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Use of N-(pyridine-4-yl) piperazine-1-formamide

A formamide and formamide compound technology, applied in the field of medicine, can solve problems such as fast metabolism, achieve low toxic and side effects, and inhibit inflammation

Active Publication Date: 2014-03-26
TIANJIN CHASE SUN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, during the use of Fasudil, people found that it metabolizes quickly in the body, and it is not easy to pass through the blood-brain barrier.

Method used

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  • Use of N-(pyridine-4-yl) piperazine-1-formamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The preparation of embodiment 1 N-(pyridine-4-)piperazine-1-carboxamide

[0058] step one:

[0059] Disperse 4-aminopyridine (3.76g, 39.95mmol) in 50mL of dichloromethane, add triethylamine (4.85g, 47.94mmol), mix well, add ethyl chloroformate (4.34g, 39.95mmol) dropwise under ice cooling mmol), followed by overnight reaction at room temperature. Evaporate the solvent under reduced pressure, adjust the solution to PH=5-6 with 5% dilute hydrochloric acid solution, extract with ethyl acetate (50mL×3), combine the organic phases, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. 5.80 g of white solid was obtained, yield 87.3%. .

[0060] Step two:

[0061] Dissolve the white solid (3.00g, 18.06mmol) and piperazine (3.03g, 35.16mmol) in 30mL of 1,4-dioxane, and add 1mL of N-methylpyrrolidine as a catalyst, then reflux for 24h, reduce The solvent was evaporated under pressure, and column chromatography [V (ethyl acetate): V (methanol)...

Embodiment 2

[0072] Example 2 Test of Rho Kinase Inhibitor Activity

[0073] Microglia are immune cells in the central nervous system. They can not only protect neurons by phagocytizing pathogens and harmful particles in brain tissue, but also activate reactive microglia under the action of inflammatory molecules. , which secretes inflammatory cytokines and has toxic effects on neurons, is an important target for the treatment of neuroinflammation and neurodegenerative diseases. BV2 cells are the most commonly used microglia for in vitro studies. Treat with N-(pyridine-4-)piperazine-1-carboxamide and PBS respectively (PBS is the abbreviation of phosphate buffer solution, generally active biological agents should be diluted with it, because it has salt balance, can Adjusted appropriate pH buffering effect) was used as a control test, and its activity was detected with a Rho kinase activity kit after 24 hours of action.

[0074] Figure 5 Is N-(pyridine-4-)piperazine-1-carboxamide Rho kin...

Embodiment 3

[0075] Example 3 Test of Cell Regeneration and Synapse Formation Ability

[0076] Image 6 is the effect of N-(pyridine-4-)piperazine-1-carboxamide on synapse formation (24h) in primary neurons and BV-2 microglia. We used mouse primary neurons and BV-2 microglial cell line to observe the effect of War-5 on cell synapses. The results showed that War-5 was able to promote synapse formation to neurons compared to the PBS control. Using the BV-2 microglial cell line, we also obtained similar results.

[0077] Figure 7 It is N-(pyridine-4-)piperazine-1-carboxamide treatment of synapse formation in BV-2 microglial cells at different times (5d). We further observed the effect of War-5 treatment at different times on cell synapse formation. The results show that War-5 can promote synapse regeneration, and the drug effect lasts longer.

[0078] Figure 8 is N-(pyridine-4-)piperazine-1-carboxamide for quantification of mean synapse length in microglia. The results show that N-(p...

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Abstract

The present invention relates to use of N-(pyridine-4-yl) piperazine-1-formamide in the preparation of a medicinal preparation for degenerative neuropathy. The degenerative neuropathy includes but is not limited to one or a plurality of Alzheimer's disease, Parkinson's disease and multiple sclerosis. The invention also relates to a synthesis method of the N-(pyridine-4-yl) piperazine-1-formamide.

Description

technical field [0001] The invention belongs to the technical field of medicine, specifically relates to the application of N-(pyridin-4-yl)piperazine-1-carboxamide in the preparation of drugs for treating degenerative diseases of the nervous system, and provides a synthesis method of the compound. Background technique [0002] Neurodegenerative disease is the pathological result of degeneration and loss of neurons in the brain and spinal cord. The brain and spinal cord are made up of neurons that have different functions, such as controlling movement, processing sensory information, and making decisions. Cells in the brain and spinal cord generally do not regenerate, so excessive damage can be devastating, irreversible, and worsen over time, leading to dysfunction. [0003] Common neurodegenerative diseases include Alzheimer's disease, Parkinson's disease, multiple sclerosis, amyotrophic lateral sclerosis, ataxia-telangiectasia, bovine spongiform encephalopathy, Creutzfeld...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/496A61P25/28A61P25/16A61P25/14A61P25/00A61P25/02A61P29/00A61P37/02
Inventor 肖保国马存根陈立功王东华董凯陈帅李宝齐姚小青孙长海王欣然闫喜龙李阳
Owner TIANJIN CHASE SUN PHARM CO LTD
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