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Pharmaceutical compositions comprising chelidonine or derivatives thereof

A technology of chelidonine and composition, applied in the field of pharmaceutical compositions containing chelidonine or its derivatives, capable of solving the problems of lack of ion channel selectivity and the like

Inactive Publication Date: 2004-07-28
殷载淳 +5
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs are known to have various side effects due to their lack of ion channel selectivity

Method used

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  • Pharmaceutical compositions comprising chelidonine or derivatives thereof
  • Pharmaceutical compositions comprising chelidonine or derivatives thereof
  • Pharmaceutical compositions comprising chelidonine or derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Example 1: Preparation of (12bR)-13,14-dihydro-13-methyl[1,3]benzodioxolo[5,6c]-1,3-dioxolo[4,5- i]phenanthridine (compound 6)

[0111] Dess-Martin Periodinane (25mg, 0.059mmol) was dissolved in anhydrous dichloromethane (0.2ml), then stirred at room temperature for 10 minutes. A solution of chelidonine (20 mg, 0.054 mmol) in anhydrous dichloromethane (0.1 ml) was added dropwise to the reaction solution. After stirring for 30 minutes, diethyl ether (0.9 ml) was added to the reaction solution. The reaction solution was added to a mixture of saturated potassium carbonate aqueous solution (0.56 ml) and sodium thiosulfate pentahydrate (0.1 g), followed by stirring for 15 minutes. The reaction solution was extracted with ethyl acetate, washed, dried and purified by column chromatography (hexane:ethyl acetate=10:1) to prepare 6.6 mg (37%) of the title compound (Compound 6). At this point, 9 mg (45%) of chelidonine were recovered.

[0112] R f = 0.24 (hexane: ethyl acetat...

Embodiment 2

[0114]Example 2: Preparation of (12bR)-7,12b,13,14-tetrahydro-13-methyl[1,3]-benzodioxolo[5,6c]-1,3-dioxolo [4,5-i]phenanthridine (Compound 7)

[0115] A solution of compound 10 (20 mg, 0.046 mmol) in dry methanol (0.3 ml) was stirred at room temperature for 10 minutes, and then potassium tert-butoxide (15 mg, 0.138 mmol) was added thereto. The reaction solution was stirred at room temperature for 13 hours. The reaction solution was extracted with ethyl acetate, washed, dried, and purified by column chromatography (hexane:ethyl acetate=4:1) to prepare 10 mg (64%) of the title compound (Compound 7).

[0116] R f =0.22 (hexane:ethyl acetate=4:1)

[0117] 1 H-NMR (500MHz, CDCl 3 ): δ7.16(d, 1H, J=6.0Hz), 7.16(d, 1H, J=8.0Hz), 6.74(d, 1H, J=8.0Hz), 6.60(s, 1H), 6.50-6.48 (m, 1H), 5.97(d, 2H, J=10Hz), 5.93(d, 2H, J=10Hz), 4.56-4.53(m, 1H), 4.43(d, 2H, J=16.5Hz), 3.92 (d, 2H, J=16.5Hz), 3.59-3.41 (m, 2H), 1.99 (s, 3H).

Embodiment 3

[0118] Example 3: Preparation of [5bR-(5bα, 6β, 12bα)]-5b, 6, 7, 12b, 13, 14-hexahydro-13-methyl[1,3]benzodioxolo[5, 6c]-1,3-dioxolo[4,5-i]phenanthridine (Compound 8)

[0119] 10% palladium (1 mg) was added to compound 7 (10 mg, 0.030 mmol) in dry methanol (0.3 ml) and stirred at room temperature for 10 minutes. Hydrogen was added while the reaction solution was stirred for 1 hour. The reaction solution was filtered through a celite filter pad, concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=6:1) to prepare 2 mg (20%) of the title compound 8 and 1.8 mg (18%) of compound 6. mixture.

[0120] R f = 0.27 (hexane: ethyl acetate = 6: 1)

[0121] 1 H-NMR (500MHz, CDCl 3 ): δ6.93(s, 1H), 6.75(d, 1H, J=8.5Hz), 6.72(d, 1H, J=8.5Hz), 6.56(s, 1H), 5.94(d, 2H, J=8.5Hz) 1 5Hz), 5.92(d, 2H, J=3Hz), 3.94(d, 1H, J=16.5Hz), 3.61(d, 1H, J=4.0Hz), 3.48(d, 1H, J=16Hz), 3.07-3.04 (m, 1H), 2.79-2.67 (m, 2H), 2.40 (s, 3H), 1.91-1.88 (m, 1H). ...

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Abstract

The present invention relation to a pharmaceutical composition comprising chelidonine or derivatives thereof, with pharmaceutically acceptable carriers. The compositions according to the present invention can selectively block hKv1.5 channels expressed preferentially in human atrial myocytes, and thus are useful as K<+> channel blockers and antiarrhythmic drugs.

Description

technical field [0001] The present invention relates to a composition comprising chelidonine or its derivatives and a pharmaceutically acceptable carrier. Background technique [0002] Cardiac arrhythmias are abnormal rhythms of the heart that cause the heart to pump less efficiently. At this point, abnormal cardiac impulse formation or impulse propagation occurs when the electrobiochemical properties of local regions of the myocardium change for a number of reasons (www.americanheart.org / heart and stroke). [0003] The shape and duration of cardiac action potentials vary with the recorded cardiac region. These regional differences are partly caused by intramyocardial K + Caused by differential expression of channel genes (Sanguinetti and Keating. Role of delayed rectifier potassium Channels in cardiac polarization and arrhythmias. News Physiol Sci 1997, 12: 152-157). [0004] All antiarrhythmic drugs affect the movement of ions in the myocardium, thereby exhibiting antia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/153A61K9/00A61K9/08A61K9/20A61K9/48A61K31/4355A61K31/4741A61K31/58A61K47/26A61P9/06C07J71/00
CPCA61K9/0019A61K31/4741A61K47/26A61K9/4866A61K9/2018A61P9/06A61K31/4355
Inventor 殷载淳郭湧根金大根蔡洙完
Owner 殷载淳
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