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2-(hydroxybenzyl) benzo [d] isothiazolone compound as well as preparation method and application thereof

A technology of isothiazolone and hydroxybenzyl, which is applied to 2-(hydroxybenzyl)benzo[d]isothiazolone compounds, and the fields of their preparation and use, can solve the problem of poor long-term curative effect and target of action in AD patients Single, multiple toxic and side effects

Active Publication Date: 2021-07-13
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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  • 2-(hydroxybenzyl) benzo [d] isothiazolone compound as well as preparation method and application thereof
  • 2-(hydroxybenzyl) benzo [d] isothiazolone compound as well as preparation method and application thereof
  • 2-(hydroxybenzyl) benzo [d] isothiazolone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 2-(Hydroxybenzyl) benzo [d] isothiazolone compound (I) preparation general method

[0040] Dissolve 1.0 mmol of 2-(hydroxybenzyl)benzo[d]isothiazolone compound (1) in 8 ml of ethanol, add 3.0 mmol of paraformaldehyde and the corresponding amine compound (HNR 4 R 5 ) 3.0 mmol, heated and refluxed and stirred for 2-48 hours (the reaction process was tracked by TLC), after the reaction was completed, the solvent was evaporated under reduced pressure, 50 ml of dichloromethane 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 column chromatography (eluent: petroleum ether-ethyl acetate=1:3 v / v) to obtain the corresponding 2-(hydroxybenzyl base) benzo [d] isothiazolone compound (I), the yield is 36.0%-80.5%, and its chemical structure has been verified 1 H-NMR, 13 It was confirmed by C-NMR and E...

Embodiment 2

[0064] Example 2 General method for the preparation of 2-(hydroxybenzyl)benzo[d]isothiazolone compound (I) and acid salt formation

[0065] Add 2.0 mmol of 2-(hydroxybenzyl) benzo [d] isothiazolone compound (I) obtained in Example 1 above and 30 ml of acetone into the reaction flask, stir evenly, add 7.0 mmol of the corresponding acid, and heat up The reaction was stirred under reflux for 30 minutes, cooled to room temperature after the reaction was completed, the solvent was evaporated under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain 2-(hydroxybenzyl)benzo[d]isothiazolone compounds (I) salts whose chemical structures have been 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a 2-(hydroxybenzyl) benzo [d] isothiazolone compound (I), pharmaceutically acceptable salts thereof, a preparation method of the compound, a pharmaceutical composition of the compound and application of the compound in preparation of drugs for treating and / or preventing nervous system related diseases, comprising but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia disease, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, glaucoma, ischemic cerebral apoplexy, hemorrhagic cerebral apoplexy, nerve injury caused by cerebral trauma and other diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a class of 2-(hydroxybenzyl)benzo[d]isothiazolone compounds (I) and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions and preparation methods for treating and / or prevention of diseases related to the nervous system, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, muscular atrophy neuropathic 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), amyotrophic late...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/04C07D275/06A61P25/00A61P25/28A61P25/16A61P31/18A61P25/04A61P27/06A61P9/10A61P25/14A61K31/5377A61K31/496A61K31/454A61K31/428A61K31/4545
CPCC07D275/04C07D275/06A61P25/00A61P25/28A61P25/16A61P31/18A61P25/04A61P27/06A61P9/10A61P25/14
Inventor 邓勇余光俊肖柑媛施怡春徐一丹
Owner SICHUAN UNIV
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