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Application of substituted cinnamamide derivative to preparation of anxiolytic medicine

一种桂皮酰胺、衍生物的技术，应用在取代桂皮酰胺衍生物在制备抗焦虑药物中的应用领域，能够解决运动性不安、未见到桂皮酰胺衍生物报道、很难静下心来等问题

Active Publication Date: 2017-08-04
TIANJIN TASLY PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(3) Motility restlessness: restlessness, restlessness, irritability, difficulty in calming down
[0014] No reports of substituted cinnamic amide derivatives in anxiolytic effects

Method used

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  • Application of substituted cinnamamide derivative to preparation of anxiolytic medicine
  • Application of substituted cinnamamide derivative to preparation of anxiolytic medicine
  • Application of substituted cinnamamide derivative to preparation of anxiolytic medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1: (E)-N-(4-methylpiperazinyl)-5-(5'-trifluoromethyl-3',4'-methylenedioxyphenyl)-1-pentene Amide hydrochloride (Ⅱ-13)

[0100]

[0101] Step 1: Put compound 1 (1.53g, 4.0mmol) in a 100ml single-necked bottle, add 15ml of chloroform to dissolve, then add compound 2 (1g, 4.0mmol) to the reaction system, stir at room temperature for 14h; TLC monitoring ( The developer PE:EA=5:1) showed that the reaction was complete; then the reactant was directly concentrated to obtain the crude product compound 3, and after purification by silica gel column chromatography (PE:EA=5:1), 1.1 g of white solid compound 3 was obtained, Yield 78.87%.

[0102] Step 2: Dissolve compound 3 (0.3g, 0.87mmol) in 5ml of dichloromethane, cool down to 0°C; add trifluoroacetic acid (1ml) dropwise to the reaction system, and then react at room temperature while the reaction system is warming up; After 1 h, TLC showed that the reaction of the raw materials was complete, and the reaction system...

Embodiment 2

[0106] Example 2: (2E,4E)-N-isobutyl-7-(5'-trifluoromethyl-3',4'-methylenedioxyphenyl)-2,4-heptadienamide (Ⅱ-14)

[0107]

[0108] Step 1: Add compound 5 (650mg, 2.6mmol), 20ml anhydrous tetrahydrofuran, lithium hydroxide (326mg, 7.8mmol) into a 50ml three-necked flask, N 2 Heated to 70°C under protection for 1 hour reaction. Compound 1 (0.76g, 2.0mmol) was dissolved in 10ml 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. A light yellow solid precipitated, which was collected by suction filtration under reduced pressure and dried in vacuo to obtain...

Embodiment 3

[0112] Example 3: (2E,4E)-N-(4-methylpiperazinyl)-7-(5'-trifluoromethyl-3',4'-methylenedioxyphenyl)-2, 4-Heptadienamide Hydrochloride (Ⅱ-15)

[0113]

[0114] Compound 6 (0.52g, 1.66mmol), N-methylpiperazine (0.5g, 5mmol), DIPEA (0.43g, 3.34mmol) were added to dichloromethane, then HATU (0.95g, 2.5mmol) was added at room temperature Stir for 6h; the reaction system was washed with water, the organic phase was dried and concentrated to obtain a crude product, which was purified by silica gel column chromatography to obtain 350 mg of a colorless oil; then dissolved with 2 ml of dioxane, and then added with 4 ml of dioxane hydrochloric acid solution , stirred at room temperature for 30 min, concentrated and dried to obtain 370 mg of compound II-15 (53%).

[0115] 1 H NMR(MeOD,400MHz):δ7.25(1H,dd,J 1 =10.8Hz,J 2 =4.4Hz),6.96(1H,s),6.87(1H,s),6.48(1H,d,J=14.8Hz),6.31(1H,dd,J 1 =10.8Hz,J 2 =4.4Hz),6.21(1H,m),6.10(2H,s),4.87(2H,br),3.77-3.50(3H,br),3.40-3.10(3H,br),3.15(3H,s...

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Abstract

The invention provides application of a substituted cinnamamide derivative to preparation of anxiolytic medicine. The substituted cinnamamide derivative uses a compound of a structure shown by a formula (I) or a pharmaceutically acceptable salt as a medicine active ingredient. The concrete formula is shown as the accompanying drawing; in the formula, R1 is -H, -OH, -F, -Cl, -Br, -I, -OCH3, -OCF3, -OCHF2, -OCH2F, -CF3, -CHF2, -CH2F, -CH3, -CH3CH2, -CF3CH2, -CN, -NO2, -NH2 or -COOR5; R2 is H, C1-C10 straight-chain alkyls, C3-C10 branch-chain alkyl groups, C3-C10 cyclic hydrocarbon groups, C1-C10 hydroxyalkyls or N-substituted piperazine derivative groups; or the R2 is a group forming a nafoxidine group, a piperidyl or a cyclohexylamine group with the adjacent X. The formula (I) is shown as the accompanying drawing.

Description

[0001] Technical field: [0002] The invention relates to a new application of medicine, in particular to the application of a substituted cinnamon amide derivative in the preparation of anxiolytic medicine. [0003] Background technique: [0004] Anxiety disorder, also known as anxiety neurosis, is the most common type of neurosis, and its main feature is the experience of anxiety. It can be divided into two forms: chronic anxiety (generalized anxiety) and acute anxiety attacks (panic disorder). The main manifestations are: nervousness and worry without a clear objective object, restlessness, and autonomic symptoms (palpitations, hand tremors, sweating, frequent urination, etc.). [0005] specific, [0006] Chronic anxiety, also known as generalized anxiety, in the absence of obvious incentives, patients often appear excessive worry, nervousness and fear, but the nervousness and fear often have no clear object and content. The main manifestations are: (1) Emotional symptoms...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/60C07D317/68C07D317/58C07C235/34C07D295/185C07C235/46A61K31/36A61K31/4525A61K31/496A61K31/165A61K31/166A61K31/4453A61P25/22
CPCA61K31/165A61K31/166A61K31/36A61K31/4453A61K31/4525A61K31/496C07C235/34C07C235/46C07D295/185C07D317/58C07D317/60C07D317/68C07D295/192A61P25/22A61K31/357
Inventor 韩民马晓慧周王谊刘雁勇李彦川王晶周水平孙鹤朱永宏
Owner TIANJIN TASLY PHARMA CO LTD
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