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Benzyl aminyl flurbiprofen compounds as well as preparation method and use thereof

A flurbiprofen and compound technology, applied to a class of benzylamino flurbiprofen compounds, their preparation and application fields, can solve the problem that flurbiprofen has poor fat solubility and cannot improve cognitive decline in patients with moderate AD and daily performance, low aggregation activity, etc.

Inactive Publication Date: 2019-06-21
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the results of Phase III clinical trials showed that ( R )- Flurbiprofen does not improve cognitive decline and daily behavior in patients with moderate AD. Single mechanism, no anti-oxidative stress and metal ion complexing properties, and inhibition of A β Factors such as low aggregation activity are closely related
Apparently, in the structural modification with flurbiprofen as the precursor, it was found that it can simultaneously have anti-oxidative stress, metal ion complexation, inhibition β -Excessive production and deposition of amyloid, and multi-targeted flurbiprofen compounds against neuroinflammation may make a breakthrough in the treatment and / or prevention of neurodegenerative related diseases

Method used

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  • Benzyl aminyl flurbiprofen compounds as well as preparation method and use thereof
  • Benzyl aminyl flurbiprofen compounds as well as preparation method and use thereof
  • Benzyl aminyl flurbiprofen compounds as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1 General method for the preparation of arylmethylaminoflurbiprofen compound (3)

[0039] Add 2.4 mmol of the corresponding aromatic formaldehyde compound (1), 2.0 mmol of the corresponding aminoflurbiprofen compound (2) and 20 ml of ethanol into the reaction flask, stir evenly, then raise the temperature and reflux and stir for 2.0 to 12.0 hours (reaction The process is monitored by TLC); after the reaction is completed, cool to room temperature, evaporate the solvent under reduced pressure, and the residue is purified by silica gel column chromatography to obtain the corresponding arylideneaminoflurbiprofen compound (3), with a yield of 46.5% -83.8%, its chemical structure has been tested 1 Confirmed by H-NMR.

Embodiment 2

[0040] Example 2 General method for the preparation of benzylaminoflurbiprofen compound (I)

[0041] Add 1.0 mmol of the corresponding arylmethanylaminoflurbiprofen compound (3) prepared in Example 1 and 16 ml of tetrahydrofuran into the reaction flask, stir at room temperature, add 3.0 mmol of sodium borohydride, and continue stirring at room temperature 1.0 to 15.0 hours (the reaction process is monitored by TLC); after the reaction, adjust the pH of the reaction solution to strong acidity with 10% hydrochloric acid aqueous solution, then adjust the pH of the reaction solution to the isoelectric point with saturated aqueous sodium bicarbonate solution, and distill off tetrahydrofuran under reduced pressure , 20 mL of deionized water was added to the residual liquid, extracted three times with 60 mL of dichloromethane, the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and filtered, and the solvent was d...

Embodiment 3

[0060] Example 3 General method for the preparation of benzylamino flurbiprofen compound (I) and acid salt formation

[0061] Add 1.0 mmol of the benzylaminoflurbiprofen compound (I) obtained in the above-mentioned Example 2 and 20 ml of acetone into the reaction flask, stir evenly, add 3.0 mmol of the corresponding acid, heat and reflux and stir for 20 minutes, and the reaction is over After being cooled to room temperature, the solvent is evaporated under reduced pressure, and the residue is recrystallized by conventional methods to obtain the corresponding salt of benzylaminoflurbiprofen compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses benzyl aminyl flurbiprofen compounds (I) as well as pharmaceutically acceptable salts and a preparation method thereof, a medicine composition and use thereof in preparation ofmedicines for treating and / or preventing nervous system-related diseases including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-associateddementia, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, glaucoma, ischemic stroke, hemorrhagic stroke and nerve damage caused by traumatic brain injury.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new class of benzylaminoflurbiprofen compounds (I) and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions and preparations for the treatment and / or prevention of nervous system Drug use in related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, amyotrophic lateral sclerosis, neurological Pain, glaucoma, ischemic stroke, hemorrhagic stroke, and neurological damage caused by traumatic brain injury. Background technique [0002] Neurodegenerative diseases refer to the general term for diseases caused by chronic progressive degeneration of central nervous tissue, including Alzheimer's disease (Alzheimer's disease, AD), Parkinson's disease (Parkinson's disease, PD), Huntington's disease (Huntington disease, HD), amyotroph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/42C07C255/59C07C251/24C07C249/02C07C227/16C07C253/30C07D295/135A61K31/216A61K31/277A61K31/402A61K31/40A61K31/4453A61K31/495A61K31/5375A61P9/00A61P25/28A61P25/16A61P25/14A61P31/18A61P9/10A61P21/00A61P25/04A61P27/06A61P25/00
Inventor 邓勇杨子仪宋青李维
Owner SICHUAN UNIV
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