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One-step synthesis method of Faropenem sodium

A technology of faropenem sodium, synthesis method, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry and other directions, can solve the problems of large catalyst dosage, unfavorable safety production and high cost, and achieves the The effect of color comparison, reduction of catalyst dosage, and low cost

Inactive Publication Date: 2009-11-25
ZHEJIANG JINGXIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The sample prepared in the last step of the patent application still needs to go through crude product and recrystallization, and the amount of catalyst used is large, the cost is high, and the solvent used is a low-boiling and explosive solvent, which is not good for safe production. In addition, the sample prepared by this method is in It is difficult to control heavy metal residues. As described in Example 5 of its patent application, there is no operation to remove palladium, and this indicator is one of the key quality indicators of faropenem sodium

Method used

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  • One-step synthesis method of Faropenem sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Dissolve 49.0g of sodium bicarbonate in 1000g of water, add 33.0g of triethyl phosphite, 6.80g of palladium acetate, 47.0g of 5,5-dimethyl-1,3-cyclohexanedione and 500ml of dichloromethane, and stir 1h, add a solution of 188.7g of desiliconized matter and 1000ml of dichloromethane, raise the temperature to 35-37°C, keep stirring for about 3h, separate the water layer, add 1500ml of dichloromethane to wash once, separate the water layer, and add the active layer to the water layer Carbon 6g, decolorize 1h, filter, the filtrate is recovered to about 700ml of water, add dropwise 3000ml of acetone, precipitate and stir for 1h, filter to obtain a wet product, rinse with acetone 100ml*2, and obtain a white solid, that is, faropenem sodium 158.6g, yield 77.7 %. HPLC 99.6%. Heavy metal content <10ppm.

Embodiment 2

[0024] Dissolve 49.0 g of sodium bicarbonate in 1000 g of water, add 33.0 g of triethyl phosphite, 3.2 g of palladium acetate, 47.0 g of 5,5-dimethyl-1,3-cyclohexanedione and 500 ml of dichloromethane, and stir 1h, add a solution of 188.7g of desilicated matter and 1000ml of dichloromethane, heat up to 30-40°C, keep stirring for about 3h, separate the water layer, add 1500ml of dichloromethane to wash once, separate the water layers, and add activity to the water layer Carbon 6g, decolorize 1h, filter, the filtrate is recovered to about 700ml of water, add dropwise 3000ml of acetone, precipitate and stir for 1h, filter to obtain a wet product, rinse with acetone 100ml*2, and obtain a white solid, namely Faropenem Sodium 155.9g, yield 76.4 %. HPLC 99.5%. Heavy metal content <10ppm.

Embodiment 3

[0026] Dissolve 49.0g of sodium bicarbonate in 1000g of water, add 330g of triethyl phosphite, 3.2g of palladium acetate, 47.0g of 5,5-dimethyl-1,3-cyclohexanedione and 500ml of dichloromethane, and stir for 1h , add a solution of 188.7g of desiliconized matter and 1000ml of chloroform, raise the temperature to 30-40°C, keep stirring for about 3h, separate the water layer, add 1500ml of chloroform to wash once, separate the water layer, add 6g of activated carbon to the water layer, and decolorize for 1h , filtered, the filtrate was recovered to about 700ml of water, 3000ml of acetone was added dropwise, precipitated and stirred for 1h, the wet product was obtained by filtration, rinsed with acetone 100ml*2, and a white solid was obtained, namely 157.6g of faropenem sodium, with a yield of 77.3%. HPLC 99.6%. Heavy metal content <10ppm.

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Abstract

The invention discloses a method for preparing Faropenem sodium. The present preparation method has long process time, all the resultant intermediates require purification, which causes low yield, high cost and little possibility to realize industrial production; a large amount of the used catalyst leads to high cost, in addition, heavy metal residues are difficulty to be controlled. The invention employs two-phase mixed system of organic solvent and water and uses palladium acetate, sodium bicarbonate, 5,5-dimethyl-1,3-cyclohexanedione, organic phosphorus and desilication substance as solvent for the purpose of reaction under 0-50 DEG C, the resultant aqueous layer, which is washed, decolorized and concentrated, is then added with acetone for crystallization, thus obtaining finished product of Faropenem sodium. The invention remarkably reduce the use amount of catalyst to thereby lower cost and residual amount of palladium; the content of heavy metals is controllable and the content of impurities is less, and the product accords with requirement of being used as medicine.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of faropenem sodium. technical background [0002] Faropenem sodium {5R-(3R,6R)-6-(1-hydroxyethyl)-7-oxo-(tetrahydro-2-furyl)-4thio-1-azabicyclo[3.2.0]heptane -2-ene-2-carboxylate}, the structural formula is as follows: [0003] [0004] Faropenem sodium is a penem β-lactam developed by Japan Suntory Company. It is similar to the carbapenem antibiotics on the market. It has broad-spectrum antibacterial, strong antibacterial activity, and is stable to β-lactamase. It can be taken orally or injected, and can effectively inhibit a wide range of Gram-positive and negative bacteria and anaerobic bacteria. It is currently the most effective anti-anaerobic β-lactam, and its efficacy and safety have been fully affirmed. [0005] Patent applications US49978929, US5820889, JP92041489 and EP410727 disclose the preparation methods of faropenem, which are 4-AA[chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/893C07D499/16B01J31/04
Inventor 金志平王法平王伟强梁洪江
Owner ZHEJIANG JINGXIN PHARMA
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