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A chiral tetrahydroisoquinoline derivative or salts thereof, and a preparing method and uses thereof

A technology for tetrahydroisoquinoline and chiral compounds, which is applied in the field of derivatives of chiral tetrahydroisoquinoline or their salts and their preparation, and can solve problems such as poor absorption and irregularity

Active Publication Date: 2015-06-10
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is poorly and irregularly absorbed orally as a quaternary ammonium salt

Method used

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  • A chiral tetrahydroisoquinoline derivative or salts thereof, and a preparing method and uses thereof
  • A chiral tetrahydroisoquinoline derivative or salts thereof, and a preparing method and uses thereof
  • A chiral tetrahydroisoquinoline derivative or salts thereof, and a preparing method and uses thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0030] Preparation method of chiral compound

[0031] The inventors prepared and separated the optical isomers in the isoquinoline compound through a chiral preparation column, and obtained (+)-C-409 and (-)-C-409 of chiral purity respectively:

[0032]

[0033] The method of chiral separation and preparation is not strictly required, as long as the (+)-C-409 and (-)-C-409 in the racemic (±)-C-409 are separated according to the conventional method of chiral separation and preparation .

[0034] Separation of (+)-C-409 and (-)-C-409 in racemic (±)-C-409 requires some separation method research.

[0035] Choose the chiral column CHIRALPAK ADHs (0.46cm I.D.×15cm L): (1) The mobile phase is n-hexane:isopropanol:diethylamine=70:30:0.1, the flow rate is 1ml / min, the column temperature is 35.0℃, and the Sample volume (4ul), sample concentration (3.2mg / ml), (+)-C-409 and (-)-C-409 are partially separated; (2) The mobile phase is n-hexane:ethanol:diethylamine=75: 25:0.1, flow rat...

Embodiment 1

[0059] (+)-1-(3-Methanesulfonamidobenzyl)-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline ((+)-C-409 ) and (-)-1-(3-methanesulfonamidobenzyl)-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline ((-)-C -409) preparation

[0060] Chiral preparative liquid phase method: Instrument: K-prep HPLC machine UV detector from YMC Company, chromatographic column: chiralpak IC column, 3cm I.D.*25cm Length, mobile phase: Hexane / Ethanol=50 / 50(v / v), The flow rate is 20ml / min, the temperature is 35°C, and the wavelength is 254nm.

[0061] 734 mg of the raw material (racemic (±)-C-409) was prepared into a mobile phase solution with a concentration of 6 mg / ml. Each injection is 6ml, that is, a sample loading is 36mg. Prepared by the above-mentioned chiral preparative liquid phase method, and collected the effluents containing (+)-C-409 and (-)-C-409 components respectively. The operation was repeated with 6 ml injections until the racemic C-409 stock solution was exhausted. The (+)-C-...

Embodiment 2

[0064] (+)-1-(3-Methanesulfonamidobenzyl)-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydroisoquinoline ((+)-C-409 ) hydrochloride and (-)-1-(3-methanesulfonamidobenzyl)-6-methoxy,7-benzyloxy-1,2,3,4-tetrahydroisoquinoline ((- )-C-409) Preparation of hydrochloride

[0065] Dissolve 301 mg of (+)-C-409 in 10 ml of methanol, add 0.3 ml of concentrated hydrochloric acid dropwise, shake until completely dissolved, evaporate the solvent with a rotary evaporator to obtain a solid product, and transfer it to a sample bottle to obtain (+) C-409 Hydrochloride 285mg. The specific rotation of (+)-C-409 hydrochloride is: [α]2D5=+20.6 (C1, 1% methanol hydrochloride). Use the following HPLC conditions for detection: Chiral column CHIRALPAK IC (0.46cm I.D.×15cm L), mobile phase is n-hexane:ethanol:diethylamine=60:40:0.1, flow rate is 1ml / min, detection wavelength is 220nm, column temperature At 35.0°C, the sample was dissolved in mobile phase, the injection volume (5ul), and the sample purity was ...

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Abstract

The invention discloses a chiral compound and a preparing method and uses thereof. The chiral compound is shown as the formula I. The invention also discloses the preparing method and the uses of the chiral compound.

Description

technical field [0001] The present invention relates to a chiral compound, in particular to a chiral tetrahydroisoquinoline derivative or a salt thereof and a preparation method and use thereof. Background technique [0002] Cardiovascular disease is a serious threat to human health and is the main cause of human death. Sudden cardiac death is the main cause of death from cardiovascular disease, and ventricular tachycardia and ventricular fibrillation are important causes of sudden cardiac death. Most patients with coronary heart disease, myocardial hypertrophy, myocardial ischemia and heart failure died because of uncontrolled ventricular tachycardia and ventricular fibrillation. [0003] Currently clinical antiarrhythmic drugs can be divided into four categories: Class I is a sodium ion channel blocker represented by quinidine; Class II is a β-receptor blocker represented by propranolol; III Class IV is a drug that prolongs the duration of the action potential represented...

Claims

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Application Information

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IPC IPC(8): C07D217/18A61P9/06A61P9/00
CPCC07D217/18
Inventor 谢美华吴泰志张福利
Owner SHANGHAI INST OF PHARMA IND
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