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Isoindoline derivative compound, preparation method and weight losing application

An isoindoline and compound technology, applied in the field of medicine, can solve the problems of small toxic and side effects, good absorption, adverse reactions, etc., and achieve the effects of reducing body weight, reducing liver fat and epididymal fat content, and improving development prospects.

Inactive Publication Date: 2021-04-16
武城县人民医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The U.S. Food and Drug Administration (FDA) approved 6 drugs for the treatment of obesity, all of which were withdrawn from the market shortly after listing due to adverse reactions in the central nervous system and cardiovascular system.
The present invention innovatively synthesizes an isoindoline derivative compound, which has good absorption and less toxic and side effects, in order to obtain a brand new compound that can be used to prepare weight-loss-related drugs or health care products. The prior art has not seen related structured reporting

Method used

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  • Isoindoline derivative compound, preparation method and weight losing application
  • Isoindoline derivative compound, preparation method and weight losing application
  • Isoindoline derivative compound, preparation method and weight losing application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, the preparation of compound 1

[0027] (1) Synthesis of 2-(2-nitro-ethyl) isoindoline:

[0028]

[0029] At 0-5°C under a nitrogen atmosphere, add isoindoline (7.1 g, 59.58 mmol), cuprous bromide (7.2 g, 50.19 mmol), triethylamine (2.0 g, 19.76 mmol) and Tetrahydrofuran (50 mL) was added dropwise with 1-bromo-2-nitroethane (18.5 g, 120.16 mmol) under stirring. After the drop was completed, the temperature was slowly raised to 30-35° C., stirred for 36 hours, and the reaction was detected by TLC. Cool to room temperature, remove insoluble matter by filtration, recover the solvent under normal pressure, and distill under reduced pressure to obtain light yellow liquid 2-(2-nitro-ethyl)isoindoline, 9.46g, yield 82.6%.

[0030] 1 H-NMR (400MHz, CDCl 3 )δ:3.11(t,2H),3.79(s,4H),4.63(t,1H),4.96(t,1H),7.33-7.46(m,4H). 13 C-NMR (125MHz, CDCl 3 )δ: 52.73, 60.97, 71.57, 124.78, 127.96, 139.81. LC-MS (ESI, pos, ion) m / z: 193.09[M+H].

[0031] (2) Synthesis of ...

Embodiment 2

[0042] The synthesis of embodiment 2, compound 2

[0043]

[0044] 2-Amino-3-(isoindolin-2-yl)-1-(4-methoxyphenyl)propan-1-ol (14.92g, 50.00mmol), 2-chloro-N-( 4-Ethoxy-3-methoxyphenethyl)acetamide (18.20g, 66.99mmol), sodium iodide (9.74g, 65.00mmol) and potassium carbonate (14.51g, 105.00mmol) were added to dimethylformaldehyde amide (120 mL) and stirred at 50°C for 80 hours. The solvent was distilled off and the crude product was dissolved in water (120 mL) and extracted with dichloromethane (4 x 30 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: EA:acetone=1:1). N-(4-ethoxy-3-methoxyphenethyl)-2-((1-hydroxy-3-(isoindolin-2-yl)-1-(4- Methoxyphenyl)propan-2-yl)amino)acetamide (compound 2), 17.48g, yield 65.5%.

Embodiment 3

[0045] The synthesis of embodiment 3, compound 3

[0046]

[0047] 2-Amino-3-(isoindolin-2-yl)-1-(4-methoxyphenyl)propan-1-ol (14.92g, 50.00mmol), 2-chloro-N-( 3,4-Diethoxyphenethyl)acetamide (19.14g, 66.99mmol), sodium iodide (9.74g, 65.00mmol) and potassium carbonate (14.51g, 105.00mmol) were added to dimethylformamide (120mL ) and stirred at 50°C for 80 hours. The solvent was distilled off and the crude product was dissolved in water (120 mL) and extracted with dichloromethane (4 x 30 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: EA:acetone=1:1). N-(3,4-diethoxyphenethyl)-2-((1-hydroxy-3-(isoindolin-2-yl)-1-(4-methoxy Phenyl)propan-2-yl)amino)acetamide (compound 3), 21.52g, yield 78.6%.

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Abstract

The invention belongs to the field of medicines, and relates to an isoindoline derivative compound, a preparation method and weight-losing application. The structural formula of the isoindoline derivative compound is shown as a formula I. The compound prepared by the invention can effectively reduce the weight of a mouse induced by high-fat diet and reduce the content of liver fat and epididymis fat, has a good weight-reducing effect, and can be used for preparing weight-reducing related medicines or health-care products.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to an isoindoline derivative compound, a preparation method and its application in the preparation of weight-loss-related medicines or health care products. Background technique [0002] Obesity refers to the pathophysiological changes of the human body caused by excessive accumulation of fat in the body. According to the statistics of the World Health Organization, it is the most neglected chronic disease with a sharp increase in incidence, and it will be accompanied by many serious complications. At present, the treatment methods for obesity mainly include exercise, drug intervention, health care therapy, and surgical intervention. Since drug treatment is the most compliant and most reliable method, the development of weight loss drugs has gradually become the focus of global drug research and development. [0003] The U.S. Food and Drug Administration (FDA) approved six drugs for treating...

Claims

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Application Information

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IPC IPC(8): C07D209/44A61P3/04A61P3/06A23L33/10
Inventor 张红梅杨明枝
Owner 武城县人民医院
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