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Novel crystallographic form of ceritinib and preparation method of novel crystallographic form

A technology of ceritinib and its crystal form, which is applied in the field of organic chemistry, can solve problems such as the unmentioned crystal form, and achieve the effect of stable physical and chemical properties and stable crystal form

Inactive Publication Date: 2016-06-01
HAINAN SIMCERE PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Patent WO2008 / 073687A1 disclosed and protected ceritinib and its preparation method. In addition, WO2009120798, WO2008073687, WO2004080980, WO20140066406, WO2011140338, WO209143389, WO2008073687, WO200912651 and other patents also published 5 methods for preparing ceritinib respectively. , but there is no mention of its crystal form

Method used

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  • Novel crystallographic form of ceritinib and preparation method of novel crystallographic form
  • Novel crystallographic form of ceritinib and preparation method of novel crystallographic form
  • Novel crystallographic form of ceritinib and preparation method of novel crystallographic form

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Effect test

Embodiment 1

[0045] Add ceritinib free base (100.0g) to a 2L four-neck flask (equipped with mechanical stirring, thermometer, nitrogen protection, constant pressure dropping funnel), then add purified water (1L) and stir, and control the system temperature to 20°C , then added hydrochloric acid (6N, 0.22L), and cooled down to 15°C under nitrogen protection. Sodium hydroxide solution (3N, 0.53L) was added dropwise to the reaction system, and the dropping time was controlled for 120 minutes. After a period of time, it began to slowly become turbid, and then a solid precipitated out quickly. After the solid was precipitated, the stirring was continued for 168 hours. Filter, wash the filter cake with purified water (500ml×3), vacuumize (under nitrogen protection), and place the product in a vacuum drying oven at 80°C for 96 hours to obtain ceritinib crystal C (64g, Yield 72%).

Embodiment 2

[0047] Add ceritinib (200.0g) to a 5L four-neck flask (equipped with mechanical stirring, thermometer, nitrogen protection, constant pressure dropping funnel), then add purified water (2L) and stir, control the system temperature at 10°C, add Hydrochloric acid (3N, 0.8L) was cooled to 5°C under nitrogen protection. Add potassium hydroxide solution (3N, 0.8L) dropwise to the reaction system, and the dropping time is controlled at 60 minutes. After dropping for a period of time, it slowly becomes cloudy, and then a solid precipitates out quickly. After the solid is precipitated, continue to Stir for 24 hours. Filter, wash the filter cake with purified water (1L×3), vacuumize (under nitrogen protection), and place the product in a vacuum drying oven at 100°C for 2 hours to obtain ceritinib crystal C (176g, Yield 88%).

Embodiment 3

[0049] Add ceritinib (200.0g) to a 5L four-neck flask (equipped with mechanical stirring, thermometer, nitrogen protection, constant pressure dropping funnel), then add purified water (2L) and stir, control the system temperature at 5°C, add Sulfuric acid solution (6N, 0.22L), temperature controlled to 20°C under nitrogen protection. Ammonia water (7N, 0.5L) was added dropwise to the reaction system, and the dropping time was controlled at 180 minutes. After a period of time, it began to slowly become cloudy, and then a solid precipitated out quickly, and the stirring was continued for 72 hours after the solid was precipitated. Filter, wash the filter cake with purified water (1L×3), vacuumize (under nitrogen protection), and place the product in a vacuum drying oven at 120°C for 2 hours to obtain ceritinib crystal C (170g, Yield 85%).

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Abstract

The invention relates to a novel crystallographic form of ceritinib. An X-ray powder diffraction pattern of the novel crystallographic form of ceritinib is as shown in Figure 1. The invention further relates to a method for preparing the crystallographic form, and application of the crystallographic form to preparation of a medicament for treating anaplastic lymphoma kinase mediated diseases.

Description

technical field [0001] The invention relates to the fields of organic chemistry and biomedicine, and relates to a new crystal form C of ceritinib, its preparation method and application. Background technique [0002] The chemical name of ceritinib is 5-chloro-N-(2-isopropoxy-5-methyl-4-(piperidin-4-ylphenyl)-N-2-(isopropylsulfonyl) Phenyl)-2,4-diamine, the structural formula is as shown in formula I below: [0003] [0004] Ceritinib (Ceritinib, formerly known as LDK378) is a progressive lymphoma enzyme (ALK) tyrosine kinase inhibitor developed by Novartis. The treatment of patients with metastatic NSCLC whose disease has progressed or cannot be tolerated after Crizotinib treatment, the trade name is Zykadia. Ceritinib is the second ALK inhibitor approved by the FDA after crizotinib, and also the second drug to be marketed through the quadruple special approval channel after Ibrutinib (Ibrutinib). [0005] Patent WO2008 / 073687A1 disclosed and protected ceritinib and it...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K31/506A61P35/00A61P35/02
Inventor 朱溪薛其俊苗兴亮廖明毅张连第张坤刘杰
Owner HAINAN SIMCERE PHARMA CO LTD
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