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Method for synthesizing carbenicillin sodium

A technology of carbenicillin sodium and synthesis method, which is applied in the field of drug synthesis, can solve the problems of high cost and unsuitability for large-scale industrial production, and achieve the effects of convenient recovery and processing, reduction of production equipment, and high purity

Inactive Publication Date: 2009-07-01
上海新先锋药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The technical problem to be solved by the present invention is to provide a low-cost, high-yield synthetic method of carbenicillin sodium aimed at the high cost of the existing carbenicillin sodium preparation method and the shortcomings of being unsuitable for large-scale industrial production

Method used

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  • Method for synthesizing carbenicillin sodium
  • Method for synthesizing carbenicillin sodium
  • Method for synthesizing carbenicillin sodium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In this embodiment, the specific operation steps are:

[0035] 1. Add 150ml of ethyl acetate and 20g of 6-aminopenicillanic acid into a 500ml three-necked bottle, stir, add 40g of N,N'-bistrimethylsilylurea, heat and reflux for 30min, cool to room temperature, and add while stirring Mesityl phenylmalonate 24g, stirred for 2.5 to 3 hours, until the reaction was complete (check the end point of the reaction with HPLC);

[0036] 2. Add 100ml of water to the reaction mixture, and adjust the pH to 6.5-7.5 with 30% sodium hydroxide solution while stirring.

[0037] 3. Stand still, after phase separation, remove the organic phase, take the water phase in a beaker, add 150ml of ethyl acetate under stirring conditions, adjust the pH to 1.0-1.5 with 10% HCl, stand still again, and after phase separation, take The organic phase.

[0038] 4. Add 60 ml of 25% sodium isooctanoate ethyl acetate solution to the organic phase, continue to stir for 1 hour after precipitation occurs, fi...

Embodiment 2

[0041] In this embodiment, the specific operation steps are:

[0042] 1. Add 150ml of ethyl acetate and 20g of 6-aminopenicillanic acid into a 500ml three-necked bottle, stir, add 44ml of hexamethyldisilazane, stir for 3h, then add 24g of mesityl phenyl malonate , and stirred for 2.5-3 hours until the reaction was complete (check the end of the reaction with HPLC).

[0043] 2. Add 100ml of water to the reaction mixture, and adjust the pH to 6.5-7.5 with 20% sodium carbonate solution while stirring.

[0044] 3. Stand still, carry out phase separation, remove the organic phase, take the water phase in a beaker, add 150ml of ethyl acetate under stirring conditions, adjust the pH to 1.0-1.5 with 10% sulfuric acid, let stand again, carry out phase separation, and take the organic phase .

[0045]4. Add 75 ml of 20% sodium isooctanoate in acetone to the organic phase while stirring, continue to stir for 1 hour after precipitation occurs, filter, and vacuum-dry the precipitate to o...

Embodiment 3

[0048] In this embodiment, the specific operation steps are:

[0049] 1. Add 150ml of ethyl acetate and 20g of 6-aminopenicillanic acid into a 500ml three-necked bottle, stir, add 50ml of N, O-bistrimethylsilylacetamide, stir for 2 hours, then add mesityl Ester 24g, stirred for 2.5 to 3 hours, until the completion of the reaction (check the end of the reaction with HPLC).

[0050] 2. Add 100ml of water to the reaction mixture, and adjust the pH to 6.5-7.5 with 8% sodium bicarbonate solution while stirring.

[0051] 3. Stand still, carry out phase separation, remove the organic phase, take the water phase in a beaker, add 150ml of ethyl acetate under stirring, adjust the pH to 1.0-1.5 with 20% phosphoric acid, let stand again, carry out phase separation, and take the organic phase.

[0052] 4. Add 150 ml of 10% sodium isooctanoate ethanol solution while stirring the filtrate, continue to stir for 1 h after precipitation occurs, filter, and vacuum-dry the precipitation to obtai...

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Abstract

The invention relates to a synthesis method for carbenicillindisodium. The carbenicillindisodium is prepared sequentially through the following steps: adding 6-amino penicillanic acid and a silanized agent into ethyl acetate, and after stirring, adding 2,2-dimethyl-5-phenyl-1,3-dioxane-4,6-diketone till the reaction is completed; adding water and alkaline into the reaction mixture, and regulating the pH value to between 5.0 and 8.5 percent; after carrying out the phase separation, collecting the water phase, adding ethyl acetate, regulating the pH value to between 1.0 and 4.0 through acid, carrying out the phase separation again, and collecting the organic phase; and adding ethyl acetate and active carbon into the organic phase for stirring and filtration, adding sodium iso-octoate solution into the filtrate, filtrating out the precipitate, cleaning the precipitate through acetone, and carrying out the vacuum drying of the precipitate to obtain the carbenicillindisodium. The synthesis method has easily obtained and cheap raw materials, moderate reaction conditions and high yield, and is suitable for the industrialized production. The solvents used are only water and ethyl acetate, thereby reducing the harm of the solvents on operating personnel, and bringing about the convenient reclamation and treatment of the solvents.

Description

technical field [0001] The invention relates to a method for synthesizing medicine, in particular to a method for synthesizing carbenicillin sodium. Background technique [0002] Carbenicillin sodium (carbenicillin sodium), also known as carbenicillin, its structural formula is: [0003] [0004] The chemical name is [2S-(2α,5α,6β)]-6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[ 3.2.0] Heptane-2-carboxylic acid disodium salt. [0005] Carbenicillin Sodium is an antibiotic developed in the 1960s by the British Beauchamp Research Institute, and the compound patent is GB1004670. Carbenicillin sodium is a broad-spectrum penicillin antibiotic, which is effective against Enterobacteriaceae such as Escherichia coli, Proteus, Enterobacter, Citrobacter, Salmonella and Shigella, as well as Pseudomonas aeruginosa , Haemophilus influenzae, Neisseria and other Gram-negative bacteria have antibacterial effect. It also has antibacterial activity against hemol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/72
Inventor 李建文祁振海郑玉林郝惠庆李晴
Owner 上海新先锋药业有限公司
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