Indolylpiperidine compound and preparation process and use thereof

A technology of indolylpiperidine and compounds, which is applied in the field of synthesis of indolylpiperidine derivatives, and can solve the problems of poor availability of donepezil biological agents and low toxicity and side effects

Inactive Publication Date: 2007-05-23
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although scientists have done a lot of research on Alzheimer's disease and made great progress, for example, the emergence of tacrine and donepezil drugs, but they still have different defects, tacrine is more toxic to the liver, and donepezil in The availability of biological agents in the body is poor, so it is still necessary to continue research on Alzheimer's disease to find a new class of compounds and develop a new generation of drugs with low toxicity and high efficacy

Method used

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  • Indolylpiperidine compound and preparation process and use thereof
  • Indolylpiperidine compound and preparation process and use thereof
  • Indolylpiperidine compound and preparation process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: N-(indole-2-formyl)-(1-benzyl-4-piperidinyl)methanamine

[0037] Suspend 0.3g of 2-indolecarboxylic acid in 6ml of dry chloroform, cool in an ice-water bath, add 0.5ml of freshly treated thionyl chloride, let it warm up naturally, and stir overnight. The solvent was distilled off under reduced pressure (control temperature T<35°C). 10 ml of dry dichloromethane were added and evaporated to dryness. Repeat this treatment twice again to obtain a pale yellow solid, which was dissolved in 10ml of dichloromethane, cooled in an ice-water bath, and a solution of 270mg of 1-benzyl-4-piperidinemethylamine in 5ml of dichloromethane was added dropwise, and after the addition was complete, Add 0.3ml of triethylamine, stir at 0°C for 30min, wash the reaction solution twice with 20ml of water, and once with 15ml of saturated sodium carbonate solution, and dry the organic layer with anhydrous potassium carbonate. The solvent was evaporated, and the residue was passed throu...

Embodiment 2

[0039] Example 2: N-(indole-2-formyl)-2-(1-benzyl-4-piperidinyl)ethylamine

[0040] The procedure was as in Example 1, except that 1-benzyl-4-piperidinylethylamine was used instead of 1-benzyl-4-piperidinylmethylamine. Acicular needle crystals were obtained, MP=168~169°C

[0041] h 1 NMR (CDCl3, AM=400): 1.26~1.42(3H, m), 1.50~1.80(4H, m), 1.90~2.00(2H, m), 2.96(2H, m), 3.48~3.58(4H, m ), 6.12(1H,br), 6.70~7.66(10H,m), 9.52(1H,S)

Embodiment 3

[0042] Example 3: N-(1-methylindole-2-formyl)-1-(1-benzyl-4-piperidinyl)methanamine

[0043] The operation process is as in Example 1, except that indole-2-carboxylic acid is replaced with 1-methylindole-2-carboxylic acid. Needle crystals were obtained, MP=141~2°C

[0044] h 1 NMR (CDCl3, AM=400): 1.30~1.42 (2H, q-d), 1.60 (1H, m), 1.68~1.76 (2H, d), 1.90~2.00 (2H, t-d), 2.90 (2H, d), 3.32(2H, t), 3.50(2H, s), 4.02(3H, s), 6.22(1H, br), 6.78(1H, s), 7.08~7.60(9H, m)

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Abstract

The present invention provides a kind of indoxyl piperidine compound. The pharmacological tests show that said kind of compound can be used as inhibitor of acetylcholin esterase, can competitively inhibit the activity of acetylcholin esterase, can delay hydrolysis of acetylcholin so as to raise the action of acetylcholin in synapsis and attain the goal of curing presenile dementia.

Description

technical field [0001] The present invention relates to the synthesis and application of indolylpiperidine derivatives. Background technique [0002] Alzheimer's disease is a disease with multiple etiologies involved in progressive brain function degeneration, and its etiology has not yet been elucidated conclusively. However, it is a common senile disease that seriously threatens the health of the elderly, especially when the society is aging gradually, and this situation becomes more and more severe, thus causing widespread concern. [0003] At present, drug research on Alzheimer's disease mainly includes the following aspects: [0004] 1. Acetylcholinesterase inhibitor (ChEI), which competitively inhibits the activity of acetylcholinesterase, slows down the hydrolysis of acetylcholine, thereby enhancing the effect of acetylcholine at the synapse to achieve the purpose of treating Alzheimer's disease. [0005] 2. Considering the precursors of acetylcholine, such as acety...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D401/06A61P25/28C07D211/06C07D209/10
Inventor 沈竞康蔡茂军蒋华良陈凯先唐希灿刘东祥罗小民
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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