Galanthamine dihydroxy naphthoate and preparation method thereof

A technology of galantamine pamoate compound and galantamine pamoate compound, which is applied in the field of amorphous galantamine pamoate and its preparation, can solve the problems of low solubility, light resistance, Problems such as solubility characteristics, poor stability, low solubility characteristics, stability and safety, etc., to achieve the effects of excellent solubility characteristics and stability, easy process, and high product yield

Active Publication Date: 2020-06-05
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems of existing galantamine salt and galanthamine hydrobromide salt with poor solubility and poor stability, the present invention aims to provide a galantamine with lower solubility, good light resistan

Method used

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  • Galanthamine dihydroxy naphthoate and preparation method thereof
  • Galanthamine dihydroxy naphthoate and preparation method thereof
  • Galanthamine dihydroxy naphthoate and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Dissolve 2g of galantamine hydrobromide in ethanol solution (30mg / mL) of 20mL sodium hydroxide, after stirring for 30min, suction filter the insoluble matter, and concentrate the filtrate to obtain galantamine free base; Dissolve 1.0 g of base in 20 mL of dimethyl sulfoxide, add 100 mL of dimethyl sulfoxide solution containing 1.29 g of pamoic acid dropwise, and stir and react at 20°C for 6 hours; after the reaction, place the reaction solution in a 5°C Stand in the environment for 24 hours, filter with suction, and dry in vacuum at 50° C. for 2 hours to obtain a light yellow powder with a yield of 88.23% and a purity of 99.92%.

Embodiment 2

[0039] Dissolve 2g of galantamine hydrobromide in ethanol solution (20mg / mL) of 20mL sodium hydroxide, after stirring for 30min, suction filter the insoluble matter, and concentrate the filtrate to obtain galantamine free base; Dissolve 1.0g of base in 30mL of N,N-dimethylformamide, add dropwise 200mL of N,N-dimethylformamide solution containing 3.51g of pamoic acid, after the dropwise completion, stir and react at 40°C for 3 hours; After completion, the reaction solution was placed in an environment at 5° C. for 24 hours, filtered with suction, and vacuum-dried at 50° C. for 2 hours to obtain a light yellow powder with a yield of 79.22% and a purity of 99.91%.

Embodiment 3

[0041]Dissolve 2g of galantamine hydrobromide in ethanol solution (50mg / mL) of 20mL sodium hydroxide, after stirring for 30min, suction filter the insoluble matter, and concentrate the filtrate to obtain galantamine free base; Dissolve 1.0 g of base in 20 mL of 1,3-dimethyl-2-imidazolidinone, add dropwise 150 mL of 1,3-dimethyl-2-imidazolidinone solution containing 2.34 g of pamoic acid, and dropwise, Stir and react at 60°C for 2 hours; place the reaction solution in an environment at 5°C for 24 hours, filter it with suction, and dry it in vacuum at 50°C for 2 hours to obtain a light yellow powder with a yield of 76.35% and a purity of 99.86%.

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Abstract

The invention provides an amorphous galanthamine dihydroxy naphthoate compound and a preparation method thereof, the compound has low solubility, good stability and high safety, and a pharmaceutical preparation prepared by using the compound as an active component has good dissolution performance. In addition, the galanthamine dihydroxy naphthoate provided by the invention is simple in preparationprocess, high in product yield, high in purity and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an amorphous galantamine pamoate, a preparation method thereof and its application in pharmacy. Background technique [0002] Galantamine was first isolated by Mashkovsky, a pathologist in the former Soviet Union, from the Amaryllidaceae plant Snowdrop woerneri. As a second-generation AchE inhibitor, galantamine mainly acts on the catalytic site of AchE. The structure-activity relationship is as follows: (1) the hydroxyl group in the molecular structure forms a hydrogen bond with Glu199 in AchE, and the double bond of the cyclohexene ring forms a hydrogen bond with Glu199 in AchE. Trp84 in AChE forms a p-p bond, thereby inhibiting AchE; (2) The modification of the N-terminal alkylation in the molecular structure is conducive to approaching the bottom of the catalytic site of AchE, which plays a very important role in the inhibition of AchE. [0003] The c...

Claims

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Application Information

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IPC IPC(8): C07D491/107A61K31/55A61P25/28
CPCC07D491/107A61P25/28C07B2200/13Y02A50/30
Inventor 张贵民秦士慧孙建合
Owner LUNAN PHARMA GROUP CORPORATION
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