Dimethylamine sphaelactone-p-hydroxybenzoate as well as preparation method and application thereof

A technology of hydroxybenzoate and p-hydroxybenzoic acid, which is applied in the field of dimethylamine lagalactone-p-hydroxybenzoate and preparation, can solve the problems of poor controllability of technological process and product quality, and easy interaction of crystal forms. Transformation, complex preparation process and other problems, to achieve the effect of convenient industrialized large-scale production and application, easy storage and transportation, and simple preparation method

Active Publication Date: 2021-07-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the problems of high hygroscopicity, poor stability, easy interconversion of crystal forms, complex preparation process, strong toxicity of solvent used, and poor controllability of process and product quality in the existing dimethylamine migna lactone salt type and its preparation method and many other technical problems, the present invention provides a kind of dimethylamine michelolactone-p-hydroxybenzoic acid salt and its preparation method and application

Method used

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  • Dimethylamine sphaelactone-p-hydroxybenzoate as well as preparation method and application thereof
  • Dimethylamine sphaelactone-p-hydroxybenzoate as well as preparation method and application thereof
  • Dimethylamine sphaelactone-p-hydroxybenzoate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Add 1.5g of dimethylamine michelactone solid, 1.414g of p-hydroxybenzoic acid solid, and 75mL of isopropyl acetate into the reaction flask, heat to 60°C, and stir for 30 minutes to fully react the raw materials. Cool to 0°C at a rate of 5°C / h, filter the obtained product, and then dry under normal pressure at 40°C for 3 hours to obtain dimethylaminomildolide-p-hydroxybenzoate.

[0061] figure 1 Prepare the crystallographic characteristics of the product for embodiment 1, from figure 1 It can be seen that the crystallographic characteristics are: the space group is P2 1 2 1 2 1 , the cell parameters are α=90°, β=90°, γ=90°, the unit cell volume is

[0062] figure 2 Prepare the powder X-ray diffraction pattern of product for embodiment 1, from figure 2 It can be seen that the diffraction angle is 2θ at 5.5°, 7.3°, 9.5°, 10.7°, 12.4°, 13.2°, 13.9°, 14.9°, 16.9°, 17.2°, 18.8°, 19.5°, 20.0°, 20.5° , 21.5°, 22.0°, 22.8°, 24.2°, 25.7°, 27.3°, 29.3° have characte...

Embodiment 2

[0091] Add 3 g of dimethylamine michelactone solid, 3.111 g of p-hydroxybenzoic acid solid, and 30 mL of methanol into the reaction flask, heat to 55°C, and stir for 10 min to fully react the raw materials. Cool to -10°C at a rate of 2°C / h, filter the obtained product, and then dry under normal pressure at 30°C for 2 hours to obtain dimethylaminomildolide-p-hydroxybenzoate.

[0092] The product that embodiment 2 obtains is carried out crystallographic test, and test result is the same as embodiment 1.

[0093] Carry out PXRD test to the product that embodiment 2 obtains, as can be known: with diffraction angle being 2θ, represent at 5.6 °, 7.5 °, 9.7 °, 10.8 °, 12.5 °, 13.4 °, 13.8 °, 14.9 °, 16.8 °, 17.2 °, There are characteristic peaks at 18.8°, 19.6°, 20.1°, 20.6°, 21.7°, 22.2°, 22.9°, 24.4°, 25.9°, 27.5°, 29.4°.

[0094] Carry out DSC test to embodiment 2, know: product has endothermic peak at 145.2 ℃.

[0095] Adopt the method identical with embodiment 1 to carry out f...

Embodiment 3

[0110] Add 6g of dimethylamine michelactone solid, 7.065g of p-hydroxybenzoic acid solid, and 120mL of acetone into the reaction flask, heat to 45°C, and stir for 20min to fully react the raw materials. Cool to 15°C at a rate of 3°C / h, filter the obtained product, and then dry under normal pressure at 25°C for 3 hours to obtain dimethylaminomildolide-p-hydroxybenzoate.

[0111] The product that embodiment 3 obtains is carried out crystallographic test, and test result is the same as embodiment 1.

[0112] Carry out PXRD test to the product that embodiment 3 obtains, as can be known: with diffraction angle being 2θ, represent at 5.3 °, 7.1 °, 9.3 °, 10.5 °, 12.2 °, 13.0 °, 13.7 °, 14.7 °, 16.8 °, 17.1 °, There are characteristic peaks at 18.6°, 19.3°, 20.1°, 20.3°, 21.3°, 21.9°, 22.6°, 24.0°, 25.5°, 27.1°, 29.1°.

[0113] Carry out DSC test to embodiment 3, know: product has endothermic peak at 145.5 ℃.

[0114] Adopt the method identical with embodiment 1 to carry out follow...

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Abstract

The invention provides dimethylamine sphaelactone-p-hydroxybenzoate as well as a preparation method and application of the dimethylamine sphaelactone-p-hydroxybenzoate. The molecular formula of the dimethylamine sphaelactone-p-hydroxybenzoate is C31H39NO9; the crystallographic characteristics of the dimethylamine sphaelactone-p-hydroxybenzoate are as follows: the space group is P212121, the cell parameters are alpha = 90 degrees, beta = 90 degrees and gamma = 90 degrees, and the cell volume is disclosed in the invention; the prepared dimethylamine sphaelactone-p-hydroxybenzoate has good hygroscopicity and physical and chemical stability, and has a good drug development prospect; the preparation method is simple to operate, mild in condition, good in repeatability, green, environment-friendly, low in toxicity and safe.

Description

technical field [0001] The invention belongs to the technical field of medicine crystallization, and in particular relates to a dimethylamine michelactone-p-hydroxybenzoic acid salt, a preparation method and an application thereof. Background technique [0002] Dimethylamine michelolactone, which belongs to sesquiterpene lactone compounds, has the molecular formula C 17 h 27 NO 3 , is a white powdery solid with poor water solubility, it will degrade when left for a long time, and its physical and chemical stability is poor. [0003] WO2015006893A1 discloses the use of sesquiterpene lactone compounds including dimethylamine microlactone and its derivatives in the treatment of rheumatoid arthritis and cancer. Method for lactone hydrochloride and fumarate. Dichloromethane belongs to the second class of organic solvents. It has certain toxicity and carcinogenicity. It has an extremely low boiling point and its vapor is narcotic. If inhaled in large quantities, it will cause ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/93C07C65/03C07C51/41C07C51/43A61P35/00A61P37/06
CPCC07D307/93C07C65/03A61P35/00A61P37/06C07B2200/13
Inventor 龚俊波李中华欧阳瑞灵赵晨阳吴送姑侯宝红
Owner TIANJIN UNIV
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