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Carbazole-rivastigmine diad and pharmaceutical composition and application thereof

A composition and drug technology, which can be used in drug combinations, medical preparations containing active ingredients, pharmaceutical formulations, etc., can solve problems such as cell function changes, oxidative imbalance, and oxidative stress, achieve good neuroprotective effects, and promote proliferation. Effect

Active Publication Date: 2016-10-26
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is a very complete set of antioxidant defense system in cells, which can maintain the level of active oxygen or oxygen free radicals. However, under certain stress conditions, the generation of free radicals far exceeds its removal, causing oxidation imbalance, which leads to Oxidative stress, which changes the function of cells and eventually causes cell death

Method used

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  • Carbazole-rivastigmine diad and pharmaceutical composition and application thereof
  • Carbazole-rivastigmine diad and pharmaceutical composition and application thereof
  • Carbazole-rivastigmine diad and pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Compound 2

[0033]

[0034] Material 1 (3.00 g) was dissolved in 100 ml of acetonitrile, and epichlorohydrin (31.00 g) and anhydrous potassium carbonate (2.50 g) were added. The reaction system was reacted at 90°C for 6 hours, 140 ml of water and 200 ml of dichloromethane were added, the layers were extracted and the organic phase was collected. The organic phase was washed once with 100 ml of 0.2 M hydrochloric acid, dried over anhydrous magnesium sulfate, filtered with suction, and concentrated in vacuo to obtain a yellow solid. The initial product was recrystallized from ethyl acetate / petroleum ether to obtain 1.37 g of white solid. Yield: 40%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 8.48 (d, J = 1.9 Hz, 2H), 7.7-7.64 (m, 2H), 7.64-7.59 (m, 2H), 4.84(dd, J = 15.8, 2.9 Hz, 1H), 4.42 (dd, J = 15.8, 5.8 Hz, 1H), 3.32-3.29 (m, 1H), 2.84-2.62 (m, 1H), 2.55-2.52 (m, 1H).

Embodiment 2

[0035] Example 2: Compound 4a

[0036]

[0037]Mix raw material 3 (0.30 g), dimethylcarbamoyl chloride (0.29 g), and triethylamine (3 g) into a flask, reflux at 95°C overnight, add 50 ml of dichloromethane to dissolve, and concentrate in vacuo at 75°C , add 50 ml of dichloromethane to redissolve, and then wash three times with 0.5 M sodium hydroxide solution. The organic phases were mixed, dried over anhydrous magnesium sulfate, and filtered with suction to obtain a viscous substance. Drying in vacuo yielded 0.29 g of a tan solid. Yield: 59%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.41 (t, J = 7.8 Hz,1H), 6.28 (dd, J = 8.0, 0.5 Hz, 1H), 6.13 (dd, J = 7.6, 0.5 Hz, 1H), 6.08(br, 1H), 2.93 (d, J = 44.0 Hz, 6H).

Embodiment 3

[0038] Example 3: Compound 4b

[0039]

[0040] Mix raw material 3 (0.30 g), N-methylethylcarbamoyl chloride (0.33 g), and triethylamine (3 g) into a flask, reflux at 95°C overnight, add 50ml of dichloromethane to dissolve, and dissolve at 75°C C was concentrated in vacuo, redissolved in 50 ml of dichloromethane, and washed three times with 0.5 M sodium hydroxide solution. The organic phases were mixed, dried over anhydrous magnesium sulfate, and filtered with suction to obtain a viscous substance. Drying in vacuo yielded 0.29 g of a tan solid. Yield: 55%. 1 H NMR (400 MHz, DMSO- d 6 ) δ 7.41 (t, J =7.8 Hz, 1H), 6.28 (d, J = 7.9 Hz, 1H), 6.13 (d, J = 7.5 Hz, 1H), 6.08 (br,2H), 3.30-3.23 (m, 2H), 2.91 (d, J = 40.2 Hz, 3H), 1.18-1.05 (m, 3H).

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Abstract

The invention provides compounds of the structure as shown in the description or pharmaceutical salt, a pharmaceutical composition and application of the compounds. The compounds relate to a series of carbazole and rivastigmine diads. The carbazole and rivastigmine diads are connected through proper joints, on one hand, a good nerve protection effect can be achieved, and on the other hand, proliferation of neural stem cells is promoted.

Description

technical field [0001] The present invention relates to the synthesis of a series of carbazole and rivastigmine dyads linked by suitable linkers. On the one hand, the compound of the present invention can exert a good neuroprotective effect; on the other hand, it can promote the proliferation of neural stem cells (such as C17.2). The present invention also relates to the pharmaceutical composition containing the doublet and its application, as well as their preparation method. Background technique [0002] Oxidative stress is considered to be one of the culprits in various neurological diseases such as Alzheimer's disease, Parkinson's disease and cerebral ischemia. There is a very complete set of antioxidant defense system in cells, which can maintain the level of active oxygen or oxygen free radicals. However, under certain stress conditions, the generation of free radicals far exceeds its removal, causing oxidation imbalance, which leads to Oxidative stress changes the f...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D209/88A61K31/4439A61K31/403A61P25/00A61P25/28A61P25/14A61P25/16A61P21/00
CPCC07D209/88C07D401/12
Inventor 皮荣标颜金武杨晓红陈紫薇王胜男陈景考
Owner SUN YAT SEN UNIV
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