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Synthesizing method of imatinib

A synthetic method, imatinib technology, applied in the field of organic compound synthesis, can solve the problems of large pollution, low cost, and prolonged cycle, and achieve the effects of reducing pollution, reducing production costs, and improving production efficiency

Inactive Publication Date: 2016-07-06
ANHUI HAIKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the most simple and economical synthesis method of imatinib is to use imaic acid and thionyl chloride to make imayl chloride, and then dock with imatinib to form imatinib. The advantage of this method is low cost, and the disadvantages are Thionyl chloride is highly corrosive and polluting, and there are patents related to the synthesis method of imatinib in the existing patented technology. Among them, a Chinese invention patent with the patent number ZL200810202634.X discloses a kind of imatinib Ni's synthetic method, it adopts imamamine and 4-(4-methylpiperazine-1-methyl)-benzoic acid ester to react, and in synthetic 4-(4-methylpiperazine-1-methyl) - The product imaic acid in the benzoate process can be directly synthesized with imatinib under the action of a suitable catalyst and dehydrating agent. Therefore, the processing method in this patent has a high cost and a prolonged cycle; And Chinese patent CN101016293A discloses another kind of synthetic method of imatinib, and the halogenated reagent used in it is highly toxic substance such as phosphorus oxychloride, which is not conducive to the protection of the environment

Method used

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  • Synthesizing method of imatinib
  • Synthesizing method of imatinib
  • Synthesizing method of imatinib

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 200ml of dimethylformamide into a 1000ml reaction bottle, then add 28g of imamic acid under stirring, stir until the reaction system is dissolved and transparent, continue stirring, and then add 41g of dicyclohexylcarbodiimide and 35g of imaic acid , 1g of 4-dimethylaminopyridine, then, the temperature in the reaction system will rise, cool with cold water on the outside of the reaction bottle, keep the reaction temperature between 20-30 degrees Celsius, the reaction time needs to be overnight; Observe that the raw material point imamamine basically disappears, and stop the reaction; then add 200ml of water to the reaction bottle, a white solid will precipitate in the system, exotherm, continue to stir for 2 hours and then filter, the filter cake is washed with a small amount of dimethyl Add 200ml of water to the filtrate and continue to stir, and the stirring time needs to be overnight; the next day, filter with suction, rinse the filter cake with a small amount of ...

Embodiment 2

[0027] Add 200ml of tetrahydrofuran into a 1000ml reaction bottle, and then add 28g of imaamine under stirring, stir until the reaction system is dissolved and transparent, continue stirring, and then add 41g of dicyclohexylcarbodiimide, 35g of imaic acid, 4-di 1g of methylaminopyridine, then, the reaction system will heat up, cool with cold water on the outside of the reaction bottle, keep the reaction temperature between 20-30 degrees Celsius, the reaction time needs to be overnight; on the second day, by spotting the plate, observe The raw material point imamamine basically disappeared, and the reaction was stopped; then 200ml of water was added to the reaction flask, and a white solid would precipitate out of the system, exothermic, continue to stir for 2 hours and then filter, the filter cake was rinsed with a small amount of tetrahydrofuran, and the filtrate was added to Continue to stir with 200ml of water, and the stirring time needs to be overnight; the next day, sucti...

Embodiment 3

[0029] Add 200ml of dichloromethane into a 1000ml reaction bottle, then add 28g of imaamine under stirring, stir until the reaction system is dissolved and transparent, continue stirring, then add 41g of dicyclohexylcarbodiimide, 35g of imaic acid, 4 -Dimethylaminopyridine 1g, then, the reaction system will heat up, cool with cold water on the outside of the reaction bottle, keep the reaction temperature between 20-30 degrees Celsius, the reaction time needs to be overnight; the second day by spotting the plate , observe that the raw material point imamamine basically disappears, and stop the reaction; then add 200ml of water to the reaction bottle, a white solid will be precipitated in the system, exothermic, continue to stir for 2 hours and then filter, and the filter cake is drenched with a small amount of dichloromethane Wash, add 200ml water to the filtrate and continue to stir, and the stirring time needs to be overnight; the next day, filter the filter cake with a small ...

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Abstract

The invention relates to the field of organic compound synthesis, in particular to a synthesizing method of imatinib.The materials of 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride, N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, dicyclohexylcarbodiimide and 4-dimethylaminopyridine are added.According to the method, 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride and N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine are added to an organic solution of dicyclohexylcarbodiimide, the catalyst 4-dimethylaminopyridine is added, imatinib is synthesized in one step, the production efficiency is improved, and meanwhile the production cost is reduced.Meanwhile, the dehydrating agent dicyclohexylcarbodiimide is used, the reaction between 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride and N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine is thorough, dicyclohexylurea (DCU) is generated from dicyclohexylcarbodiimide (DCC) after the reaction is completed, recycling can be achieved, and the degree of contamination is reduced.

Description

technical field [0001] The invention relates to the field of organic compound synthesis, in particular to a synthesis method of imatinib. Background technique [0002] Imatinib is an oral drug for the treatment of adult patients with Philadelphia chromosome-positive chronic myeloid leukemia in the blast phase, accelerated phase, and chronic phase after failure of interferon therapy. Its chemical molecular formula is: C 29 h 31 N 7 O, its chemical name is: 4-(4-methylpiperazinyl-1-methyl)-N-[4-methyl-3-[4-(3-pyridyl)pyrimidine-2-amino]- Benzamide; its structural formula is: [0003] [0004] At present, the most simple and economical synthesis method of imatinib is to use imaic acid and thionyl chloride to make imayl chloride, and then dock with imatinib to form imatinib. The advantage of this method is low cost, and the disadvantages are Thionyl chloride is highly corrosive and polluting, and there are patents related to the synthesis method of imatinib in the existin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 张小顺
Owner ANHUI HAIKANG PHARMA
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