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Cefixime compound and novel preparation method thereof

A cefixime and compound technology, applied in the field of cefixime compound and its new preparation method, can solve the problems of environmental pollution, difficulty, inability to recover mercaptobenzothiazole well, etc., and achieve the effect of improving the yield and the quality of the finished product

Inactive Publication Date: 2012-06-13
HAINAN MEIDA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Another advantage of the present invention is that the activation of (Z)-2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxy-imino)acetic acid in the present invention uses pentafluorophenol As an activator, a new cefixime active ester intermediate is obtained, which avoids the strict restrictions on anhydrous conditions caused by the use of phosphorus pentachloride and thionyl chloride, as well as the pollution caused to the environment and the impact on industrialization. The difficulty of using 2-mercaptobenzimidazole activated ester to avoid the trouble caused by the post-reaction treatment and the new impurities brought in will affect the purity of the final product; solve the problem that mercaptobenzothiazole cannot be well recovered in the original process , improve product yield and finished product quality

Method used

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  • Cefixime compound and novel preparation method thereof
  • Cefixime compound and novel preparation method thereof
  • Cefixime compound and novel preparation method thereof

Examples

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Effect test

Embodiment 1

[0042]The synthesis of embodiment 1 cefixime

[0043] 130g (0.5mol) of (Z)-2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxy-imino)acetic acid and 80ml of triethylamine were added to 500ml of acetone , the reactant was cooled to 10°C, 93g (0.5mol) of pentafluorophenol was added, and the reaction was stirred at this temperature for 1 hour, then 113g (0.5mol) of 7-AVCA and 140ml of triethylamine were added, and vigorously stirred at 10°C After 1 hour, acetone was distilled off under reduced pressure, then 3L of water was added, extracted twice with 500ml of ethyl acetate, and then 200ml of 30% sodium hydroxide solution was added, hydrolysis reaction was carried out at 10°C for 1 hour, and the reaction was adjusted with 20% hydrochloric acid When the pH is 5.5, add 20 g of activated carbon and stir for 30 minutes, filter, adjust the reaction pH to 2.6 with 20% hydrochloric acid, stir at room temperature for 1 hour, a solid precipitates, filter, wash twice with 300 ml of water, an...

Embodiment 2

[0044] The synthesis of embodiment 2 cefixime

[0045] 130g (0.5mol) of (Z)-2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxy-imino)acetic acid and 80ml of triethylamine were added to 500ml of acetone , the reactant was cooled to 5°C, 93g (0.5mol) of pentafluorophenol was added, and the reaction was stirred at this temperature for 1 hour, then 113g (0.5mol) of 7-AVCA and 140ml of triethylamine were added, and vigorously stirred at 5°C After 1 hour, acetone was distilled off under reduced pressure, then 3L of water was added, extracted twice with 500ml of ethyl acetate, and then 400ml of 20% sodium hydroxide solution was added, hydrolysis reaction was carried out at 5°C for 1 hour, and the reaction was adjusted with 25% hydrochloric acid When the pH is 5.7, add 30 g of activated carbon and stir for 30 minutes, filter, adjust the reaction pH to 2.7 with 25% hydrochloric acid, stir at room temperature for 1 hour, a solid precipitates, filter, wash twice with 300 ml of water, and ...

Embodiment 3

[0046] The synthesis of embodiment 3 cefixime

[0047] Add 260g (1mol) of (Z)-2-(2-aminothiazol-4-yl)-2-(methoxycarbonylmethoxy-imino)acetic acid and 160ml of triethylamine to 1000ml of acetone , the reactant was cooled to 8°C, 186g (1mol) of pentafluorophenol was added, and the reaction was stirred at this temperature for 1 hour, then 226g (1mol) of 7-AVCA and 280ml of triethylamine were added, and vigorously stirred at 8°C for 1 hour, Distill off acetone under reduced pressure, then add 6L of water, extract twice with 1000ml of ethyl acetate, then add 400ml of 40% sodium hydroxide solution, hydrolyze at 8°C for 1 hour, adjust the reaction pH to 5.4 with 15% hydrochloric acid , add 50 g of activated carbon and stir for 30 min, filter, adjust the reaction pH to 2.5 with 15% hydrochloric acid, stir at room temperature for 1 hour, precipitate solid, filter, wash twice with 600 ml of water, and dry under vacuum at 40 ° C to obtain the product cefixime 473.5 g, yield: 93.3%, HPLC...

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Abstract

The invention relates to a cefixime compound and a novel preparation method thereof. The invention point is that: by adopting pentafluorophenol as an active agent, the cefixime compound and the novel preparation method thereof have the advantages of high reaction stability, mild reaction condition, high product yield and purity, and are suitable for industrialized mass production.

Description

technical field [0001] The invention relates to a cefixime compound and a new preparation method thereof, belonging to the technical field of medicine. Background technique [0002] Cefixime, its chemical name is: (6R, 7R)-7[(Z)-2-(2-amino-4-thiazolyl)-2-(carboxymethoxyaminoimine)acetamido]-3 -Ethylene-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid trihydrate, molecular formula: C 16 h 15 N 5 o 7 S 2 ·3H 2 O, molecular weight: 507.50, structural formula: [0003] [0004] Cefixime is a third-generation oral cephalosporin with a broad antibacterial spectrum. Bacteriaceae bacteria have good antibacterial activity, are highly stable to β-lactamase, and have high affinity with penicillin-binding protein 3, 1a and 1b, which hinders the synthesis of bacterial cell walls, and the bacteria rapidly dissolve and die. Clinically, it is mostly used to treat pharyngitis, tonsillitis, acute bronchitis and acute exacerbation of chronic bronchitis, otitis media, urin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D501/22C07D501/06
Inventor 郝志艳
Owner HAINAN MEIDA PHARMA