4-(aminoalkyl)phthalazine-1-one compound, preparation method and use thereof

A technology of ketone compounds and amine alkyl, which is applied in the field of medicinal chemistry, can solve the problems of single target, poor long-term curative effect of AD patients, and many side effects

Active Publication Date: 2020-01-17
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 side effects in clinical use, and poor long-term curative effect on AD patients.

Method used

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  • 4-(aminoalkyl)phthalazine-1-one compound, preparation method and use thereof
  • 4-(aminoalkyl)phthalazine-1-one compound, preparation method and use thereof
  • 4-(aminoalkyl)phthalazine-1-one compound, preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1 General method for the preparation of 4-(aminoalkyl)phthalazin-1-ketone compound (I)

[0035] 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 8 to 24.0 hours (the reaction progress is tracked by TLC); after the reaction, the reaction 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;

[0036] Add 1.0 mmol of 3-triphenylphosphine salt compound (2) prepared in the previous step, 1.2 mmol of aminoalkylaldehyde compound (3) and 30 ml of dichloromethane into the reaction flask, stir well and then add triethylamine 1.2 mmol, then stirred at room temperature for 6.0 to 24.0 hours (the reaction process was tracked by TLC); after the reaction, t...

Embodiment 2

[0084] Example 2 General method for the preparation of 4-(aminoalkyl)phthalazin-1-one compound (I) and acid salt formation

[0085] Add 3.0 mmol of 4-(aminoalkyl)phthalazin-1-one compound (I) obtained according to the above-mentioned Example 1 and 25 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, heat up and reflux and stir React for 20 minutes, cool to room temperature after the reaction is over, evaporate the solvent under reduced pressure, recrystallize the residue with acetone, filter the precipitated solid, and obtain 4-(aminoalkyl)phthalazin-1-one compound (I) salt, the chemical structure of which is 1 Confirmed by H NMR and ESI-MS.

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PUM

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Abstract

The invention discloses a novel 4-(aminoalkyl)phthalazine-1-one compound (I) and pharmaceutically acceptable salts thereof, a preparation method, a pharmaceutical composition and use in the preparation of drugs for treating and / or preventing neurological 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 stroke, hemorrhagic stroke, nerve injury caused by brain trauma and other diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of 4-(aminoalkyl)phthalazin-1-one compound (I), its preparation method, pharmaceutical composition and its preparation for the treatment and / or prevention of nervous system-related diseases Uses in pharmaceuticals 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 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D237/32A61K31/502A61P25/00A61P25/28A61P9/00A61P25/14A61P25/16A61P31/18A61P25/04A61P27/06A61P9/10A61P21/00
CPCC07D237/32A61P25/00A61P25/28A61P9/00A61P25/14A61P25/16A61P31/18A61P25/04A61P27/06A61P9/10A61P21/00Y02P20/55
Inventor 邓勇徐锐曹忠诚宋青田超全
Owner SICHUAN UNIV
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