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Method for prepairng highly purity cefpodoxime proxetil

A technology of cefpodoxime and propyl oxime, which is applied in the field of cefpodoxime propyl and can solve the problems of low production yield and the like

Inactive Publication Date: 2002-12-25
HANMI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method also needs to use expensive quaternary ammonium salts, and causes low yield due to the long reaction process of about 3 days

Method used

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  • Method for prepairng highly purity cefpodoxime proxetil
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  • Method for prepairng highly purity cefpodoxime proxetil

Examples

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preparation example 1

[0017] The following examples are for illustrative purposes only and are not intended to limit the scope of the invention. Preparation Example 1: Preparation of Cefpodoxime Sodium Salt

[0018] 2.03g sodium 2-ethylhexanoate was dissolved in 12.5ml N, in the mixture of N-dimethylacetamide and 50ml methanol, 5.0g cefpodoxime (7-[2-(2-amino-4 -thiazolyl)-(Z)-2-(methoxyimino)acetamido]-3-methoxymethyl-3-cephem-4-carbonic acid), and the mixture was stirred at room temperature for 30 minutes. Methanol was then removed under reduced pressure and 50 ml of acetone was added thereto. The solution was stirred for 30 minutes and filtered. After the filtered solid was washed with 50 ml of acetone and then with 30 ml of isopropyl ether, it was vacuum-dried at room temperature to obtain 4.98 g of light yellow cefpodoxime sodium salt (yield 95%).

[0019] 1 H-NMR (δ, D 2 O): 3.15(s, 3H, C-OCH 3 ), 3.37 (ABq, 2H, C-2), 3.85 (s, 3H, =N-OCH 3 ), 4.07 (d, 2H, -CH 2 -OCH 3 ), 5.09 (d, 1H,...

preparation example 2

[0019] 1 H-NMR (δ, D 2 O): 3.15(s, 3H, C-OCH 3 ), 3.37 (ABq, 2H, C-2), 3.85 (s, 3H, =N-OCH 3 ), 4.07 (d, 2H, -CH 2 -OCH 3 ), 5.09 (d, 1H, C-6), 5.66 (d, 1H, C-7), 6.88 (s, 1H, aminothiazole ring-H). Preparation Example 2: Preparation of Cefpodoxime Sodium Salt

[0020] 1.01 g of sodium acetate was dissolved in a mixture of 1 ml of water and 5 ml of methanol, to which 5.0 g of cefpodoxime was added, followed by 15 ml of N,N-dimethylacetamide. The mixture was stirred at room temperature for 30 minutes, and then 100 ml of acetone was added thereto. The solution was stirred for 20 minutes and filtered. After the filtered solid was washed with 50 ml of acetone and then with 30 ml of isopropyl ether, it was vacuum-dried at room temperature to obtain 5.04 g of pale yellow cefpodoxime sodium salt (96% yield).

[0021] income 1 The H-NMR data are the same as those in Preparation Example 1. Preparation Example 3: Preparation of Cefpodoxime Potassium Salt

preparation example 3

[0021] income 1 The H-NMR data are the same as those in Preparation Example 1. Preparation Example 3: Preparation of Cefpodoxime Potassium Salt

[0022] 0.7 g of potassium acetate was dissolved in 5 ml of methanol, and 3.0 g of cefpodoxime was added thereto, followed by 9 ml of N,N-dimethylacetamide. The mixture was stirred at room temperature for 30 minutes, and then 60 ml of acetone was added thereto. The solution was stirred for 20 minutes and filtered. After the filtered solid was washed with 50 ml of acetone and then with 30 ml of isopropyl ether, it was vacuum-dried at room temperature to obtain 3.11 g of pale yellow cefpodoxime potassium salt (96% yield).

[0023] income 1 The H-NMR data are the same as those in Preparation Example 1. Preparation Example 4: Preparation of Cefpodoxime Magnesium Salt

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Abstract

Highly pure cefpodoxime proxetil can be prepared by a simple process comprising the step of reacting a cefpodoxime salt with 1-iodoethylisopropylcarbonate in an organic solvent in the presence of a crown ether.

Description

technical field [0001] The invention relates to a method for preparing high-purity cefpodoxime propyl axetil from cefpodoxime. Background technique [0002] Cefpodoxime Propexate, (R,S)-1-(Isopropoxycarbonyloxy)ethyl-(+)-(6R,7R)-7-[2-(2-Amino-4-thiazole) Base)-2-((Z)-methoxyimino)acetamido]-3-methoxymethyl-8-oxo-5-thio-1-azabicyclo[4,2,0]octane- 2-ene-2-carboxylate, a cephalosporin ester prodrug, when given orally, is converted to cefpodoxime, a An antibacterial agent. Cefpodoxime exhibits a broad spectrum of antibacterial activity against Gram-positive and negative bacteria such as Staphylococcus aureus, Streptococcus aureus, Escherichia coli, Klebsiella pneumoniae and Proteus vulgaris, while also being highly β- Lactamase stability. [0003] Cefpodoxime propyl axetil of molecular formula (I) is prepared by various methods Δ 3 -isomer. [0004] Hideo Nakao and Koich Huzimoto etc. have reported a kind of method (seeing J.of Antibiotics, Vol. 40, pp. 370 (1987)). Howe...

Claims

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Application Information

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IPC IPC(8): C07B61/00C07D501/00C07D501/34C07D501/36
CPCC07D501/00C07D501/36
Inventor 李宽淳张永佶李在宪朴哲玄朴柯胜郑金信
Owner HANMI PHARMA
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