IP Library Granted Patent US 11,731,981
Granted Patent B2
US 11,731,981 · App. 17/345,110 · Granted Aug 22, 2023

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 Milanese, IT); Marco Santagostino (Mittelbiberach, DE); Stefan Scheuerer (Warthausen, DE); Christofer Tautermann (Biberach, DE); Thomas Trieselmann (Mettenberg, DE)
Assignee: Centrexion Therapeutics Corporation
C07D491/107A61P25/00A61P25/02A61P25/04A61P29/00C07D405/14
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 11,731,981
App. No.
17/345,110
Granted
Aug 22, 2023
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 (32)

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

or a salt thereof; 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 —C 3 -C 5 -cycloalkyl, —C 5 -C 10 -aryl, and —C 5 -C 10 -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, and -halogen, or wherein the ring R 7 is optionally substituted with one or more groups selected from among —O—C 1 -C 6 -alkyl and —C 3 -C 8 -cycloalkyl;

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 1, 2, or 3;

G and E are N;

Z is C;

R 4 denotes —H, and R 5 is -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 -cycloalkyl or —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, and —C(O)—C 1 -C 6 -alkyl; and

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 4 , wherein R 1 is —H, and R 2 is —C 1 -C 4 -alkyl.

6. The method of claim 5 , wherein R 6 is —H.

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

or a salt thereof.

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 7 , wherein the neurologic disease is inflammatory pain.

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

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

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

14. The method of claim 11 , wherein the neuropathic pain is low back pain, hip pain, leg pain, non-herpetic neuralgia, post herpetic neuralgia, diabetic neuropathy, nerve injury-induced pain, phantom limb pain, post-surgical pain, stump pain, or trigeminal neuralgia.

15. The method of claim 1 , wherein the neurologic disease is neuropathic pain due to chemotherapy caused nerve injury.

16. The method of claim 13 , wherein the neuropathic pain is leg pain.

17. The method of claim 13 , wherein the neuropathic pain is nerve injury-induced pain.

18. The method of claim 13 , wherein the neuropathic pain is hip pain, non-herpetic neuralgia, post herpetic neuralgia, diabetic neuropathy, phantom limb pain, post-surgical pain, or stump pain.

19. The method of claim 13 , wherein the neuropathic pain is trigeminal neuralgia.

20. The method of claim 7 , wherein the neurologic disease is neuropathic pain due to chemotherapy caused nerve injury.

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 Feb 24, 2023
From: EBEL, HEINER; FRATTINI, SARA; GERLACH, KAI; GIOVANNINI, RICCARDO; HOENKE, CHRISTOPH; MAZZAFERRO, ROCCO; SANTAGOSTINO, MARCO; SCHEUERER, STEFAN; TAUTERMANN, CHRISTOFER; TRIESELMANN, THOMAS
To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
Reel/Frame 062796/0770 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 24, 2023
From: BOEHRINGER INGELHEIM INTERNATIONAL GMBH
To: CENTREXION THERAPEUTICS CORPORATION
Reel/Frame 062796/0804 →
Priority Claims (2)
EP 09179555 · Dec 17, 2009 · regional
EP 10162621 · May 12, 2010 · regional
Continuity (5)
Continuation 16233315 · Dec 27, 2018
Continuation 15606749 · May 26, 2017
Continuation 14260552 · Apr 24, 2014
Division 12969745 · Dec 16, 2010
Related Publication 20220002310A1 · Jan 6, 2022
Cited By (1)
US 12,209,094