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Method for preparing cefotiam hydrochloride

A technology of cefotiam hydrochloride and concentrated hydrochloric acid, applied in the field of drug synthesis, can solve the problems of difficult operation, low yield, difficult reaction control and the like, and achieve the effects of simple operation, high purity and simplified reaction steps

Active Publication Date: 2018-07-20
CHONGQING CHANGJIE MEDICINE CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, hydrogen chloride gas is used, and the reaction is difficult to control, difficult to operate, and the yield is low

Method used

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  • Method for preparing cefotiam hydrochloride
  • Method for preparing cefotiam hydrochloride
  • Method for preparing cefotiam hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 1.2 Synthesis of TrATA

[0042] Dissolve 2-aminothiazole-4-acetic acid (ATA) (10.0g, 0.0632mol) in 200ML acetonitrile, add triphenylbromethane (51.07g, 0.158mol), add diisopropylethylamine (24.5g, 0.1896mol), react at 25°C for 5h, TLC monitors the reaction is complete, add 100ml of purified water to quench the reaction, extract the reaction solution with dichloromethane (200ML×2), combine the organic layer and wash with saturated brine (100ML×2) Dry over anhydrous magnesium sulfate, filter and spin dry under reduced pressure to obtain 2TrATA, 36.70 g of off-white solid, yield 90.8%, HPLC purity 97.6%.

[0043] 2. Synthesis of TrCEFO

[0044] Suspend 7-ACMT (10.0g, 0.0218mol) in tetrahydrofuran 200ML as a solvent, cool down to 0°C, and slowly add diisopropylethylamine (8.45g, 0.0654mol) dropwise. After the addition is complete, the system becomes clear. The obtained clear solution was added dropwise to the tetrahydrofuran solution of 2TrATA (15.4g, 0.0239mol dissolved ...

Embodiment 2

[0048] 1. Synthesis of 2TrATA

[0049] Dissolve 2-aminothiazole-4-acetic acid (ATA) (5.80g, 0.0366mol) in 100ML acetonitrile, add triphenylbromethane (29.62g, 0.0916mol), add diisopropylethylamine (24.5g, 0.1896mol), reacted at 40°C for 3 hours, TLC monitored the reaction to be complete, added 80ml of purified water to quench the reaction, extracted the reaction solution with dichloromethane (100ML×2), combined the organic layer and washed it with saturated brine (100ML×2) Dry over anhydrous magnesium sulfate, filter and spin dry under reduced pressure to obtain 2TrATA, 21.17 g of off-white solid, yield 90%, HPLC purity 97.5%.

[0050] 2. Synthesis of TrCEFO

[0051] Suspend 7-ACMT (5.50g, 0.0149mol) in tetrahydrofuran 100ML as a solvent, cool down to 0°C, and slowly add diisopropylethylamine (5.81g, 0.0449mol) dropwise. After the addition is complete, the system becomes clear. The obtained clear solution was added dropwise to 2TrATA in THF solution (10.62g, 0.0164mol dissol...

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Abstract

The invention relates to a method for preparing cefotiam hydrochloride. The method comprises the following steps: performing double trisphenylation on 2-aminothiazol-4-acetic acid (called ATA for short) used as raw material to obtain triphenylmethyl 2-triphenylaminothiazol-4-acetate (called 2TrATA for short), connecting the 2TrATA with 7-ACMT to obtain triphenyl cefotiam (called TrCEFO for short),and finally removing a triphenyl group to obtain the target product cefotiam hydrochloride (called CEFO for short). The preparation method has the advantages of simple and easily available raw materials, simplicity in post-treatment operation, and easiness in industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing cefotiam hydrochloride, which belongs to the field of drug synthesis. Background technique [0002] Cefotiam hydrochloride is the second generation of antibiotics for injection. It was developed by Takeda Pharmaceutical Co., Ltd. in Japan. It was launched in Japan in 1981. Its dihydrochloride (Cefotiamdihydrochloride) and buffer sodium carbonate mixed powder preparation (trade name for Pansporin). The effect of this product on Gram-positive bacteria is similar to that of cefazolin, but it has excellent effects on Gram-negative bacteria, such as Haemophilus, Escherichia coli, Klebsiella, Proteus mirabilis, etc. Bacillus, indole-positive Proteus, etc. also have antibacterial effects. It is clinically used to treat infections caused by sensitive bacteria such as pneumonia, bronchitis, biliary tract infection, peritonitis, urinary tract infection, as well as infection and sepsis caused by surgery or trau...

Claims

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Application Information

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IPC IPC(8): C07D501/36C07D501/04
CPCC07D501/04C07D501/36
Inventor 翁明君王忠玉
Owner CHONGQING CHANGJIE MEDICINE CHEM
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