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Synthetic method of anti-senile dementia medicinal rivastigmine racemic body

A technology of rivastigmine racemate and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carbamic acid derivatives, etc., can solve the problems of unsuitability for industrial production, complicated operation, high cost, etc., and achieve effective It is beneficial to industrial production and popularization and application, with high reaction yield and low cost

Active Publication Date: 2012-08-01
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] The above nine methods all have disadvantages such as low yield, complicated operation, and high cost, and are not suitable for industrialized production.

Method used

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  • Synthetic method of anti-senile dementia medicinal rivastigmine racemic body
  • Synthetic method of anti-senile dementia medicinal rivastigmine racemic body
  • Synthetic method of anti-senile dementia medicinal rivastigmine racemic body

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. Compound 3 preparation of

[0040] Add m-ethylphenol (12.2 g, 0.1 mol) to 130 ml of acetone, add potassium carbonate (41.5 g, 0.3 mol) and stir for 20 min, then add compound 2 (12.5 ml, 0.105 mol), refluxed for 7 hours. Cool to room temperature, vacuum-filter and evaporate acetone to dryness, add 30 ml of ethyl acetate, add 20 ml of water under ice bath, extract the water layer twice with ethyl acetate after separation, combine the ester layers, and dry over anhydrous sodium sulfate. Concentrate by filtration to obtain the compound 3 (19.706 g), yield 95.1%.

[0041] IR (KBr,cm -1 ) : 3433, 2968, 2934, 1724, 1478, 1399, 1236, 1164.

[0042] 1H NMR (400 MHz, CDCl3) δ 7.25 (t, J = 7.8 Hz, 1H), 7.07 – 6.86 (m, 3H), 3.52 – 3.33 (m, 2H), 3.04 (m, 3H), 2.65 (q, J = 7.6 Hz, 2H), 1.21 (m, 6H).

[0043] 13C NMR (101 MHz, CDCl3) δ 154.58, 151.45, 145.59, 128.91, 124.63, 121.07, 118.86, 43.95, 34.13, 33.69, 28.56, 15.23, 13.13, 12.40.

[0044] 2. Compound 4 preparation...

Embodiment 2

[0055] 1. Compound 3 preparation of

[0056] Add m-ethylphenol (12.2 g, 0.1 mol) to 130 ml of acetone, add sodium carbonate (15.2 g, 0.3 mol) and stir for 20 min, then add the compound dropwise 2 (12.5 ml, 0.105 mol), refluxed for 7 hours. Cool to room temperature, vacuum-filter and evaporate acetone to dryness, add 30 ml of ethyl acetate, add 20 ml of water under ice bath, extract the water layer twice with ethyl acetate after separation, combine the ester layers, and dry over anhydrous sodium sulfate. Concentrate by filtration to obtain the compound 3 (19.006 g), yield 91.8%.

[0057] 2. Compound 4 preparation of

[0058] compound 3 (2 g, 9.66 mmol) was dissolved in 40 ml cyclohexane, and NBS (3.44 g, 19.32 mmol) and AIBN (80 mg, 0.48 mmol) were added at 60 ° C, and the temperature was raised to 85 ° C, and then added every 20 min AIBN (80 mg, 0.48 mmol), AIBN was added three times. After refluxing for three hours, stop the reaction, spin dry, add ethyl acetate to di...

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Abstract

The invention discloses a synthetic method of an anti-senile dementia medicinal rivastigmine racemic body, belonging to the technical field of medicinal chemistry. In the synthetic method, the rivastigmine racemic body is obtained by undergoing three steps of reactions on m-ethyl phenol serving as a raw material. The method has the advantages of readily-available raw materials, small quantity of reaction steps, easiness and safety for operating, environmental friendliness, low pollution and contribution to large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a preparation method of an anti-senile dementia drug rivastigmine. Background technique [0002] Rivastigmine, commonly known as Rivastigmine, is generally marketed as rivastigmine bitartrate, which is an acetylcholinease inhibitor and is used for the treatment of moderate to mild Alzheimer's disease. The carbamate structure of Rastigmine can be combined with the active site of cholinesterase, inhibiting the hydrolysis of acetylcholine released by cholinergic nerve endings by cholinesterase, thereby increasing the level of acetylcholine in the target tissue and improving the patient's health. memory, cognition and behavior. Moreover, Rastigmine itself will not destroy cholinesterase, but temporarily binds to the active site of the enzyme to temporarily inhibit the activity of the enzyme, so it is a reversible cholinesterase inhibitor. Rivastigmine is absorbed rapidly ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/44C07C269/06
Inventor 刘宏民张恩张保寅吕爱桥李聪方园
Owner ZHENGZHOU UNIV
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