IP Library Granted Patent US 9,650,370
Granted Patent B2
US 9,650,370 · App. 14/891,051 · Granted May 16, 2017

(Cyano-dimethyl-methyl)-isoxazoles and -[1,3,4]thiadiazoles

Inventors: Doris Riether (Biberach an der Riss, DE); Florian Paul Christian Binder (Maselheim, DE); Henri Doobs (Warthausen, DE); Stephan Georg Mueller (Warthausen, DE); Janet Rachel Nicholson (Oberhoefen, DE); Achim Sauer (Ravensburg-Torkenweiler, DE)
Assignee: Centrexion Therapeutics Corporation
C07D417/12C07D261/04C07D261/14C07D413/02C07D413/12C07D413/14
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Quick Facts
Patent No.
US 9,650,370
App. No.
14/891,051
Granted
May 16, 2017
Kind
B2
Abstract

This invention relates to novel (Cyano-dimethyl-methyl)-isoxazolesand-[1,3,4]thiadiazoles and their use as CB2 cannabinoid receptor agonists, pharmaceutical compositions containing the same, and their use for the treatment of CB2 receptor mediated disorders or conditions.

Claims (38)

1. A compound selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is

4. The compound of claim 1 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

5. A pharmaceutical composition comprising a compound according to claim 1 in admixture with a pharmaceutically acceptable adjuvant, diluent, and/or carrier.

6. A pharmaceutical composition comprising a compound according to claim 2 in admixture with a pharmaceutically acceptable adjuvant, diluent, and/or carrier.

7. A pharmaceutical composition comprising a compound according to claim 3 in admixture with a pharmaceutically acceptable adjuvant, diluent, and/or carrier.

8. A pharmaceutical composition comprising a compound according to claim 4 in admixture with a pharmaceutically acceptable adjuvant, diluent, and/or carrier.

9. A method of treating a disease or disorder selected from the group consisting of pain, osteoarthritis, and diabetic neuropathy, comprising administering to a human being an effective amount of a compound selected from the group consisting of

or a pharmaceutically acceptable salt thereof, to treat the disease or disorder.

10. The method of claim 9 , wherein the disease or disorder is pain.

11. The method of claim 10 , wherein the pain is low back pain, hip pain, or leg pain.

12. The method of claim 10 , wherein the pain is due to fibromyalgia.

13. The method of claim 10 , wherein the pain is due to trigeminal neuralgia, complex regional pain syndrome Type I, or complex regional pain syndrome Type II.

14. The method of claim 10 , wherein the pain is due to diabetic neuropathy.

15. The method of claim 10 , wherein the pain is acquired immune deficiency syndrome (AIDS) related neuropathic pain.

16. The method of claim 10 , wherein the pain is post-stroke pain, pain due to central nervous system injury, or pain due to multiple sclerosis.

17. The method of claim 10 , wherein the pain is tumour pain, pain due to carpal tunnel syndrome, pain due to irritable bowel, or pain due to osteoarthritis.

18. The method of claim 9 , wherein the disease or disorder is osteoarthritis or diabetic neuropathy.

19. The method of claim 9 , wherein the compound is a compound of claim 2 .

20. The method of claim 10 , wherein the compound is a compound of claim 2 .

21. The method of claim 11 , wherein the compound is a compound of claim 2 .

22. The method of claim 12 , wherein the compound is a compound of claim 2 .

23. The method of claim 13 , wherein the compound is a compound of claim 2 .

24. The method of claim 14 , wherein the compound is a compound of claim 2 .

25. The method of claim 15 , wherein the compound is a compound of claim 2 .

26. The method of claim 16 , wherein the compound is a compound of claim 2 .

27. The method of claim 17 , wherein the compound is a compound of claim 2 .

28. The method of claim 18 , wherein the compound is a compound of claim 2 .

29. The method of claim 10 , wherein the pain is chronic back pain.

30. The method of claim 29 , wherein the compound is a compound of claim 2 .

31. A method of treating irritable bowel syndrome, comprising administering to a human being an effective amount of a compound selected from the group consisting of

or a pharmaceutically acceptable salt thereof, to treat the irritable bowel syndrome.

32. The method of claim 31 , wherein the compound is

or a pharmaceutically acceptable salt thereof.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Nov 21, 2025
From: AVENUE VENTURE OPPORTUNITIES FUND, L.P., AS AGENT
To: CENTREXION THERAPEUTICS CORPORATION
Reel/Frame 073683/0099 →
SECURITY INTEREST Recorded Nov 21, 2025
From: CENTREXION THERAPEUTICS CORPORATION
To: ANKURA TRUST COMPANY, LLC, AS ADMINISTRATIVE AND COLLATERAL AGENT
Reel/Frame 073683/0108 →
SECURITY INTEREST Recorded Jul 12, 2023
From: CENTREXION THERAPEUTICS CORPORATION
To: AVENUE VENTURE OPPORTUNITIES FUND, L.P., AS AGENT
Reel/Frame 064256/0125 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2015
From: RIETHER, DORIS; BINDER, FLORIAN PAUL; DOODS, HENRI; MUELLER, STEPHAN GEORG; NICHOLSON, JANET RACHEL; SAUER, ACHIM
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 037274/0318 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2015
From: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
To: CENTREXION THERAPEUTICS CORPORATION
Reel/Frame 037274/0378 →
Priority Claims (1)
EP 13168165 · May 17, 2013 · regional
Continuity (1)
Related Publication 20160102085A1 · Apr 14, 2016