IP Library › Granted Patent US 10,597,411
Granted Patent B2
US 10,597,411 · App. 16/370,857 · Granted Mar 24, 2020

Compositions and methods for inhibiting arginase activity

Inventors: Eric B. Sjogren (Mountain View, CA); Jim Li (San Francisco, CA); Lijing Chen (Cupertino, CA); Roland J. Billedeau (Santa Clara, CA); Timothy F. Stanton (Daly City, CA); Michael Van Zandt (Guilford, CT); Darren Whitehouse (Westbrook, CT); Gunnar E. Jagdmann, Jr. (Branford, CT); Lene Raunkjær Petersen (Værløse, DK)
Assignee: Calithera Biosciences, Inc.
C07F5/025A61K31/4245A61K31/69A61K39/3955A61K39/39558A61K45/06A61P35/00A61P35/02C07K16/2818A61K2039/507A61K2300/00
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Quick Facts
Patent No.
US 10,597,411
App. No.
16/370,857
Granted
Mar 24, 2020
Kind
B2
Abstract

The disclosure relates to a novel class of compounds that exhibit activity inhibitory activity toward arginase, and pharmaceutical compositions comprising the compounds of the disclosure. Also provided herein are methods of treating cancer with the arginase inhibitors of the disclosure.

Claims (51)

1. A method of treating cancer, comprising administering to a patient in need thereof a therapeutically effective amount of a compound of formula (I*):

or a pharmaceutically acceptable salt thereof,

wherein:

R 1 is methyl; and

R 4 is H or (C 1 -C 6 )alkyl.

2. The method of claim 1 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

4. The method of claim 1 , wherein R 4 is (C 1 -C 6 )alkyl.

5. The method of claim 4 , wherein R 4 is methyl, ethyl, propyl, or isopropyl.

6. The method of claim 1 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

7. The method of claim 6 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

8. The method of claim 6 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

9. The method of claim 1 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

10. The method of claim 9 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

11. The method of claim 9 , wherein the compound has the structure of the following formula:

or a pharmaceutically acceptable salt thereof.

12. The method of claim 1 , wherein the patient has melanoma.

13. The method of claim 1 , wherein the patient has non-small cell lung cancer.

14. The method of claim 1 , wherein the patient has colorectal cancer.

15. The method of claim 1 , wherein the patient has bladder cancer.

16. The method of claim 1 , wherein the patient has gastric cancer.

17. The method of claim 1 , wherein the patient has head and neck cancer.

18. The method of claim 1 , wherein the patient has mesothelioma.

19. The method of claim 1 , wherein the patient has bile duct cancer.

20. The method of claim 1 , wherein the patient has ovarian cancer.

21. The method of claim 1 , wherein the patient has multiple myeloma.

22. The method of claim 1 , wherein the patient has endometrial cancer.

23. The method of claim 1 , wherein the patient has esophageal cancer.

24. The method of claim 1 , wherein the patient has a gastrointestinal carcinoid tumor.

25. The method of claim 1 , wherein the patient has a gastrointestinal stromal tumor (GIST).

26. The method of claim 1 , further comprising conjointly administering one or more additional chemotherapeutic agents, wherein the one or more additional chemotherapeutic agents is selected from ipilimumab, MGA012, nivolumab, pembrolizumab, pidilizumab, and epacadostat.

27. The method of claim 26 , wherein the additional chemotherapeutic agent is epacadostat.

28. The method of claim 8 , further comprising conjointly administering one or more additional chemotherapeutic agents, wherein the one or more additional chemotherapeutic agents is selected from ipilimumab, MGA012, nivolumab, pembrolizumab, pidilizumab, and epacadostat.

29. The method of claim 28 , wherein the additional chemotherapeutic agent is epacadostat.

30. The method of claim 26 , wherein the additional chemotherapeutic agent is ipilimumab.

31. The method of claim 26 , wherein the additional chemotherapeutic agent is MGA012.

32. The method of claim 26 , wherein the additional chemotherapeutic agent is nivolumab.

33. The method of claim 26 , wherein the additional chemotherapeutic agent is pembrolizumab.

34. The method of claim 26 , wherein the additional chemotherapeutic agent is pidilizumab.

35. The method of claim 28 , wherein the additional chemotherapeutic agent is ipilimumab.

36. The method of claim 28 , wherein the additional chemotherapeutic agent is MGA012.

37. The method of claim 28 , wherein the additional chemotherapeutic agent is nivolumab.

38. The method of claim 28 , wherein the additional chemotherapeutic agent is pembrolizumab.

39. The method of claim 28 , wherein the additional chemotherapeutic agent is pidilizumab.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2023
From: CALITHERA BIOSCIENCES, INC.
To: PRECISION PHARMACEUTICALS, INC.
Reel/Frame 064091/0777 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: BILLEDEAU, ROLAND J; SJOGREN, ERIC B.; LI, JIM; CHEN, LIJING; STANTON, TIMOTHY F.; GROSS, MATTHEW I.; PARLATI, FRANCESCO
To: CALITHERA BIOSCIENCES, INC.
Reel/Frame 050982/0054 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: VAN ZANDT, MICHAEL; WHITEHOUSE, DARREN; JAGDMANN, GUNNAR E., JR.
To: NEW ENGLAND DISCOVERY PARTNERS, LLC
Reel/Frame 050982/0239 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: NEW ENGLAND DISCOVERY PARTNERS, LLC
To: CALITHERA BIOSCIENCES, INC.
Reel/Frame 050983/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: NCK A/S
To: CALITHERA BIOSCIENCES, INC.
Reel/Frame 050983/0947 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2019
From: PETERSEN, LENE RAUNKJAER
To: NCK A/S
Reel/Frame 050991/0361 →
Continuity (4)
Division 15853310 · Dec 22, 2017
Provisional Application 62438092 · Dec 22, 2016
Provisional Application 62439614 · Dec 28, 2016
Related Publication 20190330244A1 · Oct 31, 2019