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Substituted bicyclo(3,3,1)nonane ether compound and application thereof

A technology of salt compounds and compounds, applied in organic chemistry, drug combinations, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2011-05-04
马宏志
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But there is no report about the ether compounds of 3-azabicyclo (3,3,1) nonanol and its optical isomers and quaternary ammonium salts

Method used

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  • Substituted bicyclo(3,3,1)nonane ether compound and application thereof
  • Substituted bicyclo(3,3,1)nonane ether compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Rac-9-(2'-anthracenyl-2'-naphthyl-2'-hydroxy-ethoxy)-N-methyl-3-azabicyclo(3.3.1)nonane (Rac-1 ) preparation

[0051] Under the protection of nitrogen, put 0.6g (15mmol) NaH in a dry three-necked flask, add 10mL of anhydrous DMSO, after stirring for 5min, dropwise add N-methyl-3-azabicyclo(3.3.1) nonanol ( 2.0g (14.2mmol) of 10mL DMSO solution, stirred at 60°C for 1h. Cooled to room temperature, slowly added dropwise 2'-anthracenyl-2'-naphthyl-1,2-oxirane 2.61g (14mmol) 10mL DMSO solution. Stir the reaction at 50°C for 3h, cool, and carefully add 20mL of water dropwise. Extract with ether, wash with water, wash the ether layer with 10% hydrochloric acid solution, and combine the aqueous phase; After drying over sodium sulfate, 9-(2'-anthracenyl-2'-naphthyl-2'-hydroxyl-ethoxyl)-N-methyl-3-azabicyclo (3.3.1 ) nonane colorless liquid, 3.02g, yield 67%. 1 H-NMR: δ (ppm, CD 3 Cl), 7.44(m, 2H), 7.25(m, 3H), 5.02(s, 1H), 3.71-3.85(m, 2H), 2.91-3.05(m, 4H), 2.91(s...

Embodiment 2

[0052] Example 2 Rac-9-(2'-anthracenyl-2'-naphthyl-2'-hydroxy-ethoxy)-N-methyl-3-azabicyclo(3.3.1)nonane hydrochloride ( Preparation of Rac-1·HCl)

[0053]Dissolve 2.0g of (1) in 5mL of ether, cool the ether layer, add 5ml of 2N hydrochloric acid solution, and stir to precipitate a solid. The solid was collected by filtration, washed with ice water, and recrystallized from 95% ethanol to obtain 1.8 g of the title compound as a white solid, yield 81%, melting point: 189-191°C.

[0054] H-NMR: δ (ppm, CD 3 Cl), 10.87(s, 1H), 7.61(m, 2H), 7.25(m, 3H), 5.08(s, 1H), 3.63-3.80(m, 2H), 2.92-3.05(m, 4H), 2.82 (s, 3H), 2.21 (s, 1H), 2.03 (s, 1H), 2.01 (m, 2H), 1.31-1.75 (m, 12H).

Embodiment 3

[0055] Example 3Rac-9-(2'-Anthracenyl-2'-Naphthyl-2'-Hydroxy-ethoxy)-N,N-Dimethyl-3-azabicyclo(3.3.1)nonane quaternary Amiodonium salt (Rac-1-CH 3 I) Preparation

[0056] Dissolve 1.0g (1) and excess methyl iodide in 20mL of acetonitrile, stir and reflux for 5 days, TLC detects that the reaction has reached equilibrium, cool to room temperature, evaporate the solvent, wash the residue 3 times with ethyl acetate, and recrystallize from ethanol , the target compound was obtained as 0.86 g of yellow solid, yield 61%, melting point: 161-163°C. H-NMR: δ (ppm, DMSO), 11.27 (s, 1H), 7.58 (m, 2H), 7.37 (m, 3H), 4.98 (s, 1H), 3.43-3.70 (m, 2H), 2.82- 3.10(m, 4H), 2.88(s, 3H), 2.76(s, 3H), 2.25(s, 1H), 2.06(s, 1H), 2.04(m, 2H), 1.37-1.81(m, 12H) .

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Abstract

The invention relates to a substituted bicyclo(3,3,1)nonane ether compound and application thereof. The compound comprises an optical isomer, quaternary ammonium salt and medicinal compositions thereof. The compound can be used for treating diseases or symptoms which are associated with a central nervous system, a peripheral nervous system, smooth muscle contraction, endocrine, neurodegeneration, inflammation, pain, withdrawal symptoms caused by termination of abuse of chemical substances and the like.

Description

technical field [0001] The invention relates to the preparation and use of substituted bicyclic (3,3,1) nonanyl ether compounds, including optical isomers and quaternary ammonium salts thereof, and their pharmaceutical compositions. The compounds of the present invention can be used in the treatment of diseases or conditions related to the central nervous system, peripheral nervous system, diseases or conditions related to smooth muscle contraction, endocrine diseases or conditions, diseases or conditions related to neurodegeneration, diseases related to inflammation or disorders, pain, and withdrawal symptoms caused by cessation of chemical substance abuse. Background technique [0002] Substituted bicyclic (3,3,1) nonanyl ether compounds have significant therapeutic effects on some major diseases such as Kinson's syndrome, senile dementia, chronic obstructive pulmonary disease, urinary incontinence and the like. [0003] CN1089838A and US6028198 disclose the use of an est...

Claims

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Application Information

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IPC IPC(8): C07D221/22C07D401/14C07D409/14C07D401/12C07D405/14A61K31/439A61K31/444A61K31/475A61K31/4709A61P25/00A61P25/02A61P21/00A61P5/00A61P25/28A61P29/00A61P25/30
Inventor 马宏志
Owner 马宏志
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