Crystals of N-acetylneuraminic acid ammonium salt anhydrate, and method for producing same

A technology of neuraminic acid ammonium salt and anhydrous, which is applied in the preparation of sugar derivatives, organic chemical methods, chemical instruments and methods, etc., can solve the problems of stability and storage stability, and achieve storage stability sex high effect

Active Publication Date: 2017-09-26
KYOWA HAKKO BIO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the crystal and its solution gradually change color to brown, etc., and there is also a problem in terms of storage stability.
[0004] On the other hand, as a crystal of the ammonium salt of NeuAc, a monohydrate crystal is known (Patent Document 1), but its melting point is as low as around 105°C, so there is a problem with stability under high temperature conditions

Method used

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  • Crystals of N-acetylneuraminic acid ammonium salt anhydrate, and method for producing same
  • Crystals of N-acetylneuraminic acid ammonium salt anhydrate, and method for producing same
  • Crystals of N-acetylneuraminic acid ammonium salt anhydrate, and method for producing same

Examples

Experimental program
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Effect test

reference example 1

[0083] Obtaining of Non-crystalline Amorphous Form of NeuAc Ammonium Salt

[0084] 519.4 g of NeuAc anhydrate crystals were dissolved in water, and the pH was adjusted to 6.80 using ammonia water to prepare 650 mL of an aqueous NeuAc-containing ammonium salt solution. A part of this aqueous solution was freeze-dried to obtain a white powder. When the powder was subjected to powder X-ray diffraction measurement, no X-ray diffraction peak was confirmed, so it was found that the powder was an amorphous amorphous substance.

[0085] Examples are shown below, but the present invention is not limited to the following examples.

Embodiment 1

[0087] Crystal Obtaining of NeuAc Ammonium Salt Anhydrate-1

[0088] 1546.7 g of NeuAc in terms of anhydrous matter was dissolved in water, and the pH was adjusted to 7.67 using ammonia water to obtain 3800 mL. This aqueous solution was concentrated to 1800 mL, and 500 mL of the obtained concentrated solution was used in the next step.

[0089] While maintaining the 500 mL concentrated solution at 45° C., 1500 mL (3 times the amount) of methanol was added dropwise thereto over 3 hours, and then 400 mL of acetone was added thereto. After aging for 1 hour, 1100 mL of acetone (final addition amount: 3 times the amount) was additionally added over 3 hours to precipitate crystals. The crystal slurry was cooled to 5° C., aged for 3 hours, and the crystals were collected by filtration, washed with 80% methanol aqueous solution, and dried under reduced pressure at 25° C. to obtain 430.8 g of crystals.

[0090] Table 1 shows the results of powder X-ray diffraction of this crystal. I...

Embodiment 2

[0102] Crystal Obtaining of NeuAc Ammonium Salt Anhydrate-2

[0103] 1475.8 g of NeuAc in terms of anhydrous matter was dissolved in water, and the pH was adjusted to 6.81 using ammonia water to prepare 4000 mL. This aqueous solution was concentrated to 1810 mL, and 40 mL of the obtained concentrated solution was used in the next step.

[0104] 10 mL of water was added to 40 mL of this concentrated solution to make 50 mL. While maintaining this 50 mL solution at 40° C., 40 mL of ethanol was added dropwise thereto over 1 hour. The crystal obtained in Example 1 was added as a seed crystal, and the crystal was precipitated. After aging the crystals over 9 hours, 110 mL (final addition amount: 3 times the amount) of ethanol was added dropwise over 8 hours. The crystal slurry was cooled to 10° C., aged for 3 hours, and the crystals were collected by filtration, washed with 80% ethanol aqueous solution, and dried under reduced pressure at 25° C. to obtain 32.9 g of crystals.

[...

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Abstract

The present invention makes it possible to provide: crystals of N-acetylneuraminic acid ammonium salt anhydrate; and a method for producing crystals of N-acetylneuraminic acid ammonium salt anhydrate. The method is characterized in that crystals of N-acetylneuraminic acid ammonium salt anhydrate are precipitated by addition or dropwise addition of a solvent selected from the group consisting of alcohols and ketones to an aqueous solution of N-acetylneuraminic acid that contains an ammonium-containing compound having a pH of 3.0-9.0, and the crystals of N-acetylneuraminic acid ammonium salt anhydrate are collected from this aqueous solution.

Description

technical field [0001] The present invention relates to a crystal of an ammonium salt anhydrate of N-acetylneuraminic acid useful as products, raw materials, or intermediates of, for example, health foods, pharmaceuticals, cosmetics, and the like, and a method for producing the same. Background technique [0002] N-acetylneuraminic acid (hereinafter referred to as NeuAc) is a type of acidic amino sugars collectively referred to as sialic acid, and is widely used as a pharmaceutical raw material for anti-influenza drugs and the like, as a component of foods, cosmetics, and cell culture media. [0003] NeuAc can be produced by a fermentation method, an enzymatic method, an extraction method from a natural product, or a chemical synthesis method. As known crystals of NeuAc, dihydrate (Non-Patent Document 1) and anhydrous (Non-Patent Document 2) crystals are known, but the solution of these crystals shows strong acidity, and their solubility is compared at room temperature Smal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H7/027
CPCC07H1/00C07H7/027C07B2200/13C07H13/04C07H5/06
Inventor 福本一成
Owner KYOWA HAKKO BIO CO LTD
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