Novel BAPTA derivative, preparation method thereof and medicinal use thereof

A pharmacy, drug technology, applied in the field of improved BAPTA derivatives, which can solve problems affecting R&D and production

Inactive Publication Date: 2013-09-11
HENGXING PHARMA INST HEFEI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, BAPTA-AM is completely insoluble in water, which affects its development and production as a pharmaceutical preparation for clinical application

Method used

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  • Novel BAPTA derivative, preparation method thereof and medicinal use thereof
  • Novel BAPTA derivative, preparation method thereof and medicinal use thereof
  • Novel BAPTA derivative, preparation method thereof and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of BAPTA methyl ester

[0027] In a 10L dry reaction kettle, add 370g (1.5mol) of 2,2'-diaminoethylene glycol diphenyl ether and 3500ml of anhydrous acetonitrile, stir at room temperature for 10min, and 2 Under protection, 1440ml (8.32mol) of diisopropylethylamine and 70g (0.446mol) of anhydrous sodium iodide were added, and the temperature was raised slowly. When the temperature of the reaction solution reached 60°C-65°C, 768ml of methyl bromoacetate ( 8.32mol), after the dripping is completed, seal the reactor, raise the temperature to 80℃~83℃, react and stir for 27h, TLC controls the reaction end point, the developer is DMF-ethyl acetate=6:20, the reaction is completed, cooled to At room temperature, add 4000ml of toluene, stir for 10min, separate the toluene layer, continue to stir and separate the solid compound with 1000ml×4 toluene, combine the toluene layer, wash the toluene layer with 1000ml×4 deionized water, discard the water lay...

Embodiment 2

[0034] Embodiment 2: the preparation of BAPTA

[0035]In a 10L clean reaction kettle, add 532g (1.0mol) of BAPTA methyl ester and 5500ml of ethanol, heat slowly until the solids are completely dissolved, and slowly add 2667ml (5.0mol) of 15% sodium hydroxide solution [prepared by 15% sodium hydroxide solution Method: Weigh 400g of sodium hydroxide, dissolve in 2600ml of distilled water, stir to clarify, and cool to obtain], after the dropwise addition, reflux the mixture for 3 hours, TLC to control the reaction end point, the developer is DMF-ethyl acetate=1:2, After the reaction is over, cool slightly, add 15g of activated carbon, stir and reflux for 20min, remove insoluble matter by filtration, concentrate under reduced pressure to leave one-tenth of the solvent, cool to room temperature, add 1L of distilled water, cool to 5°C-10°C, use 0.1N Adjust the pH ester to 2-2.5 with hydrochloric acid, keep stirring for 20 minutes, filter, wash the solid with distilled water until th...

Embodiment 3

[0037] Example 3: Preparation of 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetra(dimethylaminoethanol)tetraacetate

[0038] In a 5000ml dry and clean four-neck flask, add BAPTA95g (0.2mol), anhydrous acetonitrile 1100ml, stir at room temperature for 10min, and 2 Under protection, add 208ml (1.2mol) of diisopropylethylamine and 12g (0.08mol) of anhydrous sodium iodide, and slowly raise the temperature. When the temperature of the reaction solution reaches 60℃~65℃, slowly drop in dimethylaminoethyl Bromine 216g (1.2mol) [Dimethylaminoethyl bromide preparation method: Take 500g of commercially available dimethylaminoethyl bromide hydrobromide, dissolve it in 1500ml distilled water, adjust the pH to 9 with saturated sodium bicarbonate solution , extracted with 3000ml of toluene, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness], after the dropwise addition, seal the reactor, raise the temperature to 80°C to 83°C, stir the reaction for 30h, and control the e...

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Abstract

The invention relates to the field of pharmaceutical chemistry, and particularly relates to an improved BAPTA derivative general formula (I), a preparation method of the improved BAPTA derivative, a medicinal preparation containing the improved BAPTA derivative, and medicinal use of the improved BAPTA derivative, wherein R, R1, R2 and n are defined as in the description. The invention further provides a preparation method of the derivative compounds and applications in medicine.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an improved BAPTA derivative, its preparation method, including its pharmaceutical preparation and its medical application. Background technique [0002] Calcium is widely distributed in the cells and body fluids of the human body, and plays an important role in regulating the metabolism and function of cells. Calcium not only participates in short-term processes such as nerve conduction, transmitter release, and cell secretion, but also participates in long-term responses of cell differentiation and proliferation. It widely affects physiological processes such as neuron growth, axon elongation, and synaptic strength. Calcium is one of the important element components of the human body, in the body in the bound state and ion state Ca 2+ exist. but only Ca 2+ have biological activity. Ca in vivo 2+ intracellular Ca 2+ and extracellular Ca 2+ +Two, among them, cytosolic ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/18C07C227/18A61K31/223A61P9/10A61P1/16A61P1/18
Inventor 许璇徐奎刘经星吴仁荣鞠芳
Owner HENGXING PHARMA INST HEFEI
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