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Cefradine compound containing one-fifth water and pharmaceutical composition preparation thereof

A cefradine and compound technology, which is applied in the field of chemical engineering and pharmaceutical crystallization, can solve the problems of poor product quality, waste of raw materials, instability between batches, etc.

Inactive Publication Date: 2019-01-04
赵建宇
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existence of these problems leads to poor product quality and instability between batches on the one hand, and also leads to increased production costs and waste of raw materials to a certain extent.

Method used

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  • Cefradine compound containing one-fifth water and pharmaceutical composition preparation thereof
  • Cefradine compound containing one-fifth water and pharmaceutical composition preparation thereof
  • Cefradine compound containing one-fifth water and pharmaceutical composition preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of 1 / 5 water cephradine compound

[0036](1) Add 300.2 g of dichloromethane and 60.1 g of 7-ADCA to Reactor 1, cool to -10°C; add 40.2 g of tetramethylguanidine dropwise therein, and stir until completely dissolved to obtain 7-ADCA tetramethyl Dichloromethane solution of guanidinium salt;

[0037] (2) Add 87.3g of dihydrophenylglycine sodium salt, 441.2g of dichloromethane, and 30.4g of dimethylacetamide into reactor 2, cool down to 5°C, and add 3.1g of 2,6-lutidine , the temperature was lowered to -30°C for the second time, 41.4 g of pivaloyl chloride was added, and reacted at -10°C for 1 hour to obtain a mixed acid anhydride;

[0038] (3) Quickly transfer the tetramethylguanidine salt solution of 7-ADCA to the mixed acid anhydride, react at -30°C for 2h; add 4.1g of diethylamine, continue the reaction for 0.5h; cool the reaction solution to 0°C, add deionized 500.1g of water and 50.2g of concentrated hydrochloric acid, let stand for 0.5...

Embodiment 2

[0042] Embodiment 2: the preparation of 1 / 5 water cephradine compound

[0043] (1) Add 400.1 g of dichloromethane and 60.1 g of 7-ADCA to Reactor 1, cool to -15°C; add 45.1 g of tetramethylguanidine dropwise therein, and stir until completely dissolved to obtain 7-ADCA tetramethyl Dichloromethane solution of guanidinium salt;

[0044] (2) Add 90.2g of dihydrophenylglycine sodium salt, 440.1g of dichloromethane, and 30.3g of dimethylacetamide to reactor 2, cool down to 0°C, and add 3.1g of 2,6-lutidine , the temperature was lowered to -25°C for the second time, 42.4 g of pivaloyl chloride was added, and reacted at -10°C for 1 hour to obtain a mixed anhydride;

[0045] (3) Quickly transfer the tetramethylguanidine salt solution of 7-ADCA to the mixed acid anhydride, react at -30°C for 2h; add 4.5g of diethylamine, continue the reaction for 0.5h; cool the reaction solution to 0°C, add deionized 500.3g of water and 41.7g of concentrated hydrochloric acid, let stand for 0.5h, tak...

Embodiment 3

[0049] Embodiment 3: the preparation of 1 / 5 water cephradine compound

[0050] (1) Add 300.2 g of dichloromethane and 50.3 g of 7-ADCA to Reactor 1, cool to -12°C; add 40.5 g of tetramethylguanidine dropwise therein, and stir until completely dissolved to obtain 7-ADCA tetramethyl Dichloromethane solution of guanidinium salt;

[0051] (2) Add 89.4g of dihydrophenylglycine Deng sodium salt, 441.5g of dichloromethane, and 31.2g of dimethylacetamide into reactor 2, cool down to 5°C, and add 3.5g of 2,6-lutidine , the temperature was lowered to -20°C for the second time, 41.5 g of pivaloyl chloride was added, and reacted at -10°C for 1 hour to obtain a mixed acid anhydride;

[0052] (3) Quickly transfer the tetramethylguanidine salt solution of 7-ADCA to the mixed acid anhydride, react at -30°C for 2h; add 4.4g of diethylamine, continue the reaction for 0.5h; cool the reaction solution to 0°C, add deionized 500.1g of water and 50.5g of concentrated hydrochloric acid, let stand f...

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Abstract

The invention discloses a cefradine compound containing one-fifth water and a pharmaceutical composition preparation thereof. Each mole of cefradine contains one-fifth mole of water. The cefradine compound has characteristic peaks at the positions with the X-ray diffraction spectrum diffraction angle 2 theta of 5.50+ / -0.2 degrees, 7.21+ / -0.2 degrees, 14.49+ / -0.2 degrees, 15.69+ / -0.2 degrees, 16.24+ / -0.2 degrees, 16.66+ / -0.2 degrees, 20.16+ / -0.2 degrees and 22.04+ / -0.2 degrees. First, a dichloromethane solution and mixed anhydride of 7-ADCA tetramethylguanidine are separately synthesized and then reacted with each other to obtain the cefradine compound containing one-fifth water. The operation is simple, reactants are easy to obtain, the reaction conditions are mild, and the yield is high.The cefradine compound containing one-fifth water has low hygroscopicity and impurity content, high fluidity and thermodynamic stability and a wider application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical engineering medicine crystallization, and relates to a 1 / 5 water cephradine compound and a pharmaceutical composition preparation thereof. Background technique [0002] Cefradine (Cefradine) is a semi-synthetic cephalosporin antibiotic successfully researched by Bristol-Myers Squibb in 1972. It belongs to the first generation of cephalosporins and entered the pharmaceutical market in the 1970s. The chemical name is (6R,7R)-7-[(R)-2-amino-2-(1,4-cyclohexen-1-yl)acetamido]-3-methyl-8-oxo-5 -Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. The structural formula is as follows: [0003] [0004] Cefradine has good curative effect and high safety in clinical treatment of respiratory tract infection, urinary tract infection, skin and soft tissue infection, gastrointestinal infection, bone and joint infection, sepsis, endocarditis, etc., and is widely used in clinical practice . [0005] At p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/22C07D501/06C07D501/12A61K31/545A61P31/04
CPCC07B2200/13C07D501/06C07D501/12C07D501/22
Inventor 赵建宇
Owner 赵建宇
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