A class of benzylamino flurbiprofen amide compounds, its preparation method and use

A technology of benzylamino flurbiprofen amide and arylamide amino flurbiprofen amide, which is applied to the preparation of organic compounds, carboxylic acid amide preparation, chemical instruments and methods, etc., and can solve the problem of single action mechanism and inability to Improve cognitive decline, daily behavior, and low aggregation activity in patients with moderate AD

Inactive Publication Date: 2021-06-18
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A class of benzylamino flurbiprofen amide compounds, its preparation method and use
  • A class of benzylamino flurbiprofen amide compounds, its preparation method and use
  • A class of benzylamino flurbiprofen amide compounds, its preparation method and use

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 , add 20mL deionized water to the residual liquid, extract three times with 90 mL dichloromethane, wash the organic layer with saturated aqueous sodium chloride solution after combining, filter after drying over anhydrous sodium sulfate, distill off the solvent un...

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 in Example 2 above 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, the reaction 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 compounds (I), whose chemical structure was 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a class of benzylamino flurbiprofen amide compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation of medicines for treating and / or preventing nervous system related diseases. Uses, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, glaucoma, Hemorrhagic stroke, hemorrhagic stroke, and nerve damage caused by traumatic brain injury and other diseases;

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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Patent Type & Authority Patents(China)
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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