IP Library Granted Patent US 9,670,222
Granted Patent B2
US 9,670,222 · App. 14/260,552 · Granted Jun 6, 2017

CCR2 receptor antagonists and uses thereof

Inventors: Heiner Ebel (Biberach an der Riss, DE); Sara Frattini (Castelleone, IT); Kai Gerlach (Mittelbiberach, DE); Riccardo Giovannini (Verona, IT); Christoph Hoenke (Biberach an der Riss, DE); Rocco Mazzaferro (San Giuliano, IT); Marco Santagostino (Mittelbiberach, DE); Stefan Scheuerer (Warthausen, DE); Christofer Tautermann (Biberach, DE); Thomas Trieselmann (Mettenberg, DE)
Assignee: Centrexion Therapeutics Corporation
C07D491/107C07D405/14
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 9,670,222
App. No.
14/260,552
Granted
Jun 6, 2017
Kind
B2
Abstract

The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.

Claims (36)

1. A method for treating a neurologic disease selected from inflammatory and neuropathic pain, comprising administering an effective amount of a compound of Formula I to a patient in need thereof to treat the neurologic disease, wherein Formula I is represented by:

or an acid addition salt thereof with a pharmacologically acceptable acid; wherein:

R 1 is a group selected from among —H, -halogen, —CN, —O—C 1 -C 4 -alkyl, —C 1 -C 4 -alkyl, —CH═CH 2 , —C≡CH, —CF 3 , —OCF 3 , —OCF 2 H, and —OCFH 2 ;

R 7 is a ring selected from among phenyl and —C 5 -C 6 -heteroaryl,

wherein the ring R 7 is optionally substituted with one or more groups selected from among —CF 3 , —O—CF 3 , —S—CF 3 , —CN, —C 1 -C 6 -alkyl, —C(CH 3 ) 2 —CN—O—C 1 -C 6 -alkyl, —C 3 -C 8 -cycloalkyl, and -halogen;

R 2 is selected from among —H, -halogen, —CN, —O—C 2 -C 4 -alkyl, —C 1 -C 4 -alkyl, —CH═CH 2 , —C≡CH, —CF 3 , —OCF 3 , —OCF 2 H, and —OCFH 2 ;

R 3 is selected from among —H, -methyl, -ethyl, -propyl, -i-propyl, -cyclopropyl, —OCH 3 , —CF 3 , and —CN;

n is 2;

G and E are N;

Z is C;

R 4 denotes —H, and R 5 is a group of the structure -L 1 -R 18 , wherein L 1 is selected from among —NH—, —N(C 1 -C 4 -alkyl)-, and a bond, and R 18 is —C 3 -C 8 -heterocyclyl,

wherein R 18 is optionally substituted by one or more groups selected from among halogen, —CF 3 , —OCF 3 , —CN, —OH, —O—C 1 -C 4 -alkyl, —C 1 -C 6 -alkyl, —NH—C(O)—C 1 -C 6 -alkyl, —N(C 1 -C 4 -alkyl)-C(O)—C 1 -C 6 -alkyl, —C(O)—C 1 -C 6 -alkyl, —S(O) 2 —C 1 -C 6 -alkyl, —NH—S(O) 2 —C 1 -C 6 -alkyl, —N(C 1 -C 4 -alkyl)-S(O) 2 —C 1 -C 6 -alkyl, and —C(O)—O—C 1 -C 6 -alkyl; and

wherein R 6 is selected from among —H, —C 1 -C 4 -alkyl, —OH, —O—C 1 -C 4 -alkyl, -halogen, —CN, —CF 3 , and —OCF 3 .

2. The method of claim 1 , wherein L 1 is —NH—.

3. The method of claim 2 , wherein R 18 is —C 3 -C 8 -heterocyclyl substituted by one or more groups selected from among halogen, —CF 3 , —OCF 3 , —CN, —OH, —O—C 1 -C 4 -alkyl, and —C 1 -C 6 -alkyl.

4. The method of claim 3 , wherein R 7 is phenyl optionally substituted with one or more groups selected from among —CF 3 , —O—CF 3 , —CN, —C 1 -C 6 -alkyl, —C(CH 3 ) 2 —CN, and halogen.

5. The method of claim 1 , wherein the compound is

6. The method of claim 1 , wherein the compound is

or an acid addition salt thereof with a pharmacologically acceptable acid.

7. The method of claim 1 , wherein the compound is an acid addition salt with a pharmacologically acceptable acid of the following compound:

8. The method of claim 1 , wherein the neurologic disease is inflammatory pain.

9. The method of claim 4 , wherein the neurologic disease is inflammatory pain.

10. The method of claim 6 , wherein the neurologic disease is inflammatory pain.

11. The method of claim 7 , wherein the neurologic disease is inflammatory pain.

12. The method of claim 1 , wherein the neurologic disease is neuropathic pain.

13. The method of claim 4 , wherein the neurologic disease is neuropathic pain.

14. The method of claim 6 , wherein the neurologic disease is neuropathic pain.

15. The method of claim 7 , wherein the neurologic disease is neuropathic pain.

16. The method of claim 1 , wherein the inflammatory or neuropathic pain is low back pain, hip pain, or leg pain.

17. The method of claim 4 , wherein the inflammatory or neuropathic pain is low back pain, hip pain, or leg pain.

18. The method of claim 6 , wherein the inflammatory or neuropathic pain is low back pain, hip pain, or leg pain.

19. The method of claim 7 , wherein the inflammatory or neuropathic pain is low back pain, hip pain, or leg pain.

20. The method of claim 1 , wherein the inflammatory or neuropathic pain is diabetic neuropathy or trigeminal neuralgia.

21. The method of claim 4 , wherein the inflammatory or neuropathic pain is diabetic neuropathy or trigeminal neuralgia.

22. The method of claim 6 , wherein the inflammatory or neuropathic pain is diabetic neuropathy or trigeminal neuralgia.

23. The method of claim 7 , wherein the inflammatory or neuropathic pain is diabetic neuropathy or trigeminal neuralgia.

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: EBEL, HEINER, MR.; FRATTINI, SARA, MS.; GERLACH, KAI, MR.; GIOVANNINI, RICCARDO, MR.; HOENKE, CHRISTOPH, MR.; MAZZAFERRO, ROCCO, MR.; SANTAGOSTINO, MARCO, MR.; SCHEUERER, STEFAN, MR.; TAUTERMANN, CHRISTOFER, MR.; TRIESELMANN, THOMAS, MR.
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 037273/0285 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2015
From: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
To: CENTREXION THERAPEUTICS CORPORATION
Reel/Frame 037273/0311 →
Priority Claims (2)
EP 09179555 · Dec 17, 2009 · regional
EP 10162621 · May 12, 2010 · regional
Continuity (2)
Division 12969745 · Dec 16, 2010
Related Publication 20140235661A1 · Aug 21, 2014