IP Library Granted Patent US 9,724,316
Granted Patent B2
US 9,724,316 · App. 15/262,852 · Granted Aug 8, 2017

Bicyclic analgesic compounds

Inventor: Kevin Duane Bunker (Escondido, CA)
Assignee: Kalyra Pharmaceuticals, Inc.
A61K31/16A61K9/0014A61K9/0019A61K31/13A61K31/133A61K31/14A61K31/215A61K31/216A61K31/22A61K31/221A61K31/235A61K31/24A61K45/06C07C211/62C07C217/52C07C233/06C07C233/23C07C233/41C07C233/52C07C233/63C07C235/74C07C2102/38
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Quick Facts
Patent No.
US 9,724,316
App. No.
15/262,852
Granted
Aug 8, 2017
Kind
B2
Abstract

Analgesic compounds for treatment of pain or fever that include a bicyclopentane moiety linked to an amine, combinations of the compounds with opioid analgesic drugs, and methods for treating pain or fever by administering a compound described herein.

Claims (37)

1. A method for reducing pain comprising administering an effective amount of a compound of Formula (I), or a pharmaceutically acceptable salt thereof, wherein Formula (I) has the structure:

wherein:

R 1 is H, —CH 3 or an unsubstituted (C 2 to C 5 ) alkyl;

R 2 is H or —C(═Y)R 4 ;

R 3 is a substituted or unsubstituted (C 1 to C 30 ) alkyl, a substituted or unsubstituted (C 2 to C 30 ) alkenyl, a substituted or unsubstituted (C 3 to C 30 ) cycloalkyl, a substituted or unsubstituted (C 3 to C 30 ) cycloalkenyl, a substituted or unsubstituted (C 8 to C 30 ) cycloalkynyl, a substituted or unsubstituted (C 6 to C 30 ) aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl(C 1-6 alkyl), or a substituted or unsubstituted heteroaryl(C 1-6 alkyl);

R 4 is a substituted or unsubstituted (C 1 to C 10 ) alkyl; and

Y is O.

2. The method of claim 1 , further comprising administering an opioid analgesic.

3. The method of claim 2 , wherein the opioid analgesic is selected from the group consisting of codeine, hydrocodone and oxycodone.

4. The method of claim 1 , wherein the administration is intravenous.

5. The method of claim 1 , wherein the administration is oral.

6. The method of claim 1 , wherein the pain is acute pain.

7. The method of claim 1 , wherein R 2 is H.

8. The method of claim 7 , wherein R 1 is H.

9. The method of claim 1 , wherein R 3 is a substituted or unsubstituted (C 6 to C 30 ) aryl.

10. The method of claim 1 , wherein R 3 is a substituted or unsubstituted heteroaryl.

11. The method of claim 1 , wherein R 3 is a substituted or unsubstituted heterocyclyl.

12. The method of claim 1 , wherein R 3 is a substituted or unsubstituted aryl(C 1-6 alkyl) or a substituted or unsubstituted heteroaryl(C 1-6 alkyl).

13. A compound of Formula (I), or a pharmaceutically acceptable salt thereof:

wherein:

R 1 is H, —CH 3 or an unsubstituted (C 2 to C 5 ) alkyl;

R 2 is —C(═Y)R 4 ; and

R 3 is a substituted or unsubstituted (C 1 to C 30 ) alkyl, a substituted or unsubstituted (C 2 to C 30 ) alkenyl, a substituted or unsubstituted (C 3 to C 30 ) cycloalkyl, a substituted or unsubstituted (C 3 to C 30 ) cycloalkenyl, a substituted or unsubstituted (C 8 to C 30 ) cycloalkynyl, a substituted or unsubstituted (C 6 to C 30 ) aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, or a substituted or unsubstituted aryl(C 1-6 alkyl); or

R 1 is H, —CH 3 , —CF 3 , or a substituted or unsubstituted (C 2 to C 5 ) alkyl;

R 2 is H; and

R 3 is a substituted or unsubstituted (C 3 to C 30 ) cycloalkyl, a substituted or unsubstituted (C 3 to C 30 ) cycloalkenyl, a substituted or unsubstituted (C 8 to C 30 ) cycloalkynyl, a substituted (C 6 to C 30 ) aryl, an unsubstituted (C 7 to C 30 ) aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclyl, a substituted or unsubstituted aryl(C 1-6 alkyl), a substituted or unsubstituted heteroaryl(C 1-6 alkyl);

R 4 is or a substituted or unsubstituted (C 1 to C 10 ) alkyl; and

Y is or O.

14. The compound of claim 13 , wherein R 2 is H.

15. The compound of claim 14 , wherein R 1 is H.

16. The compound of claim 13 , wherein R 3 is a substituted (C 6 to C 30 ) aryl.

17. The compound of claim 13 , wherein R 3 is a substituted or unsubstituted heteroaryl.

18. The compound of claim 13 , wherein R 3 is a substituted or unsubstituted heterocyclyl.

19. The compound of claim 13 , wherein R 3 is a substituted or unsubstituted aryl(C 1-6 alkyl) or a substituted or unsubstituted heteroaryl(C 1-6 alkyl).

20. A pharmaceutical composition comprising an effective amount of a compound of claim 13 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent, excipient or combination thereof.

21. The method of claim 1 , wherein the pain is chronic pain.

22. The method of claim 1 , wherein the administration is intramuscular.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 27, 2025
From: RECURIUM IP HOLDINGS, LLC
To: KTHERA, LLC
Reel/Frame 070653/0373 →
CHANGE OF NAME Recorded Jan 3, 2020
From: ZENO ROYALTIES & MILESTONES, LLC
To: RECURIUM IP HOLDINGS, LLC
Reel/Frame 051478/0353 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2018
From: KALYRA PHARMACEUTICALS, INC.
To: ZENO ROYALTIES & MILESTONES, LLC
Reel/Frame 047695/0432 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2018
From: KALYRA PHARMACEUTICALS, INC.
To: ZENO ROYALTIES & MILESTONES, LLC
Reel/Frame 047414/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 15, 2016
From: BUNKER, KEVIN DUANE
To: KALYRA PHARMACEUTICALS, INC.
Reel/Frame 039760/0074 →
Continuity (3)
Continuation 14439636
Provisional Application 61781580 · Mar 14, 2013
Related Publication 20160374968A1 · Dec 29, 2016