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Preparation method and application of bencycloquidium bromide optical isomer and composition of bencycloquidium bromide optical isomer

A technology for optical isomers and benzoquinium bromide, which is applied in the field of preparation and application of a group of benzoquine bromide optical isomers and compositions thereof, and can solve the problems of short half-life and the like

Active Publication Date: 2009-11-25
YINGU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the half-life of this type of drug is short, the half-life of the terminal clearance period is about 1.6 hours, and the half-life of drug and metabolite clearance is 3.6 hours, so frequent administration is required

Method used

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  • Preparation method and application of bencycloquidium bromide optical isomer and composition of bencycloquidium bromide optical isomer
  • Preparation method and application of bencycloquidium bromide optical isomer and composition of bencycloquidium bromide optical isomer
  • Preparation method and application of bencycloquidium bromide optical isomer and composition of bencycloquidium bromide optical isomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation of embodiment 1 (+)-3-quinoline alcohol and (-)-3-quinoline alcohol

[0021] Dissolve 60 g of 3-quinoline alcohol in 80% ethanol, add 58 g of L(+) tartaric acid, heat and reflux in a water bath for 30 minutes, cool to 45°C, precipitate crystals, filter and recrystallize to obtain (+)-3-quinoline alcohol salt , and the filtrate is set aside. Take the above filtrate, add K 2 CO 3 Adjust the pH to 8, add D(-) tartaric acid, heat to reflux, cool to 45°C, crystallize, filter and recrystallize to obtain (-)-3-quinoline alkoxide. Dissolve (+)-3-quinoline salt and (-)-3-quinoline salt in water, add K 2 CO 3 Adjust the pH to 8, extract with chloroform, combine the extracts, and evaporate the chloroform to dryness to obtain (+)-3-quinoline and (-)-3-quinoline respectively.

Embodiment 2

[0022] The preparation of four kinds of pure optical isomers of embodiment 2 phencycloquinium bromide

[0023] Respectively get (+)-3-quinoline alcohol and (-)-3-quinoline alcohol prepared in Example 1 to react with 1-phenyl-1-cyclopentyl oxirane to obtain (+)-pentethyclone Ether mixtures and (-)-penthyclidine mixtures. The (+)-pentehyclidine mixture was subjected to silica gel (100-200 mesh) column chromatography (the eluent was an appropriate proportion of chloroform, methanol, and ammonia water). Take an appropriate amount of (+)-pentehyclidine eluent at different time points, use chloroform / methanol / ammonia water=90 / 10 / 0.02 as the developing solvent, perform TLC analysis, develop color with bismuth potassium iodide reagent, combine the above point and Next point the eluate and evaporate the chloroform to dryness, and react with methyl bromide respectively. Reaction of the upper point with methyl bromide gives the IV isomer, and reaction of the lower point with methyl bro...

Embodiment 3

[0038] The preparation of embodiment 3 phencycloquinium bromide isomer I, II mixture and isomer III, V mixture

[0039]Get the (-)-penthyclidine mixture and the (+)-penthyclidine mixture prepared in Example 2 to react with methyl bromide respectively, and the resulting products are respectively isomer I, II mixture and isomer III, V mixture. The two isomer mixtures were quantitatively analyzed by HPLC, and the chromatographic conditions were as follows:

[0040] Chromatographic column: Dikma company C 18 Chromatographic column

[0041] Mobile phase: Phosphate buffer at pH=5.0: Methanol=4:6

[0042] Detection wavelength: 210nm

[0043] Detection results; the purity of the mixture of isomers I and II is 99.5%, and the purity of the mixture of isomers III and V is 99.2%.

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Abstract

The invention relates to the technical field of medicaments, in particular to a preparation method and application of a bencycloquidium bromide optical isomer. The isomer is obtained by a chemical resolution method, the activity of the isomer is far beyond that of other isomers and racemic forms; when the isomer is taken as a medicament to be taken, the taking dosage is reduced, and side effects caused by other isomers are simultaneously eliminated; moreover, the bencycloquidium bromide optical isomer has a romurtide cyclodextrin inclusion compound with higher pharmaceutical value and a preparation thereof. The romurtide is coated by the cyclodextrin, so that the problems of low water-solubility, unstable preparation prepared by the romurtide cyclodextrin inclusion compound and the like are solved. The romurtide cyclodextrin inclusion compound has the characteristics of high stability, good water-solubility, and low toxic and side effects, and is a quite good immunomodulator.

Description

technical field [0001] The invention belongs to the field of chemical medicines, in particular to a group of phencycloquinium bromide (chemical name: 3-{(2-cyclopentyl-2-hydroxyl-2-phenyl)ethoxy}-1-methyl-bromo Fe-1-azabicyclo[2,2,2]octane, molecular formula: C 21 h 32 NBrO 2 ) optical isomers and preparation methods thereof, compositions containing the optical isomers, and applications of the optical isomers in the preparation of medicines for treating nasal cavity hypersecretion and chronic obstructive pulmonary disease. Background technique [0002] Chronic Obstructive Pulmonary Disease (COPD) referred to as COPD refers to a group of associated diseases with airway obstruction such as chronic bronchitis, emphysema, and pulmonary heart disease. It includes chronic bronchitis, chronic obstructive emphysema and chronic pulmonary heart disease. Its main features are chronic inflammation of the airway and progressive airway obstruction, which is a long-term accumulation pr...

Claims

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Application Information

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IPC IPC(8): C07D453/04A61K31/49A61P11/00C07B57/00
Inventor 陈小平温守明赵锋孟小平丁浩
Owner YINGU PHARMA
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