Pseudoephedrine derivative and preparation method and application thereof

A kind of technology of ephedrine and derivatives, applied in the field of pseudoephedrine derivatives and preparation thereof

Active Publication Date: 2016-04-06
上海秉丰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the rapid mutation of related targets during the replication process, influenza viruses have also developed varying degrees of resistance to these drugs

Method used

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  • Pseudoephedrine derivative and preparation method and application thereof
  • Pseudoephedrine derivative and preparation method and application thereof
  • Pseudoephedrine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1,6-bis((S)-2-(methylamino)propyl)isochroman-3-one (Ia-1,R 1 =R 2 =CH 3 )

[0040] Weigh 1.71g of 2-(5-chloro-2-methylphenyl)ethan-1-ol into a 150mL three-necked flask, measure 20mL of acetonitrile, stir and dissolve at room temperature, add 0.4g of glucose isomerase , 0.2g of chromium trioxide, continue to stir at room temperature for 10min, weigh 2.28g of periodic acid and dissolve in 10mL of acetonitrile, gradually and slowly dropwise add to the reaction system, and continue to react at room temperature for 36h. After the reaction of Ia-1 was completed, the reaction was stopped, and the solvent was concentrated under reduced pressure. Through column chromatography, the developer was acetone:ether=1:5, and Ia-2 was obtained, 1.32g (yield 66.3%).

[0041] Weigh 1.99g of 2-(5-chloro-2-formylphenyl)acetic acid (Ia-2) into a 150mL round bottom flask, measure 20mL of ethanol, stir and dissolve at room temperature, add 1.83g of N -Dimethylpropan-2-amine, add 0.5g of α-a...

Embodiment 2

[0045] 1,6-bis((S)-2-(methylamino)butyl)isochroman-3-one (R 1 =CH 3 , R 2 =CH 2 CH 3 )

[0046] The preparation method is as in Example 1, except that N-methylbutan-2-amine is used. White solid, mp: 216~220℃, MSm / z: 341.46 (M+Na); 1 H-NMR (DMSO-d 6 , ppm) δ: 7.42~7.09 (m, 3H), 6.85 (m, 1H), 3.52~3.49 (d, 2H), 3.12~3.06 (m, 4H), 2.93~2.54 (m, 4H), 1.92~ 1.48 (m, 2H), 0.87 (t, 2H); 13 C-NMR (DMSO-d 6 , ppm) δ: 167.4, 138.1, 137.3, 135.4, 132.5, 130.9, 125.3, 68.9, 67.9, 66.4, 58.4, 42.2, 39.9, 36.9, 34.0, 27.8, 10.7.

Embodiment 3

[0048] 1,6-bis((S)-2-(ethylamino)butyl)isochroman-3-one (R 1 =R 2 =CH 2 CH 3 )

[0049] The preparation method is the same as in Example 1, except that N-diethylbutyl-2-amine is used. White solid, mp: 201~215°C, MSm / z: 347.09 (M+H), 369.26 (M+Na); 1 H-NMR (DMSO-d 6 , ppm) δ: 7.37~7.18(m, 3H), 5.72(m, 1H), 3.52~3.38(m, 4H), 2.91(d, 1H), 2.79(d, 1H), 2.59~2.54(m, 3H), 2.13(m, 1H), 1.97~1.53(m, 4H), 1.11(s, 2H), 0.84(t, 2H); 13 C-NMR (DMSO-d 6 , ppm) δ: 169.4, 138.1, 136.7, 135.4, 130.5, 128.7, 126.9, 66.6, 62.4, 55.9, 42.2, 40.1, 36.9, 28.6, 27.4, 15.9, 10.3.

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Abstract

The invention discloses a pseudoephedrine derivative and belongs to the field of organic synthesis. The invention relates to a pseudoephedrine derivative as shown in the general structural formula I, or pharmaceutically acceptable salt, ester or prodrug, a preparation method thereof, and an application of a composition containing one or more of the compounds in preparing a medicine for treating and preventing influenza.

Description

technical field [0001] The invention relates to an organic substance, in particular to a pseudoephedrine derivative and its preparation method and application. Background technique [0002] Influenza (flu) is a respiratory infectious disease that seriously threatens human life and health. It has the characteristics of strong pathogenicity, wide epidemic range and rapid transmission. The main symptoms of patients after influenza infection are fever, headache, myalgia, and Typical respiratory symptoms such as cough, rhinitis and sore throat. Influenza viruses are single-stranded negative-sense RNA viruses belonging to the Orthomyxoviridae family. According to the antigenicity of influenza virus matrix protein and nucleoprotein, it can be divided into A, B, C (or A, B, C) three different subtypes. Influenza C viruses rarely cause illness, influenza A and B viruses cause seasonal flu almost every year, and only influenza A viruses are capable of causing influenza pandemics. A...

Claims

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Application Information

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Patent Type & AuthorityApplications(China)
IPC IPC(8): C07D311/76A61K31/366A61P31/16
CPCC07D311/76
Inventor黄林海
Owner上海秉丰生物科技有限公司