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New ibrutinib crystal form and preparation method thereof

A technology of ibrutinib and crystal form, which is applied in the field of medicinal chemistry and can solve problems such as unsuitable preparation development

Inactive Publication Date: 2016-11-16
SHANGHAI ACEBRIGHT PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] WO2016025720A discloses acetic acid solvate crystal form G and anisole solvate crystal form J of ibrutinib, which are also unsuitable for further formulation development

Method used

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  • New ibrutinib crystal form and preparation method thereof
  • New ibrutinib crystal form and preparation method thereof
  • New ibrutinib crystal form and preparation method thereof

Examples

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preparation example Construction

[0055] The present invention also provides a preparation method of the crystal III, comprising the steps of:

[0056] (i) dissolving crude ibrutinib I in an organic solvent, with a weight-to-volume ratio of 1:1-1:30 g / ml;

[0057] (ii) crystallization at -10°C to 90°C to obtain the crystal form III;

[0058] Wherein, the crude ibrutinib I is selected from the following group: ibrutinib crystal form C, ibrutinib amorphous substance, ibrutinib crystal form A, or a combination thereof.

[0059] In another preferred example, in the step (i), the organic solvent is selected from the group consisting of alcohol solvents, ester solvents, ketone solvents, alkanes, or combinations thereof, preferably alcohol solvents A mixed solvent with an alkane, a mixed solvent with an ester solvent and an alkane, a mixed solvent with a ketone solvent and an alkane, or a combination thereof.

[0060] As used herein, the number of carbon atoms of each of the alcohol solvents, ester solvents, ketone...

Embodiment 1

[0093] Example 1 Preparation of ibrutinib crystal form III

[0094] Add amorphous ibrutinib (5.0 g) into 50 ml of n-propanol, and heat to reflux to dissolve. Continue stirring for 30 minutes after dissolving. Stop heating, cool down at a speed of about 1 °C / min, cool to 50 °C, solids precipitate out, keep stirring for 2 hours, filter, the filtrate is rinsed with ethyl acetate, and the filter cake is vacuum-dried at 50 °C to obtain 3.2 g of product.

[0095] Result: The powder X-ray diffraction pattern of the obtained solid is as follows figure 1 Characterized by the differential thermal scanning spectrum as figure 2 As shown, thermogravimetric analysis such as image 3 As shown, the infrared Fourier transform spectrum is shown as Figure 4 shown.

Embodiment 2

[0096] Example 2 Preparation of ibrutinib crystal form III

[0097] Ibrutinib Form C (5.0 g) was added to 75 ml of isopropanol, stirred overnight at room temperature, the resulting suspension was filtered, and vacuum-dried at 50° C. to constant weight to obtain 3.9 g of a white solid.

[0098] Result: the powder X-ray diffraction pattern of the obtained solid is the same as the crystal form obtained in Example 1.

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Abstract

The invention provides a new ibrutinib crystal form and a preparation method thereof. More specifically, the invention provides an ibrutinib crystal form III and a preparation method thereof. The ibrutinib crystal form III prepared by the preparation method has good heat stability, and is stably stored under the conventional conditions, thus being suitable for industrial application.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, specifically, the present invention relates to 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d A new crystal form III of ]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one, and a preparation method and use of the new crystal form. Background technique [0002] Ibrutinib (Ibrutinib) is jointly developed by American Pharmacyclics Company and Johnson & Johnson, the trade name is Imbruvica, and its chemical name is: 1-[(3R)-3-[4-amino-3-(4-phenoxybenzene Base)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one, the structural formula X is as follows: [0003] [0004] Ibrutinib is a first-in-class oral Bruton's tyrosine kinase (BTK) inhibitor, which selectively co-activates cysteine ​​residues (Cys-481) with the target protein Btk active site. It binds to BTK and irreversibly inhibits BTK, thereby effectively preventing the migration of tumors from B cells to lymphoid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00
CPCC07D487/04C07B2200/13
Inventor 任华森蔡志刚杨勤刚
Owner SHANGHAI ACEBRIGHT PHARMA GRP
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