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Method for preparing mecillinam

A technology for the reaction of azemidine penicillin, which is applied in the field of preparation of azemidine penicillin, can solve problems such as harsh operating conditions, inconvenient production, unmentioned yield, etc., and achieve easy industrialization, good stability, and convenient process Effect

Inactive Publication Date: 2007-08-29
上海新先锋药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The yield is not mentioned in these two methods, and both are anhydrous reactions under deep freezing conditions, so the operating conditions are relatively harsh, and the reaction solvent ether chloroform used is also a highly dangerous solvent, which has many inconveniences in production
And the product purity is not ideal, even after refining, it is difficult to make the purity reach more than 90%, and it is difficult to meet the pharmacopoeia standard

Method used

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  • Method for preparing mecillinam
  • Method for preparing mecillinam
  • Method for preparing mecillinam

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 20g of 6-APA and 400ml of absolute ethanol to a 1000ml three-neck bottle equipped with a stirring and thermometer, cool to 5°C, slowly add 13.2g of triethylamine in 100ml of ethanol solution in about 30 minutes, and continue to stir until completely dissolved , still at 5°C, slowly add dropwise a 50ml ethanol solution containing 22g of acetal, after the addition, the temperature was raised to 10°C, and the reaction was continued with stirring for 4 hours. Use a rotary evaporator to control the temperature of the water bath below 30°C, concentrate under reduced pressure in vacuo until about 1 / 3 of the volume remains, add 2g of activated carbon to decolorize and stir at 5°C for 30 minutes, and filter. Wash with a small amount of absolute ethanol, combine and shake the filtrate washing liquid, measure and divide into two equal parts, each 26ml.

[0033] A. A portion of 26ml of feed liquid is cooled to 5°C, and it takes about 2 minutes to add 10g of p-toluenesulfonic ac...

Embodiment 2

[0036] Add 300ml of propanol and 20g of 6-APA to a 1000m three-neck bottle equipped with a stirring and thermometer, cool to 5°C, add dropwise 50ml of ethanol solution containing 9.5g of diethylamine in about 30 minutes, and maintain the internal temperature at 0°C , stir to fully dissolve. At 5°C, 22g of acetal in 50ml of ethanol was slowly added dropwise, and after the addition, the temperature was raised to 10°C, and stirring was continued for 5 hours.

[0037] Concentrate to about 1 / 3 of the residual volume as in Example 1, add 20ml of acetone and 2g of activated carbon, decolorize and stir at 2°C for half an hour, filter, wash with propanol, shake the lotion filtrate, and divide into two equal parts, each 37ml.

[0038] A. One portion of feed solution was cooled to 5°C, gradually added dropwise 10 g of p-toluenesulfonic acid in 30 ml of acetone solution with stirring for about 30 minutes, then stood still for 2 hours, filtered and dried to obtain 9.7 g of dry product. HP...

Embodiment 3

[0041] The feeding ratio and reaction device are the same as Example 1. After the reaction, concentrate to about 1 / 3 of the residual volume, add 2g of activated carbon for decolorization for 30 minutes, filter, wash the filter cake with 20ml of absolute ethanol, combine the lotion and stock solution, and shake well Divide into 2 parts, 31ml each.

[0042]A. A portion of feed solution at 10°C, after stirring, gradually add 10g of p-toluenesulfonic acid in 30ml of acetone solution dropwise, stop adding when crystallization appears, continue adding after stirring for 30 minutes, and finish adding dropwise in about 30 minutes. After the addition, it was left to stand at 5°C for 2 hours, filtered, washed with acetone, and dried under vacuum at room temperature to obtain 10.7 g of the product. HPLC 97.7%, moisture 0.47%, PH4.7 (10% aqueous solution), color grade < yellow No. 4, residual acetone 0.42%.

[0043] B. Another part of feed liquid was added dropwise to 10 g of p-toluenesu...

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Abstract

The invention supplies a manufacture method for mecillinam. It uses acetal as raw material, and using organic alkali as catalyst, and the product needn't recrystallization. The purity could be over 95%, and the yield is about 75%. It could be used in industrial producing.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a preparation method of azemidine penicillin. Background technique [0002] Mecillin is also known as azemidine penicillin, and the American trade name is Coactin. [0003] The INN name is Mecillinam, the common name in the United States is Amdinocillin, [0004] Chemical name (2S, 5R, 6R)-6-[(azepanyl-1)-methenylamino]-3,3-dimethyl-7-oxo-4-mercapto-1-nitrogen Heterobicyclo[3.2.0]heptane-2-carboxylic acid. [0005] Structural formula: [0006] [0007] Molecular formula: C 15 h 23 N 3 o 3 S [0008] Molecular weight: 325 [0009] This product is a bactericidal antibiotic, characterized by a narrow antibacterial spectrum, limited to G - Bacilli - except Pseudomonas aeruginosa. Among them, it has the strongest activity against Escherichia coli (including ampicillin-resistant strains), and its MIC for inhibiting Escherichia coli is 0.015-0.1ug / ml, which is 40-100 tim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/10C07D499/21
CPCY02P20/582
Inventor 郝惠庆
Owner 上海新先锋药业有限公司
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