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Preparation method of pomalidomide

A technology for pomalidomide and a compound is applied in the field of preparation of anticancer drug pomalidomide, which can solve the problems of numerous steps, complicated operation, and difficulty in realizing industrialized production, and achieves reduction of production cost, short synthesis route and raw materials. easy-to-get effect

Active Publication Date: 2017-11-07
LIANYUNGANG RUNZHONG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The raw material 3-aminophthalate hydrochloride used in this route is produced by crystallization of 3-aminophthalic acid in concentrated hydrochloric acid. The production process is dangerous and corrosive to production equipment, and the method is complicated to operate. , there are many steps, precise temperature control is required, and it is difficult to realize industrial production

Method used

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  • Preparation method of pomalidomide
  • Preparation method of pomalidomide
  • Preparation method of pomalidomide

Examples

Experimental program
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Effect test

Embodiment 1

[0020]

[0021] Acetonitrile (100 mL), acetic acid (25.41 mL, 444.2 mmol), triethylamine (22.48 g, 222.1 mmol), disodium 3-aminophthalate (10 g, 44.4 mmol), 3-aminopiperidine-2, Add 6-diketone hydrochloride (7.68g, 46.6mmol) into the reaction flask, heat to 80-85°C and reflux. After 6 hours of reaction, the reaction is complete. Cool the reaction solution to 20-25°C, slowly add purified water, stir and analyze Crystallized for 2 hours, filtered, and the filter cake was dried under reduced pressure at 60±5°C for 8 hours to obtain 8.98 g of a black solid with a yield of 74.0% and a purity of 99.1%.

Embodiment 2

[0023] Acetonitrile (100 mL), acetic acid (25.41 mL, 444.2 mmol), triethylamine (12.62 mL, 88.8 mmol), disodium 3-aminophthalate (10 g, 44.4 mmol), 3-aminopiperidine-2, Add 6-diketone hydrochloride (7.68g, 46.6mmol) into the reaction flask, heat to 80-85°C to reflux, react for 8 hours, cool the reaction solution to 20-25°C, slowly add purified water, stir and crystallize for 2 hours , filtered, and the filter cake was dried under reduced pressure at 60±5° C. for 8 hours to obtain 8.9 g of yellow solid, yield: 73.3%, purity: 99.2%. Example 3

Embodiment 3

[0024] Acetonitrile (100mL), acetic acid (25.41mL, 444.2mmol), anhydrous sodium acetate (18.22g, 222.1mmol), disodium 3-aminophthalate (10g, 44.4mmol), 3-aminopiperidine-2 , Add 6-diketone hydrochloride (7.68g, 46.6mmol) into the reaction flask, heat to 80-85°C to reflux, react for 8 hours and complete the reaction, cool the reaction solution to 20-25°C, slowly add purified water, stir Crystallize for 2 hours, filter, and dry the filter cake under reduced pressure at 60±5°C for 8 hours to obtain 10.2 g of a yellow solid with a yield of 84.0% and a purity of 99.4%.

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Abstract

The invention relates to a preparation method of pomalidomide. The preparation method includes a process of using 3-aminopiperidine-2, 6-dione hydrochloride (which is a compound shown in the formula I) and disodium 3-amino phthalate (which is a compound shown in the formula II) as raw materials. The method is simple and short in route, simple to operate, available in raw materials, reduced in production cost, and suitable for massive industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of an anti-cancer drug pomalidomide. Background technique [0002] Pomalidomide is an oral TNF-α synthesis inhibitor developed by Celgene Crop in the United States. In the treatment of relapsed and refractory multiple myeloma (MM), its racemic mixture is clinically used, and its structural formula is shown in the following formula: [0003] [0004] CN101253163 discloses a preparation method of pomalidomide: a mixture of 3-aminophthalic acid hydrochloride, 3-aminoglutarimide hydrochloride, acetonitrile and acetic acid is added to the reactor. After stirring the mixture for 15 minutes, triethylamine was added dropwise over 30-35 minutes while maintaining the reaction temperature at 20-25°C. The reaction mixture is then stirred for a further 10-15 minutes and then refluxed at about 85-87°C for about 5-7 hours or until in-process controls indica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 高策程兴栋张爱明夏春光张喜全
Owner LIANYUNGANG RUNZHONG PHARMA CO LTD
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