Salt of an aminopyridine derivative compound, a crystalline form thereof, and a process for preparing the same

Patent metadata

Field	Value
Publication number	US-12428401-B2
Application number	US-202418618379-A
Country	US
Kind code	B2
Filing date	Mar 27, 2024
Priority date	Apr 21, 2017
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

The present invention relates to novel mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, a novel crystalline form thereof, and a process for preparing the same. More specifically, the present invention relates to mesylate salt of N-(5-(4-(4-((dimethylamino)methyl)-3-phenyl-1H-pyrazol-1-yl)pyrimidine-2-ylamino)-4-methoxy-2-morpholinophenyl)acrylamide, which is excellent in stability, solubility, and bioavailability when it is administered not only alone but also in combination with other drugs and which has a high purity, a crystalline form thereof, and a process for preparing the same.

First claim

What is claimed:

1. A process for preparing a mesylate salt of Formula 1

which comprises:
(1) mixing the compound represented by the following Formula 2

and a single organic solvent or a mixed solvent, followed by adding methanesulfonic acid thereto, to prepare a mixture of the mesylate salt represented by the Formula 1; and
(2) adding an organic solvent to the mixture to crystallize the mesylate salt according to Formula 1.

2. The process of claim 1 , wherein the single organic solvent used in the step (1) is one selected from the group consisting of acetone, methyl ethyl ketone, and ethyl acetate.

3. The process of claim 1 , wherein the mixed solvent used in the step (1) is a mixed solvent of water and at least one organic solvent selected from acetone and methyl ethyl ketone.

4. The process of claim 3 , wherein the mixed ratio of water and the organic solvent is 1:1 to 1:10 by volume.

5. The process of claim 1 , wherein the step (1) is carried out at a temperature of 20 to 70° C.

6. The process of claim 1 , wherein the step (1) is carried out at a temperature of 45 to 60° C.

7. The process of claim 1 , wherein the organic solvent used in the step (2) is at least one selected from the group consisting of acetone, methyl ethyl ketone, and ethyl acetate.

8. The process of claim 1 , wherein in the step (2), the organic solvent is added in a volume ranging from 3 mL to 20 mL based on 1 g of the compound represented by the Formula 2.

Assignees

• Yuhan Corp

Inventors

• Oh Sang Ho
• Kim Jong Gyun
• Oh Se-Woong
• Han Tae Dong
• Chung Soo Yong
• Lee Seong Ran
• Kim Kyeong Bae
• Lee Young Sung
• Shin Woo Seob
• Ju Hyun
• Kang Jeong Ki
• Park Su Min
• Kim Dong Kyun

Classifications

• C07C309/04

  containing only one sulfo group · CPC title

• C07C303/22

  from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups} · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61K31/5377

  not condensed and containing further heterocyclic rings, e.g. timolol · CPC title