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Method for preparing hydrobromic acid teneligliptin

A technology of hydrobromic acid and glutamic acid, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of high cost, low yield and purity, and achieve the effect of low cost

Inactive Publication Date: 2017-01-25
南通普悦生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the prior art, the method for preparing teneligliptin hydrobromide generally has higher cost, lower yield and purity

Method used

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  • Method for preparing hydrobromic acid teneligliptin
  • Method for preparing hydrobromic acid teneligliptin
  • Method for preparing hydrobromic acid teneligliptin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] This embodiment relates to a preparation method of Teliliptin hydrobromide, which includes the following steps:

[0045] S1: Add glutamic acid to the reaction tank, heat the oil bath to 220-290°C, stir and dehydrate, react at 130-180°C for 40-70 minutes, put it in water, cool, and filter to obtain crude pyroglutamic acid. Add water to the crude pyroglutamic acid to saturate it at 40-70°C, cool to 30-40°C to crystallize, separate the crystals, wash with detergent, and dry to obtain a refined pyroglutamic acid;

[0046] S2: Add absolute ethanol to the flask, cool to below -5°C with an ice-salt bath, add the catalyst and the pyroglutamic acid obtained in step S1, stir and slowly raise the temperature to react at 20-45°C for 24 to 48 hours; in use Adjust the pH to 7-8 with alkali, collect the filtrate by filtration, wash the filter residue with detergent, combine the washing and filtrate and concentrate to obtain a crude product, which is purified by distillation under the condi...

Embodiment 2

[0062] This embodiment relates to a preparation method of Teliliptin hydrobromide, which includes the following steps:

[0063] S1: Add glutamic acid to the reaction tank, heat the oil bath to 220-290°C, stir and dehydrate, react at 130-180°C for 40-70 minutes, put it in water, cool, and filter to obtain crude pyroglutamic acid. Add water to the crude pyroglutamic acid to saturate it at 40-70°C, cool to 30-40°C to crystallize, separate the crystals, wash with detergent, and dry to obtain a refined pyroglutamic acid;

[0064] S2: Add absolute ethanol to the flask, cool to below -5°C with an ice-salt bath, add the catalyst and the pyroglutamic acid obtained in step S1, stir and slowly raise the temperature to react at 20-45°C for 24 to 48 hours; in use Adjust the pH to 7-8 with alkali, collect the filtrate by filtration, wash the filter residue with detergent, combine the washing and filtrate and concentrate to obtain a crude product, which is purified by distillation under the condi...

Embodiment 3

[0080] This embodiment relates to a preparation method of Teliliptin hydrobromide, which includes the following steps:

[0081] S1: Add glutamic acid to the reaction tank, heat the oil bath to 220-290°C, stir and dehydrate, react at 130-180°C for 40-70 minutes, put it in water, cool, and filter to obtain crude pyroglutamic acid. Add water to the crude pyroglutamic acid to saturate it at 40-70°C, cool to 30-40°C to crystallize, separate the crystals, wash with detergent, and dry to obtain a refined pyroglutamic acid;

[0082] S2: Add absolute ethanol to the flask, cool to below -5°C with an ice-salt bath, add the catalyst and the pyroglutamic acid obtained in step S1, stir and slowly raise the temperature to react at 20-45°C for 24 to 48 hours; in use Adjust the pH to 7-8 with alkali, collect the filtrate by filtration, wash the filter residue with detergent, combine the washing and filtrate and concentrate to obtain a crude product, which is purified by distillation under the condi...

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Abstract

The invention provides a method for preparing hydrobromic acid teneligliptin. The method includes steps of preparing L-hydroxyproline; mixing the L-hydroxyproline and sodium bicarbonate with each other to obtain mixtures, dissolving the mixtures in water, adding acetone into the water, dropping di-tert-butyl dicarbonate into the water, carrying out room-temperature reaction overnight and then treating reaction products to obtain t-butyloxycarboryl-N-hydroxyproline; preparing t-butyloxycarboryl-N-4-oxo-proline from the t-butyloxycarboryl-N-hydroxyproline; preparing (2S)-4-oxo-2-(3-thiazolidine carbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester from the t-butyloxycarboryl-N-4-oxo-proline; preparing compounds III from compounds IV; preparing compounds II from the compounds III; preparing compounds 1-(3-methyl-1-phenyl-1H-pyrazole-5-base) piperazine from the compounds II; preparing intermediates I; preparing the hydrobromic acid teneligliptin from the intermediates I. The method has the advantages that the method is low in cost, and the cost of the method is only two-thirds of the cost of an existing method in the prior art; the yield of the hydrobromic acid teneligliptin is higher than 95%, and the purity of the hydrobromic acid teneligliptin is higher than 98%.

Description

Technical field [0001] The invention relates to a preparation method of Teliliptin hydrobromide, and belongs to the technical field of medicine synthesis. Background technique [0002] Diabetes (Diabetes Mellitus) is a chronic comprehensive disease mainly caused by glucose metabolism disorder caused by absolute or relative lack of insulin or decreased sensitivity of target cells to insulin, which seriously affects the health and quality of life of patients. Diabetes is clinically divided into insulin-dependent diabetes (type I diabetes) and non-insulin-dependent diabetes (type II diabetes), among which type II diabetes patients account for more than 90%. [0003] The prevalence of diabetes in my country is relatively low, but due to the large population base, the number of diabetic patients in my country ranks second in the world, second only to India. China currently has the largest number of type 2 diabetes patients in the world. Due to the increase in type 2 diabetes patients, ...

Claims

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Application Information

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IPC IPC(8): C07D417/14
CPCY02P20/55C07D417/14
Inventor 王林
Owner 南通普悦生物医药有限公司
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