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Sulbenicillin sodium compound and new preparation method thereof

A technology of sulfobenicillin sodium and compound, applied in the field of medicine, can solve the problems of complicated operation, low product purity, high corrosiveness of hydrogen chloride gas and the like

Inactive Publication Date: 2012-02-29
HAINAN MEILAN SMITH KLINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In this method, the sulfonation reaction of phenylacetic acid is relatively complicated, the cost is high, and the direct use of hydrogen chloride gas is more corrosive, and the splitting adopts L(+)-lysine hydrochloride product to be easily racemized, the operation is complicated, and the effect is poor. The resulting product is less pure

Method used

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  • Sulbenicillin sodium compound and new preparation method thereof
  • Sulbenicillin sodium compound and new preparation method thereof
  • Sulbenicillin sodium compound and new preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0026] The synthesis of embodiment 1α-sulfophenylacetyl chloride

[0027] Put 216g (1mol) of α-sulfophenylacetic acid into 400ml of anhydrous diethyl ether, stir well, slowly add 357g (3mol) of thionyl chloride dropwise, after the dropwise completion, add 20ml of triethylamine, at 40°C Stir the reaction for 20 hours, then evaporate diethyl ether and excess thionyl chloride under reduced pressure below 40°C, add 200ml of ether to the residue, evaporate the ether after fully stirring, then add 1000ml of petroleum ether, shake fully, and store at -25°C Freeze for 24 hours, pour off the supernatant, and add 1000ml of dry dichloromethane to the residue to dissolve.

Embodiment 2D

[0028] The synthesis of embodiment 2DL-sulfabenicillin sodium

[0029] Dissolve 216g (1mol) of 6-APA in 2000ml of dichloromethane, slowly add 290ml of triethylamine dropwise under vigorous stirring, then vigorously stir at about 10°C until the solids are completely dissolved, then drop slowly below 0°C Add the dichloromethane solution of α-sulfophenylacetyl chloride obtained in the step, and maintain the pH=7.5 of the reaction with triethylamine at the same time. After dropping, stir and react at room temperature for 2 hours, and pour the reaction solution into 2500ml of ice-water mixture , stirred, allowed to stand for layering, decolorized the water layer with activated carbon, then added 2500ml of n-butanol, adjusted the pH of the reaction solution to 1.5 with 5% sulfuric acid under stirring, collected the organic phase, and used 1000ml of n-butanol for the water layer Alcohol extraction, combined organic phases, and then adding saturated aqueous sodium carbonate to adjust ...

Embodiment 3

[0030] The synthesis of embodiment 3 sulbenicillin sodium

[0031] 300g of DL-sulfbenicillin sodium was added to the reaction flask, then 1500ml of methanol and isopropanol mixed solvent (1:3), heated to reflux for 2 hours, then cooled to room temperature, stirred for 3 hours, and filtered to obtain a white 105 g of solid (D-sulbenicillin sodium: L-sulbenicillin sodium = 3:1), yield 70%.

[0032] [α] 20 : +179°~+181°.

[0033] IR(KBr)ν: 2965 (phCH, stretching), 1767 (lactamC=O), 1673 (-CONH-), 1608 (-COO-), 1527, 1404, 1316, 1214, 1047 (-SO 3 H), 697cm -1 ;

[0034] 1 HNMR (D 2 O) δ: 1.409 (6H, t-CH 3 ×2), 4.130 (1H, d, -CH-COONa), 4.983 (1H, d, Ar-CH-C=O), 5.446 (2H, m, lactam C-H), 7.442 (5H, m, Ar-H ).

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Abstract

The invention relates to a sulbenicillin sodium compound and a new preparation method thereof. A racemic body containing not less than 75% of D-sulbenicillin sodium and not more than 25% of L-sulbenicillin sodium is obtained by a recrystallization method through the differences of dissolubilities of the D-sulbenicillin sodium and the L-sulbenicillin sodium in a mixed solvent of methanol and isopropyl alcohol. The invention has the advantages of simple reaction process, easy operation, low cost, and high product purity.

Description

technical field [0001] The invention relates to a sulbenicillin sodium compound and a new preparation method thereof, belonging to the technical field of medicine. Background technique [0002] Sulbenicillin sodium, the chemical name is (2S, 5R, 6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetamido)-7-oxo-4-thia- 1-Azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt, molecular formula C 16 h 16 N 2 Na 2 o 7 S 2 , molecular weight 458.42, structural formula: [0003] [0004] Sulbenicillin sodium is a broad-spectrum semi-synthetic penicillin antibiotic, which is effective against Enterobacteriaceae such as Escherichia coli, Proteus, Enterobacter, Citrobacter, Salmonella and Shigella, as well as Pseudomonas aeruginosa Bacteria, Haemophilus influenzae, Neisseria and other Gram-negative bacteria have antibacterial activity; it also has antibacterial activity against hemolytic streptococcus, Streptococcus pneumoniae and staphylococcus that does not produce penicillinase; ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/62C07D499/16
Inventor 郝志艳
Owner HAINAN MEILAN SMITH KLINE PHARMA
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