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Hydroxyflurbiprofen mannich base compounds as well as preparation method and applications thereof

A compound and hydroxyl technology, applied to a class of hydroxyflurbiprofen Mannich base compounds, their preparation and application fields, can solve the problems of single action target, poor long-term efficacy in AD patients, and many toxic and side effects

Active Publication Date: 2019-07-12
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have problems such as a single target, more toxic and side effects in clinical use, and poor long-term curative effect on AD patients.

Method used

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  • Hydroxyflurbiprofen mannich base compounds as well as preparation method and applications thereof
  • Hydroxyflurbiprofen mannich base compounds as well as preparation method and applications thereof
  • Hydroxyflurbiprofen mannich base compounds as well as preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 General method for the preparation of hydroxyflurbiprofen Mannich base compound (I)

[0037] Dissolve 2.0 mmol of the corresponding 4′-hydroxyflurbiprofen compound (2) in 15 ml of methanol, add 4.0 mmol of paraformaldehyde and the corresponding amine compound (HNR 1 R 2 ) 4.0 mmol, heated and refluxed and stirred for 2-48 hours (the reaction process was tracked by TLC). After the reaction, the solvent was evaporated under reduced pressure, and 40 ml of ethyl acetate was added to the residue, washed with 20 ml of saturated brine, and the organic layer was After drying over anhydrous sodium sulfate and filtering, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the corresponding hydroxyflurbiprofen Mannich base compound (I) with a yield of 20.0%-73.0%. Its chemical structure has been 1 H-NMR, 13 It was confirmed by C-NMR and ESI-MS that the purity of the obtained target substance ...

Embodiment 2

[0063] Example 2 General method for the preparation of hydroxyflurbiprofen Mannich base compound (I) and acid salt formation

[0064] Add 2.0 mmol of the hydroxyflurbiprofen Mannich base compound (I) obtained in the above-mentioned Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 5.0 mmol of the corresponding acid, heat up and reflux and stir for 20 minutes, After the reaction is finished, cool to room temperature, evaporate the solvent under reduced pressure, recrystallize the residue by a conventional method, and filter the precipitated solid to obtain the salt of hydroxyflurbiprofen Mannich base compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses novel hydroxyflurbiprofen mannich base compounds (I) as well as pharmaceutically acceptable salts thereof, a preparation method, pharmaceutical composition and applications inthe preparation of drugs for treating and / or preventing neurodegenerative associated diseases, including but not limited to vascular dementia, AD (Alzheimer's disease), Parkinson's disease, Huntington's disease, HIV-associated dementia, MS (multiple sclerosis), progressive lateral sclerosis of spinal cord, neuropathic pains, glaucoma and other neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of hydroxyflurbiprofen Mannich base compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation treatment and / or prevention Use in drugs for neurodegenerative-related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, progressive lateral sclerosis, Neuropathic pain, glaucoma and other neurodegenerative diseases. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD, senile dementia) is a degenerative disease of the central nervous system mainly characterized by progressive cognitive impairment and memory impairment. Vascular diseases and cancers are high-incidence diseases, which have risen to the fourth cause of death in developed countries such as Europe and the United Stat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/34C07C227/10C07C237/20C07C231/12C07D295/155A61K31/216A61K31/40A61K31/4453A61K31/5375A61K31/495A61K31/165A61P25/28A61P25/16A61P25/14A61P31/18A61P27/06A61P25/04A61P9/10
CPCC07C229/34C07C237/20C07D295/155
Inventor 邓勇强晓明田超全宋青
Owner SICHUAN UNIV
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