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Zucapsaicin crystal, and preparation method and application thereof

A technique for jurcassecin and crystals, which is applied in the field of zhucalcetin crystals and its preparation and application, can solve the problems of no zhucalcetin crystal form, etc., and achieve simple preparation methods, good stability, easy filtration and washing effect

Inactive Publication Date: 2015-07-29
SHANGHAI INST OF PHARMA IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are no relevant literature or patent reports on the crystal form of zucassecin

Method used

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  • Zucapsaicin crystal, and preparation method and application thereof
  • Zucapsaicin crystal, and preparation method and application thereof
  • Zucapsaicin crystal, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of Zucassecin Crystals 1

[0041] Dissolve 2.0 g of the crude product of Zhucacesin in 16 ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, and filter after stirring for 2 hours to obtain 1.5 g of the first refined product of Zhucacesin (cis-trans isopropyl ether). conformation content 0.50%).

[0042] Dissolve 1.5 g of the first refined product of zhucacesin in 12 ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, and filter after stirring for 2 hours to obtain 1.2 g of the second refined product of zhucacesin ( The cis-trans isomer content is 0.29%). The crystals are white crystals, and the melting point of the crystals is 72-74°C as tested by a melting point apparatus.

Embodiment 2

[0044] Preparation of Zucassecin Crystals 2

[0045] Dissolve 2.0 g of the crude product of zhucacetin in 20 ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, add 20 ml of n-hexane, stir for 2 hours, and then filter to obtain the first refined product of zucacetin 1.9g (the cis-trans isomer content is 1.50%).

[0046] Dissolve 1.9 g of the first refined product of Zhucalcetin in 20 ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, add 20 ml of n-hexane, stir for 2 hours, and then filter to obtain the second Sub-refined product 1.7g (cis-trans isomer content 0.98%).

[0047] Dissolve 1.7g of the second refined product of Zhucalcetin in 20ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, add 20ml of n-hexane, stir for 2 hours, and then filter to obtain the third Sub-refined product 1.5g (cis-trans isomer content 0.45%).

[0048] Dissolve 1.5 g of the third refined pr...

Embodiment 3

[0050] Preparation of Zucassecin Crystals 3

[0051]Dissolve 2.0 g of the crude product of zucasicin in 10 ml of methyl tert-butyl ether, heat to reflux to dissolve, cool naturally to room temperature, and filter after stirring for 2 hours to obtain 1.6 g of the first refined product of zucasicin ( The cis-trans isomer content is 1.2%).

[0052] Dissolve 1.6 g of the first refined product of Zhucalcetin in 8 ml of isopropyl ether, heat to reflux to dissolve, cool naturally to room temperature, and filter after stirring for 48 hours to obtain 1.4 g of the second refined product of Zhucalcetin ( The content of cis-trans isomers is 0.45%), the crystals are white crystals, and the melting point of the crystals is 72-74 ° C after the melting point tester.

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Abstract

The present invention discloses a Zucapsaicin crystal, and a preparation method and application thereof. The crystal has characteristic peaks at diffraction angle 2theta of 5.9 and 11.9 DEG in a powder X-ray diffraction spectrum using radiation source of Cu-Kalpha, wherein the error range of 2theta is + / - 0.2 DEG. The Zucapsaicin crystal has purity of more than 99.5%, cis-trans isomer content of less than 0.3%, good stability, and easiness for filtration and washing, thus contributing to improve the bioavailability. The preparation method of the Zucapsaicin crystal is simple, and products between different batches have stable properties. Zucapsaicin samples from different points of a same batch have basically the same content. After twice crystallization, the cis-trans isomer content is less than 0.3%, which decreases significantly compared with the reported cis and trans isomer content of 7.1% after twice crystallization.

Description

technical field [0001] The present invention relates to a crystal of zucasexin and its preparation method and application. Background technique [0002] Zucapsaicin (Zucapsaicin) is a capsaicin isomer as described in formula I, also known as cis-capsaicin, a new type of painkiller developed by Winston Pharma of Canada. [0003] [0004] Zucassecin, its preparation method refers to Journal of Organic Chemistry; vol.54; 1989; P3477-34785. Zurcasexin inhibits pain through the same mechanism as capsaicinoids, which may act through the transient receptor potential vanilloid receptor 1 (TRPV1), reducing the CGRP (calcitonin gene-related protein, from the trigeminal neuron release) and substance P, thereby reducing the sensation of pain, and can be used to treat related diseases such as osteoarthritis pain, postherpetic neuralgia, chronic neuralgia, and cluster headache. [0005] At present, there are no relevant literature or patent reports on the crystal form of zucassecin. ...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C231/24
Inventor 唐超隋强刘帅欧阳群香时惠麟
Owner SHANGHAI INST OF PHARMA IND
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