Heterocyclic compounds as LSD1 inhibitors

• US 9,944,647 B2
• Filed: 04/01/2016
• Issued: 04/17/2018
• Est. Priority Date: 04/03/2015
• Status: Active Grant

• Current Assignee: Incyte Corporation, Incyte Holdings Corporation (Incyte Corporation)
• Original Assignee: Incyte Corporation
• Inventors: He, Chunhong, Li, Zhenwu, Wu, Liangxing, Yao, Wenqing, Zhang, Fenglei
• Primary Examiner(s): Bakshi, Pancham
• Application Number:
  US15/088,259
• Publication Number:
  US 20160289238A1
• Time in Patent Office: 746 Days
• Field of Search: 5142282, 514230, 5142302, 514249, 514229
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 13/00 Drugs for disorders of the urinary system
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

The present invention is directed to compounds of Formula I which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

Claims

1. A compound which is 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl -1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile, or a pharmaceutically acceptable salt thereof.

3. A pharmaceutical composition comprising the compound of claim 1, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier or excipient.

2. A compound which is 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl -1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile.

4. A pharmaceutical composition comprising the compound of claim 2 and at least one pharmaceutically acceptable carrier or excipient.

5. A compound which is 4-[5-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-8-(1-methyl -1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile, or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition comprising the compound of claim 5, or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier or excipient.

6. A compound which is 4-[5-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-8-(1-methyl -1H-pyrazolo[3,4-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile.

8. A pharmaceutically composition comprising the compound of claim 6 and at least one pharmaceutically acceptable carrier or excipient.

9. A compound which is 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl -1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile, or a pharmaceutically acceptable salt thereof.

11. A pharmaceutical composition comprising the compound of claim 9, a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier or excipient.

10. A compound which is 4-[5-[4-(dimethylamino)piperidin-1-yl]-8-(1-methyl -1H-pyrrolo[2,3-b]pyridin-5-yl)imidazo[1,2-c]pyrimidin-7-yl]benzonitrile.

12. A pharmaceutical composition comprising the compound of claim 10 and at least one pharmaceutically acceptable carrier or excipient.