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Cefpiramide sodium compound of new way

A technology of cefpiramide sodium and its compounds, which is applied in the field of drug synthesis, can solve the problems of uneven crystal form, poor stability, and low purity, and achieve the effects of improved purity and yield, simple equipment, and simple synthesis process

Inactive Publication Date: 2010-03-17
HAINAN LINGKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Chinese patent CN1594324A and CN101037444A all disclose a kind of preparation method of cefpiramide sodium, all are to react cefpiramide sodium with transsodium agent, make cefpiramide sodium crystal, the shortcoming is crystal form inhomogeneous, purity is low, stable Poor performance, and none of the above-mentioned patents relates to the synthetic method of cefpiramide

Method used

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  • Cefpiramide sodium compound of new way
  • Cefpiramide sodium compound of new way
  • Cefpiramide sodium compound of new way

Examples

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Embodiment 1

[0026] The synthesis of embodiment 1 cefpiramide sodium

[0027] Dissolve 600 grams of triphosgene in 1 liter of dichloromethane, and add dropwise to 302 grams of D-α-(6-methyl-4-hydroxynicotinamide)-p-hydroxyphenylacetic acid and 556 grams of triphenyl In the system of phosphine and 2 liters of dichloromethane, react at -5°C for 4 hours, then add dropwise to 1 liter of water containing 328 grams of 7-TMCA, adjust pH=7.5 with sodium hydroxide in the reaction, The reaction temperature was controlled at 0°C. After the dropwise addition, reacted for 2 hours, distilled off part of the organic solvent under reduced pressure, added 3 liters of acetone, stirred, precipitated crystals, filtered, and vacuum-dried at 40°C to obtain 584 grams of the product, with a yield of 92 %.

Embodiment 2

[0028] The synthesis of embodiment 2 cefpiramide sodium

[0029] Dissolve 800 grams of triphosgene in 2 liters of xylene and add dropwise to 604 grams of D-α-(6-methyl-4-hydroxynicotinamide)-p-hydroxyphenylacetic acid and 988 grams of triphenyl In the system of oxonphos and 3.5 liters of xylene, react at -3°C for 5 hours, then add dropwise to 3 liters of water containing 656 grams of 7-TMCA, adjust pH=7.8 with sodium hydroxide in the reaction, and the reaction temperature Controlled at 2°C, after dropwise addition, reacted for 3 hours, distilled off part of the organic solvent under reduced pressure, added 3 liters of acetone, stirred, precipitated crystals, filtered, and vacuum dried at 45°C to obtain 1182 grams of product, yield 93.1%.

Embodiment 3

[0030] The synthesis of embodiment 3 cefpiramide sodium

[0031] Dissolve 300 grams of triphosgene in 1 liter of 1,2-dichloroethane, and add dropwise to 151 grams of D-α-(6-methyl-4-hydroxynicotinamide)-p-hydroxyphenylacetic acid and In the system of 282 grams of triphenylphosphine and 2 liters of 1,2-ethylene dichloride, react at 0°C for 6 hours, then add dropwise to 1 liter of water containing 164 grams of 7-TMCA, in the reaction Use sodium hydroxide to adjust PH=7.3, and control the reaction temperature at 5°C. After the dropwise addition, react for 4 hours, remove part of the organic solvent by distillation under reduced pressure, add 2 liters of acetone, stir, precipitate crystals, filter, and vacuum at 40°C After drying, 291 grams of the product were obtained, with a yield of 91.8%.

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Abstract

The invention relates to a cefpiramide sodium compound of a new way. The target product, i.e. cefpiramide sodium compound, is prepared by dissolving triphosgene, D-alpha-(6-methyl-4-hydroxy niacinamide)-p-hydroxy phenylacetic acid and triphenylphosphine oxide into an organic solvent, mixing and reacting the D-alpha-(6-methyl-4-hydroxy niacinamide)-p-hydroxy phenylacetic acid with the triphenylphosphine oxide, and then dripping reaction liquid into an aqueous 7-TMCA solution for reaction.

Description

technical field [0001] The invention relates to a cephalosporin compound, in particular to a method for synthesizing a new route of cefpiramide sodium compound, which belongs to the field of drug synthesis. Background technique [0002] Cefpiramide sodium, its chemical name is: (6R, 7R)-7-[(R)-2-(4-hydroxy-6-methyl-3-pyridinecarbonylamino)-2-(p-hydroxyphenyl) Acetylamino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4,2,0 ]oct-2-ene-2-carboxylic acid sodium salt, molecular formula: C 25 h 23 N 8 NaO 7 S 2 , molecular weight: 634.62, structural formula: [0003] [0004] It is a semi-synthetic third-generation cephalosporin antibiotic with broad antibacterial spectrum and bactericidal activity. It has strong antibacterial activity against Gram-positive bacteria, negative bacteria and anaerobic bacteria, and is quite stable against β-lactamase. Clinically, it is mainly used for pharyngitis, tonsillitis, acute and chronic bronchitis, pneumonia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36C07D501/06B01J31/02B01J27/20A61P31/04
Inventor 邱民
Owner HAINAN LINGKANG PHARMA CO LTD
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