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Synthesis method of Teneligliptin dimer impurity

A technology of tiagliptin and synthetic method, applied in the field of synthesis of tiagliptin dimer impurities, achieving the effects of reasonable process design, easy availability of raw materials, and high purity

Active Publication Date: 2020-07-24
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on the study of tiagliptin dimer impurities

Method used

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  • Synthesis method of Teneligliptin dimer impurity
  • Synthesis method of Teneligliptin dimer impurity
  • Synthesis method of Teneligliptin dimer impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] A kind of synthetic method for Geglitin dimer impurity, comprises the following steps:

[0054] (1) Dissolve 10.00g of edaravone in tetrahydrofuran, add 12.32g of thionyl chloride dropwise at room temperature, stir at 80°C for 5 hours to obtain a brown solution, spot the plate to monitor the complete reaction; pour the reaction solution slowly Quenched in ice water, a solid product precipitated out of the water, the water phase was removed by filtration, and the filter cake was vacuum-dried to obtain 9.00 g of brown solid compound II, with a reaction yield of 71.04%.

[0055](2) Dissolve 5.00g of compound II in N,N-dimethylformamide, add 6.81g of tert-butylpiperazine N-formate and 6.36g of cesium carbonate, heat up to 90°C and stir for 3 hours, the reaction is complete to obtain a brown The turbid solution, after returning the reaction solution to room temperature, adjusted the pH to less than 5 with dilute hydrochloric acid in an ice bath, extracted with ethyl acetate ...

Embodiment 2

[0064] A kind of synthetic method for Geglitin dimer impurity, comprises the following steps:

[0065] (1) Dissolve 10.00g of edaravone in N,N-dimethylformamide, add 18.22g of phosphorus oxychloride dropwise at room temperature, stir at 60°C for 12 hours to obtain a light green solution, and spot the plate The completion of the reaction was monitored; the reaction solution was slowly poured into ice water to quench, a solid product was precipitated from the water, the water phase was removed by filtration, and the filter cake was vacuum-dried to obtain 9.08 g of brown solid compound II, with a reaction yield of 71.06%.

[0066] (2) Dissolve 6.00g of compound II in N,N-dimethylformamide, add 4.81g of tert-butylpiperazine N-formate and 8.36g of sodium hydroxide, raise the temperature to 100°C and stir for 15 hours, and the reaction is complete to obtain a Brown-gray turbid liquid. After returning the reaction liquid to room temperature, adjust the pH to less than 5 with dilute h...

Embodiment 3

[0074] A kind of synthetic method for Geglitin dimer impurity, comprises the following steps:

[0075] (1) Dissolve 10.00g of edaravone in N,N-dimethylformamide, add 16.24g of NCS dropwise at room temperature, stir at 70°C for 12 hours to obtain a brown solution, and spot the plate to monitor the completion of the reaction; The reaction solution was slowly poured into ice water to quench, and a solid product was precipitated from the water. The water phase was removed by filtration, and the filter cake was vacuum-dried to obtain 8.57 g of brown solid compound II, with a reaction yield of 67.64%.

[0076] (2) Dissolve 8.00g of compound II in N,N-dimethylformamide, add 15.81g of tert-butylpiperazine N-formate and 20.36g of sodium carbonate, raise the temperature to 80°C and stir for 18 hours, the reaction is complete to obtain a brown The turbid solution, after returning the reaction solution to room temperature, adjusted the pH to less than 5 with dilute hydrochloric acid in an...

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Abstract

The invention discloses a synthesis method of a Teneligliptin dimer impurity, and the method comprises the following steps: by using edaravone and 1-(3-methyl-1-phenyl-5-pyrazolyl) piperazine as raw materials, carrying out eight-step reaction to synthesize the Teneligliptin dimer impurity. The method is reasonable in whole process design, high in operability, mild in reaction condition and high inyield, and industrial production can be achieved; the prepared Teneligliptin dimer is high in impurity purity, provides a basis for quality control and safety and efficiency evaluation of Teneligliptin, and can be developed and used for treating type II diabetes mellitus.

Description

technical field [0001] The invention belongs to medicine synthesis technology, in particular to a method for synthesizing tiagliptin dimer impurities. Background technique [0002] Tiagliptin is a dipeptidyl peptidase-IV inhibitor oral hypoglycemic drug researched and developed by Mitsubishi Tanabe Pharmaceutical Co., Ltd. in Japan. It is mainly used for the treatment of type Ⅱ diabetes in clinical practice. Tiagliptin reduces the inactivation of glucagon-like peptides in the body by inhibiting the activity of DPP-IV, promotes the production of insulin by islet cells, and at the same time reduces the concentration of glucagon, thereby lowering blood sugar. The drug has good tolerance, low incidence of adverse reactions, no adverse reactions such as hypoglycemia and weight gain, and the combined drug also has obvious hypoglycemic effect. [0003] With the reduction of physical activity and unhealthy diet, diabetes has become a serious disease that endangers human health. Pr...

Claims

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Application Information

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IPC IPC(8): C07D403/14
CPCC07D403/14
Inventor 何旭王加燕张池刘春王忠义崔希林
Owner TLC NANJING PHARMA RANDD CO LTD
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