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Preparation method of compound serving as neuroprotective agent

A compound and hydroxyl technology, applied in the field of compound preparation, can solve the problems of difficult large-scale industrial production, low yield, and many steps, and achieve the effect of alleviating Parkinson's disease and improving Parkinson's symptoms

Inactive Publication Date: 2017-11-24
深圳瀜新生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although this synthetic route is feasible, there are many steps (10 steps), and the yield is relatively low, so it is difficult to carry out kilogram-level or large-scale industrial production

Method used

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  • Preparation method of compound serving as neuroprotective agent
  • Preparation method of compound serving as neuroprotective agent
  • Preparation method of compound serving as neuroprotective agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesize (R,S)-4-(2-hydroxy-5-methylphenyl)-5-methylhexanoic acid according to the following procedure

[0050]

[0051] Add 1220g (10mol, 1eq) of p-methylanisole (2) into 12L of dichloromethane (room temperature), cool down to -5 to 0 degrees and add 1600g (12mol, 1.2eq) of aluminum trichloride in batches, After the addition, 1200g of succinic anhydride (12mol, 1.2eq) was added dropwise to the reaction system, and the temperature was controlled at about 10°C to react overnight. After the reaction is completed, add 10L of water dropwise to quench, separate the layers, extract the water phase with dichloromethane three times (5L*3), combine the dichloromethane phases, wash with 5% sodium bicarbonate solution and saturated brine until neutral (5L), dried over anhydrous sodium sulfate, dried with dichloromethane and spin-dried to obtain 1.6kg of crude product (3), which was used for the next reaction without purification.

[0052] Dissolve 1.6 kg of intermediate 3 in...

Embodiment 2

[0058] First prepare 4-(2-hydroxymethyl-5-ethylphenyl)-4-carbonyl butyric acid methyl ester according to the method similar to Example 1, then 1.4 kg of 4-(2-hydroxyl Methyl-5-ethylphenyl)-4-carbonylbutanoic acid methyl ester was dissolved in 15L tetrahydrofuran at room temperature, and the tetrahydrofuran solution (2.0M, 4.5L) of ethylmagnesium chloride was slowly added under temperature control below 0 degrees, and the dropwise after reaction. After the reaction is complete, add 3L of sulfuric acid to quench the reaction, stir for 10 hours, concentrate to remove most of the tetrahydrofuran, add 10L of dichloromethane, separate layers, extract the aqueous phase with dichloromethane three times, (5L*3), combine dichloromethane The methane phase was washed with 5% sodium bicarbonate solution and saturated brine to neutrality (5 L), dried over anhydrous sodium sulfate, and the dichloromethane phase was dried by spinning to obtain 0.8 kg of crude product, which was used for the n...

Embodiment 3

[0062] First prepare 4-(2-hydroxymethyl-5-propylphenyl)-4-carbonyl butyric acid methyl ester according to the method similar to Example 1, then 1.4 kg of 4-(2-hydroxyl Methyl-5-propylphenyl)-4-carbonylbutanoic acid methyl ester was dissolved in 15L tetrahydrofuran at room temperature, and the tetrahydrofuran solution (2.0M, 4.5L) of ethylmagnesium chloride was slowly added under temperature control below 0 degrees, and the dropwise after reaction. After the reaction is complete, add 3L of concentrated sulfuric acid to quench the reaction, stir for 10 hours, concentrate to remove most of THF, add 10L of dichloromethane, separate layers, extract the aqueous phase three times with dichloromethane (5L*3), and combine the two Chloromethane phase, washed with 5% sodium bicarbonate solution and saturated brine until neutral (5L), dried over anhydrous sodium sulfate, dichloromethane phase was dried and spin-dried to obtain 0.75kg of crude product, which was used for the next reaction ...

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Abstract

The invention relates to a preparation method of a compound serving as a neuroprotective agent. By using the method, the original ten-step synthesis is simplified into six-step synthesis, so that the method is simpler and more feasible and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a preparation method of a compound used as a neuroprotective agent. Background technique [0002] Parkinson's disease (PD) is one of the most common neurodegenerative diseases of middle-aged and elderly people. It seriously endangers the health of middle-aged and elderly people with physical dysfunction such as tremor, stiffness, and slow movement, and affects their quality of life. The prevalence rate of epidemiological statistics is 15-328 / 100,000 population, the average age of onset is about 60 years old, and the population >65 years old is about 1.7%. Statistics in Shenzhen show that the number of Parkinson's patients is between 10,000 and 30,000, and less than 1 / 5 of them have received formal treatment. The incidence of Parkinson's disease in Shenzhen is 16 out of 100,000. The incidence rate was 1.6%. [0003] The etiology of Parkinson's is still unclear, but aging i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C59/52
CPCC07C51/083C07C51/09C07C67/00C07C67/08C07D307/33C07C59/90C07C59/52C07C69/738C07C69/734
Inventor 余慧东张维李铭源李国辉侯廷军
Owner 深圳瀜新生物科技有限公司
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