IP Library Granted Patent US 10,576,080
Granted Patent B2
US 10,576,080 · App. 15/818,082 · Granted Mar 3, 2020

Compounds and compositions as protein kinase inhibitors

Inventors: Shenlin Huang (San Diego, CA); Xianming Jin (San Ramon, CA); Zuosheng Liu (San Diego, CA); Daniel Poon (Piedmont, CA); John Tellew (La Jolla, CA); Yongqin Wan (Irvine, CA); Xing Wang (San Diego, CA); Yongping Xie (San Diego, CA)
Assignee: Array BioPharma Inc.
A61K31/506A61K9/0053A61K31/4184A61K45/06C07D401/14C07D403/04C07D405/14
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Quick Facts
Patent No.
US 10,576,080
App. No.
15/818,082
Granted
Mar 3, 2020
Kind
B2
Abstract

The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with abnormal or deregulated kinase activity, particularly diseases or disorders that involve abnormal activation of B-Raf.

Claims (22)

1. A method of reducing the size of a tumor in a subject in need thereof, the method comprising administering to said subject a therapeutically effective amount of a pharmaceutical composition comprising a Raf kinase inhibitor, which is methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof, wherein said tumor is melanoma.

2. The method of claim 1 , wherein the tumor is melanoma having a B-RAF V600E mutation.

3. The method of claim 1 further comprising administering to the subject an additional therapeutic agent.

4. The method of claim 3 , wherein the additional therapeutic agent comprises an anticancer compound.

5. The method of claim 4 , wherein the additional therapeutic agent is a different Raf kinase inhibitor or an inhibitor of MEK, mTOR, HSP90, AKT, PI3K, CDK9, PAK, Protein Kinase C, a MAP kinase, a MAPK Kinase, or ERK.

6. The method of claim 5 , wherein the additional therapeutic agent is a MEK inhibitor.

7. The method of claim 6 , wherein the MEK inhibitor is selected from: AS703026; MSC1936369B; GSK1120212; AZD6244; PD-0325901; ARRY-438162; RDEA119; GDC0941; GDC0973; TAK-733; RO5126766; and XL-518.

8. The method of claim 7 , wherein the MEK inhibitor is ARRY-438162.

9. The method of claim 8 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered as a fixed combination.

10. The method of claim 8 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered as a non-fixed combination.

11. The method of claim 10 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered sequentially.

12. The method of claim 10 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered concurrently.

13. The method of claim 2 further comprising administering to the subject an additional therapeutic agent.

14. The method of claim 13 , wherein the additional therapeutic agent comprises an anticancer compound.

15. The method of claim 14 , wherein the additional therapeutic agent is a different Raf kinase inhibitor or an inhibitor of MEK, mTOR, HSP90, AKT, PI3K, CDK9, PAK, Protein Kinase C, a MAP kinase, a MAPK Kinase, or ERK.

16. The method of claim 15 , wherein the additional therapeutic agent is a MEK inhibitor.

17. The method of claim 16 , wherein the MEK inhibitor is selected from: AS703026; MSC1936369B; GSK1120212; AZD6244; PD-0325901; ARRY-438162; RDEA119; GDC0941; GDC0973; TAK-733; RO5126766; and XL-518.

18. The method of claim 17 , wherein the MEK inhibitor is ARRY-438162.

19. The method of claim 18 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered as a fixed combination.

20. The method of claim 18 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered as a non-fixed combination.

21. The method of claim 20 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered sequentially.

22. The method of claim 20 , wherein said methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-1-(propan-2-yl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate or a pharmaceutically acceptable salt thereof and said ARRY-438162 are administered concurrently.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2019
From: HUANG, SHENLIN; LIU, ZUOSHENG; TELLEW, JOHN; WAN, YONGQIN; WANG, XING; XIE, YONGPING
To: IRM LLC
Reel/Frame 049355/0833 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2019
From: JIN, XIANMING; POON, DANIEL
To: NOVARTIS AG
Reel/Frame 049355/0872 →
MERGER Recorded Jun 4, 2019
From: IRM, LLC
To: NOVARTIS INTERNATIONAL PHARMACEUTICAL LTD.
Reel/Frame 049355/0921 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2019
From: NOVARTIS INTERNATIONAL PHARMACEUTICAL LTD.
To: NOVARTIS AG
Reel/Frame 049355/0960 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 4, 2019
From: NOVARTIS AG
To: ARRAY BIOPHARMA INC.
Reel/Frame 049355/0982 →