Method for purifying D (-)-sulbenicillin sodium

A technology of sulfobenicillin sodium and a purification method, which is applied in the field of β-cyclodextrin purification of D-sulfobenicillin sodium, can solve the problems of easy racemization of levoform, complicated process, inability to use, etc., and achieves the effect of improving production efficiency

Active Publication Date: 2011-10-19
HUNAN ER KANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are certain defects in each method, such as the reaction process is difficult to control when the chiral source synthesis method is used for the production of sulbenicillin sodium, and the L-isomer in the product is easy to racemize; the asymmetric synthesis method and high-performance liquid chromatography have complex processes. , high equipment costs and other issues that cannot be applied to industry

Method used

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  • Method for purifying D (-)-sulbenicillin sodium
  • Method for purifying D (-)-sulbenicillin sodium
  • Method for purifying D (-)-sulbenicillin sodium

Examples

Experimental program
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Effect test

Embodiment 1

[0053] (a) mixing and dissolving the crude sulfobenicillin sodium with water in a weight ratio of 2:1;

[0054] (b) The solution temperature was maintained at 30°C through a porous ceramic tube with a pore size of 60 μm loaded with β-cyclodextrin membrane, and the solution flow rate was 6 dl / sec;

[0055] (c) add dehydrated alcohol of 1 / 2 of Sulfonbenicillin Sodium crude product weight and the isopropanol of Sulfonbenicillin Sodium crude product weight, stir and grow crystal in reaction tank until there is a large amount of crystals to separate out, open frozen brine and cool down 8h;

[0056] (d) centrifugal separation to obtain D(-)-sulfobenicillin sodium.

[0057] The yield of sulfenbenicillin sodium was 60%, and the content of D(-)-sulfenbenicillin sodium was 80%. The optical rotation of the product is determined to be [α]D: +160°~+180°.

Embodiment 2

[0059] (a) mixing and compatibilizing sulfobenicillin sodium crude product with water at a weight ratio of 9:1;

[0060] (b) A ceramic tube with a pore size of 2 μm passed through a loaded L-lysine-β-cyclodextrin membrane at room temperature, and the solution flow rate was 2 dl / sec;

[0061] (c) add dehydrated alcohol of 1 / 2 of Sulfonbenicillin Sodium crude product weight and the isopropanol of Sulfonbenicillin Sodium crude product weight, stir and grow crystal in reaction tank until there is a large amount of crystals to separate out, open frozen brine and cool down 9h;

[0062] (d) centrifugal separation to obtain D(-)-sulfobenicillin sodium.

[0063] The yield of Sulfonicillin Sodium was 65%, and the content of D(-)-Sulfonbenicillin Sodium was 99%. The optical rotation of the product is determined to be [α]D: +175°~+180°.

[0064] NMR test results of the obtained product: 1H-NRM (400MHz, D2O)δ(ppm): 1.4025(t, 6H, -CH3), 4.1153(d, H, -CH-COONa), 4.9275(s, H, Ar- CH), 5.46...

Embodiment 3

[0066] (a) mixing and compatibilizing sulfobenicillin sodium crude product with water at a weight ratio of 7:1;

[0067] (b) Passing through a carboxymethyl-β-cyclodextrin membrane loaded with a carboxymethyl-β-cyclodextrin membrane while keeping the solution temperature at 27°C, a ceramic tube with a pore size of 100 μm and a solution flow rate of 10 dl / sec;

[0068] (c) add the dehydrated alcohol of 1 / 2 of the Sulfonicillin Sodium crude product weight and the isopropanol of Sulfonbenicillin Sodium crude product weight, stir and grow crystals in the reaction tank until a large amount of crystals separate out, open the frozen brine and cool down 10h;

[0069] (d) centrifugal separation to obtain D(-)-sulfobenicillin sodium.

[0070] The yield of sulfobenicillin sodium was 50%, and the content of D(-)-sulfobenicillin sodium was 93%. The optical rotation of the product is determined to be [α]D: +170°~+180°.

[0071] It can be seen from the above that the optical rotation range...

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Abstract

The invention provides a method for purifying D (-)-sulbenicillin sodium, which comprises the following steps of: mixing a sulbenicillin sodium crude product and water in a weight ratio of (1-10):1, and dissolving; allowing solution to pass through a beta-cyclodextrin membrane-loaded porous ceramic tube at the flow speed of between 1 and 10 dl/second; adding a solvent, stirring until crystals are not precipitated, and cooling at a low temperature; and centrifuging to obtain the D (-)-sulbenicillin sodium. The content of the D (-)-sulbenicillin sodium processed by the method is 99 percent, and the yield is 65 percent; and the method is simple and convenient and low in requirement on equipment, and the cost of generating the D (-)-sulbenicillin sodium is reduced effectively.

Description

technical field [0001] The invention relates to a method for purifying D(-)-sulfobenicillin sodium, in particular to a method for purifying D(-)-sulfobenicillin sodium with beta-cyclodextrin. Background technique [0002] The molecular structure of sulfobenicillin sodium has chirality, so it is divided into levorotatory, dextrorotatory and racemate. The crude sulfobenicillin sodium in industry is a mixture of levorotatory (D(-)) and dextrorotatory (L(+)), with a mass ratio of about 3:1. It has been found that the biological activity of D(-)-sulfobenicillin sodium is 4 to 8 times higher than that of L(+) sulfobenicillin sodium. method. [0003] Common methods for separating chiral compounds include chiral source synthesis, asymmetric synthesis and high performance liquid chromatography. Each method has certain defects. For example, when the chiral source synthesis method is used for the production of sulfobenicillin sodium, the reaction process is not easy to control, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D499/62C07D499/18
Inventor 帅放文王向峰章家伟
Owner HUNAN ER KANG PHARMA
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