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Cefminox sodium preparation method

A technology for cefminox sodium and compound, which is applied in the field of preparation of cefminox sodium and can solve the problems of expensive raw materials, high risk factor, harsh conditions for deprotecting groups and the like

Inactive Publication Date: 2019-12-20
重庆天地药业有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first synthetic route is simple to operate, but the raw materials are expensive. The second synthetic route has little damage to other groups during the methoxidation process, but the conditions for deprotection are harsh and the risk factor is high.

Method used

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  • Cefminox sodium preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] A kind of preparation method of cefminox sodium of the present embodiment, comprises the steps:

[0075] (1) At room temperature, 45g of 7-amino-3-[(acetoxy)methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]-2-ene -2-carboxylic acid (7-ACA) and 200g dimethyl carbonate were mixed and evenly mixed, 31g 1-methyl 5-mercapto-tetrazolium was added, the temperature was raised to 30°C with stirring, and 128.5g boron trifluoride (40 %), temperature control reaction for 120min, and the reaction is over, slowly drip ammonia water (15%) to the system until the system is turbid, grow the crystal for 30min, suction filter, 210g acetone beating and washing, filter off the solvent, and dry in vacuo to obtain intermediate 7- Amino-3-(1-methyl-1-H-tetraaza-5-thiomethyl)-3-cephem-4-carboxylic acid 46.5 g, yield 118.5%.

[0076] (2) At room temperature, add 36.5g of intermediate 7-amino-3-(1-methyl-1-H-tetraza-5-thiomethyl)-3-cephem-4-carboxylic acid to 195.5g of acetic acid In ethyl ester, stir a...

Embodiment 2

[0080] A kind of preparation method of cefminox sodium of the present embodiment, comprises the steps:

[0081] (1) At room temperature, 40g of 7-amino-3-[(acetoxy)methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]-2-ene -2-carboxylic acid (7-ACA) and 220g dimethyl carbonate were mixed and evenly mixed, 31.5g 1-methyl 5-mercapto-tetrazolium was added, the temperature was raised to 30°C with stirring, and 127.7g boron trifluoride ( 40%), temperature controlled reaction for 120min, after the reaction was completed, ammonia water (15%) was slowly added dropwise to the system until the system became turbid, the crystal was grown for 30min, suction filtered, 200g of acetone was beaten and washed, the solvent was filtered off, and vacuum-dried to obtain intermediate 7 -Amino-3-(1-methyl-1-H-tetraza-5-thiomethyl)-3-cephem-4-carboxylic acid 48g, yield 120%.

[0082] (2) At room temperature, add 37.5g of intermediate 7-amino-3-(1-methyl-1-H-tetraza-5-thiomethyl)-3-cephem-4-carboxylic acid to 19...

Embodiment 3

[0086] A kind of preparation method of cefminox sodium of the present embodiment, comprises the steps:

[0087] (1) At room temperature, 50g of 7-amino-3-[(acetoxy)methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0]-2-ene -2-carboxylic acid (7-ACA) and 250g dimethyl carbonate were mixed and evenly mixed, 32g 1-methyl 5-mercapto-tetrazolium was added, the temperature was raised to 30°C with stirring, and 125g boron trifluoride (40% ), temperature controlled reaction for 120min, and the reaction was completed, slowly drip ammonia water (15%) to the system until the system was turbid, grow crystals for 30min, filter with suction, wash with 200g of acetone beating, filter to remove the solvent, and dry in vacuo to obtain the intermediate 7-amino - 47 g of 3-(1-methyl-1-H-tetraza-5-thiomethyl)-3-cephem-4-carboxylic acid, yield 119.2%.

[0088] (2) At room temperature, add 38g of intermediate 7-amino-3-(1-methyl-1-H-tetraza-5-thiomethyl)-3-cephem-4-carboxylic acid to 185g of ethyl acetate In...

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Abstract

The invention provides a cefminox sodium preparation method, which comprises: (1) dispersing a compound having a structure represented by a formula (VII) in an organic solvent A to prepare a solutionor a suspension, adding a compound having a structure represented by a formula (VII), and carrying out vacuum drying to obtain a compound having a structure represented by a formula (VI); (2) dispersing the compound with the structure represented by the formula (VI) into an organic solvent C, adding a compound having a structure represented by a formula (V) in a dropwise manner, and drying to obtain a compound having a structure represented by a formula (IV); (3) dispersing the compound having the structure represented by the formula (IV) in an organic solvent, and removing the solvent by rotary evaporation under a pressure reducing condition to obtain an organic phase containing a compound having a structure represented by a formula (II); and (4) adding purified water into the solution containing the compound having the structure represented by the formula (II), heating, adjusting the pH value, adding a compound having a structure represented by a formula (III), carrying out temperature control stirring, transferring the water phase into a crystallizing tank, crystallizing, and carrying out pressure reducing drying to obtain the cefminox sodium heptahydrate. According to the invention, the synthesis process is shortened, the cost is reduced, and the product yield and the purity are high.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of cefminox sodium. Background technique [0002] Cefminox sodium, English name: Cefminox Sodium, chemical name: (6R, 7S)-7β-[(S)-2-(2-amino-2-carboxyethylmercapto)acetamido]-7α-methoxy Sodium-3-[(1-methyl-1H-5-yl)thio]methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-ene-2-carboxylate, mainly It exists in the form of heptahydrate crystals, and its molecular formula is: C16H20N7NaO7S3·7H2O. Cefminox sodium has broad-spectrum antibacterial activity on Gram-positive bacteria and Gram-negative bacteria, especially Escherichia coli, Klebsiella, Haemophilus influenzae, Proteus and Bacteroides fragilis. Antibacterial effect. It can be used for respiratory, urinary, abdominal and pelvic infections and sepsis caused by the above bacteria. [0003] Patent CN 101696214 discloses a 7-MAC as the starting mother nucleus, which first reacts with bromoacetyl bromide to ...

Claims

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Application Information

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IPC IPC(8): C07D501/57C07D501/04
CPCC07D501/04C07D501/57
Inventor 唐洪张可人陈娅琼杨成白智全吴建军
Owner 重庆天地药业有限责任公司
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