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Use of a cyclohexenyl-dl-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations

A technology of aspartic acid and neuraminidase, applied in the field of medicine

Active Publication Date: 2021-06-22
ZHONGSHAN WANHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, studies by Satoh K et al. (Biol Pharm Bull. 2007 Sep; 30(9):1816-8.) found that neither compound I nor compound II affected the reuptake and / or Therefore, the inventor speculates that the neuropsychiatric adverse reactions such as depression in compound I may be related to other related substances in its preparation

Method used

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  • Use of a cyclohexenyl-dl-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations
  • Use of a cyclohexenyl-dl-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations
  • Use of a cyclohexenyl-dl-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations

Examples

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preparation Embodiment 2

[0021] Compound Preparation Example 2 Preparation and Structure Confirmation of Compound A

[0022] Take 1mmol ethyl (3R,4R,5S)-4-acetylamino-5-amino-3-(pent-3-yloxy)cyclohex-1-ene-1-carboxylate (compound S) and 1.2 Mmol fumaric acid was dissolved in 70% acetonitrile to obtain a saturated solution, and the pH of the solution was adjusted to 9 with 0.1N sodium hydroxide. The resulting solution was stirred in a 70°C water bath for 24 hours. Distilled to dryness under reduced pressure, the resulting solid was washed three times with 0.01N sodium hydroxide, and purified by HPLC to obtain a white powdery solid with a melting point of 88.9°C to 90.2°C. The H-NMR spectrum data of the starting material and the product are shown in Table 2. The HPLC analysis results showed that the retention time of the obtained product in the HPLC measured by the method described in Test Example 1 was 43.985 min.

[0023] Table 2 Proton NMR spectrum data of relevant compounds

[0024]

[0025] ...

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Abstract

One aspect of the invention provides a use of a cyclohexenyl-DL-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations, the cyclohexenyl-DL-aspartic acid derivative For the specific definition of the neuraminidase inhibitor, see the instructions. HPLC and structural confirmation studies show that the commercially available original preparation of the neuraminidase inhibitor contains a small amount of the cyclohexenyl-DL-aspartic acid derivative, and the cyclohexenyl-DL-aspartic acid derivative Aspartic acid derivatives are one of the main causes of neuropsychiatric adverse reactions caused by the original preparation of the neuraminidase inhibitor, so controlling them is crucial to improving the quality of medicines and reducing the incidence of adverse reactions.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to the use of a cyclohexenyl-DL-aspartic acid derivative in the quality control of neuraminidase inhibitor pharmaceutical preparations. Background technique [0002] Research by Hoffmann G et al. (Antimicrob Agents Chemother.2009 Nov; 53(11):4753-61.) pointed out that the neuraminidase inhibitor compound Ⅰ and its in vivo active metabolite compound Ⅱ for the treatment of influenza virus infection Crossing the blood-brain barrier into the CNS is relatively low and therefore unlikely to be neuropsychiatrically related as it occurs in influenza-infected patients. [0003] [0004] However, many literatures have reported cases of neuropsychiatric adverse reaction events during the clinical use of compound I, including depression, abnormal behavior, etc. (Sungho Chung et al. Psychiatry Investig. 2010 Dec; 7(4):302-4. Wait). It is well known in the art that the reuptake ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/245A61P25/24A61P31/16
CPCA61K31/245A61P25/24A61P31/16
Inventor 何秋云杨衍秋王浩然杜志博向飞彭韪
Owner ZHONGSHAN WANHAN PHARM CO LTD
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