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Substituted cinnamide derivative, its preparation method and application

By synthesizing and screening 5'-methoxy-3',4'-methylenedioxycinnamic acid isobutylamide and its derivatives, the problems of toxic side effects and poor efficacy of existing antidepressant drugs have been solved and achieved It has significant antidepressant activity and minor side effects and is suitable for the treatment of depression.

Active Publication Date: 2013-01-02
JIANGSU TASLY DIYI PHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, due to the limited resources of large-leaved medicinal plants and the low content of 5'-methoxy-3', 4'-methylenedioxycinnamic acid isobutylamide in plants, extraction and separation from plants alone cannot meet the basic needs. Theoretical and clinical application research needs

Method used

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  • Substituted cinnamide derivative, its preparation method and application
  • Substituted cinnamide derivative, its preparation method and application
  • Substituted cinnamide derivative, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0157] Example 1: 5'-methoxy-3', 4'-methylenedioxycinnamic acid isobutylamide (I-1)

[0158]

[0159] Add triethyl phosphonoacetate (300mg, 1.3mmol), 10ml anhydrous tetrahydrofuran, lithium hydroxide (163mg, 3.9mmol) in 50ml there-necked flask, N 2 Heated to 70°C under protection for 1 hour reaction. 3,4-Dioxymethylene-5-methoxybenzaldehyde (200mg, 1.1mmol) was dissolved in 5ml of anhydrous tetrahydrofuran, and it was dropped into the reaction flask within 0.5 hours. The reaction solution was reacted at 70° C. for 10 hours. TLC detection, stop heating after the reaction is complete. The reaction solution was concentrated to dryness by rotary evaporation, and 20 ml of distilled water was added to dissolve the solid. 2N hydrochloric acid was slowly added dropwise to the above solution to pH 2.0, and the stirring was continued for 1 hour, and a pale yellow solid was precipitated. The solid was collected by suction filtration under reduced pressure and dried in vacuo to obt...

Embodiment 2

[0164] Example 2: 5'-nitro-3', 4'-methylenedioxycinnamic acid isobutylamide (I-2)

[0165]

[0166] Add triethyl phosphonoacetate (300mg, 1.3mmol), 10ml anhydrous tetrahydrofuran, lithium hydroxide (163mg, 3.9mmol) in 50ml there-necked flask, N 2 Heated to 70°C under protection for 1 hour reaction. 3,4-Dioxymethylene-5-nitrobenzaldehyde (215mg, 1.1mmol) was dissolved in 5ml of anhydrous tetrahydrofuran, and it was dropped into the reaction flask within 0.5 hours. The reaction solution was reacted at 70° C. for 10 hours. TLC detection, stop heating after the reaction is complete. The reaction solution was concentrated to dryness by rotary evaporation, and 20 ml of distilled water was added to dissolve the solid. 2N hydrochloric acid was slowly added dropwise to the above solution until the pH was 2.0, and the stirring was continued for 1 hour, and a yellow solid was precipitated. The solid was collected by suction filtration under reduced pressure and dried in vacuo to o...

Embodiment 3

[0171] Example 3: 5'-iodo-3', 4'-methylenedioxycinnamic acid isobutylamide (I-3)

[0172]

[0173] Add triethyl phosphonoacetate (300mg, 1.3mmol), 10ml anhydrous tetrahydrofuran, lithium hydroxide (163mg, 3.9mmol) in 50ml there-necked flask, N 2 Heated to 70°C under protection for 1 hour reaction. 3,4-Dioxymethylene-5-iodobenzaldehyde (300mg, 1.1mmol) was dissolved in 5ml of anhydrous tetrahydrofuran, and it was dropped into the reaction flask within 0.5 hours. The reaction solution was reacted at 70° C. for 10 hours. TLC detection, stop heating after the reaction is complete. The reaction solution was concentrated to dryness by rotary evaporation, and 20 ml of distilled water was added to dissolve the solid. 2N hydrochloric acid was slowly added dropwise to the above solution to pH 2.0, and the stirring was continued for 1 hour, and a pale yellow solid was precipitated. The solid was collected by suction filtration under reduced pressure and dried in vacuo to obtain th...

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Abstract

The invention relates to a substituted cinnamide derivative of formula (i), its preparation method and application. The invention further discloses a method for preparing substituted cinnamide and its derivative by using a substituted heliotropin derivative as a raw material and conducting Wittig reaction and acid amine condensation, and an application of substituted cinnamide and its derivative in medicines for treating and preventing depressive psychosis.

Description

technical field [0001] The present invention relates to the field of organic chemistry and pharmacy, specifically, the present invention relates to a kind of pharmaceutical compound, described compound has formula (I) structure, the present invention also includes the pharmaceutically acceptable acid addition salt of formula (I) compound, Their preparation methods, pharmaceutical compositions containing them, and their application in the preparation of drugs for treating and preventing depressive mental diseases. Background technique [0002] Depression is an affective disorder, a mental illness syndrome characterized by low mood. Its clinical manifestations are depression, slow thinking, decreased speech and movement, and loss of interest in work. According to the World Health Report, depression has become the fourth largest disease in the world, and by 2020, depression may become the second largest disease after heart disease. At present, the number of depression patient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/50A61K31/36A61K31/4525A61P25/24
CPCC07D317/60C07D317/50A61K31/4525C07D317/62C07D317/64A61K31/36C07D317/68A61P25/00A61P25/24C07D317/52C07D405/06
Inventor 马晓慧靳元鹏韩民周水平周王谊罗学军王国成颜璐璐张兰兰朱永宏
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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