IP Library Granted Patent US 9,862,690
Granted Patent B2
US 9,862,690 · App. 14/890,147 · Granted Jan 9, 2018

Treatment of pulmonary and other conditions

Inventor: Raju Reddy (Cheswick, PA)
Assignees: University of Pittsburgh—Of the Commonwealth System of Higher Education; The United States of America as Represented by the Department of Veterans Affairs
C07D241/20C07D239/26C07D239/30C07D239/34C07D239/38C07D239/42C07D239/47C07D239/52C07D241/12C07D241/16C07D241/18
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Quick Facts
Patent No.
US 9,862,690
App. No.
14/890,147
Granted
Jan 9, 2018
Kind
B2
Abstract

Disclosed is a compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of: X 1 -L-X 2 wherein L is a linking moiety comprising an enone; and X 1 and X 2 are each independently an optionally-substituted N-heterocycle. Also disclosed are method for treating pulmonary conditions and other organ or system conditions with the compounds.

Claims (26)

1. A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of:

wherein represents a single bond;

A is CH(S—R 5 ), wherein R 5 is an acylamino-substituted carboxylalkyl, a sulfonate-substituted alkyl, or an acylamino-substituted amido; and

X 1 and X 2 are each independently an optionally substituted 6-membered N-heterocycle.

2. The compound of claim 1 , wherein X 1 has a structure of:

and X 2 has a structure of:

wherein Z 1 , Z 2 , and Z 3 are each independently C or N, provided that at least one of Z 1 , Z 2 , or Z 3 is N; and

Y 1 , Y 2 , Y 3 , Y 4 and Y 5 are each independently H, optionally-substituted alkyl, amino, hydroxyl, optionally-substituted alkoxy, optionally-substituted thiol, acyl, or halogen.

3. The compound of claim 1 , wherein the compound has a structure of:

4. The compound of 3 , wherein the compound has a structure of:

wherein Y 2 , Y 3 , Y 4 and Y 5 are each independently H, optionally-substituted alkyl, amino, hydroxyl, optionally-substituted alkoxy, optionally-substituted thiol, acyl, or halogen.

5. The compound of claim 3 , wherein X 1 and X 2 are each optionally-substituted pyrazinyl or optionally-substituted pyrimidinyl.

6. The compound of claim 5 , wherein X 1 and X 2 are each the same.

7. The compound of claim 5 , wherein X 1 and X 2 are each different.

8. The compound of claim 3 , wherein R 5 is an acylamino-substituted carboxylalkyl, a sulfonate-substituted alkyl, or an acylamino-substituted amido.

9. The compound of claim 3 , wherein —S—R 5 is a N-acetylcysteine moiety, a 2-mercaptoethane sulfonate moiety, or a glutathione moiety.

10. A pharmaceutical composition comprising a compound of claim 1 , and at least one pharmaceutically acceptable excipient.

11. The pharmaceutical composition of claim 10 , wherein the composition is in the form of an aerosol.

12. The pharmaceutical composition of claim 10 , wherein the composition is in the form of a dry powder.

13. The compound of claim 4 , wherein R 5 is an acylamino-substituted carboxylalkyl, a sulfonate-substituted alkyl, or an acylamino-substituted amido.

14. The compound of claim 4 , wherein —S—R 5 is a N-acetylcysteine moiety, a 2-mercaptoethane sulfonate moiety, or a glutathione moiety.

15. The compound of claim 1 , wherein the compound has a structure of:

16. The compound of claim 1 , wherein the compound has a structure of:

17. The compound of claim 4 , wherein Y 2 , Y 3 , Y 4 and Y 5 are each independently H.

18. The compound of claim 13 , wherein Y 2 , Y 3 , Y 4 and Y 5 are each independently H.

19. The compound of claim 14 , wherein Y 2 , Y 3 , Y 4 and Y 5 are each independently H.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2016
From: REDDY, RAJU
To: UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; THE UNITED STATES GOVERNMENT AS REPRESENTED BY THE DEPARTMENT OF VETERANS AFFAIRS
Reel/Frame 039162/0213 →
Continuity (2)
Provisional Application 61822224 · May 10, 2013
Related Publication 20160090366A1 · Mar 31, 2016