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Method for synthesizing intermediate benzene sulfonamide of type 2 diabetes mellitus drug glimepiride

A technology for isobenzenesulfonamide and diabetes drugs, which is applied in the field of compound preparation, can solve the problems of complex process steps and inconvenient operation, and achieve the effect of simple process and high product yield

Inactive Publication Date: 2013-09-11
姜树林
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Problems solved by technology

[0004] Glimepiride and its intermediate N-4-[2-(3-ethyl-4-methyl-2-oxide-3-pyrroline-1 -Carboxamido)ethyl]-benzenesulfonamide (abbreviated as benzenesulfonamide in the text) is a core intermediate of type Ⅱ diabetes drug, and its synthesis method has been reported a lot, Indian Pat. Appl., 2006MU00502, and Journal of China Pharmaceutical University 38(1), 1-5; 2007; Fine Chemical Intermediates 36(3), 16-18; 2006, etc. reported that the synthesis of this intermediate is to first make phenylethylamine into phenylethyl isocyanate, and then combine with 3-ethyl-4-methylpyrrolidone reaction, further progressive sulfonation and amination, this method has complicated process steps and is not easy to operate

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  • Method for synthesizing intermediate benzene sulfonamide of type 2 diabetes mellitus drug glimepiride
  • Method for synthesizing intermediate benzene sulfonamide of type 2 diabetes mellitus drug glimepiride

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Embodiment 1

[0014] Add 1200 ml of dichloromethane, 170 g of phenethylamine, and 175 g of 3-ethyl-4-methylpyrrolidinone into a 3000 ml three-necked flask, and control the temperature at -10 to 0°C to feed in metered phosgene 132 gram, passed through in about 2 hours, continued to react for 3 hours after passing through, then warmed up to room temperature and stirred for 2 hours to the end of the reaction, added 800 milliliters of water and stirred, concentrated to remove solvent methylene chloride, then added 1000 milliliters of water, stirred and cooled to 0°C, and stirred at this temperature for 3 hours, filtered, washed with 100 milliliters of ethanol, and dried to obtain 195 grams of intermediate N-[2-(3-ethyl-4-methyl-2-oxidized-3-pyrroline -1-Carboxamido)ethyl]-benzene.

[0015] Pump 640 grams of chlorosulfonic acid into a 2000 milliliter reactor, put the jacket into the ice brine and cool down to about 10°C, keep the internal temperature at 10-15°C, and add 195 grams of the inte...

Embodiment 2

[0017] Add 1200 ml of dichloromethane, 170 g of phenethylamine, and 175 g of 3-ethyl-4-methylpyrrolidinone into a 3000 ml three-necked flask, and control the temperature from -10 to 0 ° C to feed metered phosgene 152 gram, passed through in about 2 hours, continued to react for 3 hours after passing through, then warmed up to room temperature and stirred for 2 hours to the end of the reaction, added 800 milliliters of water and stirred, concentrated to remove solvent dichloromethane, then added 1000 milliliters of water, stirred and cooled to 0 ℃, and stirred at this temperature for 3 hours, filtered, washed with 100 milliliters of ethanol, and dried to obtain 198 grams of intermediate N-[2-(3-ethyl-4-methyl-2-oxidized-3-pyrroline- 1-formamido)ethyl]-benzene.

[0018] Pump 640 grams of chlorosulfonic acid into a 2000 milliliter reactor, put the jacket into ice brine to cool down to about 10°C, keep the internal temperature at 10-15°C, and add 198 grams of the intermediate N-[2...

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Abstract

The invention discloses a method for synthesizing the intermediate benzene sulfonamide of type 2 diabetes mellitus drug glimepiride. The method comprises the following steps of: reacting phenylethylamine with 3-ethyl-4-methylpyrrolinone in a solvent under the conditions that a certain temperature is controlled and phosgene is introduced, and after the reaction, performing corresponding treatment to obtain N-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-formylamino)ethyl] benzene (3), and reacting the N-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-formylamino)ethyl] benzene (3) with chlorosulfonic acid to obtain a sulfonated product; reacting the sulfonated product with ammonia water to obtain the crude product of benzene sulfonamide, and then performing solvent refining to obtain the finished product. A reaction formula involved is as shown in the specification. The method provided by the invention is simple in process, easy to operate and high in product yield.

Description

[0001] technical field [0002] The invention relates to a method for synthesizing benzenesulfonamide, an intermediate of glimepiride, a drug for type II diabetes, and belongs to the field of compound preparation. Background technique [0003] 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. 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 oxidative biotransformation, the main metabolites are cyclohexyl hydroxymethyl derivatives (M1) and carboxylated...

Claims

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Application Information

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IPC IPC(8): C07D207/38
Inventor 王德峰朱小飞俞健钧
Owner 姜树林
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