IP Library › Granted Patent US 11,787,793
Granted Patent B2
US 11,787,793 · App. 17/672,351 · Granted Oct 17, 2023

Heterocyclic compounds as immunomodulators

Inventors: Liangxing Wu (Wilmington, DE); Jingwei Li (Westfield, NJ); Wenqing Yao (Chadds Ford, PA)
Assignee: Incyte Corporation
C07D413/14A61K31/4375A61P37/00A61P37/02C07D413/06C07D413/12C07D471/04C07D487/04C07D498/04C07D513/04
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Quick Facts
Patent No.
US 11,787,793
App. No.
17/672,351
Granted
Oct 17, 2023
Kind
B2
Abstract

Disclosed are compounds of Formula (I), methods of using the compounds as immunomodulators, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating, preventing or ameliorating diseases or disorders such as cancer or infections.

Claims (25)

1. A method of treating lung cancer comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

2. The method of claim 1 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1, 7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

3. The method of claim 1 , wherein the lung cancer is selected from non-small cell lung cancer (NSCLC), small cell lung cancer, bronchogenic carcinoma, alveolar carcinoma, bronchial adenoma, chondromatous hamartoma, and mesothelioma.

4. The method of claim 1 , wherein the lung cancer is non-small cell lung cancer (NSCLC).

5. The method of claim 1 , wherein the lung cancer is small cell lung cancer.

6. A method of treating hepatic cancer comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

7. The method of claim 6 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1, 7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

8. The method of claim 6 , wherein the hepatic cancer is selected from hepatocellular carcinoma, cholangiocarcinoma, hepatoblastoma, angiosarcoma, hepatocellular adenoma, and hemangioma.

9. The method of claim 6 , wherein the hepatic cancer is hepatocellular carcinoma.

10. A method of treating skin cancer comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

11. The method of claim 10 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1, 7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

12. A method of treating cancer of the bladder comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

13. The method of claim 12 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1, 7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

14. The method of claim 12 , wherein the cancer of the bladder is selected from urothelial cancer, urothelial carcinoma, squamous cell carcinoma of the bladder, transition cell carcinoma of the bladder, and adenocarcinoma of the bladder.

15. A method of treating cancer of the urethra comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

16. The method of claim 15 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1, 7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

17. The method of claim 15 , wherein the cancer of the urethra is selected from squamous cell carcinoma of the urethra, transition cell carcinoma of the urethra, and adenocarcinoma of the urethra.

18. A method of treating renal cancer comprising administering to a patient in need thereof a therapeutically effective amount of a compound, wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a pharmaceutically acceptable salt thereof.

19. The method of claim 18 , wherein the compound is (R)-1-((7-cyano-2-(3′-(3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-ylamino)-2,2′-dimethylbiphenyl-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid.

20. The method of claim 18 , wherein the renal cancer is selected from renal cell carcinoma, clear cell carcinoma, adenocarcinoma of the kidney, and Wilm's tumor.

21. The method of claim 18 , wherein the renal cancer is renal cell carcinoma.

22. The method of claim 10 , wherein the skin cancer is selected from melanoma, basal cell carcinoma, squamous cell carcinoma, Kaposi's sarcoma, moles dysplastic nevi, lipoma, angioma, dermatofibroma, and keloids.

23. The method of claim 22 , wherein the skin cancer is melanoma.

24. The method of claim 23 , wherein the melanoma is selected from cutaneous malignant melanoma, intraocular malignant melanoma, metastatic malignant melanoma, and ocular melanoma.

25. The method of claim 22 , wherein the skin cancer is squamous cell carcinoma.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2022
From: WU, LIANGXING; LI, JINGWEI; QI, CHAO; ZHANG, FENGLEI; LI, ZHENWU; ZHU, WENYU; YU, ZHIYONG; XIAO, KAIJIONG; LU, LIANG; MEI, SONG; QIAN, DING-QUAN; HE, CHUNHONG; YE, YINGDA; XU, MEIZHONG; YAO, WENQING
To: INCYTE CORPORATION
Reel/Frame 059824/0910 →
Continuity (7)
Continuation 16996507 · Aug 18, 2020
Division 16373150 · Apr 2, 2019
Continuation 15850170 · Dec 21, 2017
Provisional Application 62551033 · Aug 28, 2017
Provisional Application 62487336 · Apr 19, 2017
Provisional Application 62438009 · Dec 22, 2016
Related Publication 20220194931A1 · Jun 23, 2022
Cited By (6)
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