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Preparation method for Dasatinib compound

A dasatinib and compound technology, applied in the field of drug synthesis, to achieve the effects of fewer by-products, improved product yield and purity, and easy operation

Active Publication Date: 2016-11-09
SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] In the above synthetic route of dasatinib, the introduction of the pyrimidine ring is mostly synthesized by reacting 4,6-dichloro-2-methylpyrimidine or 2-methyl-4-amino-6-chloropyrimidine with other intermediates, But all there are certain defectives, so it is necessary to seek a kind of preparation method that can not only simplify process steps, but also can operate simply, reduce by-product, improve product yield and purity new dasatinib

Method used

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  • Preparation method for Dasatinib compound
  • Preparation method for Dasatinib compound
  • Preparation method for Dasatinib compound

Examples

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Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of compound IV

[0033] Take 13.0g of N-hydroxyethylpiperazine and place it in a 1000ml three-necked flask, add 500ml of dichloromethane, stir until dissolved, and react at room temperature; start to add 13.7g of methyl malonate chloride dropwise, and during the dropwise addition process 31.8g of sodium carbonate was added in batches, and after the low price was completed, stirred for 1.5h, the reaction was completed, filtered with suction, washed with distilled water, recrystallized with ethyl acetate, and dried in vacuo to obtain 20.6g of crystal powder with a yield of 88.9%. HPLC purity 99.3%.

Embodiment 2

[0034] Embodiment 2: the preparation of compound IV

[0035] Take 13.0g of N-hydroxyethylpiperazine and place it in a 1000ml three-neck flask, add 500ml of ethyl acetate, stir until dissolved, and react at room temperature; start to add 15.0g of methyl malonate chloride dropwise, Add 12.0 g of sodium hydroxide in batches, after the reduction is completed, stir for 1.5 h, after the reaction is complete, filter with suction, wash with distilled water, recrystallize with ethyl acetate, and dry in vacuo to obtain 21.1 g of crystal powder with a yield of 91.2%. , HPLC purity 99.5%.

Embodiment 3

[0036] Embodiment 3: the preparation of compound IV

[0037] Take 13.0g of N-hydroxyethylpiperazine and place it in a 1000ml three-necked flask, add 500ml of N,N-dimethylformamide, stir until dissolved, and react at room temperature; g, during the dropwise addition, add 10.0 g of potassium bicarbonate in batches, after the low price is completed, stir for 1.5 h, after the reaction is completed, filter with suction, wash with distilled water, recrystallize with ethyl acetate, and dry in vacuo to obtain crystal powder 20.1 g, yield 86.5%, HPLC purity 99.2%.

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Abstract

The invention discloses a preparation method for a Dasatinib compound. The synthetic method provided by the invention comprises the following steps: reacting initial raw material N-piperazine with methyl 3-chloro-3-oxopropanoate, thereby acquiring a compound IV; causing the compound IV react with the compound V, thereby acquiring a compound VI; cyclizing the compound VI and acetamidine hydrochloride, thereby acquiring the Dasatinib. According to the invention, the synthetic route is short, the operation is simple, the reaction condition is mild, the purity and yield are high and the method is fit for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a preparation method of a dasatinib compound. Background technique [0002] Dasatinib is a potent multi-target inhibitor of tyrosine kinases. It is another drug for imatinib-resistant and intolerant CML in the chronic phase after nilotinib. Compared with imatinib and nilotinib, which target the single target of Bcr-Abl fusion protein, dasatinib is a multi-target drug, targeting five key oncogenic tyrosine protein kinases, namely BCR-ABL, SRC, c-KIT, PDGFR and Ephrin (EPH) all played a role. The product was first developed by Bristol-Myers Squibb. It was approved for marketing in the US in June 2006 and launched in the EU in November. Trade name: SPRYCEL. Dasatinib tablets have been approved for marketing in 64 countries. [0003] Dasatinib (Dasatanib, I), the chemical name is N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl ]-2-methyl-4-pyrimidinyl...

Claims

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Application Information

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IPC IPC(8): C07D417/12
CPCC07D417/12
Inventor 刘新泉武玉梅李玉胜
Owner SHANDONG LUOXIN PHARMA GRP HENGXIN PHARMA CO LTD
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