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Pharmaceutical compound, its preparation method and application in making medicine

A pharmaceutical compound and pharmaceutical technology, applied in the preparation of anticholinergic drugs and drugs for the treatment of respiratory diseases, bromide-1-cyclopropylmethyl-3-quinuclidane pharmaceutical compound and its preparation field, can solve the problem of Accumulation of poisoning in the patient's brain, affecting learning and memory, etc., to achieve long-lasting bronchodilation and protection, relaxation of bladder detrusor, and reduction of medication frequency

Inactive Publication Date: 2006-06-14
CHENGDU LIST PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] When the existing anticholinergic drugs (such as: ipratropium bromide, etc.) are used to treat respiratory diseases, they have almost no selectivity to the three muscarinic receptor subtypes when they act on the airway of the human body, and they are easy to penetrate through the human body. Blood-brain barrier, long-term medication can lead to accumulation of poisoning in the brain of patients and affect learning and memory

Method used

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  • Pharmaceutical compound, its preparation method and application in making medicine
  • Pharmaceutical compound, its preparation method and application in making medicine

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Preparation of 3-(2-phenyl-2-cyclopentyl-2-hydroxyethoxy)quinuclidane

[0027] In a three-necked reaction flask, weigh 1 g of phenyl-cyclopentyl oxirane and 1.5 g of 3-quinine alcohol, dissolve it in 20 ml of DMSO, add 1 g of sodium hydride, stir and react for 3 hours, cool, extract with ether, and remove the ether layer Extract with 3mol / L hydrochloric acid, neutralize the acid water with 40% NaOH, then extract with ether, dry over anhydrous magnesium sulfate, filter, evaporate the solvent, and the product is purified by distillation for use, with a yield of 57%.

Embodiment 2

[0029] Preparation of 1-cyclopropylmethyl-3-(2-phenyl-2-cyclopentyl-2-hydroxyethoxy)quinuclidine bromide

[0030] Dissolve 5 g of the compound obtained in Example 1 with anhydrous ether, add excess bromomethylcyclopropane, react overnight, pour off the supernatant, and recrystallize the remaining solid with acetone to obtain a white solid with a yield of 67%. The melting point measured by YRT-3 melting point apparatus is 153-154°C.

Embodiment 3

[0032] Antispasmodic effect of 1-cyclopropylmethyl-3-(2-phenyl-2-cyclopentyl-2-hydroxyethoxy)quinuclidine bromide on isolated guinea pig bronchi

[0033] Guinea pigs were killed by bloodletting from the femoral artery after violently hitting the head, and the trachea from the larynx to the bifurcation of the trachea was quickly taken out, placed in a petri dish filled with Krebson’s solution, and the trachea was cut into 20×3cm 2 Fix the lower end of the helical strip of the trachea to the bottom of the McFarland bath filled with 15ml of Krebson's solution, and a thin line at the upper end is connected to the tension transducer, which is connected to the second physiological recorder, and the tracheal load is adjusted to 1.5 ~2g, and feed 95% oxygen and 5% carbon dioxide gas, keep the temperature at 37 degrees, and stabilize for 60-90 minutes. Add different concentrations of Ach into the bath by cumulative dosing method, record the shrinkage amplitude of each concentration, and...

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Abstract

The present invention relates to a bromo-1-cyclopropylmethyl-3-(2-phenyl-2-cyclopentyl-2-hydroxyoxyethyl) quinuclidane medicine compound, its preparation method and application of said medicine compound in preparation of anticholinergic and medicine for curing respiratory diseases. The invented medicine compound can selectively act on receptor M1 and receptor M3 and does not act on receptor M2, and is not easy to permeate through blood-brain barrier, so that it can reduce pharmacy frequency of patient and can reduce therapeutic cost.

Description

technical field [0001] The present invention relates to a pharmaceutical compound, in particular to bromide-1-cyclopropylmethyl-3-(2-phenyl-2-cyclopentyl-2-hydroxyethoxy)quinuclidane pharmaceutical compound and its The preparation method and the application of the drug compound in the preparation of anticholinergic drugs and drugs for treating respiratory diseases. Background technique [0002] Anticholinergic drugs can compete with acetylcholine or its analogues to bind to choline receptors, but have no intrinsic activity, hinder the stimulatory effect of cholinergic drugs on choline receptors, and exert anticholinergic effects. According to the mechanism of action, they can be divided into The following two categories: M choline receptor blocking drugs, N choline receptor blocking drugs. [0003] Anticholinergic drugs play a very important role in the treatment of respiratory diseases. [0004] There are three subtypes of muscarinic receptors in the parasympathetic gangl...

Claims

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Application Information

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IPC IPC(8): C07D453/02A61K9/00A61K9/12A61K31/439A61P11/00
Inventor 朱登军
Owner CHENGDU LIST PHARMA
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