Pyridine methylamino phthalide compound and preparation method and application thereof

A picolinylaminophthalide and compound technology, which is applied to a class of picolinylaminophthalide compounds, and the fields of their preparation and use, can solve the problem of single action target, poor long-term efficacy in AD patients, and many toxic and side effects, etc. question

Inactive Publication Date: 2020-12-01
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these drugs have problems such as a single target, more toxic and...

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  • Pyridine methylamino phthalide compound and preparation method and application thereof
  • Pyridine methylamino phthalide compound and preparation method and application thereof
  • Pyridine methylamino phthalide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 General method for the preparation of pyridylamino-3-substituted phthalides (3)

[0037] Add 2.4 mmol of the corresponding 2-pyridinecarbaldehyde compound (1), 2.0 mmol of the corresponding amino-3-substituted phthalide compound (2) and 20 ml of ethanol into the reaction flask, stir evenly, then raise the temperature and reflux and stir for 2.0~ 12.0 hours (the reaction 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 pyridyl imino-3-substituted phthalide compound ( 3), the yield is 52.6%-83.5%, and its chemical structure has been tested 1 Confirmed by H-NMR and ESI-MS.

Embodiment 2

[0038] Example 2 The General Method for the Preparation of Pyridylaminophthalides (I)

[0039] Add 1.0 mmol of the corresponding pyridylidene amino-3-substituted phthalide compound (3) prepared in Example 1 and 10 ml of tetrahydrofuran into the reaction flask, stir evenly at room temperature, add 3.0 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 weak alkalinity with saturated aqueous sodium bicarbonate solution, and evaporate under reduced pressure Add 20 mL of deionized water to the residual liquid, extract three times with 60 mL of ethyl acetate, wash the organic layers with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate, and filter, evaporate the solvent under reduced pressure, and th...

Embodiment 3

[0052] Example 3 General method for the preparation of pyridylaminophthalide compound (I) and acid salt formation

[0053]Add 1.0 mmol of the picolylaminophthalide 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, after the reaction is completed Cool to room temperature, evaporate the solvent under reduced pressure, and recrystallize the residue by a conventional method to obtain the corresponding salt of the pyridylaminophthalide compound (I), whose chemical structure has been confirmed by 1 Confirmed by H NMR and ESI-MS.

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PUM

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Abstract

The invention discloses a novel pyridine methylamino phthalide compound (I) and pharmaceutically acceptable salts, a preparation method and a pharmaceutical composition thereof and application thereofin preparation of medicines for treating and/or preventing nervous system related diseases. The diseases include but are 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, cerebral arterial thrombosis, cerebral hemorrhagic stroke, nerve injury causedby cerebral trauma and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of pyridylaminophthalide compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation of therapeutic and / or prevention of nervous system-related Use in medicines for 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, neuropathic pain , glaucoma, ischemic stroke, hemorrhagic stroke, and nerve 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), amyotrophic lateral scl...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K31/443A61K31/5377A61K31/496A61K31/4545A61P25/28A61P25/16A61P25/14A61P31/18A61P25/00A61P27/06A61P9/10
CPCC07D401/12A61P25/28A61P25/16A61P25/14A61P31/18A61P25/00A61P27/06A61P9/10
Inventor 邓勇宋青曹忠诚
Owner SICHUAN UNIV
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