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Piperidine alkyl phthalide compounds, preparation method and application thereof

A technology for piperidinyl phthalide and compound, which is applied to a class of piperidinyl phthalide, the field of preparation and use thereof, can solve AD patients with poor long-term curative effect, many toxic and side effects, single action target, etc. question

Active Publication Date: 2018-11-02
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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  • Piperidine alkyl phthalide compounds, preparation method and application thereof
  • Piperidine alkyl phthalide compounds, preparation method and application thereof
  • Piperidine alkyl phthalide compounds, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 When A 1 -A 2 When C=CH, the preparation method of piperidine alkylphthalide compound (I)

[0036] 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;

[0037] Add 1.0 mmol of 3-triphenylphosphine salt compound (2) prepared in the previous step, 1.2 mmol of piperidine-4-alkylaldehyde compound (3) and 30 ml of dichloromethane into the reaction flask, stir well Add 1.2 mmol of triethylamine, then stir and react at room temperature for 12 to 24.0 hours (the reaction progress is tracked by TLC); after the reaction, evaporate the solvent und...

Embodiment 2

[0058] Example 2 When A 1 -A 2 Indicates CH-CH 2 When, the preparation general method of piperidine alkyl phthalide compound (I)

[0059] The piperidinylphthalide compound (I) (i.e.: A in the general chemical structure formula) prepared according to the method of Example 1 1 -A 2 means C=CH) E / Z Add 1.0 mmol of the configuration mixture and 25 ml of ethanol into the reaction flask, stir evenly, add 40 mg of 10% Pd / C, replace with hydrogen for three times, and react with hydrogen at room temperature and pressure for 2.0 to 24.0 hours (the reaction process is determined by TLC tracking), after the reaction, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane:methanol=20~30:1 v / v) to obtain the corresponding piperidine alkylbenzene Phthalo compound (I) (A 1 -A 2 Indicates CH-CH 2 ), the yield is 65.0%-95.0%, and its chemical structure has been tested 1 H-NMR, 13 Confirmed by C-NMR ...

Embodiment 3

[0084] Example 3 General method for preparation of piperidine alkylphthalide compound (I) and acid salt formation

[0085]Add 1.0 mmol of the piperidine alkylphthalide compound (I) obtained according to the above-mentioned Example 1 or 2 and 25 ml of acetone into the reaction flask, stir evenly, add 4.0 mmol of the corresponding acid, heat up and reflux and stir for 20 minutes, and the reaction After cooling to room temperature, the solvent was evaporated under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain the salt of piperidinylphthalide compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses piperidine alkyl phthalide compounds (I), pharmaceutically acceptable salt, a preparation method, a pharmaceutical composition and an application thereof in preparing drugs fortreating and / or preventing neurodegeneration related diseases, including but not being limited by neurodegenerative diseases such as vascular dementia, Alzheimer's disease, Parkinsonism, Huntington disease, HIV related dementia, multiple sclerosis, progressive lateral sclerosis spinal cord, neuropathic pain and glaucoma. The formula is as shown in the description.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry, and relates to a new class of piperidinylphthalide compound (I), its preparation method, pharmaceutical composition and its use in the preparation of drugs for the treatment and / or prevention of 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 States. According to the repor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D401/06C07D409/06A61K31/4525A61K31/4535A61K31/454A61P25/28A61P25/16A61P31/18A61P25/14A61P9/10A61P25/00A61P27/06
CPCA61P9/10A61P25/00A61P25/14A61P25/16A61P25/28A61P27/06A61P31/18C07D401/06C07D405/06C07D409/06
Inventor 邓勇谭正怀李岩宋青徐锐曹忠诚
Owner SICHUAN UNIV
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