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Cephalosporin nucleus derivative compound, cephaene onium salt compound prepared from same, and method for preparing cefpiramide sulfate from cephalosporin nucleus derivative compound and cephaene onium salt compound

Inactive Publication Date: 2010-07-21
YANTAI BAOHUA BIO TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented new chemical structure describes different methods for making certain types of molecules called Ceftazolin or Cefpiridone that can be useful against various diseases like tuberculosis caused by bacterial strains resistant to drugs currently available at this time. These structures are made from specific substances found naturally within plants, but they may also contain other components added during production. By combining these materials together, it becomes possible to create more effective medications without requiring costly reagent processes.

Problems solved by technology

This patented describes methods for making certain types of chemical called Ceftiprofen Sulphapy® or CFIBN® from beta-substitute imidocarbazoles made up of 3-(4'-thienzo-5') acroleic molded carboxymultonium bacterial strains. These techniques involve converting these molecules into their corresponding α-,ß-unsaturated derivatives followed by various modifications such as protecting them under specific conditions before further processing.

Method used

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  • Cephalosporin nucleus derivative compound, cephaene onium salt compound prepared from same, and method for preparing cefpiramide sulfate from cephalosporin nucleus derivative compound and cephaene onium salt compound
  • Cephalosporin nucleus derivative compound, cephaene onium salt compound prepared from same, and method for preparing cefpiramide sulfate from cephalosporin nucleus derivative compound and cephaene onium salt compound
  • Cephalosporin nucleus derivative compound, cephaene onium salt compound prepared from same, and method for preparing cefpiramide sulfate from cephalosporin nucleus derivative compound and cephaene onium salt compound

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Embodiment 1, the first step: the synthesis of 7β-amino-3-hydroxyl-3-cephalosporin-4-carboxylic acid (II): 20 milliliters of methyl alcohol is loaded into a 100 milliliter three-necked flask, 20 milliliters of water, add 6 grams of 7- ACA, cooled to -40°C, added dropwise 1.76 g of sodium hydroxide in 5 ml of aqueous solution, after the addition, kept stirring for 30 min, adjusted the pH to 1-2 with 15% hydrochloric acid, stirred for 2 h, suction filtered, and filtered the cake with water Washing and vacuum drying at 40°C gave 4.5 g of a white solid with a yield of 90% and a purity of 98.7%;

[0041] 1 H-NMR (DMSO-d 6 )δ3.45 (1H, d, J = 18Hz), 3.55 (2H, d, J = 18Hz), 4.18 (1H, d, J = 13.6Hz), 4.23 (1H, d, J = 13.6Hz), 4.72 ( 1H, d, J = 4.8Hz), 4.92 (1H, d, J = 4.8Hz), 6.25 (2H, brs)

[0042] The second step: 7β-[2-(2-formylaminothiazol-4-yl)-2-(methoxyiminoacetamide)]-3-hydroxyl-3-cephem-4-carboxylic acid (III ) synthesis: put 40 ml tetrahydrofuran and 20 ml water in...

Embodiment 2

[0050] Embodiment 2, the first step is with embodiment 1;

[0051] The second step: 7β-[2-(2-formylaminothiazol-4-yl)-2-(methoxyiminoacetamide)]-3-hydroxyl-3-cephem-4-carboxylic acid (III ) synthesis: 30 milliliters of acetonitrile and 20 milliliters of water are loaded into a 200 milliliter three-necked flask, 4 grams of compound (II) synthesized in the first step are added, saturated sodium bicarbonate solution is added dropwise to pH=7-8, cooled to 0- Add 4.0 grams of active ester in batches at 5°C, while adding, use saturated sodium bicarbonate solution to control pH=7-8, after the addition, slowly heat up to about 40°C, stir for 6 hours, filter, add 30ml of water to the filtrate, and cool At about 5°C, adjust the pH to 1-2 with 10% hydrochloric acid, stir for 8 hours after dripping, filter with suction, wash with ice water, and vacuum-dry at 30°C to obtain 6.6 g of a light yellow solid with a yield of 87% and a purity of 95%;

[0052] The third step: 7β-[2-(2-formylamino...

Embodiment 3

[0055] Embodiment 3, the first step is with embodiment 1;

[0056] The second step: 7β-[2-(2-formylaminothiazol-4-yl)-2-(methoxyiminoacetamide)]-3-hydroxyl-3-cephem-4-carboxylic acid (III ) synthesis: 20 milliliters of N, N-dimethylformamide, 20 milliliters of water are charged into a 200 milliliter three-necked flask, 3 grams of compound (II) synthesized in the first step are added, and saturated sodium bicarbonate solution is added dropwise to pH= 7-8, cool to 0-5°C, add 4.0 grams of active ester in batches, control the pH=7-8 with saturated sodium bicarbonate solution while adding, slowly raise the temperature to about 50°C after the addition, stir for 4 hours, filter , add 30 ml of water to the filtrate, cool to about 5°C, adjust the pH to 1-2 with 10% hydrochloric acid, stir for 8 hours after dripping, filter with suction, wash with ice water, and dry in vacuum at 30°C to obtain 6.5 g of a light yellow solid. 86% yield, 95% purity;

[0057] The third step: 7β-[2-(2-form...

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Abstract

The invention discloses cephalosporin nucleus derivative compound and cephaene onium salt compound prepared from the cephalosporin nucleus derivative compound, which are respectively intermediates for synthesizing cefpiramide sulfate, and a method for preparing the cefpiramide sulfate from the two intermediates, namely preparing 7beta-[2-(2-alkanol aminothiazol-5-yl)-2-methoxyimino acetamid]]-3-[3-alkanol amino-2-(2-alkanol oxy ethyl)-1-pyrazol onium]methyl-3-cephem-4-carboxylate (IV) by coupling 7beta-[2(2-alkanol aminothiazol-5-yl)-2-methoxyimino acetamid]]-3-(hydrocarbon sulfonate)-3-cephem-4-carboxylic acid (I) serving as a raw material with 5-alkanol amino-2-(2-alkanol oxy ethyl)-1-pyrazol, and then converting to obtain the cefpiramide sulfate. The method has the advantages of mild reaction conditions, short steps, cheap raw materials, industrial production, no special reagents, simple process and easy amplification.

Description

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Claims

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Application Information

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Owner YANTAI BAOHUA BIO TECH
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