Isoquinolinium compound or its salts, pharmaceutical composition containing the same, preparation and use thereof

A compound and isoquinoline technology, applied in the field of isoquinoline compounds or their salts, can solve the problems of increased myocardial oxygen consumption, accelerated heart rate and the like, and achieve the effect of good antiarrhythmic activity and small inhibitory effect

Active Publication Date: 2011-05-11
JIANGSU KANION PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, Uigenamine (the main component extracted from the traditional Chinese medicine Aconite with β-receptor stimulant effect) can enhance myocardial contractility, but at the same time it will increase the heart rate and increase myocardial oxygen consumption, thereby limiting its clinical use

Method used

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  • Isoquinolinium compound or its salts, pharmaceutical composition containing the same, preparation and use thereof
  • Isoquinolinium compound or its salts, pharmaceutical composition containing the same, preparation and use thereof
  • Isoquinolinium compound or its salts, pharmaceutical composition containing the same, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline

[0049] Dissolve 2.75g (10mmol) N-2-thiopheneacetyl-3,4-methylenedioxyphenethylamine in 60ml chloroform, add 2ml (20mmol) POCl dropwise 3 , after the addition, heat to reflux until the point plate reaction shows that the reactants are completely consumed (about 3 hours), and the excess POCl is evaporated under reduced pressure. 3 and chloroform, the residue was washed with 1:1 benzene-hexane, solidified, and the crude product was collected by filtration, recrystallized from methanol-ether (volume ratio 1:1) (volume ratio 1:1) to obtain 6,7-methylene di Oxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline 2.89 g, yield 98.8%.

Embodiment 2

[0050] Example 2 6,7-methylenedioxy-1-(2-thienyl)-3,4-dihydroisoquinoline

[0051] Dissolve 2.75g (10mmol) N-2-thiopheneacetyl-3,4-methylenedioxyphenethylamine in 60ml chloroform, add 1.5ml (15mmol) POCl dropwise 3 , the addition is completed, heated to 50 ° C, until the point plate reaction shows that the reactants are completely consumed (about 3 hours), and the excess POCl is evaporated under reduced pressure 3 and chloroform, the residue was washed with 1:1 benzene-hexane, solidified, and the crude product was collected by filtration, recrystallized from methanol-ether (volume ratio 1:1), and the crystals were collected to obtain 6,7-methylenedioxy-1 -(2-thienylmethyl)-3,4-dihydroisoquinoline 2.83g, yield 97%.

Embodiment 3

[0052] Example 3 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline

[0053] Dissolve 2.75g (10mmol) N-2-thiopheneacetyl-3,4-methylenedioxyphenethylamine in 60ml benzene, add dropwise 1ml (10mmol) POCl 3 , the addition is complete, heated to 80 ° C, the reactant disappears (about 3 hours), and the excess POCl is evaporated under reduced pressure 3 and chloroform, the residue was washed with 1:1 benzene-hexane, solidified, and the crude product was collected by filtration, recrystallized from methanol-ether (volume ratio 1:1), and the crystals were collected to obtain 6,7-methylenedioxy-1 -(2-thienylmethyl)-3,4-dihydroisoquinoline 2.63 g, yield 90%.

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Abstract

The invention discloses isoquinolin compounds shown as formula I and salts thereof, wherein R1 represents H, -CH3 or Br. The invention also discloses a preparation method for the compounds, which comprises the step of reacting compounds shown as formula IV under the action of a reducing agent in an alcohol solvent. The invention also discloses a medicine composition containing the compounds, and application of the compounds to preparing medicines for treating arrhythmia. The isoquinolin compounds and the salts thereof have good antiarrhythmic activity and small function of inhibiting myocardial contraction force.

Description

technical field [0001] The present invention relates to a class of novel compounds, as well as pharmaceutical compositions containing them, their preparation methods and applications, in particular to a class of isoquinoline compounds or their salts, and their pharmaceutical compositions, their preparation methods and applications. Background technique [0002] Sudden cardiac death (SCD) is one of the leading causes of cardiovascular death. The generation of SCD is due to the instability of myocardial electrophysiology, which leads to the disappearance of regular heart rhythm, and the most serious ones are sustained ventricular tachycardia (VT, vetricular tachycardia) and ventricular fibrillation (VF, vetricalar fibrillation). [0003] At present, there are many antiarrhythmic drugs, such as sodium channel blockers, β-receptor blockers, calcium channel blockers, and potassium ion channel blockers. In clinical application, it is necessary for antiarrhythmic drugs to slow dow...

Claims

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Application Information

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IPC IPC(8): C07D491/04A61K31/4355A61P9/06
Inventor 魏建梅谢美华奚家瑞
Owner JIANGSU KANION PHARMA CO LTD
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