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Penicillin G sulfoxide dimethylacetamide (DMA) composite crystal and preparation method thereof

A technology of composite crystal and penicillin, applied in the field of medicine and chemical industry, can solve the problems of affecting the protection effect of esterification, increasing by-product impurities, affecting the yield of ring expansion and rearrangement, etc., and achieves high product yield, good stability and controllability strong effect

Active Publication Date: 2015-04-08
NORTH CHINA PHARMA COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the composite crystal contains methanol that may destroy the esterification protection group, it will affect the effect of esterification protection, and then affect the yield of ring expansion rearrangement, increasing the by-product impurities

Method used

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  • Penicillin G sulfoxide dimethylacetamide (DMA) composite crystal and preparation method thereof
  • Penicillin G sulfoxide dimethylacetamide (DMA) composite crystal and preparation method thereof
  • Penicillin G sulfoxide dimethylacetamide (DMA) composite crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] At room temperature, put 50 g of penicillin G sulfoxide (water content 0.3%) into a 100 ml one-mouth eggplant-shaped bottle, add 53 ml of DMA, and dissolve in an ultrasonic pool at 40°C to form a DMA solution of penicillin G sulfoxide. Then the temperature of the one-mouth eggplant bottle was slowly lowered to -30°C, and crystallization was carried out at low temperature for 24 hours. Filter and wash the filter cake with 50ml petroleum ether. After drying, 20.0 g of penicillin G sulfoxide DMA complex crystals were obtained (32.0% molar yield).

[0045] The penicillin G sulfoxide DMA complex crystal was taken to measure the melting point, and the melting point was found to be 103.5°C~103.9°C.

[0046] Take the penicillin G sulfoxide DMA composite crystal for X-ray powder diffraction analysis (see the table below for details), and the spectrum is obtained by passing the λ=1.54059 Angstrom copper ray through the silk filter of the monochromator.

[0047] X-ray powder dif...

Embodiment 2

[0051] At room temperature, drop 35 grams of penicillin G sulfoxide with a moisture content of 15% into a single-mouth eggplant-shaped bottle, add the filtered mother liquor of Example 1, and dissolve in an ultrasonic pool at 30° C. to form DMA of penicillin G sulfoxide solution. Then the temperature of the one-mouth eggplant bottle was slowly lowered to -30°C, and crystallization was carried out at low temperature for 24 hours. Filter and wash the filter cake with 80ml petroleum ether. After drying, 37.2 g of penicillin G sulfoxide DMA complex crystals were obtained (100% molar yield).

[0052] The penicillin G sulfoxide DMA complex crystal was taken to measure the melting point, and the melting point was found to be 103.5°C~103.8°C.

[0053] Get the penicillin G sulfoxide DMA composite crystal to do X-ray powder diffraction analysis, and obtain a collection of spectra similar to Example 1.

Embodiment 3

[0055] At room temperature, put 25 grams of penicillin G sulfoxide (water content 0.2%) into a 100ml one-mouth eggplant-shaped bottle, add 53ml of DMA and 13ml of water, and dissolve in an ultrasonic pool at 35°C to form a DMA solution of penicillin G sulfoxide . Then slowly cool down the one-mouth eggplant bottle to -20°C, and crystallize at low temperature for 24 hours. Filter and wash the filter cake with 60ml petroleum ether. After drying, 26.5 g of penicillin G sulfoxide DMA complex crystals were obtained (84.9% molar yield).

[0056] The penicillin G sulfoxide DMA complex crystal was taken to measure the melting point, and the melting point was found to be 103.3°C~103.8°C.

[0057] Get the penicillin G sulfoxide DMA composite crystal to do X-ray powder diffraction analysis, and obtain a collection of spectra similar to Example 1.

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Abstract

The invention discloses a penicillin G sulfoxide dimethylacetamide (DMA) composite crystal and a preparation method thereof. The molecular formula of the composite crystal is C20H27N3O6S and the molecular weight of the composite crystal is 437.5. The pareparation method comprises the following steps: (a) dissolving penicillin G sulfoxide into a DMA solution or an aqueous solution containing the DMA or a mixed organic solution containing the DMA; (b) cooling the solution containing the penicillin G sulfoxide and the DMA so as to enable the penicillin G sulfoxide and the DMA to gradually reach a saturated or supersaturated state and separate out the crystal; and separating and drying the crystal to obtain the penicillin G sulfoxide DMA composite crystal. The composite crystal provided by the invention has high stability, does not contain impurities which damage esterification protective reaction, is extremely favorable for esterification protection reaction and ring expanding rearrangement reaction, increases the yield of the ring expanding rearrangement reaction, and improves the product quality.

Description

technical field [0001] The invention relates to a penicillin G sulfoxide DMA composite crystal and a preparation method thereof, belonging to the field of medicine and chemical industry. Background technique [0002] Penicillin antibiotics are commonly used antibacterial drugs by the public, and are the general term for a large class of antibiotics in β-lactams. Penicillin antibiotics include penicillin G, penicillin V, ampicillin and other subclasses. In order to improve the antibacterial effect of drugs, researchers have continuously modified and optimized natural penicillins to synthesize a variety of new cephalosporin antibiotics. [0003] Penicillin G sulfoxide is usually obtained by oxidation of penicillin G as a starting material, and is an important intermediate for the synthesis of various new cephalosporins. Penicillin G sulfoxide can be protected by esterification, ring expansion and rearrangement, etc., to obtain 7-aminodesacetoxy cephalosporin (7-ADCA), 7-phen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D499/46C07C233/05C07D499/04C07D499/18C07C231/24
Inventor 米振瑞魏青杰段志钢刘明儒王东杨帆马金玉闫峰王立强米建伟张伟
Owner NORTH CHINA PHARMA COMPANY
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