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Galanthamine intermediate compound V

A technology of galantamine and compound, applied in the field of galantamine intermediate compound V, can solve the problems of serious environmental pollution, high technical requirements and high production cost, achieve economical and environmental protection yield, high product purity and easy operation Effect

Pending Publication Date: 2021-03-19
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In order to solve the problems in the prior art, such as long route, complicated operation, low yield and low purity in the preparation process of galantamine; or high technical requirements, serious environmental pollution and high production cost, the invention provides a galantamine Sensitive intermediate V, and provides the preparation method of the compound; and a new method of using the compound to synthesize galantamine, the method has a short reaction route, easy operation, milder reaction, economical and environmental protection and high yield, and is suitable for industrialization Production

Method used

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  • Galanthamine intermediate compound V
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  • Galanthamine intermediate compound V

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add compound II (19.3g, 0.10mol), paraformaldehyde (13.51g, 0.15mol), compound IV (14.64g, 0.12mol), p-toluenesulfonic acid (3.44g, 0.02mol), 100mL toluene into the there-necked flask . Stir to dissolve, heat to reflux, remove the generated water from the reaction system with a water separator, stop heating when the water in the water separator no longer increases, and slowly cool down to room temperature. Add 100 mL of ethyl acetate, shake vigorously and let it stand still, collect the organic phase and dry it with anhydrous sodium sulfate. The desiccant was removed by filtration and concentrated under reduced pressure to obtain a white solid powder with a yield of 92.5% and an HPLC purity of 99.92%.

Embodiment 2

[0059] Add compound II (19.3 g, 0.10 mol), paraformaldehyde (9.91 g, 0.11 mol), compound IV (14.64 g, 0.12 mol), benzenesulfonic acid (3.16 g, 0.02 mol), and 100 mL of toluene into the three-neck flask. Stir to dissolve, heat to reflux, remove the generated water from the reaction system with a water separator, stop heating when the water in the water separator no longer increases, and slowly cool down to room temperature. Add 100 mL of dichloromethane, shake vigorously and let stand, collect the organic phase, dry with anhydrous sodium sulfate, filter to remove the desiccant, and concentrate under reduced pressure to obtain a white solid powder with a yield of 85.1% and an HPLC purity of 99.87%.

Embodiment 3

[0061] Add compound II (19.3 g, 0.10 mol), paraformaldehyde (9.01 g, 0.10 mol), compound IV (14.64 g, 0.12 mol), acetic acid (1.20 g, 0.02 mol), and 80 mL of benzene into the three-neck flask. Stir to dissolve, heat to reflux, remove the generated water from the reaction system with a water separator, stop heating when the water in the water separator no longer increases, and slowly cool down to room temperature. Add 100 mL of chloroform, shake vigorously and let stand, collect the organic phase, dry with anhydrous sodium sulfate, filter to remove the desiccant, and concentrate under reduced pressure to obtain a white solid powder with a yield of 81.3% and an HPLC purity of 99.44%.

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Abstract

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to a galanthamine intermediate compound V. According to the invention, 4-(2-(methylamino)ethyl)phenyl acetate,paraformaldehyde and 1,3-benzodioxole are used as raw materials to synthesize the novel intermediate compound V. The invention also provides a novel method for synthesizing galanthamine by using the intermediate. According to the method, use of dangerous chemical reagents is avoided, the synthesized intermediate does not generate new impurities, a green catalyst is used for replacing a traditionalcatalyst, a reaction is milder, economical and environment-friendly, yield is higher, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a galantamine intermediate compound V. Background technique [0002] Galanthamine, chemical name 11-methyl-3-methoxy-4a,5,9,10,11,12-hexahydro-6H-benzofuran-[3a,3,2ef] [2] Azepine-6-ol, molecular formula: C 17 h 21 NO 3 ; Molecular weight: 323.81; CAS registration number: 357-70-0, the structural formula is as follows: [0003] [0004] Galantamine was first researched and produced by Sopharma Pharmaceutical Company in Bulgaria, and its trade name is Nivalin. Pharmacological studies have proved that it is a potent inhibitor of acetylcholinesterase (AChE), and it also has a good regulatory effect on neuronal nicotinic receptors. It is widely used in the treatment of Alzheimer's disease ( Alzheimer's disease, AD) and myasthenia gravis and other diseases. At present, the drug has been launched in the United Kingdom, Ireland, the United States, China...

Claims

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Application Information

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IPC IPC(8): C07D317/54C07D491/08
CPCC07D317/54C07D491/08C07B2200/07Y02P20/55
Inventor 张贵民时江华姜龙
Owner LUNAN PHARMA GROUP CORPORATION
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