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Green synthesis method for ibuprofen piconol and medicinal preparation thereof

A green synthesis technology of ibuprofen pyridoxine, which is applied in the field of western medicine, can solve the problems of non-recycling, high production cost, and unfriendly environment, and achieve the effects of less three wastes, eliminating troublesome disposal, and easy control of reaction conditions

Inactive Publication Date: 2012-01-04
湖南医药工业研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of this method is that the operation is complicated, the total yield is low, and a large amount of unfriendly raw materials such as thionyl chloride, triethylamine or pyridine are used in the reaction, and it can be seen from the reaction process that there is no recovery The value and measures of utilization produce a large amount of hydrogen chloride and sulfur dioxide gas, which can generate a large amount of waste water, cause environmental pollution, troublesome post-reaction treatment, high industrial production costs, and increase the manufacturer's investment in environmental protection.

Method used

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  • Green synthesis method for ibuprofen piconol and medicinal preparation thereof
  • Green synthesis method for ibuprofen piconol and medicinal preparation thereof
  • Green synthesis method for ibuprofen piconol and medicinal preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Add 206.2g (1.0mol) ibuprofen and 2000ml dichloromethane into a 5000ml dry single-necked bottle, stir mechanically, dissolve, add 109g (1.0mol) 2-hydroxymethylpyridine, then add 206.3g (1.0mol) N , N'-dicyclohexylcarbodiimide and 3.6g (0.03mol) 4-dimethylaminopyridine, stirred overnight at room temperature in the dark, and a large amount of white crystals were precipitated. After the reaction was completed, filter and wash with an appropriate amount of dichloromethane. Obtain filter residue dicyclohexyl urea, combine and wash filtrate, use 200ml 5%Na 2 CO 3 , 300ml water washing twice to neutral, anhydrous Na 2 SO 4 Drying, vacuum distillation to recover the solvent, and high vacuum rectification to obtain 280.1 g of ibuprofen pyridoxine (170-172 / 0.133kPa) as an oily liquid, with a yield of 94.5%.

[0052] Analyze the product as figure 1 , 2 , 3, 4, 5, 6, 7, the following conclusions are obtained:

[0053] Light yellow clear liquid, boiling point 178℃ / 0.133kPa. E...

Embodiment 2

[0055] Add 224.3g (1.0mol) of dicyclohexylurea and 800ml of dichloromethane into a 2000ml dry single-necked bottle, stir and dissolve, keep the reaction temperature at about 40°C, and slowly add 212g (1.2mol) of benzene Sulfonyl chloride, stirred and reacted for 2 hours, cooled to room temperature, slowly added dropwise 15% sodium hydroxide solution to neutrality, continued to stir for 30 minutes, separated the organic layer, washed with water, anhydrous Na 2 SO 4 Dry, distill to recover the solvent, vacuum distill and collect the 156-159°C / 15mmHg fraction to obtain 171g of N,N'-dicyclohexylcarbodiimide with a yield of 83%. After solidification, the melting point is 33-35°C.

Embodiment 3

[0057] Add 206.2g (1.0mol) ibuprofen and 2000ml dichloromethane into a 5000ml dry single-necked bottle, stir mechanically, dissolve, add 109g (1.0mol) 2-hydroxymethylpyridine, then add 126.2g (1.0mol) N , N'-diisopropylcarbodiimide and 3.6g (0.03mol) 4-dimethylaminopyridine, stirred overnight at room temperature in the dark, after the reaction was completed, washed with 300ml of water, 200ml of 5% Na 2 CO 3 , 300ml water washing twice to neutral, anhydrous Na 2 SO 4 Drying, vacuum distillation to recover the solvent, and high vacuum rectification to obtain 275.1 g of ibuprofen pyridoxine (170-172 / 0.133kPa) as an oily liquid, with a yield of 92.6%.

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Abstract

The invention discloses a green synthesis method for ibuprofen piconol and a medicinal preparation method thereof and provides a formula process of and a green chemical synthesis method of a medicinal compound, in particular the method for preparing ibuprofen piconol, a medicinal composition prepared by using ibuprofen piconol as an active ingredient, and a new formula of an externally-applied preparation for diminishing inflammation, relieving pain and treating infectious diseases. Compared with the prior art, the method has the advantages that: the technical route is advanced, the technical conditions are reasonable, the use of halogenating agents such as thionyl chloride which produce lots of toxic and harmful gases is avoided, a reactions are replaced by one reaction, the operation is simple, convenient and safe, the reaction yield is high, the reaction conditions are easy to control, the solvent and a dehydration condensation agent can be recycled and reused, the problems of trouble of treatment after a reaction process, serious waste gas, waste water and waste residue pollution and the like in the conventional process are solved from the source, environment pollution is avoided, little waste gas, waste water and water residue are produced, and high implementation value and great social and economic benefit are realized.

Description

technical field [0001] The present invention relates to the field of western medicine invention, and relates to a pharmaceutical compound formulation process and green chemical synthesis, specifically a method for preparing a compound with the following structural formula, and a pharmaceutical composition containing the compound as an effective active ingredient. [0002] Background technique [0003] Ibuprofen is an aryl alkanoic acid compound with anti-inflammatory, analgesic and antipyretic effects. Since its listing in the late 1970s, ibuprofen has developed rapidly and has become one of the anti-inflammatory, antipyretic and analgesic drugs with the largest production and usage, and has been accepted by patients. [0004] Ibuprofen pyridoxine is a derivative of ibuprofen, which belongs to the external use of non-steroidal anti-inflammatory analgesics for dermatology treatment. Ibuprofen pyridoxine has strong analgesic and anti-inflammatory effects, minimal toxic and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30A61K31/4402A61P29/00A61P17/00A61P17/10A61P17/02
Inventor 肖方青刘旭桃王树华杨世平肖艳萍陈海波龙彤
Owner 湖南医药工业研究所有限公司
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