Quinine compound containing quaternary ammonium groups and preparation method of quinine compound

A technology of quaternary ammonium groups and compounds, which is applied in the field of quinine compounds containing quaternary ammonium groups and their preparation, and can solve problems such as quinine compounds that have not been reported yet

Inactive Publication Date: 2019-05-21
山东博洛德生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the existing literature, the report of the quinine compound containing the quaternary ammonium group of the present invention has not been seen so far

Method used

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  • Quinine compound containing quaternary ammonium groups and preparation method of quinine compound
  • Quinine compound containing quaternary ammonium groups and preparation method of quinine compound
  • Quinine compound containing quaternary ammonium groups and preparation method of quinine compound

Examples

Experimental program
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Embodiment 1

[0023] Preparation of 3-(2-cyclopentyl-2-hydroxy-2-phenylethoxy)quinuclidane

[0024] Add 12.71g (0.1mol) of 3-quinine alcohol into a 500ml there-necked flask, add 100ml of DMSO, stir to dissolve, slowly add 4.2g (0.105mol) of sodium hydride with a content of 60%, raise the temperature to 60°C, stir for 1 hour, and dissolve 20.7 Add g (0.11mol) 1-phenyl-1-cyclopentyl-oxirane in 80mL of DMSO solution, continue stirring at this temperature for 4 hours, cool down to 10°C, add 150ml of water, and extract with methyl tert-butyl ether The organic phases were combined three times, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain 26.1 g of light yellow viscous oil.

[0025] Preparation of 3-[2-cyclopentyl-2-phenyl-2-(2-cyclopentyl-2-hydroxy-2-phenyl-ethoxy)ethoxy]quinuclidine

[0026] Add 18.90 g (0.06 mol) of penehyclidine into a 500 ml three-necked flask, add 150 mL of DMSO, add 2.40 g (0.06 mol, 1 eq) of sodium hydride with a conten...

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Abstract

The invention discloses a quinine compound containing quaternary ammonium groups and a preparation method of the quinine compound, and relates to a novel compound with the general formula I and a preparation method of the novel compound. The preparation method comprises the steps that 1-phenyl-1-R1-ethylene oxide and 3-quinuclidinol react in an organic solvent under the action of strong base to obtain 3-(2-R1-2-oxhydryl-2-phenyl ethyoxyl)quinuclidine; the obtained product reacts with 1-phenyl-1-R1-ethylene oxide in the organic solvent under the action of strong base to obtain 3-[2-R1-2-phenyl-2-(2-R1-2-oxhydryl-2-phenyl-ethyoxyl)ethyoxyl] quinuclidine; the obtained product reacts with alkyl halide R2X to obtain (I) (see the formula in the specification).

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a quinine compound containing a quaternary ammonium group and a preparation method thereof [0002] Background technique [0003] Acetylcholine (ACh) is a neurotransmitter released from cholinergic nerve endings. It has strong biological activity and exerts its effects by acting on muscarinic receptors (M receptors) and nicotinic receptors (N receptors). . Choline receptor blocking drugs are a class of drugs that work by blocking choline receptors, and are divided into M-choline receptor blocking drugs and N-choline receptor blocking drugs. M-choline receptor blocking drugs can block the choline receptors on the effectors innervated by the central and postganglionic cholinergic nerves, manifested as psychotropic effects of the central nervous system and smooth muscle relaxation, glandular secretion inhibition, and pupil dilation , increased heart rate, etc., has a wide range of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/02
Inventor 蔡连辉
Owner 山东博洛德生物科技有限公司
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