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Furoylureide penicillin crystal and preparation method thereof

A technology of furacillin and furacillin acid, which is applied in the field of semi-synthetic penicillin purification, crystallization and preparation, can solve problems such as difficult filtration and drying, poor product stability, and poor product quality, and achieve convenient transportation and storage , good industrial applicability, and stable properties

Active Publication Date: 2008-08-20
GUANGZHOU BAIYUNSHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Even if there is a report ("Journal of Taiyuan University of Technology" 2004, 9, 35 (5), 575) to take out fururonil acid solid, but because it is directly separated from the water phase without a special purification process, crystallization is difficult , sticky, difficult to filter and dry, unable to obtain crystals of the present invention, the product has poor relative stability, and is not suitable for storage and transportation
The current market sale furacillin sodium (potassium) product is to take to directly prepare with the method for reacting and making the acid solution to neutralize, and product quality is relatively poor, adopts titration method to measure content, and content requires more than 80%

Method used

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  • Furoylureide penicillin crystal and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] According to the synthesis method of USP 3959258, 300 mL of 0.148 mol / L ethyl fururonyl penicillin acetate solution was prepared, cooled in an ice-salt bath to 0 ° C, and 0.5 mol / L sodium carbonate solution was added dropwise to make the pH = about 7, and stirred for 10 min , stand still for phase separation, remove ethyl acetate, move the water phase into a reaction flask, add 200 mL of ethyl acetate, dropwise add 3N hydrochloric acid to adjust pH=2.5, stir for 10 min, stand still for phase separation; extract once with 50 mL of ethyl acetate, combine The organic phase was dried by adding anhydrous magnesium sulfate. Filter, add 100 mL of petroleum ether dropwise with stirring, and grow the crystal for 30 minutes; then continue to add 200 mL of petroleum ether dropwise, and stir for 2 hours. Cool to 5°C in an ice-water bath, filter, wash and dry the slurry, and dry in vacuum to obtain the product with a yield of 89.2%.

[0025] Use D / max-IIIA DIFFRATOMETER (RIGAKU COR...

Embodiment 2

[0030] The reaction product prepared according to the synthesis method of Example 1 was 300 mL of 0.137mol / L fururacillin acid dichloromethane solution, and the obtained fururacil acid dichloromethane solution was cooled to 0° C. in an ice-salt bath, and 0.5 mol / L sodium bicarbonate solution to make the pH=7, stir for 10min, stand still and separate the phases, transfer the water phase into the reaction flask, add 200mL of dichloromethane, add 2N sulfuric acid dropwise below 0°C to adjust the pH=2, stir for 10min, Stand still and separate the phases; the aqueous phase was extracted once with 50 mL of dichloromethane, the organic phases were combined, and dried by adding anhydrous magnesium sulfate. Filter, add 100mL isopropyl ether dropwise for 30min while stirring, then add 200mL isopropyl ether dropwise, and stir for 2 hours. Cool to 5°C in an ice-water bath, filter, wash and dry the slurry, and dry in vacuum to obtain the product with a yield of 86.3%. Measured X-ray powde...

Embodiment 3

[0032] According to the synthetic method of ("Chinese Journal of Medicinal Chemistry" 2006, 2, 16 (1), 51), 300 mL of 0.137 mol / L fururonyl penicillin acid trichloromethane solution was prepared, cooled to 0 ° C in an ice-salt bath, and slowly added dropwise 0.5 mol / L sodium hydroxide solution to make the pH = about 7, control the temperature, then add 200mL ice water, stir for 10min, let stand to separate the phases, move the water phase into the reaction bottle, add 200mL chloroform, and cool in an ice-salt bath to Below 0°C, slowly add 2N phosphoric acid dropwise to adjust the pH to 2, stir for 10 minutes, and let stand to separate the phases; extract the aqueous phase once with 50 mL of chloroform, combine the organic phases, and add anhydrous magnesium sulfate to dry. Filter, add 100mL isopropanol dropwise with stirring, grow the crystal for 30min, then continue to add 200mL isopropanol dropwise, and stir for 2 hours. Cool to 5°C in an ice-water bath, filter, wash and dry...

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Abstract

The invention discloses a furbenicillin crystal and the preparation method, and Alpha-ray powder diffraction spectrum is used for the representation of the crystal. A furbenicillin acidic solution is neutralized by a soda solution, impurities are removed by extraction, the furbenicillin solution undergoes acidification to be adjusted to a product isoelectric point, then the impurities are removed by washing, and finally the furbenicillin acid crystal is separated out by adopting solvent crystallization. The furbenicillin crystal obtained by the invention has stable properties, convenient transportation and storage as well as good industrial applicability.

Description

technical field [0001] The invention relates to a preparation method of a broad-spectrum semi-synthetic penicillin, in particular to the purification, crystallization and preparation method of the semi-synthetic penicillin. Background technique [0002] Furbenicillin sodium is also known as furbenicillin sodium, furbenicillin sodium, and furbenicillin sodium, and its English name is Furbenicillin Sodium. [0003] Fubenicillin sodium (potassium) is a broad-spectrum semi-synthetic penicillin that acts like ampicillin. It has antibacterial effect on most Gram-positive bacteria and Gram-negative bacteria. The antibacterial activity against Escherichia coli, Proteus mirabilis, Alcaligenes, Dicoccus pneumoniae, Streptococcus viridans, and Streptococcus faecalis is stronger than ampicillin and carbenicillin; the effect on Pseudomonas aeruginosa is stronger than carbenicillin4 -16 times; the antibacterial effect on other Gram-positive bacteria and Gram-negative bacteria is similar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/68
Inventor 于沛叶海鸿
Owner GUANGZHOU BAIYUNSHAN PHARM CO LTD
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