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6-(hydroxybenzyloxy) phthalide Mannich base compound, and preparation method and application thereof

A phthalide Mannich base and hydroxybenzyloxy technology, applied to 6-(hydroxybenzyloxy) phthalide Mannich base compounds, their preparation and application fields, can solve the problem of single action target and AD patients Problems such as poor long-term efficacy and many toxic and side effects

Pending Publication Date: 2022-05-13
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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  • 6-(hydroxybenzyloxy) phthalide Mannich base compound, and preparation method and application thereof
  • 6-(hydroxybenzyloxy) phthalide Mannich base compound, and preparation method and application thereof
  • 6-(hydroxybenzyloxy) phthalide Mannich base compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 General method for the preparation of 6-(hydroxybenzyloxy) phthalide Mannich base compound (I)

[0038] Dissolve 2.0 mmol of the corresponding 6-(hydroxybenzyloxy)phthalide compound (2) in 20 ml of methanol, add 4.0 mmol of paraformaldehyde and the corresponding amine compound (HNR 2 R 3 ) 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, 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 6-(hydroxybenzyloxy)phthalide Mannich base compound (I), with a yield of 32.6 %-66.5%, its chemical structure has been 1 H-NMR, 13 C-NMR and ESI-MS confirmed that the purity of the...

Embodiment 2

[0071] Example 2 General method for the preparation of 6-(hydroxybenzyloxy)phthalide Mannich base compound (I) and acid salt formation

[0072] Add 1.0 mmol of 6-(hydroxybenzyloxy)phthalide Mannich base compound (I) obtained in Example 1 above and 30 ml of methanol into the reaction flask, stir well, add 2.0 mmol of the corresponding acid, and stir at room temperature After reacting for 25 minutes, the solvent was evaporated under reduced pressure, and the residue was recrystallized to obtain the salt of 6-(hydroxybenzyloxy)phthalide Mannich base compound. 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a 6-(hydroxybenzyloxy) phthalide mannich base compound (I), pharmaceutically acceptable salts thereof, a preparation method thereof, a pharmaceutical composition and application thereof in preparation of drugs for treating and / or preventing nervous system related diseases. Comprising but not limited to vascular dementia, Alzheimer's disease, frontotemporal dementia, Prion disease, dementia with Lewy bodies, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, cerebral arterial thrombosis, hemorrhagic stroke, 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 6-(hydroxybenzyloxy)phthalide Mannich base compounds (I) and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions and preparation methods for treatment and treatment. / or use in drugs for the prevention of nervous system-related diseases, including but not limited to vascular dementia, Alzheimer's disease, frontotemporal dementia, Prion's disease, dementia with Lewy bodies, Parkinson's disease, Huntington's disease, HIV-related Dementia, multiple sclerosis, amyotrophic lateral sclerosis, neuropathic pain, 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), Parkin...

Claims

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Application Information

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IPC IPC(8): C07D307/88C07D333/72C07D209/46A61P25/00A61P25/28A61P25/16A61P25/14A61P31/18A61P21/00A61P9/10A61P25/04A61K31/343A61K31/381A61K31/4035A61K31/4025A61K31/5377A61K31/496A61K31/4525A61K31/4535A61K31/454
CPCC07D307/88C07D333/72C07D209/46A61P25/00A61P25/28A61P25/16A61P25/14A61P31/18A61P21/00A61P9/10A61P25/04
Inventor 邓勇施怡春余光俊吴承训张小玉
Owner SICHUAN UNIV
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