (C≤12) .

9. The compound according to claim 1 , wherein R 4 is i-butyl.

10. The compound according to claim 1 , wherein R 3 is alkyl (C≤12) or substituted alkyl (C≤12) .

11. The compound according to claim 1 wherein R 3 is i-butyl.

12. The compound according to claim 1 , wherein R 5b is heteroaryl (C≤12) or substituted heteroaryl (C≤12) .

13. The compound according to claim 1 , wherein R 5b is heteroaryl (C≤12) .

14. The compound according to claim 1 , wherein R 5b is cycloalkyl (C≤12) or substituted cycloalkyl (C≤12) .

15. The compound according to claim 1 , wherein R 5b′ is heteroaryl (C≤12) or substituted heteroaryl (C≤12) .

16. The compound according to claim 1 , wherein R 5b is heteroaryl (C≤12) .

17. The compound according to claim 1 , wherein R 5b is quinolin-3-yl.

18. The compound according to claim 1 , wherein R 1 is —NO 2 .

19. The compound according to claim 1 , wherein R 1 is alkyl (C≤12) or substituted alkyl (C≤12) .

20. The compound according to claim 1 , wherein R 1 is halo.

21. The compound according to claim 1 , wherein R 1 is fluoro.

22. The compound according to claim 1 , wherein R 1 is amido (C≤12) or substituted amido (C≤12) .

23. The compound according to claim 1 , wherein R 1a is aralkyl (C≤18) or substituted aralkyl (C≤18) .

24. The compound according to claim 1 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

25. A pharmaceutical composition comprising:

a) a compound according to claim 1 ; and

b) an excipient and/or a pharmaceutically acceptable carrier.

26. A method of treating a disease or disorder in a patient in need thereof comprising administering to the patient a therapeutically effective amount of a compound according to claim 1 , wherein the disease or disorder is breast cancer, ovarian cancer, pancreatic cancer, or brain cancer.

27. The method of claim 26 , wherein the compound or composition is administered in an amount sufficient to induce endoplasmic reticulum stress and/or shut down protein synthesis.

28. The method according to claim 26 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

29. The pharmaceutical composition according to claim 25 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

30. The method according to claim 27 , wherein the compound is further defined as:

or a pharmaceutically acceptable salt thereof.

31. The compound according to claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

32. The compound according to claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

33. The compound according to claim 1 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

Assignments (3)
LICENSE Recorded Aug 19, 2024
From: THE UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO
To: NATIONAL INSTITUTES OF HEALTH
Reel/Frame 068691/0526 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2022
From: RAJ, GANESH; VADLAMUDI, RATNA K.
To: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 059928/0900 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2022
From: AHN, JUNG-MO
To: BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 059930/0530 →
Continuity (3)
Continuation In Part PCTUS2019064073 · Dec 2, 2019
Provisional Application 62774671 · Dec 3, 2018
Related Publication 20220017454A1 · Jan 20, 2022
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