Compound with dual inhibitory activities to acetylcholine esterase and cholinesterase

A compound, selected technology, applied in the field of medicine

Active Publication Date: 2013-12-04
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The description of the pathogenesis mainly includes the theory of cholinergic damage and abnormal deposition of β-amyloid protein, but it is not yet clear

Method used

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  • Compound with dual inhibitory activities to acetylcholine esterase and cholinesterase
  • Compound with dual inhibitory activities to acetylcholine esterase and cholinesterase
  • Compound with dual inhibitory activities to acetylcholine esterase and cholinesterase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of 1,1'-([1,1'-biphenyl]-4,4'-diyl)bis(2-(dimethylamino)ethanone

[0058]

[0059] Add biphenyl (7.71g, 50mmol), anhydrous AlCl 3 (20g, 150mmol), 100ml CS 2 , under mechanical stirring, heated to 50°C, added dropwise chloroacetyl chloride (11.94ml, 150mmol), after addition, raised the temperature to 80°C, reacted for 4h, stopped heating, poured the reaction solution into ice water, stirred, pumped Filter, wash with water, and dry to obtain 10.10 g of a yellow solid (intermediate), with a yield of 66%.

[0060] In a 250 mL dry round bottom flask add K 2 CO 3 (1.38g, 10mmol), KI (0.83g, 5mmol), 20ml of acetonitrile, heated to 50°C, stirred for 30min, then added dimethylamine hydrochloride (0.81g, 10mmol), and the intermediate synthesized above (1.53g , 5mmol). Raise the temperature to 80°C, react for 10h, stop heating, after cooling, concentrate the reaction mixture under reduced pressure, add water to the residue, CH 2 Cl 2 Extracted three times, the ...

Embodiment 2

[0063] Synthesis of 1,1'-([1,1'-biphenyl]-4,4'-diyl)bis(2-(morpholinyl)ethanone

[0064]

[0065] The operating steps were the same as in Example 1, except that dimethylamine hydrochloride was replaced by morpholine: to obtain the title compound as a pale yellow solid. The yield is 65%.

[0066] 1 H-NMR (300MHZ, CDCl 3 )δ: 8.039(d,4H), 7.744(d,4H), 3.781(s,4H), 3.724(t,8H), 2.574(t,8H).

Embodiment 3

[0068] Synthesis of 1,1'-([1,1'-biphenyl]-4,4'-diyl)bis(2-(4-methylpiperazin-1-yl)ethanone

[0069]

[0070] The operation steps were the same as in Example 1, except that dimethylamine hydrochloride was replaced by N-methylpiperazine to obtain the title compound as a pale yellow solid. The yield is 70%.

[0071] 1 H-NMR (300MHZ, CDCl 3 )δ: δ8.106(d,4H),7.706(d,4H),3.859(s,4H),2.654(d,16H),2.323(s,6H).

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PUM

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Abstract

The invention provides an inhibitor of acetylcholine esterase and cholinesterase shown in the general formula (I), wherein R1, R2 and N form an aliphatic heterocyclic ring with 3-7 carbons containing 1-2 hetero atoms, and X is selected from a covalent bond, CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, and C[(CH2)mCH3]2 (m=5). The compound shows inhibitory activities to acetylcholine esterase and cholinesterase, and can be used for treating and / or preventing cognitive diseases and neurodegeneration diseases.

Description

field of invention [0001] The invention relates to a class of biphenyl and diphenyl compounds with symmetrical structures and a method for preparing such compounds. These compounds not only have strong acetylcholinesterase (AChE) inhibitory activity, but also have strong butyrylcholinesterase (BuChE) inhibitory activity, so they are useful in the treatment of such diseases as cognitive and neurodegenerative diseases (including senile Dementia) and other diseases involving acetylcholinesterase inhibitors and butyrylcholinesterase inhibitors have potential applications, and belong to the field of medical technology. Background of the invention [0002] Alzheimer's disease (AD), also known as senile dementia, is a common degenerative disease of the central nervous system. Manifestations include memory loss, often forgetting the names of relatives and friends including children, unable to distinguish time and seasons, and getting lost in familiar places; hallucinations, delusio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/108C07C225/16A61K31/55A61K31/496A61K31/5377A61K31/135A61K31/4545A61P25/28
Inventor 吴松杜冠华王琳王冬梅刘艾林周丹
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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