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Crystal form of lenalidomide and preparation method thereof

A technology of lenalidomide and crystal form, applied in antipyretic drugs, antineoplastic drugs, organic chemistry, etc., can solve the problems of increasing the complexity of the manufacturing process and increasing the manufacturing cost

Inactive Publication Date: 2011-12-07
GENERICS UK LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This again increases the manufacturing cost and further increases the complexity of the manufacturing process

Method used

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  • Crystal form of lenalidomide and preparation method thereof
  • Crystal form of lenalidomide and preparation method thereof
  • Crystal form of lenalidomide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1 : Preparation of anhydrous lenalidomide according to the first aspect of the invention from 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-nitro-isoindole amine.

[0107] Suspend 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-nitro-isoindole (10.0 g, 0.035 mol) in ethanol (120 ml), And iron powder (9.6 g, 0.175 mol) was added thereto. Hydrochloric acid (18.5 ml) diluted with an equal volume of water was added to the mixture. The reaction mixture was heated to about 65-70 °C and maintained at this temperature for about 1 1 / 2 -2 hours. Cool the reaction mixture and pass Filter through a pad and concentrate the resulting clear filtrate. The pH of the filtrate was adjusted to 7 to 8 with ammonia solution and passed The concentrated filtrate was further filtered through a pad. The filtrate was concentrated again under reduced pressure. The product was finally dissolved in ethanol (50ml) and heated at 45-50°C until a clear solution formed. The solution was cooled ...

Embodiment 2

[0111] Example 2 : The anhydrous crystalline form of lenalidomide according to the first aspect of the present invention is converted into the crystalline form B of lenalidomide of the prior art.

[0112]Anhydrous crystalline lenalidomide (1.5 g) prepared according to Example 1 was dissolved in a mixture of methanol:water (80:20) (22.5 ml) by heating the reaction mixture at 45-50° C. until a clear solution was formed . The solution was cooled slowly to about 25-30°C. When the solution started to appear cloudy, it was cooled to about 0-5°C and held at temperature while stirring at this temperature for 2-3 hours. The crystalline product was filtered, washed with cold methanol (3ml), then dried by vacuum filtration. Finally the product was dried at 45-50°C for about 3 hours under a pressure of 100 mmHg. The resulting dried solid was subjected to XRPD, DSC and TGA analysis, which confirmed that Form B had been prepared as disclosed in WO 2005 / 023192.

[0113] The chemical pu...

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Abstract

The present invention relates to a new crystalline form of lenalidomide having the formula (I) and chemically known as 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl )-piperidine-2,6-dione. The invention further relates to a process for the preparation of said new crystalline form and its use in pharmaceutical formulations for the treatment of autoimmune diseases, inflammation, inflammatory diseases and the management of diseases such as cancer, especially multiple myeloma application.

Description

technical field [0001] The present invention relates to a new crystalline form of lenalidomide having formula (I) and chemically known as 3-(4-amino-1-oxo-1,3-dihydro-isoindole-2 -yl)-piperidine-2,6-dione. The invention further relates to a process for the preparation of said new crystalline form and its use in pharmaceutical formulations for the treatment of autoimmune diseases, inflammation, inflammatory diseases and the management of diseases such as cancer, especially multiple myeloma application. [0002] Background technique [0003] Lenalidomide is used to treat a variety of conditions, including autoimmune disorders, inflammation, inflammatory diseases, and cancer. Structurally, it is closely related to thalidomide. [0004] US 5,635,517 and US 6,281,230 describe the preparation of lenalidomide and structural analogs. US 5,635,517 relates to the use of lenalidomide to reduce undesired levels of tumor necrosis factor alpha (TNFα). 1,3-dioxo-2-(2,6-dioxopiperid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04A61P29/00A61P35/00A61P37/00A61P37/02
Inventor 普里扬卡·博萨莱维纳亚克·戈雷阿肖克·佩赫尔维纳伊·舒克拉
Owner GENERICS UK LTD
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