Isoquinolinium compound, 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 effects of enhanced myocardial contractility and good anti-arrhythmic activity

Active Publication Date: 2009-07-01
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, pharmaceutical composition containing the same, preparation and use thereof
  • Isoquinolinium compound, pharmaceutical composition containing the same, preparation and use thereof
  • Isoquinolinium compound, pharmaceutical composition containing the same, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline

[0043] 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 reactant is 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) to obtain 6,7-methylenedioxy-1-(2 -2.89 g of -thienylmethyl)-3,4-dihydroisoquinoline, yield 98.8%.

Embodiment 2

[0044] Example 2 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline hydrochloride

[0045] Dissolve 2.75g (10mmol) N-2-thiopheneacetyl-3,4-methylenedioxyphenethylamine in 60ml chloroform, add 1ml (10mmol) 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), collected crystals, dissolved in ethanol, and dripped into a saturated ethanol solution of HCl to pH=1, 2.0 g of 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline hydrochloride was obtained, the yield was 68%, and the melting point was 201.8-203.0°C .

[0046] Elemental Analysis: C 15 h 14 cNO 2 S: Calculated %: C 58.53, H 4.58, N 4.55, Cl 11.52

[004...

Embodiment 3

[0049] Example 3 6,7-methylenedioxy-1-(2-thienylmethyl)-3,4-dihydroisoquinoline tartrate

[0050] Dissolve 2.75g (10mmol) N-2-thiopheneacetyl-3,4-methylenedioxyphenethylamine in 60ml benzene, add 1.5ml (15mmol) POCl dropwise 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-methylenedichloro-1 -(2-thienylmethyl)-3,4-dihydroisoquinoline, dissolved in ethyl acetate, dropwise add saturated 8wt% tartaric acid ethyl acetate solution until pH=1.5, stir to precipitate crystals, filter , The filter cake was washed with ethyl acetate and dried to give 6,7-methylenedichloro-1-(2-thienylmethyl)-3,4-dihydroisoquinoline tartrate.

[0051] Reference Example 2 N-2--5'-m...

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PUM

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Abstract

The invention discloses isoquinolin compounds shown as a formula I and salts thereof, wherein R1 refers to H, -CH3 or Br. The invention also discloses a preparation method for the compounds, which comprises the step of reacting compounds shown as III under the action of a condensing agent in halogenated alkane or benzene. 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 certain function of strengthening 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/04A61K31/436A61P9/06
Inventor 魏建梅谢美华奚家瑞
Owner JIANGSU KANION PHARMA CO LTD
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