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Cephalosporin derivatives

A technology of compounds and halogen atoms, applied in the field of medicine, can solve problems such as affecting the antibacterial efficacy of cephalosporin antibiotics

Inactive Publication Date: 2009-04-15
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, due to long-term clinical use, bacteria have developed resistance to cephalosporin antibiotics, which has greatly affected the antibacterial efficacy of cephalosporin antibiotics.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114] Embodiment 1 Compound A, the preparation of compound B

[0115] (1) (6R, 7R)-7-[2-furyl (cis-methoxyimino)acetamido]-3-[[(5-carboxymethyl-4-methyl-2-thiazolyl)sulfur Preparation of ]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Compound A)

[0116] Add cefuroxime sodium 1.3g (0.003mol), MMTA 0.6g (0.0032mol), NaHCO 3 0.32g (0.0038mol), 15ml of water, stirred to form a solution, heated in a water bath, and reacted at 60°C for 8h. After the reaction, add a small amount of activated carbon, stir for about 15 min, filter, add hydrochloric acid dropwise to the filtrate under cooling in an ice-water bath until the pH is about 6, then extract 3 times with 20 ml of ethyl acetate (60 ml in total), and the water layer is decompressed to remove residual Ethyl acetate, and then adjust the pH to about 2 with 2N hydrochloric acid, and filter at low temperature for 1 h to obtain 0.9 g of compound A as a yellow solid, with a yield of 54.3%.

[0117] Molecula...

Embodiment 2

[0129] Embodiment 2 Preparation two of compound A and compound B

[0130] (1) Preparation of intermediate TACS (7-amino-3-(5-carboxymethyl-4-methyl-1,3-thiazole-2-mercaptomethyl)ceph-2-ene-2-carboxylic acid)

[0131] Add 2.8g (0.01mol) of 7-ACA and 15ml of water into the Erlenmeyer flask, oscillate to make a uniform suspension for use. Add 2.9g (0.015mol) of MMTA and 40ml of water into a 250ml three-necked flask, add 0.56g (0.014mol) of NaOH solid in batches under stirring, and then use saturated NaHCO 3 Adjust the pH of the solution to 6.0, control the temperature in a water bath at 70°C, then add 7-ACA suspension dropwise and add saturated NaHCO dropwise 3 Solution The pH of the reaction solution was about 6.0, the addition was completed in 15 minutes, and the reaction was performed for 1 hour after the addition. Then add activated carbon and stir for 10 minutes, then filter while it is hot, adjust the pH of the filtrate to 2 with 2N HCl in an ice-water bath, and filter ...

Embodiment 3

[0148] Example 3 Preparation of the compound of the present invention aseptic powder injection

[0149] 1. Prescription:

[0150] Prescription 1:

[0151] Compound B 250g

[0152]

[0153] A total of 1000 sticks were prepared

[0154] Prescription 2:

[0155] Compound B 500g

[0156]

[0157] A total of 1000 sticks were prepared

[0158] Prescription 3:

[0159] Compound B 1000g

[0160]

[0161] A total of 1000 sticks were prepared

[0162] Prescription 4:

[0163] Compound B 2000g

[0164]

[0165] A total of 1000 sticks were prepared

[0166] 2. Preparation process:

[0167] (1) Aseptically process the antibiotic glass bottles, rubber stoppers, etc. used for the preparation;

[0168] (2) Weigh the raw materials according to the prescription, place the...

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PUM

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Abstract

The invention belongs to the medicine technical field and especially relates to cephalosporin derivatives of formula (I), the pharmaceutically acceptable salts, the hydrolysable esters and the isomers thereof, wherein, R1, R2, R3 and R4 are defined as in the description; the invention also relates to the method for preparing the compounds, pharmaceutical combination which contains the compounds and the application of the compounds in preparing medicines for treating and / or preventing infectious diseases.

Description

1. Technical field [0001] The present invention relates to cephalosporin derivatives, pharmaceutically acceptable salts thereof, easily hydrolyzed esters or isomers thereof, preparation methods of these compounds, pharmaceutical compositions containing these compounds, and preparation of these compounds for the treatment of And / or the purposes in the medicine of prevention infectious disease, belong to the technical field of medicine. 2. Background technology [0002] Cephalosporin antibiotics are widely used in clinical antibacterial drugs, and have been developed to the fourth generation. [0003] Cefuroxime (Cefuroxime) is a semi-synthetic second-generation cephalosporin antibiotic, which is stable to the β-lactamase produced by negative bacilli, and has stronger anti-gram-negative bacilli than the first generation; Similar or slightly weaker first-generation cephalosporins. It is used for respiratory tract, urinary tract, skin and soft tissue infection, biliary tract i...

Claims

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Application Information

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IPC IPC(8): C07D501/36A61K31/546A61P31/04
CPCY02P20/55
Inventor 黄振华
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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