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Novel route cefprozil compound

A technology of cefprozil and compounds, applied in the field of medicine, can solve the problems of large isomer content, only yield, and low product purity, and achieve the effects of small isomer content, easy scale-up production, and improved reaction yield

Inactive Publication Date: 2010-08-11
HAINAN MEIDA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The synthesis method of cefprozil is introduced in domestic and foreign patents, but its common disadvantage is that the reaction steps are too complicated, the product obtained is not high in purity, and the content of isomers is too high
U.S. Patent No.4694079 discloses a kind of preparation method of cefprozil DMF solvate, not only reaction step is complicated, and yield only has 65%; The separation of isomers by adsorption chromatography is difficult for this method to be implemented on an industrial scale; Chinese patent CN1694888A discloses a preparation method of cefprozil DMF solvate. Big

Method used

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Embodiment

[0037] 1. Preparation of Cefprozil

[0038] (1) Mix 50 g of p-methoxybenzyl 7-phenylacetamide-3-chloromethyl cephalosporin acid and 28.3 g of triphenyl phosphate, add 300 ml of chloroform and 300 ml of water, and react at 60°C under nitrogen protection After 3 hours, separate the organic phase, cool to 10°C, add 200ml of 1mol / L sodium hydroxide solution to react for 3 hours, collect the organic phase, wash with 200ml of water, then add 200ml of chloroform, 250ml of isopropanol and 40% 130ml of acetaldehyde was stirred and reacted for 16 hours, then 250ml of water was added, stirred for 30 minutes, the organic phase was separated, concentrated under reduced pressure, 100ml of ice water was added, stirred for 3 hours, filtered, and vacuum dried at 45°C to obtain 7-phenylacetamido- 46 g of p-methoxybenzyl 3-(Z-prop-1-enyl)-4-cephalosporanic acid, with a yield of 93.3%.

[0039] (2) Add 136g of phosphorus pentachloride to 625ml of dichloromethane, cool to 15°C, add 45g of pyridine und...

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Abstract

The invention provides a novel route cefprozil compound, which simplifies the processes of 7-phenylacetamide-3-chloromethyl cephalosporanic acid anisyl acetate and triphenylphosphine phyllocaline Benedict's reagents, and activating reagents such as sodium iodide and the like do not need to be added, so the post treatment is simple and convenient, the production amplification can be realized more easily, and at the same time, para hydroxybenzene glycine is adopted to react with 2, 4, 6-trichlorophenol to generate a novel intermediate product of para hydroxybenzene glycine 2, 4, 6- phenyl ester trichlorine. The stability and the activity of the compound are mild, by-products produced in the reaction are fewer, the reaction yield is improved, and in addition, the obtained products have high purity and low isomeride content.

Description

Technical field [0001] The invention relates to a new route of cefprozil compound and belongs to the technical field of medicine. Background technique [0002] Cefprozil, its chemical name is: (6R, 7R)-7-[(R)-2-amino-2-(p-hydroxyphenyl)acetamido]-8-oxo-3-propene-5-thiol -1-Azabicyclo-(4.2.0)oct-2-ene-2-carboxylic acid monohydrate, molecular formula: C 18 H 19 N 3 O 5 S·H 2 O, molecular weight: 407.45, structural formula: [0003] [0004] Cefprozil is a second-generation cephalosporin antibiotic with a broad-spectrum antibacterial effect. The mechanism of action is to inhibit the synthesis of bacterial cell walls and quickly rupture and dissolve the bacteria. It can be used for the following mild and moderate infections caused by sensitive bacteria: 1. Respiratory tract infections: (1) Streptococcus pyogenes pharyngitis, tonsillitis. (2) Streptococcus pneumoniae, Haemophilus influenzae (including β-lactamase-producing strains) and Moraxella catarrhalis (including β-lactamase-prod...

Claims

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Application Information

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IPC IPC(8): C07D501/22C07D501/04C07C229/36C07C227/18
Inventor 邱民
Owner HAINAN MEIDA PHARMA
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