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New Optical active derivative of flavo acidamide, its preparation method and its medicinal composition and use

A kind of xanthoamide, photoactive technology, applied in the direction of drug combination, organic chemistry, etc., can solve the problem that can not be directly used to prepare xanthanamide and its derivatives, etc.

Active Publication Date: 2007-01-17
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The prior art cannot be directly used for preparing the optically active xanthamide and its derivatives described in the present invention

Method used

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  • New Optical active derivative of flavo acidamide, its preparation method and its medicinal composition and use
  • New Optical active derivative of flavo acidamide, its preparation method and its medicinal composition and use
  • New Optical active derivative of flavo acidamide, its preparation method and its medicinal composition and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1 photoactive new xanthamide (I 2 ) preparation (see route 1)

[0068] Separation of racemic neobantamide ketone:

[0069] Add 2.7 g of racemic neopantyl ketone to 30 mL of dichloromethane solution of (-)-menthol oxyacetyl chloride prepared from 2.7 g of (-)-menthol oxyacetic acid, cool in an ice-water bath, and then add 1.5 mL of pyridine, stirred at room temperature until the reaction was complete, the reaction solution was diluted with 50 mL of dichloromethane, washed with 2N hydrochloric acid, saturated sodium carbonate solution and brine successively, and the organic layer was dried over anhydrous sodium sulfate. Concentrate to obtain 6g of oily matter, add hexane to solidify, filter the solid, and recrystallize from methanol to obtain 1.48g of 3-O-[(-)mentholoxyacetyl]--(3R,4S,5R)-neopanthamide Ketone [ester (a)], mp: 170-172°C, [α] D 15 =-50.9(c, 1.25, CHCl 3 ), yield 33.8%. The column chromatography of the filtrate gave 3-O-[(-)menthol oxyacetyl...

Embodiment 2

[0073] Embodiment 2 light active table new xanthamide (I 4 ) preparation

[0074] (+)-(3S, 4R, 5S)-Neospermide ketone 1.05g (3.56mmol.), aluminum isopropoxide 2.4g (11.75mmol.) dissolved in 30ml of anhydrous anhydrous isopropanol, heated and stirred , slowly evaporate isopropanol and acetone, and at the same time add anhydrous isopropanol dropwise at a constant speed, the reaction is completed in about 6.5 hours, evaporate most of the solvent, cool to room temperature, add 60ml water and 20ml 3N hydrochloric acid and stir at room temperature, a large amount of White solid, recrystallized from methanol to obtain (-)-(3S, 4R, 5S, 6S)-epipanthamide, yield 85%, m.p.217-219℃, [α] D 24 = -36.5 (c, 0.128, MeOH). Recrystallized again from methanol, m.p. 221-222°C, [α] D 20 = -37.3 (c, 0.15, MeOH).

[0075] (-)-(3R, 4S, 5R)-neopsinamide ketone is used as raw material, the same operation as above, and reduction with aluminum isopropoxide, to obtain (+)-(3R, 4S, 5R, 6R)-epideneopsi...

Embodiment 3

[0076] Embodiment 3 epibantamide (I 3 ) preparation (see route 2)

[0077] A: (±)-Epidermide ((±)-I 3 ) preparation

[0078] (±)-(4R*, 5R*, 6R*)-3-deoxyepixanthamide (3-deoxyl 3 )90mg (0.032mmol.), dissolved with 2.5mL anhydrous THF and 0.7mL hexamethylphosphoramide (N 2 under protection), cool to -70°C, stir for 5 minutes, add 1mL (0.32mmol.) fresh THF solution of lithium diisopropylamide with a syringe, stir for 1 hour at -60°C to -70°C, add triphosphite Ethyl ester 53ul, pass into O 2 , keep the temperature at -60°C to -70°C, stop ventilation after 2 hours, adjust the reaction solution to pH value = 3-4 with 0.5mol / L hydrochloric acid in an ice-water bath, then wash with ethyl acetate, water, and chlorination Wash with sodium aqueous solution, dry with anhydrous sodium sulfate, evaporate the solvent, and obtain 40 mg of the title compound by column chromatography. The recovered raw material is 40 mg, with a yield of 40%. Recrystallization mp: 193-195°C.

[0079] B: (-...

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Abstract

The present invention relates to the stereo-isomers of gamma-lactam (clausenamide) substituted by hydroxyl benzyl group, hydroxyl group and phenyl group, light active stereo-isomers thereof, process for producing same, pharmaceutical composition adopting same as active substances, and therein applications for preparing intelligence promoting and anti-aging pharmaceutical agents.

Description

technical field [0001] The present invention relates to the stereoisomers of hydroxybenzyl, hydroxyl, and phenyl substituted gamma-lactams (campamide), optically active stereoisomers, their preparation methods, and pharmaceutical compositions using them as active substances , and their application in the preparation of drugs for treating mental decline, anti-cerebral ischemia-hypoxia, neurodegenerative diseases, senile dementia, presenile dementia, and vascular dementia. Background technique [0002] At present, the average life expectancy of our country's population has exceeded 70 years, which is double the average life expectancy at the time of liberation. A foreign scientific study predicts that by 2025, the proportion of children under the age of 15 will account for 18.6% of the total population, while the elderly aged 65 and over will exceed the number of children, reaching 18.8%. After more than 20 years, there will be 1 elderly person in every 5 people. Alzheimer's...

Claims

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Application Information

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IPC IPC(8): C07D207/267A61K31/4015A61P43/00
Inventor 黄量张均田吴克美郑国钧冯志强陈世明
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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