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Method for preparing cefodizime sodium

A technology of cefodizime sodium and its compound, which is applied in the field of drug synthesis, can solve the problems of complex operation, low yield, and high cost, and achieve the effects of simple operation, high yield, and low cost

Active Publication Date: 2008-08-13
QILU ANTIBIOTICS PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Compound 7-amino-3-(5-carboxymethyl-4-methyl-1.3-thiazole-2-mercaptomethyl) cef-2-ene-2-carboxylic acid (IV) generated in route C needs to use Purification of macroporous resin, complicated operation and high cost; in route D, the reaction of cefotaxime acid and MMTA at high temperature has poor color and low yield, which increases the production cost
The post-processing work of these two routes is relatively cumbersome and the yield is low

Method used

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  • Method for preparing cefodizime sodium
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  • Method for preparing cefodizime sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] [Example 1] Synthesis of 7-amino-3-(5-carboxymethyl-4-methyl-1.3-thiazole-2-mercaptomethyl)ceph-2-ene-2-carboxylic acid (IV)

[0035] Suspend 25g of the compound of formula (II) and 20g of the compound of formula (III) in 100ml of acetonitrile, add 250ml of boron trifluoride acetonitrile, stir at room temperature for 1 hr, cool with ice water, add 300ml of water, and adjust the pH to 3.0 with ammonia. The crystals were grown for 1 hr, filtered with suction, and the filter cake was washed with 50 ml of water and 50 ml of acetone, respectively, and dried in vacuum to obtain 26.7 g (yield 72.4%, purity 98.5%) of the compound of formula (IV).

Embodiment 2

[0036] [Example 2] Synthesis of 7-amino-3-(5-carboxymethyl-4-methyl-1.3-thiazole-2-mercaptomethyl)ceph-2-ene-2-carboxylic acid (IV)

[0037] 25g of the compound of formula (II) and 20g of the compound of formula (III) were suspended in 100ml of ethyl chloroacetate, passed into 19.5g of boron trifluoride gas, stirred at room temperature for 1hr, cooled with ice water, added 200ml of water, ammoniacal liquor The pH was adjusted to 2.8, the crystals were grown for 1 hr, filtered with suction, the filter cake was washed with 50 ml of water and 50 ml of acetone, and dried in vacuum to obtain 27.5 g (73.3% yield, 98.2% purity) of the compound of formula (IV).

Embodiment 3

[0038] [Example 3] (6R, 7R)-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido]-3-[[(5-carboxymethyl-4-methyl Synthesis of yl-2-thiazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2carboxylic acid (VI)

[0039] 26g of the compound of formula (IV) and 25g of the compound of formula (V) were suspended in 250ml of dichloromethane and 20ml of methanol, cooled with ice water, added with 18ml of triethylamine, reacted at the same temperature for 3hr, added with 200ml of water for extraction, and separated out water. Layer, add 2g activated carbon to decolorize, filter, add 3N HCl to the filtrate to adjust pH to 2.8, grow crystals for 1hr, filter with suction, and wash the filter cake with 100ml of water and 50ml of methanol respectively. Vacuum drying gave 35.5 g (yield 93.9%, purity 98.3%) of the compound of formula (VI).

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Abstract

The invention relates to preparation of a cefodizime sodium. The preparation includes reacting compound of formula (II) and compound of formula (III) in presence of acid catalyst to obtain compound of formula (IN); acidylating compound of formula (IN) and compound of formula (V) to obtain compound of formula (VI) in mixed solution; generating compound of formula (I) by compound of formula (VI) in presence of salt forming agents in mixed solution. The invention is easy to operate, high in yield, and low in cost.

Description

technical field [0001] The invention relates to a preparation method of a cephalosporin antibacterial drug, in particular to a preparation method of cefodizime sodium, and belongs to the technical field of drug synthesis. Background technique [0002] Cefidiazine sodium is a third-generation cephalosporin antibacterial drug, its chemical name is (6R, 7R)-7-[(2-amino-4-thiazolyl)-(methoxyimino)acetamido]- 3-[[(5-Carboxymethyl-4-methyl-2-thiazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo(4.2.0)octane-2 -alkene-2 ​​carboxylic acid disodium salt (I), the chemical structural formula is as follows: [0003] [0004] The drug was developed by the German company Hoechst, and has been widely used in clinical practice due to its dual nature of antibacterial and immunomodulatory properties. [0005] At present, ceftizime sodium (I) is mainly prepared from ceftizime acid (VI), and the most important thing in the preparation process is the dissolution of ceftizime acid (VI). [0006]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36A61K31/546A61P31/04
Inventor 李凤侠范美菊王勇进
Owner QILU ANTIBIOTICS PHARMA
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