Erythromycin ethylsuccinate crystalline hydrate and preparation method and application thereof

A technology of erythromycin and compounds, applied in the field of medicine, to achieve good storage stability at room temperature, easy storage and transportation

Active Publication Date: 2014-12-10
胡梨芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] The literature only reported erythromycin ethylsuccinate [C 43 h 75 NO 16 , molecular weight 862.07, CAS No.: 1264-62-6], and its use, so far, there is no open literature to report macrolide derivatives-erythromycin ethylsuccinate crystalline hydrate [C 43 h 75 NO 16 ·nH 2 O, n=0.2~0.6, and its preparation method and use

Method used

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  • Erythromycin ethylsuccinate crystalline hydrate and preparation method and application thereof
  • Erythromycin ethylsuccinate crystalline hydrate and preparation method and application thereof
  • Erythromycin ethylsuccinate crystalline hydrate and preparation method and application thereof

Examples

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Embodiment 1

[0058] Example 1 Preparation of erythromycin ethylsuccinate 0.5 hydrate: in a three-necked flask, add 35ml of tetrahydrofuran, 10ml of acetone, 8g of erythromycin, 15ml of 47% potassium carbonate, 10ml of water and stir, cool to below 15°C, add Succinic acid monoethyl chloride 4.8g, monitor by TLC until the reaction is complete, slowly add 5M sodium phosphate aqueous solution, stir, control the pH value at about 7.0-8.5, settle and separate the organic phase, slowly add about 60ml into the organic phase under stirring of water, cooled to -15~0°C, after the solid precipitation is complete, filter, the obtained solid is recrystallized with ethanol and water, cooled to about -10°C, after the solid precipitation is complete, suction filtration, the obtained solid is at about 50°C After drying for 8 hours, 4.2 g of off-white solid was obtained; melting point: 109.2~111.7°C (uncorrected), this sample was tested according to the identification items (1) and (2) of erythromycin ethylsu...

Embodiment 2

[0059] Example 2 Preparation of erythromycin ethylsuccinate 0.5 hydrate: In a three-necked flask, add 40ml of acetone, 50ml of tetrahydrofuran, 20g of erythromycin thiocyanate, stir at 30-45°C, add 40ml of 12g potassium carbonate aqueous solution, and stir to react For 1 hour, add 4M sodium dihydrogen phosphate aqueous solution dropwise, stir, control the pH value at about 7.0-8.5, settle and separate the organic phase, add 40ml of 47% potassium carbonate and 10ml of water to the organic phase, stir, cool to below 15°C, Add 10 grams of monoethyl succinic acid chloride, monitor with TLC until the reaction is complete, add dropwise 5M sodium citrate aqueous solution, stir, control the pH value at about 7.0-8.5, settle and separate the organic phase, slowly add to the organic phase while stirring About 100ml of water, cooled to -15 ~ 0 ℃, after the solid precipitation is complete, suction filtration, the obtained solid is recrystallized with isopropanol and water, suction filtrati...

Embodiment 3

[0060] Example 3. The preparation of erythromycin ethylsuccinate 0.25 hydrate: at room temperature, in a 500ml three-necked flask, add 10 g of erythromycin ethylsuccinate 0.5 hydrate, add acetone to make it completely dissolve and slightly excessive, and stir Slowly add 50-70ml of pure water, cool to -10~4°C, let the precipitate precipitate out, filter, rinse the solid with water, filter to obtain a off-white solid, recrystallize with acetone and water, and filter with suction at about 60°C Vacuum drying at about 0.09MPa for about 16 hours yielded 6.7g of off-white crystals; melting point: 109-113°C (uncorrected); this sample was identified according to the identification items (1) and ( 2) Do the identification test, and the result is in line with the corresponding regulations; the water content measured by the Karl Fischer method is 0.68% (theoretical value is 0.52%), and the TG: weight loss is about 0.53% (see attached image 3 ) and the sample contains 0.25 crystal water w...

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Abstract

Disclosed is an anti-infective drug-macrolide derivate, preparation and uses thereof. Macrolide derivate, namely erythromycin ethylsuccinate crystalline hydrate, which has less moisture absorption and good storage stability, can be used in the preparation of medicaments for the treatment and prevention of human or animal infectious diseases caused by Gram-positive or negative bacteria.

Description

technical field [0001] The invention relates to the technical field of medicine, and specifically provides an anti-infection drug-erythromycin ethylsuccinate crystalline hydrate and its preparation and application. Background technique [0002] The literature only reported erythromycin ethylsuccinate [C 43 h 75 NO 16 , molecular weight 862.07, CAS No.: 1264-62-6], and its use, so far, there is no open literature to report macrolide derivatives-erythromycin ethylsuccinate crystalline hydrate [C 43 h 75 NO 16 ·nH 2 O, n=0.2~0.6, and its preparation method and application. Contents of the invention [0003] The present invention relates to an anti-infection drug—a macrolide derivative—a hydrate of Erythromycin Ethylsuccinate (CAS No.: 1264-62-6), its use, and its preparation and use. Erythromycin ethylsuccinate crystalline hydrate of the present invention, its molecular formula is C 43 h 75 NO 16 ·nH 2 O, n=0.2~0.6, n can be a number between 0.25, 0.5, and the eryt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/08C07H1/00A61K31/7048A61P31/04A61P29/00
CPCC07C43/06C07C255/03C07D407/14C07H17/08C07C31/08C07D307/06A61K31/7048C07C19/03C07C49/08C07C69/14C07C31/10A61P29/00A61P31/04Y02A50/30
Inventor 刘力
Owner 胡梨芳
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