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Crystal, pharmaceutical composition and application of compound n-butyl-2,2'-imino-bis(8-quinolinamine)

An imino and quinolinamine technology, applied in the field of crystals of two-type derivatives, can solve the problems of no crystallography, research, etc., and achieve easy packaging, improved water solubility and fat solubility, and good water solubility and fat solubility. Effect

Active Publication Date: 2022-05-27
GUANGZHOU XIN CHUANG YI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, many studies have been carried out on the coordination compound formed by the complexation of compound A and metal copper ions, but there is no crystallographic study on compound A itself.

Method used

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  • Crystal, pharmaceutical composition and application of compound n-butyl-2,2'-imino-bis(8-quinolinamine)
  • Crystal, pharmaceutical composition and application of compound n-butyl-2,2'-imino-bis(8-quinolinamine)
  • Crystal, pharmaceutical composition and application of compound n-butyl-2,2'-imino-bis(8-quinolinamine)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] An example of the crystal of N-butyl-2,2'-imino-bis(8-quinolinamine) according to the present invention, the N-butyl-2,2'-imino described in this example -The preparation method of the crystal of bis(8-quinolinamine) is:

[0052] (1) get N-butyl-2,2'-imino-bis(8-quinolinamine) crude product 8.0g, add dichloromethane to make it dissolve, add 400mL of HCl with a concentration of 1mol / L in the solution, N-butyl-2,2'-imino-bis(8-quinolinamine) was precipitated;

[0053] (2) filter, add 100mL mass percent concentration of sodium bicarbonate aqueous solution of 5% in the obtained filter cake to make it dissolve, then extract with ethyl acetate, concentrate the extract to obtain refined product, which is identified as N through nuclear magnetic resonance analysis -Butyl-2,2'-imino-bis(8-quinolinamine);

[0054] (3) Take 200 mg of the above-mentioned N-butyl-2,2'-imino-bis(8-quinolinamine) refined product, dissolve it in 30 mL of methanol, place it in an environment of 0-5 °C...

Embodiment 2

[0063] An example of the crystal of N-butyl-2,2'-imino-bis(8-quinolinamine) according to the present invention, the N-butyl-2,2'-imino described in this example -The preparation method of the crystal of bis(8-quinolinamine) is:

[0064] (1) get N-butyl-2,2'-imino-bis(8-quinolinamine) crude product 10.0g, add chloroform to make it dissolve, add 600mL concentration of HCl to the solution and be 1mol / L, N-butyl-2,2'-imino-bis(8-quinolinamine) was precipitated;

[0065] (2) filtering, adding 400 mL of sodium carbonate aqueous solution with a mass percent concentration of 5% to the obtained filter cake to dissolve it, then extracting with ethyl acetate, concentrating the extract to obtain a refined product, which is identified as N-butyl by NMR -2,2'-imino-bis(8-quinolinamine);

[0066](3) Take 300 mg of the above-mentioned N-butyl-2,2'-imino-bis(8-quinolinamine) refined product, heat it to dissolve it in 40 mL of ethanol, slowly cool down to -5~0°C, here After standing at the t...

Embodiment 3

[0074] An example of the crystal of N-butyl-2,2'-imino-bis(8-quinolinamine) according to the present invention, the N-butyl-2,2'-imino described in this example -The preparation method of the crystal of bis(8-quinolinamine) is:

[0075] (1) Take 12.0 g of N-butyl-2,2'-imino-bis(8-quinolinamine) crude product, add dichloromethane to dissolve it, and add 1 mol / L of HCl to the solution until it no longer produces precipitation;

[0076] (2) filtering, adding 300 mL of sodium hydroxide solution with a mass percent concentration of 1% to the obtained filter cake to dissolve it, then extracting with ethyl acetate, concentrating the extract to obtain a refined product, which is identified as N-butyl by NMR base-2,2'-imino-bis(8-quinolinamine);

[0077] (3) Take 500 mg of the above-mentioned N-butyl-2,2'-imino-bis(8-quinolinamine) refined product, heat it to dissolve it in 40 mL of methanol, and slowly cool down to 0-5 °C, at this temperature After standing, a yellow crystalline su...

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PUM

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Abstract

The invention provides crystals, pharmaceutical compositions and applications of the compound N-butyl-2,2'-imino-bis(8-quinolinamine). The crystalline compound N-butyl-2,2'-imino-bis(8-quinolinamine) of the present invention has good medicinal properties, and can be used to treat diseases related to metal ion metabolic imbalance, as well as disorders including Tau protein metabolism, Beta-amyloid-related disorders such as amyotrophic lateral sclerosis, spinal muscular atrophy, ataxia-telangiectasia, Creutzfeldt-Jakob disease, Huntington's disease, cerebellar atrophy, multiple sclerosis , Parkinson's disease, Alzheimer's disease, primary lateral sclerosis and other diseases including neurodegenerative diseases.

Description

technical field [0001] The present invention relates to crystals of bis(8-quinolinamine) derivatives, compositions and applications thereof, in particular to crystals of the compound N-butyl-2,2'-imino-bis(8-quinolinamine), Its composition and application. Background technique [0002] N-butyl-2,2'-imino-bis(8-quinolinamine) (compound A) is a polyquinoline compound. US8324196 discloses that bis(8-substituted quinoline) derivatives including compound A are metal ion chelators, which can effectively reduce the accumulation of metal ions in the human body. [0003] Na + , K + , Ca 2+ , Cu 2+ , Zn 2+ , Fe 3+ , Al 3+ The accumulation of such metal ions can cause damage to related neurons in the brain or spinal cord, leading to a series of neurodegenerative diseases, such as amyotrophic lateral sclerosis, spinal muscular atrophy, and ataxia. Telangiectasia, Creutzfeldt-Jakob disease, Huntington's disease, cerebellar atrophy, multiple sclerosis, Parkinson's disease, Alzhei...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/40A61K31/4709A61P25/00A61P25/16A61P25/28A61P21/00A61P3/12
CPCC07D215/40C07B2200/13
Inventor 不公告发明人
Owner GUANGZHOU XIN CHUANG YI CO LTD
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