Preparation method of penicillin antibiotic impurity

A penicillin and antibiotic technology, applied in the field of preparation of penicillin antibiotic impurities, can solve problems such as the preparation of penicillin antibiotic impurities that have not been seen

Pending Publication Date: 2020-05-26
CHONGQING MEDICAL & PHARMA COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] No preparation of penicillin antibiotic impurities

Method used

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  • Preparation method of penicillin antibiotic impurity
  • Preparation method of penicillin antibiotic impurity
  • Preparation method of penicillin antibiotic impurity

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preparation example Construction

[0050] The invention discloses a method for preparing penicillin-type antibiotic impurities, and those skilled in the art can learn from the contents of this article and appropriately improve the process parameters to realize the method. In particular, it should be pointed out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention. The method and application of the present invention have been described through preferred embodiments, and the relevant personnel can obviously make changes or appropriate changes and combinations to the method and application described herein without departing from the content, spirit and scope of the present invention to realize and Apply the technology of the present invention.

[0051] All the reagents used in the present invention can be purchased from the market.

Embodiment 1

[0053] The preparation method of mezlocillin sodium impurity, this impurity has structure as shown below:

[0054]

[0055] Add 2 g of mezlocillin sodium, 2.5 ml of penicillinase and 25 ml of water to the reaction flask in sequence, and stir at a temperature of 25°C for 30 min. The reaction solution was directly purified by preparative chromatography (eluent: acetonitrile: methanol = 3:1, filler: C18 silica gel) to obtain the target product solution, and then concentrated under reduced pressure to obtain a white solid. Add 10 ml of methanol to the above crude product to dissolve, leave it at room temperature for 2 days, and concentrate under reduced pressure to obtain an off-white powdery solid. HPLC purity: 95.1%. MS [M-H]: 512.1.

[0056] Proton NMR spectrum: 1 H-NMR (500NHz,D 2 O), δ3.803~3.958(m,6H), δ3.378(s,3H), δ5.339-5.347(d,1H), δ7.418~7.502(m,5H), δ4.726-4.735 (d,1H), δ2.055(S,1H), δ3.670(S,1H), δ1.308(S,3H), δ1.393(S,3H).

[0057] Carbon NMR spectrum: 13 C...

Embodiment 2

[0059] The preparation method of mezlocillin sodium impurity, this impurity has structure as shown below:

[0060]

[0061] Take 2g of mezlocillin sodium, 2.5ml of cephalosporinase and 25ml of water and add them to the reaction flask in sequence, and stir the reaction at a temperature of 30°C for 60min. The reaction solution was directly purified by preparative chromatography (eluent: acetonitrile: methanol = 3:1, filler: C18 silica gel) to obtain the target product solution, and then concentrated under reduced pressure to obtain a white solid. Add 10 ml of ethanol to the above crude product to dissolve, leave it at room temperature for 2 days, and concentrate under reduced pressure to obtain an off-white powdery solid. HPLC purity: 90.1%.

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PUM

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Abstract

The invention relates to a preparation method of a penicillin antibiotic impurity. The penicillin antibiotic impurity has a structure represented by formula (I), and in the formula (I), R represents side chains of penicillin, mezlocillin, piperacillin sodium and flucloxacillin. The method comprises the following steps: (1) mixing penicillin antibiotic, beta-lactamase and water; (2) controlling thetemperature to be 37 DEG C or below; (3) purifying by preparative chromatography, and concentrating; and (3) mixing and reacting with an alcohol solvent. The method is simple to operate and short inreaction time, the purity of the product is 90% or above, and the product can be directly used as a reference substance to qualitatively and quantitatively research penicillin antibiotics, so that theproduct quality is effectively controlled.

Description

technical field [0001] The invention relates to a preparation method of penicillin antibiotic impurities, which belongs to the technical field of medicinal chemistry. Background technique [0002] Penicillin is the first natural antibiotic with strong antibacterial activity against Gram-positive bacteria, Gram-negative cocci and actinomycetes. It is famous for curing British Prime Minister Winston Churchill's pneumonia. The mechanism of action of penicillin antibiotics is to combine with the penicillin-binding protein (PBP) on the bacterial cell membrane to hinder the synthesis of bacterial cell wall mucopeptides, so that they cannot be cross-linked and cause cell wall defects, resulting in bacterial cell rupture and death. This process occurs during the reproductive period of bacterial cells, so this class of drugs is a fungicide during the reproductive period. Bacterial cells have cell walls, but human and mammalian cells do not have cell walls, so the toxicity of penicil...

Claims

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Application Information

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IPC IPC(8): C12P17/14C12P17/16C07D277/06C07D417/12
CPCC12P17/14C12P17/167C07D277/06C07D417/12
Inventor 杨延音孙化富杨治国
Owner CHONGQING MEDICAL & PHARMA COLLEGE
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