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

A technology of benzylamino flurbiprofenamide and arylmethyleneamino flurbiprofenamide, which is applied in the preparation of organic compounds, the preparation of carboxylic acid amides, chemical instruments and methods, etc., can solve the problems of low aggregation activity, fluorine Problems such as poor fat solubility and single mechanism of action of biprofen

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 The general method for the preparation of arylmethylaminoflurbiprofen amide compounds (3)

[0039] Add 2.3 mmol of the corresponding aromatic formaldehyde compound (1), 2.0 mmol of the corresponding aminoflurbiprofen amide 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 ( The reaction process was monitored by TLC); after the reaction was completed, it was cooled to room temperature, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the corresponding arylideneaminoflurbiprofen amide compound (3), with a yield of 52.6 %-88.2%, its structure is 1 Confirmed by H-NMR.

Embodiment 2

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

[0041] Add 1.0 mmol of the corresponding arylmethylaminoflurbiprofen amide compound (3) prepared in Example 1 and 20 ml of tetrahydrofuran into the reaction flask, stir at room temperature, add 2.5 mmol of sodium borohydride, and continue stirring at room temperature React for 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 neutrality 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 90 mL of dichloromethane, the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and filtered, and the sol...

Embodiment 3

[0061] Example 3 General method for the preparation of benzylaminoflurbiprofen amides (I) and acid salt formation

[0062] Add 1.0 mmol of the benzylaminoflurbiprofen amide compound (I) obtained according to the above-mentioned Example 2 and 20 ml of acetone into the reaction flask, stir well, add 3.0 mmol of the corresponding acid, heat and reflux and stir for 20 minutes, and react After cooling to room temperature, the solvent was evaporated under reduced pressure, and the residue was recrystallized by conventional methods to obtain the corresponding salt of benzylamino flurbiprofen amide compound (I), whose chemical structure was confirmed by 1 Confirmed by H NMR and ESI-MS.

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PUM

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Abstract

The invention discloses benzyl aminyl flurbiprofen amides compounds (I) as well as pharmaceutically acceptable salts and a preparation method thereof, a medicine composition and use thereof in preparation of medicines 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-associated dementia, 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 type of benzylamino flurbiprofen amide compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation for treating and / or preventing neuropathy. Use in drugs for system-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 Sexual 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), amyotr...

Claims

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Application Information

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IPC IPC(8): C07C237/20C07C231/12C07C255/59C07C253/30C07D213/38C07D213/61C07D213/64C07D213/65C07D213/74C07D213/68C07D295/135A61P25/28A61P25/16A61P25/14A61P25/00A61P25/04A61P9/10A61P21/00A61P27/06A61K31/165A61K31/277A61K31/40A61K31/4453A61K31/44A61K31/495A61K31/5375A61K31/455A61K31/4439
Inventor 邓勇杨子仪田超全叶蝉媛
Owner SICHUAN UNIV
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