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Novel 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindole-2-yl)-2,6-piperidinedione crystal forms and preparation method thereof

A technology of piperidinedione and piperidinedione salt is applied in the field of preparation of new crystal forms, and can solve the problems of long cycle, large amount of solvent, high energy consumption and cost

Inactive Publication Date: 2014-09-03
SHANGHAI ACEBRIGHT PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that acetonitrile is about 150 times the solute, the amount of solvent is very large, energy consumption and cost are high, and the cycle is long and the production capacity is low

Method used

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  • Novel 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindole-2-yl)-2,6-piperidinedione crystal forms and preparation method thereof
  • Novel 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindole-2-yl)-2,6-piperidinedione crystal forms and preparation method thereof
  • Novel 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindole-2-yl)-2,6-piperidinedione crystal forms and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0194] Preparation of new crystal form X of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

[0195] Mix 43g of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione methanesulfonate raw material with 690ml of deionized water, Add it into a 1L three-necked flask, stir and mix well at room temperature until the solute is completely dissolved; filter the solution under reduced pressure, and transfer the resulting clear solution into another 2L three-necked flask. Adjust the mechanical stirrer, add dropwise 400ml of aqueous sodium bicarbonate solution with a concentration of 0.525mol / L, and start the reaction crystallization process; after dropping, under the protection of nitrogen, raise the temperature of the system to 80-82°C and keep it warm for 30 hours, then lower the temperature of the system to 53~56°C, filter the crystalline slurry with suction, wash the filter cake three times with a certain volume of deionized water at about 55°C; vacuum...

Embodiment 2

[0199] Preparation of new crystal form X of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

[0200] Mix 30g of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione methanesulfonate raw material with 750ml of deionized water, Add it into a 1L three-necked flask, stir and mix well at room temperature until the solute is completely dissolved; filter the solution under reduced pressure, and transfer the resulting clear solution into another 2L three-necked flask. Adjust the mechanical stirrer, add dropwise 300ml of aqueous sodium bicarbonate solution with a concentration of 0.525mol / L, and start the reaction crystallization process; after dropping, under the protection of nitrogen, raise the temperature of the system to 80-83°C and keep it warm for 28 hours, then lower the temperature of the system to 55~58°C, filter the crystalline slurry with suction, wash the filter cake twice with a certain volume of deionized water at about 55°C; dry the filt...

Embodiment 3

[0203] Preparation of new crystal form XI of 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione

[0204] The volume ratio of 37g 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione methanesulfonate raw material to 400ml is 20 : 80 deionized water / methanol mixed solvent, add in a 1L three-necked flask, stir and mix well at room temperature until the solute is completely dissolved; filter the solution under reduced pressure, and transfer the resulting clear solution into another 1L three-necked flask. Stir fully, slowly add triethylamine to the solution, and start the reaction crystallization process; during the dropwise addition, a large amount of off-white solids precipitate; when the pH of the system is adjusted to 8.3, under nitrogen protection, stir at room temperature for 4 hours, and filter the crystal slurry , the filter cake was washed 3 times with deionized water; the filter cake was vacuum-dried for 20 hours at room temperature to obtain...

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Abstract

The invention relates to novel 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindole-2-yl)-2,6-piperidinedione crystal form and a preparation method thereof, and particularly to four novel crystal forms, namely, crystal form X, crystal form XI, crystal form XII and crystal form XIII, and the preparation method of the novel crystal forms. The four novel crystal forms are stable to store, good in flowability, small in static electricity, more applicable to medicine preparations, simple and efficient in preparation process, capable of achieving on-scale production and environmental friendly.

Description

technical field [0001] The present invention relates to crystalline forms of organic chemical and pharmaceutical compounds, more particularly to 3-(4-amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2, Four new crystal forms X, XI, XII and XIII of 6-piperidinedione, and the preparation method of the new crystal forms. Background technique [0002] 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione, molecular formula: C 13 h 13 N 3 o 3 , molecular weight: 259.26, CAS number: 191732-72-6, its molecular structure formula is as follows: [0003] [0004] 3-(4-Amino-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-2,6-piperidinedione, Chinese name Lenalidomide, commodity Revlimid is a drug developed by Celgene Corporation of the United States for the treatment of fatal blood diseases and cancer. It is currently the most effective drug for the treatment of multiple myeloma. More than half of the patients who take this drug can prolong their survival time by 3 more than a year...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61K31/454A61P35/00A61P7/00
CPCC07D401/04
Inventor 安晓霞吕峰李祯祖远远邓义
Owner SHANGHAI ACEBRIGHT PHARMA CO LTD
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