Derivative of macrolides, method for preparing same and application thereof

A technology of macrolides and derivatives, which is applied in the field of medicine to achieve good dissolution performance and improve bioavailability

Inactive Publication Date: 2010-01-13
刘力
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] The literature only reported erythromycin lactobionate [C 37 h 67 NO 13 ·C 12 h 22 o 12 , CAS No.: 3847-29-8], erythromycin thiocyanate C 37 h 67 NO 13 · HCNS (CAS No.: 7704-67-8) etc. and its application, so far, there is no open literature report macrolide derivatives -- the hydrate of the salt of erythromycin [C

Method used

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  • Derivative of macrolides, method for preparing same and application thereof
  • Derivative of macrolides, method for preparing same and application thereof

Examples

Experimental program
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Embodiment 1

[0064] Example 1 Preparation of erythromycin lactobionic acid 11 hydrate: In a three-necked flask, add 50ml of acetone and 8g of erythromycin, stir, add lactobionic acid or its aqueous solution, stir at 5-35°C, make the reaction complete, slowly add Anhydrous acetone, cooled to about -30~5℃, wait for the solid to precipitate, filter, rinse the solid with anhydrous acetone, and drain to obtain off-white crystalline powder, easily soluble in water, HPLC: the main peak of the sample and red The retention time of the main peak of the mycin reference substance is the same, and the content of erythromycin is 56.79% (56.88%); melting point: 95.1~116.3°C (uncorrected), moisture measured by Karl Fischer method is 15.53% (theoretical value 15.36%), TG: 200 The weight loss of the platform before ℃ is about 15.56% (see attached figure 1 ), MS (ESI) m / z: 1092,734,358. Elemental analysis measured values: C 45.73, H 8.54, N 1.15; theoretical values: C 45.61, H 8.67, N 1.09.

Embodiment 2

[0065] Example 2 Preparation of erythromycin lactobionic acid hexahydrate: In a three-necked flask, add 50 ml of acetone, 10 g of erythromycin, add equimolar lactobionic acid or its acetone aqueous solution under stirring at 10 to 40 ° C, and react for 0.2 to 4 Hours, after the reaction is complete, slowly add 1 to 8 times the amount of anhydrous acetone, cool to -45 to -10°C, filter, rinse the solid with acetone, drain, and dry at about 80°C to obtain off-white powder, very Soluble in water, HPLC: the retention time of the main peak of the sample is consistent with the main peak of the erythromycin reference substance, the content of erythromycin is 61.91% (theoretical 62.08%); melting point: 132.6-137.7°C (uncorrected); : 9.16%, TG: about 9.09% (theoretical value 9.01%) of platform weight loss before 200 ℃ (see attached figure 2 ), MS (ESI, FAB) m / z: 1092, 1091, 734, 733, 358, 357; elemental analysis measured values: C 49.11, H 8.55, N 1.21; theoretical values: C 49.03, H 8...

Embodiment 3

[0066] Example 3. Put 10 g of lactobionic acid and erythromycin in a molar ratio (1:1) into a reaction flask, add water, stir, and control the temperature between 5 and 40° C. to dissolve. After the reaction is completed, fill each bottle with 1 ml In a 20ml bottle, freeze it to -50°C, keep it for 0.5 to 6 hours, lower the temperature of the condenser to -55°C, vacuumize, and gradually raise the temperature to about -16°C through the shelf, then cool it down at about -16°C Keep it for about 28 hours, continue heating to raise the temperature of the drug to about 30°C, keep it for about 10 hours, and get a white powder with a yield of 99%. The sample is very soluble in water. HPLC: the retention of the main peak of the sample and the main peak of the erythromycin reference substance The time is the same; melting point: 137.2-138.7 ° C (uncorrected); Karl Fischer's method to determine the moisture is 4.67% (theoretical value 4.72%), TG-DTG: weight loss before 200 ° C is about 4.3...

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Abstract

The invention provides a derivative of macrolides, a method for preparing the same and application thereof. The derivative is a hydrate of erythrocin and salt, the molecular formula is C37H67NO13.A.nH2O, and n is between 1.0 and 11.0; and A is selected from an organic acid or inorganic acid, and one of lactobionic acid, thiocyanic acid, maleic acid, fumaric acid, thiocyanic acid, acetic acid, methanesulfonic acid, benzene sulfonic acid, nicotinic acid, lactic acid, citric acid, tartaric acid, aspartic acid, glutamic acid and phosphoric acid. The hydrate has better water solubility and storing stability, and is suitably used for preparing medicaments of treating and preventing infectious diseases of human or animals caused due to sensitive bacteria of Gram-positive or negative bacteria.

Description

technical field [0001] The invention relates to the technical field of medicine, and specifically provides macrolide derivatives and their preparation and application. Background technique [0002] The literature only reported erythromycin lactobionate [C 37 h 67 NO 13 ·C 12 h 22 o 12 , CAS No.: 3847-29-8], erythromycin thiocyanate C 37 h 67 NO 13 · HCNS (CAS No.: 7704-67-8) etc. and its application, so far, there is no open literature report macrolide derivatives -- the hydrate of the salt of erythromycin [C 37 h 67 NO 13 ·A·nH 2 O, n=1.0~11.0, A can be lactobionic acid, gluconic acid, thiocyanic acid, acetic acid, methanesulfonic acid, benzenesulfonic acid, maleic acid, fumaric acid, nicotinic acid, lactic acid, citric acid, tartaric acid, One of aspartic acid, glutamic acid and phosphoric acid] and its preparation method and use. Contents of the invention [0003] What the present invention relates to is the hydrate of macrolide derivatives-erythromycin sal...

Claims

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Application Information

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IPC IPC(8): C07H17/08A61K31/7048A61P31/00
CPCA61K31/7048A61P31/00Y02A50/30
Inventor 刘力
Owner 刘力
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