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Method for preparing torasemide and derivative thereof

A technology of torasemide and derivatives, applied in the field of drug synthesis, can solve the problems of high price, skin irritation, high toxicity of isopropyl isocyanate, etc., and achieve production capacity improvement, reaction time shortening, and reaction conditions. mild effect

Inactive Publication Date: 2015-07-01
NANJING CHANGAO PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The disadvantage of this method is that isopropyl isocyanate is very toxic, strongly irritating to the respiratory tract, can cause pulmonary edema, is also irritating to eyes and skin, can cause burns, and its price is very expensive
Isopropyl isocyanate is also flammable, which brings certain safety hazards to production

Method used

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  • Method for preparing torasemide and derivative thereof
  • Method for preparing torasemide and derivative thereof
  • Method for preparing torasemide and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The preparation of embodiment 1N-ethyl-[4-(3-methylphenylamino)pyridine-3-sulfonamido]formamide

[0020] Add 500mL ethanol to a 1L three-necked flask, add N-ethyl-1H-imidazole-1-carboxamide (69.58g, 0.50mol), 4-(3-methylphenylamino)pyridine-3-sulfonamide (105.3g , 0.40mol), and mix well under stirring. Heat to reflux, react for 7-8 hours, distill under reduced pressure, and concentrate to dryness. Add 125mL of concentrated ammonia water (25-28%) and 500mL of purified water to the residue, heat and dissolve under stirring, and after complete clarification, add 1.0g of activated carbon, keep warm and decolorize and stir for 15-30min. Filtrate while it is hot, cool the filtrate to 40-50°C, neutralize the filtrate with glacial acetic acid to pH=6-7, cool to 10-20°C, crystallize for 4 hours and then filter. The filter cake was washed twice with purified water. The wet product is air-dried at 60-65°C for 6-8 hours. Weigh, weight is 80g, and yield is 60.0%. ESI-MS(m / z): 3...

Embodiment 2

[0021] The preparation of embodiment 2N-ethyl-[4-(3-methylphenylamino)pyridine-3-sulfonamido]formamide

[0022] Add 500mL ethanol to a 1L three-necked flask, add N-ethyl-1H-imidazole-1-carboxamide (69.58g, 0.50mol), 4-(3-methylphenylamino)pyridine-3-sulfonamide (105.3g , 0.40mol) and pyridine (79.1g, 1.0mol), mix well under stirring. Heat to reflux and react for 4-6 hours. TLC monitoring, after the completion of the reaction, vacuum distillation, concentrated to dryness. Add 125mL of concentrated ammonia water (25-28%) and 500mL of purified water to the residue, heat and dissolve under stirring, and after complete clarification, add 1.0g of activated carbon, keep warm and decolorize and stir for 15-30min. Filtrate while it is hot, cool the filtrate to 40-50°C, neutralize the filtrate with glacial acetic acid to pH=6-7, cool to 10-20°C, crystallize for 4 hours and then filter. The filter cake was washed twice with purified water. The wet product is air-dried at 60-65°C for ...

Embodiment 3

[0023] The preparation of embodiment 3N-isopropyl-[4-(3-methylphenylamino)pyridine-3-sulfonamido]formamide

[0024] Add 500mL of acetone into a 1L three-necked flask, add N-isopropyl-1H-imidazole-1-carboxamide (76.60g, 0.50mol), 4-(3-methylphenylamino)pyridine-3-sulfonamide (105.3 g, 0.40mol) and triethylamine (101.2g, 1.0mol), mix well under stirring. Heat up to 40-50°C and react for 4-6 hours. TLC monitoring, after the reaction is complete, distill under reduced pressure and concentrate to dryness. Add 125mL of concentrated ammonia water (25-28%) and 500mL of purified water to the residue, heat and dissolve under stirring, and after complete clarification, add 1.0g of activated carbon, keep warm and decolorize and stir for 15-30min. Filtrate while it is hot, cool the filtrate to 40-50°C, neutralize the filtrate with glacial acetic acid to pH=6-7, cool to 10-20°C, crystallize for 4 hours and then filter. The filter cake was washed twice with purified water. The wet produc...

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Abstract

The invention belongs to the field of medicine synthesis and provides a method for preparing torasemide and a derivative thereof. The method comprises the following steps: by taking N-alkyl-1H-imidazole-1-formamide as the raw material, reacting with 4-(m-toluene amino) pyridine-3-sulfamide to obtain the torasemide and the derivative thereof. The method for preparing the torasemide and the derivative thereof has the advantages of low toxin, low pollution, high safety, short production period and simple operation and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a preparation method of torasemide and derivatives thereof. Background technique [0002] Torsemide (trade name Developed by Swiss Nycomed pharma company, it is used for the treatment of acute renal failure, chronic renal failure and essential hypertension. It was first launched in Germany in 1993 and in the United States the following year. Torasemide is a powerful diuretic, and its mechanism of action is similar to that of furosemide. It mainly acts on the thick segment of the ascending limb of the renal loop of Henle, inhibiting the active reabsorption of Cl-, reducing the reabsorption of NaCl in the ascending limb of the Henle of Henle, and the renal medulla The osmotic pressure of the substance decreases, and the osmotic pressure in the lumen increases, which interferes with the process of urine concentration. Unlike other loop diuretics, torasemide ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74
CPCC07D213/74
Inventor 魏伟业霍立茹杨晓兵王正泽陈慧林辉高忠旗
Owner NANJING CHANGAO PHARMA SCI & TECH CO LTD
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