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A kind of preparation method of vildagliptin cyclic amidine impurity

A vildagliptin cyclic amidine and impurity technology, applied in the field of medicinal chemistry, can solve the problems of complex process and high cost, and achieve the effects of high yield, reduced research and development costs, and mild reaction conditions

Active Publication Date: 2020-02-21
SHANGHAI PHARMA GRP QINGDAO GROWFUL PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The vildagliptin cyclic amidine impurity is a specific degradation impurity in vildagliptin preparations. The synthesis method of this impurity has not been reported in the literature so far. It can only be extracted from the preparation during the current research and development process, and the impurity is extracted from the preparation The process is complicated and the cost is extremely high

Method used

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  • A kind of preparation method of vildagliptin cyclic amidine impurity
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  • A kind of preparation method of vildagliptin cyclic amidine impurity

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Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of vildagliptin cyclic amidine impurity

[0025]

[0026] Add 30.3g vildagliptin (I) (0.1mol) and 200ml ethanol to a 1000ml four-necked bottle equipped with mechanical stirring, condenser, thermometer and heating device, and then add 200ml aqueous solution of 20g sodium hydroxide (0.5mol) , the temperature was raised to 40° C., and the reaction was carried out for 5 hours, and the reaction was completed. Cool to room temperature and filter, evaporate the filtrate to dryness, then add 500ml of a mixed solution of methanol and dichloromethane (methanol:dichloromethane=1:10 (v:v)), stir to dissolve, filter, and evaporate the filtrate to obtain a white solid , which is the degradation impurity (II) of vildagliptin amide, with a yield of 85%.

Embodiment 2

[0027] Embodiment 2: Preparation of vildagliptin cyclic amidine impurity

[0028] Add 30.3g vildagliptin (I) (0.1mol) and 200ml methanol to a 1000ml four-necked bottle equipped with mechanical stirring, condenser, thermometer and heating device, then add 200ml aqueous solution of 28g potassium hydroxide (0.5mol) , the temperature was raised to 60° C., and the reaction was carried out for 5 hours, and the reaction was completed. Cool to room temperature and filter, evaporate the filtrate to dryness, then add 500ml of a mixed solution of methanol and dichloromethane (methanol:dichloromethane=1:10 (v:v)), stir to dissolve, filter, and evaporate the filtrate to obtain a white solid , which is the degradation impurity (II) of vildagliptin amide, with a yield of 80%.

Embodiment 3

[0029] Embodiment 3: Preparation of vildagliptin cyclic amidine impurity

[0030] Add 30.3g vildagliptin (I) (0.1mol) and 200mlDMF in the 1000ml four-necked bottle equipped with mechanical stirring, condenser, thermometer, heating device, add 200ml aqueous solution of 28g potassium hydroxide (0.5mol) again, The temperature was raised to 70° C., and the reaction was completed for 5 hours. Cool to room temperature and filter, evaporate the filtrate to dryness, then add 500ml of a mixed solution of methanol and dichloromethane (methanol:dichloromethane=1:10 (v:v)), stir to dissolve, filter, and evaporate the filtrate to obtain a white solid , which is the degradation impurity (II) of vildagliptin amide, with a yield of 90%.

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Abstract

The invention discloses a method for preparing a vildagliptin cyclic amidine impurity. Vildagliptin (I) is added into a reaction solvent, an alkali is added, the temperature is raised to 30-180° C., and the reaction time is 2-8 hours, and the reaction solution is carried out After purification, the vildagliptin cyclic amidine impurity (II) can be obtained. The present invention proposes the synthetic method of vildagliptin cyclic amidine impurity for the first time, uses vildagliptin as raw material, adopts one-step cyclization reaction to prepare vildagliptin cyclic amidine impurity, reaction condition is mild, easy to operate, yield high. Products meeting quality standards can be obtained after simple purification, effectively reducing research and development costs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of vildagliptin cyclic amidine impurity. Background technique [0002] Vildagliptin was developed by Novartis and was approved for marketing by the European Union in 2007. On August 15, 2011, CFDA officially approved vildagliptin to be launched in China. Vildagliptin can be used in combination with biguanides, thiazolidinediones, and sulfonylureas to treat type 2 diabetes. Vildagliptin can reduce fasting and postprandial blood glucose levels, postprandial glucagon secretion and improve β-cell function, which provides a new option for the treatment of type Ⅱ diabetes patients. Vildagliptin's sales grew strongly after its launch, reaching US$677 million in 2011, and the total sales in the first three quarters of 2012 were close to US$655 million. [0003] The following is the structure of the degradation impurity of vildagliptin cyclic amidine:...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 卢伟伸周振宇祖金祥张欣
Owner SHANGHAI PHARMA GRP QINGDAO GROWFUL PHARMA CO LTD
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