Cefotiam hydrochloride for reducing anaphylaxis and preparation thereof

A technology for cefotiam hydrochloride and allergic reaction, applied in the field of antibiotics, can solve the problems of low yield, difficult transportation, unsuitable for industrial production and the like, and achieves the effects of high product yield, simple reaction process and low impurity content

Active Publication Date: 2016-06-08
福安药业集团庆余堂制药有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The 4-chloro-3-oxobutanoyl chloride used in the first method has strong reactivity and is not easy to transport, so this method is not suitable for industrial production
The second method requires the operation steps of protecting and deprotecting groups, resulting in high cost and low yield

Method used

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  • Cefotiam hydrochloride for reducing anaphylaxis and preparation thereof
  • Cefotiam hydrochloride for reducing anaphylaxis and preparation thereof
  • Cefotiam hydrochloride for reducing anaphylaxis and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Dissolve 7-ACMT385g in 2L of acetone, add 300g of tert-butyldimethylsilyl chloride and 202g of triethylamine, stir the reaction at room temperature, TLC detects that the reaction is complete, cool to 0°C, and remove the solvent to obtain formula 1 compound.

[0030] (2) Dissolve 204 g of 2-formylaminothiazole-4 acetyl chloride in 2L of dichloromethane, then add 598 g of the compound of formula 1 obtained in step (1), stir and react at room temperature for 3 hours, and TLC detects that the reaction is complete. The solvent is removed under reduced pressure to obtain the compound of formula 1 .

[0031] (3) The compound of formula 2 prepared in step (2) was dissolved in 2L of acetone, then an excess of aqueous hydrochloric acid was added, heated to 35° C. for 3 hours, crystals were precipitated after the reaction was complete, washed, and vacuum-dried to obtain cefotiam hydrochloride Salt 550kg, yield is 92%.

[0032] Determination of content: according to size excl...

Embodiment 2

[0038] (1) Dissolve 7-ACMT385g in 2L ethyl acetate, add 315g tert-butyldimethylsilyl chloride and 212g triethylamine, stir the reaction at room temperature, TLC detects that the reaction is complete, cool to -5°C, and remove the solvent Compound of formula 1 is obtained.

[0039] (2) Dissolve 204 g of 2-formylaminothiazole-4 acetyl chloride in 2 L of chloroform, then add 592 g of the compound of formula 1 obtained in step (1), stir and react at room temperature for 2.5 hours, TLC detects that the reaction is complete, and depressurizes Removal of the solvent affords the compound of formula 1 .

[0040] (3) Dissolve the compound of formula 2 prepared in step (2) in 2L of methyl isobutyl ketone, then add excess hydrochloric acid aqueous solution, heat to 40°C and react for 2.5 hours, after the reaction is complete, crystals are precipitated, washed, and vacuum-dried to obtain cephalosporin Thiam hydrochloride 545g, the yield is 91%.

[0041] The content of cefotiam hydrochlori...

Embodiment 3

[0043] (1) Dissolve 7-ACMT385g in 2L tetrahydrofuran, add 308g tert-butyldimethylsilyl chloride and 207g triethylamine, stir the reaction at room temperature, TLC detects that the reaction is complete, cool to 5°C, and remove the solvent to obtain formula 1 compound.

[0044](2) Dissolve 204 g of 2-formylaminothiazole-4 acetyl chloride in 2L of acetone, then add 596 g of the compound of formula 1 obtained in step (1), stir and react at room temperature for 2.5 hours, TLC detects that the reaction is complete, and depressurizes Removal of the solvent affords the compound of formula 1 .

[0045] (3) The compound of formula 2 prepared in step (2) was dissolved in 2L of acetone, then an excess of hydrochloric acid aqueous solution was added, heated to 45° C. for 2 hours, crystals were precipitated after the reaction was complete, washed, and vacuum-dried to obtain cefotiam hydrochloride Salt 538g, the yield is 90%.

[0046] The content of cefotiam hydrochloride in Example 3 was ...

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Abstract

The invention relates to an antibiotic drug, in particular to cefotiam hydrochloride for reducing anaphylaxis. The compound has the advantages of high yield, high purity and the like, and is suitable for industrial production, and product stability and anaphylaxis reducing and clinic application of a preparation are all obviously improved.

Description

technical field [0001] The invention relates to an antibiotic, in particular to a cefotiam hydrochloride capable of reducing allergic reactions. Background technique [0002] Cefotiam is a second-generation bactericidal cephalosporin broad-spectrum antibiotic, and its effect on Gram-positive bacteria is similar to that of Cefazolin, while it is effective against Gram-negative bacteria such as Haemophilus, Escherichia coli, Klebsiella Bacillus, Proteus mirabilis, etc. have strong antibacterial effects, and also have antibacterial effects on Enterobacter, Citrobacter, and indole-positive Proteus. Its mechanism of action is to bind to penicillin-binding proteins (PBPs) on the bacterial cell membrane, acylate transpeptidase, inhibit the synthesis of bacterial septum and cell wall, affect the cross-linking of cell wall mucopeptide components, and inhibit cell division and growth. The bacterial morphology becomes elongated and eventually dissolves and dies. [0003] Cefotiam hyd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/04A61K31/546A61K9/14A61P31/04
CPCA61K9/0019A61K9/143A61K31/546C07D501/04C07D501/36
Inventor 蒋晨胡昌勤周晓东
Owner 福安药业集团庆余堂制药有限公司
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