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Synthesis process of dasatinib analogue

A synthesis process and dasatinib technology, which are applied in the field of dasatinib analog synthesis technology, can solve the problems of low bioavailability of drug tablets, low yield, and high preparation cost of dasatinib, and achieve The effect of improving bioavailability, high yield, and shortening synthesis time

Inactive Publication Date: 2018-05-15
湖北广辰药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to solve the problems of high preparation cost of dasatinib in the prior art, low yield and low bioavailability of pharmaceutical tablets, and provides a synthesis process of dasatinib analogues

Method used

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  • Synthesis process of dasatinib analogue

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Effect test

Embodiment 1

[0028] A synthesis technique of dasatinib analogues, comprising the following steps:

[0029] A. Preparation of Intermediate I

[0030] Add xylene and a catalyst into the reaction kettle, feed nitrogen to exhaust the air, then feed CO, after the reaction is complete, the product is subjected to oil-water separation, washing, drying and distillation to obtain 3-5-dimethylbenzaldehyde; then Add the 3-5-dimethylbenzaldehyde, malonic acid, pyridine, and piperidine into another reactor, stir evenly, and heat until the reaction is complete, then add toluene and potassium carbonate solution in the reactor, Adjust the pH value to 8, continue to stir and react for 35 minutes, separate the liquid, take the water layer, then adjust the pH value of the liquid to 3, filter, take the filter residue, wash with water 3 times, and dry to obtain the intermediate product I;

[0031] B. Preparation of Intermediate II

[0032] Add the intermediate product I prepared in step A into the reaction k...

Embodiment 2

[0043] A synthesis technique of dasatinib analogues, comprising the following steps:

[0044] A. Preparation of Intermediate I

[0045] Add xylene and a catalyst into the reaction kettle, feed nitrogen to exhaust the air, then feed CO, after the reaction is complete, the product is subjected to oil-water separation, washing, drying and distillation to obtain 3-5-dimethylbenzaldehyde; then Add the 3-5-dimethylbenzaldehyde, malonic acid, pyridine, and piperidine into another reactor, stir evenly, and heat until the reaction is complete, then add toluene and potassium carbonate solution in the reactor, Adjust the pH value to 10, continue to stir and react for 45 minutes, separate the liquid, take the water layer, then adjust the pH value of the liquid to 4, filter, take the filter residue, wash with water 3 times, and dry to obtain the intermediate product I;

[0046] B. Preparation of Intermediate II

[0047] Add the intermediate product I prepared in step A into the reaction ...

Embodiment 3

[0058] A synthesis technique of dasatinib analogues, comprising the following steps:

[0059] A. Preparation of Intermediate I

[0060] Add xylene and a catalyst into the reaction kettle, feed nitrogen to exhaust the air, then feed CO, after the reaction is complete, the product is subjected to oil-water separation, washing, drying and distillation to obtain 3-5-dimethylbenzaldehyde; then Add the 3-5-dimethylbenzaldehyde, malonic acid, pyridine, and piperidine into another reactor, stir evenly, and heat until the reaction is complete, then add toluene and potassium carbonate solution in the reactor, Adjust the pH value to 9 and continue to stir for 40 n, separate the liquid, take the water layer, then adjust the pH value of the liquid to 4, filter, take the filter residue, wash with water 3 times, and dry to obtain the intermediate product I;

[0061] B. Preparation of Intermediate II

[0062] Add the intermediate product I prepared in step A into the reaction kettle, then a...

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Abstract

The invention discloses a synthesis process of a dasatinib analogue and belongs to the technical field of organic chemistry. The synthesis process comprises the following steps: A, preparing an intermediate product I; B, preparing an intermediate product II; and C, adding a solvent to dissolve the intermediate product II prepared in the step B, adding mixed liquid of tetrahydrofuran, 2-amino-N-(2-chlorine-6-methyl phenyl)-5-thiazole carboxamide and N,N'-diisopropyl ethylamine dropwise at 0 DEG C, performing complete reaction under the condition of room temperature after dropwise addition, heating and evaporating the redundant tetrahydrofuran, adding dichloromethane and water, performing suction filtration and collecting a solid material to obtain the dasatinib analogue. Compared with the dasatinib in the prior art, the product dasatinib analogue obtained by the synthesis process has the advantage of higher bioavailability; and furthermore, the synthesis method is low in cost and the yield of the products is high.

Description

technical field [0001] The invention relates to a synthesis process of dasatinib analogues, belonging to the technical field of organic chemistry. Background technique [0002] Dasatinib (Dasatinib / Sprycel), used for all stages of chronic myelogenous leukemia (chronic phase, accelerated phase, lymphoid adult patients with lineage blast phase and myeloid blast phase). At the same time, the FDA also approved dasatinib through normal procedures for the treatment of adult patients with Philadelphia chromosome-positive acute lymphoblastic leukemia who are resistant or intolerant to other therapies. [0003] Dasatinib is a multi-tyrosine kinase inhibitor, mainly based on the safety and efficacy results and other supporting data from 4 international, multi-center phase II trials including 911 patients. Indications. Its most commonly reported side effects in clinical studies are fluid retention, gastrointestinal symptoms, and bleeding events; the most commonly reported serious si...

Claims

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Application Information

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IPC IPC(8): C07D277/56
CPCC07D277/56
Inventor 桂平年雷绍青
Owner 湖北广辰药业有限公司
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