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Preparation method of glimepiride

A glimepiride and anti-diabetic technology, which is applied in the field of organic synthesis route design and preparation, can solve the problems of harsh reaction conditions, difficult post-processing, many reaction steps, etc., and achieves improved reaction yield, simple reaction steps, and high reaction efficiency. mild effect

Inactive Publication Date: 2018-05-25
董丹丹
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are many synthetic methods for preparing anti-diabetic glimepiride, and the target product can be obtained, there are still many reaction steps, high production costs, difficult post-processing and harsh reaction conditions. Therefore, it is necessary to seek a process step Preparation method of antidiabetic drug glimepiride characterized by simplification, low production cost and mild reaction conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid②

[0031] 3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-(N-phenylethyl)-formamide ① (36g, 7.6mol) was added to tert-amyl alcohol (80ml) , Fuming sulfuric acid (40ml) in a reaction vessel, heated in a water bath to 18°C, TLC detection of the end of the reaction, diluted with dichloromethane (120ml) in the vessel, and adjusted the pH to 6 with saturated sodium bicarbonate, concentrated the organic phase, and added water (60ml) and ethanol (60ml) were recrystallized to obtain 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid②( 33.78g), the yield was 98.27%, and the purity was 99.64%.

Embodiment 2

[0033] Preparation of 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid②

[0034]3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-(N-phenylethyl)-formamide ① (36g, 7.6mol) was added to tert-amyl alcohol (133ml) , Fuming sulfuric acid (58ml) in a reaction vessel, heated to 20°C in a water bath, TLC detection of the end of the reaction, diluted with dichloromethane (150ml) in the vessel, and adjusted the pH to 6.6 with saturated sodium bicarbonate, concentrated the organic phase, and added water (70ml) and ethanol (70ml) were recrystallized to obtain 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid②( 33.81g), the yield was 99.12%, and the purity was 99.7%.

Embodiment 3

[0036] Preparation of 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonic acid②

[0037] (1) Add 3-ethyl-4-methyl-2-oxo-3-pyrroline-1-(N-phenylethyl)-carboxamide ① (36g, 7.6mol) to the tert-amyl alcohol (180ml) and fuming sulfuric acid (73ml) in a reaction vessel, heated to 22.5°C in a water bath, and the reaction was detected by TLC. Dilute (170ml) into the vessel with dichloromethane, adjust the pH to 7 with saturated sodium bicarbonate, and concentrate the organic phase , adding water (85ml) and ethanol (85ml) for recrystallization to obtain 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonate Acid ② (33.79g), the yield was 98.28%, and the purity was 99.66%.

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Abstract

Disclosed is a preparation method of glimepiride. The chemical name of glimepiride is 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-formamido)-ethyl]-phenylsulfonyl]-3-(trans-4-methyl cyclohexyl)-urea, and the chemical formula of glimepiride is C24H34N4O5S. The preparation method of glimepiride aims at solving the deficiency in existing glimepiride preparing methods and is simplified in technicalprocesses, low in production cost and mild in reaction conditions.

Description

Technical field [0001] The invention relates to the technical field of organic synthesis route design and preparation thereof, in particular to the antidiabetic drug glimepiride. Background technique [0002] Glimepiride is a sulfonyl hypoglycemic drug developed by the German company Hoechst Marion Roussel in the 1980s and first launched in Germany. Glimepiride is a third-generation sulfonylurea oral hypoglycemic drug. The main mechanism of its hypoglycemic effect is to stimulate the secretion of insulin by pancreatic β cells and partially increase the sensitivity of surrounding tissues to insulin. This product binds and dissociates faster than glibenclamide with the insulin receptor, and causes less severe hypoglycemia. After oral administration, glimepiride is 100% absorbed in the gastrointestinal tract, and the plasma concentration reaches the peak (Cmax) within 2-3 hours, and the protein binding rate is greater than 99.5%. Glimepiride is completely metabolized through ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/38
CPCC07D207/38
Inventor 董丹丹
Owner 董丹丹
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