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3-amine alkyl phthalide compound as well as preparation method and application thereof

An amine alkyl phthalide and compound technology, which is applied in the field of medicinal chemistry, can solve the problems of AD patients with poor long-term curative effect, many toxic and side effects, and single action target.

Active Publication Date: 2020-01-17
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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  • 3-amine alkyl phthalide compound as well as preparation method and application thereof
  • 3-amine alkyl phthalide compound as well as preparation method and application thereof
  • 3-amine alkyl phthalide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation general method of embodiment 1 compound (4)

[0039] Add 2.0 mmol of the corresponding 3-bromide (1), 2.4 mmol of triphenylphosphine and 20 ml of toluene into the reaction flask, raise the temperature and reflux and stir for 12 to 24.0 hours (track the reaction process with TLC); Cool the liquid to room temperature, filter with suction, wash the filter cake with toluene and petroleum ether successively, and dry to obtain the corresponding 3-triphenylphosphine salt compound (2), with a yield of 60.0%-88.0%. 1 Confirmed by H-NMR;

[0040] Add 1.0 mmol of 3-triphenylphosphine salt compound (2) prepared in the previous step, 1.3 mmol of aminoalkylaldehyde compound (3) and 30 ml of dichloromethane into the reaction flask, stir well and then add triethylamine 1.5 mmol, then stirred at room temperature for 12 to 24.0 hours (the reaction process was tracked by TLC); after the reaction, the solvent was evaporated under reduced pressure, 30 mL of deionized water ...

Embodiment 2

[0041] Example 2 General method for the preparation of 3-aminoalkylphthalides (I)

[0042] Add 1.0 mmol of compound (4) mixture prepared according to the method in Example 1, and 25 ml of ethanol into the reaction flask. After stirring evenly, add 40 mg of 10% Pd / C. Stir the reaction with hydrogen for 2.0 to 24.0 hours (the reaction process is tracked by TLC). After the reaction, the solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: dichloromethane: methanol = 20 to 30:1 v / v), to obtain the corresponding 3-aminoalkylphthalide compound (I), the yield is 60.5%-92.0%, and its chemical structure has been verified by 1 H-NMR, 13 Confirmed by C-NMR and ESI-MS; the purity of the obtained target was greater than 97.0% as determined by HPLC. The structure of the target object prepared by the above-mentioned general method is as follows:

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[004...

Embodiment 3

[0083] Example 3 General method for the preparation of 3-aminoalkylphthalide compound (I) and acid salt formation

[0084] Add 1.0mmol of the 3-aminoalkylphthalide compound (I) obtained according to the above-mentioned Example 1 and Example 2 and 25 ml of acetone into the reaction flask, stir evenly, add 2.5 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, and separate and purify by conventional methods to obtain the salt of 3-aminoalkylphthalide compound (I). 1 Confirmed by H NMR and ESI-MS.

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PUM

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Abstract

The invention discloses a type of novel 3-amino alkyl phthalein compound (I) as well as a pharmaceutical acceptable salt, a preparation method, a medicine composition and application thereof in preparing medicines for treating and / or preventing diseases associated with nervous systems, and the diseases comprise but not limited to, vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related dementia, multiple sclerosis, muscular atrophy amyotrophic lateral sclerosis, neuropathic pain, glaucoma, ischemic stroke, hemorrhagic stroke, nerve damage caused by brain injury, and the like.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry and relates to a new type of 3-aminoalkylphthalide compound (I), its preparation method, pharmaceutical composition and its use in the preparation of drugs for the treatment and / or prevention of nervous 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, neuropathic pain, glaucoma, ischemic brain Stroke, hemorrhagic stroke, and neurological damage caused by traumatic brain injury. 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 ...

Claims

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Application Information

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IPC IPC(8): C07D307/88A61K31/365A61K31/4525A61P25/28A61P25/16A61P25/14A61P31/18A61P25/00A61P27/06A61P9/10
CPCC07D307/88A61P25/28A61P25/16A61P25/14A61P31/18A61P25/00A61P27/06A61P9/10Y02P20/55
Inventor 邓勇罗礼刘红艳曹忠诚田超全
Owner SICHUAN UNIV
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