IP Library Granted Patent US 11,207,302
Granted Patent B2
US 11,207,302 · App. 16/849,610 · Granted Dec 28, 2021

1,2,5-oxadiazoles as inhibitors of indoleamine 2,3-dioxygenase

Inventors: Andrew P. Combs (Kennett Square, PA); Eddy W. Yue (Landenberg, PA); Richard B. Sparks (Wilmington, DE); Wenyu Zhu (Media, PA); Jiacheng Zhou (Newark, DE); Qiyan Lin (Newark, DE); Lingkai Weng (Phoenixville, PA); Tai-Yuen Yue (Hockessin, DE); Pingli Liu (Wilmington, DE)
Assignees: Incyte Corporation; Incyte Holdings Corporation
A61K31/4245A61K39/3955C07D271/08C07D413/04C07D413/12
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Quick Facts
Patent No.
US 11,207,302
App. No.
16/849,610
Granted
Dec 28, 2021
Kind
B2
Abstract

The present invention is directed to 1, 2, 5-oxadiazole derivatives, and compositions of the same, which are inhibitors of indoleamine 2, 3-dioxygenase and are useful in the treatment of cancer and other disorders, and to the processes and intermediates for making such 1, 2, 5-oxadiazole derivatives.

Claims (20)

1. A method of treating cervical cancer in a patient, comprising administering to said patient a therapeutically effective amount of a compound, which is 4-({2-[(amino sulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide, or a pharmaceutically acceptable salt thereof, in combination with an antibody therapeutic, wherein the treating is inhibiting or ameliorating the cancer.

2. The method of claim 1 , wherein the antibody therapeutic is an anti-PD-1 antibody.

3. The method of claim 1 , wherein the antibody therapeutic is an anti-CTLA-4 antibody.

4. A method of treating cervical cancer in a patient, comprising administering to said patient a therapeutically effective amount of a compound, which is 4-({2-[(amino sulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide in combination with an antibody therapeutic, wherein the treating is inhibiting or ameliorating the cancer.

5. The method of claim 4 , wherein the antibody therapeutic is an anti-PD-1 antibody.

6. The method of claim 4 , wherein the antibody therapeutic is an anti-CTLA-4 antibody.

7. The method of claim 4 , wherein the compound and the antibody therapeutic are administered simultaneously.

8. The method of claim 4 , wherein the compound and the antibody therapeutic are administered sequentially.

9. The method of claim 5 , wherein the compound and the antibody therapeutic are administered simultaneously.

10. The method of claim 5 , wherein the compound and the antibody therapeutic are administered sequentially.

11. The method of claim 6 , wherein the compound and the antibody therapeutic are administered simultaneously.

12. The method of claim 6 , wherein the compound, and the antibody therapeutic are administered sequentially.

13. A method of treating cervical cancer in a patient, comprising administering to said patient a therapeutically effective amount of a compound, which is 4-({2-[(amino sulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide, or a pharmaceutically acceptable salt thereof, or 4-({2-[(amino sulfonyl)amino]ethyl}amino)-N-[(4-bromo-2-furyl)methyl]-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide, or a pharmaceutically acceptable salt thereof, in combination with an anti-cancer vaccine, wherein the treating is inhibiting or ameliorating the cancer.

14. The method of claim 13 , wherein the anti-cancer vaccine is selected from dendritic cells, a synthetic peptide, a DNA vaccine, and a recombinant virus.

15. A method of treating cervical cancer in a patient, comprising administering to said patient a therapeutically effective amount of a compound, which is 4-({2-[(amino sulfonyl)amino]ethyl}amino)-N-(3-bromo-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide or 4-({2-[(aminosulfonyl)amino]ethyl}amino)-N-[(4-bromo-2-furyl)methyl]-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide in combination with an anti-cancer vaccine, wherein the treating is inhibiting or ameliorating the cancer.

16. The method of claim 15 , wherein the anti-cancer vaccine is selected from dendritic cells, a synthetic peptide, a DNA vaccine, and a recombinant virus.

17. The method of claim 15 , wherein the compound and the anti-cancer vaccine are administered simultaneously.

18. The method of claim 15 , wherein the compound and the anti-cancer vaccine are administered sequentially.

19. The method of claim 16 , wherein the compound and the anti-cancer vaccine are administered simultaneously.

20. The method of claim 16 , wherein the compound and the anti-cancer vaccine are administered sequentially.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2020
From: COMBS, ANDREW P.; YUE, EDDY W.; SPARKS, RICHARD B.; ZHU, WENYU; ZHOU, JIANCHENG; LIN, QIYAN; WENG, LINGKAI; YUE, TAI-YUEN; LIU, PINGLI
To: INCYTE CORPORATION
Reel/Frame 052603/0146 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2020
From: INCYTE CORPORATION
To: INCYTE HOLDINGS CORPORATION; INCYTE CORPORATION
Reel/Frame 052603/0228 →
Continuity (11)
Continuation 16446253 · Jun 19, 2019
Continuation 15903414 · Feb 23, 2018
Continuation 15442876 · Feb 27, 2017
Continuation 15093420 · Apr 7, 2016
Continuation 14661191 · Mar 18, 2015
Continuation 14322362 · Jul 2, 2014
Continuation 13294711 · Nov 11, 2011
Division 12498782 · Jul 7, 2009
Provisional Application 61150873 · Feb 9, 2009
Provisional Application 61078876 · Jul 8, 2008
Related Publication 20210030722A1 · Feb 4, 2021