IP Library Granted Patent US 8,993,758
Granted Patent B2
US 8,993,758 · App. 13/883,026 · Granted Mar 31, 2015

Substituted quinoxalines and uses thereof

Inventors: Amarnath Natarajan (Elkhorn, NE); Qianyi Chen (Shanghai, CN); Vashti C. Bryant (Cary, NC); Rajkumar Rajule (Omaha, NE)
Assignees: Board of Regents of the University of Nebraska; The Board of Regents, University of Texas System
C07D241/42C07D241/44C07D405/04C07D405/14C07D409/14C07D401/12C07D401/14C07D403/12C07D471/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,993,758
App. No.
13/883,026
Granted
Mar 31, 2015
Kind
B2
Abstract

Disclosed herein are compounds of formula (I) and methods of inhibiting IKKβ and the NF-κB signaling and mTOR pathways.

Claims (35)

1. A compound having a structure of formula (I)

wherein

each R 1 is independently heteroaryl, aryl, or alkyl;

L is selected from —NHC(O)NH—, —NHC(O)CH 2 —,

X is halo, alkyl, alkoxy, aryl, CO 2 alkyl, COalkyl, or haloalkyl;

R 2 is H, alkyl, alkoxy, CO 2 alkyl, COalkyl, or haloalkyl; and

R 3 is H, alkyl, or alkoxy;

or a salt thereof.

2. The compound of claim 1 , wherein each R 1 is independently selected from furanyl, thiophenyl, pyridinyl, and phenyl.

3. The compound of claim 1 , wherein at least one R 1 is methyl, ethyl, propyl, or isopropyl.

4. The compound of claim 1 , wherein L is

5. The compound of claim 1 , wherein L is

6. The compound of claim 1 , wherein X is alkoxy.

7. The compound of claim 1 , wherein X is CF 3 , CHF 2 , CH 2 F, CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CHBr 2 , or CH 2 Br.

8. The compound of claim 1 , wherein R 2 is alkyl.

9. The compound of claim 1 , wherein R 2 is CF 3 , CHF 2 , CH 2 F, CCl 3 , CHCl 2 , CH 2 Cl, CBr 3 , CHBr 2 , or CH 2 Br.

10. A method of decreasing inhibitor of kappa B kinase β (IKKβ) activity in a cell comprising contacting the cell with the compound of claim 1 in an amount effective to decrease activity of IKKβ.

11. The method of claim 10 , wherein the compound has a structure:

or a salt thereof.

12. A method of inhibiting nuclear factor kappa Kβ(NFκB) signaling pathway in a cell comprising contacting the cell with the compound of claim 1 in an amount effective to inhibit the NFκB signaling pathway.

13. The method of claim 12 , wherein the compound has a structure:

or a salt thereof.

14. A method of inhibiting mammalian target of rapamycin (mTOR) signaling pathway in a cell comprising contacting the cell with the compound of claim 1 in an amount effective to inhibit the mTOR signaling pathway.

15. The method of claim 14 , wherein the compound has a structure:

or a salt thereof.

16. A compound selected from the group consisting of:

or a salt thereof.

17. A compound having a structure selected from:

or a salt thereof.

18. A compound having a structure selected from:

or a salt thereof.

19. A compound having a structure selected from:

or a salt thereof.

20. A compound having a structure:

or a salt thereof.

Assignments (3)
CONFIRMATORY LICENSE Recorded Feb 13, 2015
From: UNIVERSITY OF NEBRASKA MEDICAL CENTER
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 034996/0353 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2013
From: NATARAJAN, AMARNATH
To: THE BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM
Reel/Frame 031082/0893 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2013
From: NATARAJAN, AMARNATH; CHEN, QIANYI; BRYANT, VASHTI C.; RAJULE, RAJKUMAR
To: BOARD OF REGENTS OF THE UNIVERSITY OF NEBRASKA
Reel/Frame 031083/0383 →
Continuity (3)
Provisional Application 61416001 · Nov 22, 2010
Provisional Application 61415934 · Nov 22, 2010
Related Publication 20130289041A1 · Oct 31, 2013