Compound with antidepressant activity and preparation method thereof

A compound and antidepressant technology, applied in the field of medicine and chemical industry, can solve the problems of few antidepressant drugs and slow onset of action, and achieve the effect of good antidepressant activity

Inactive Publication Date: 2019-06-25
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The antidepressant drug promazine hydrochloride (Imipramine hydrochloride) with traditional tricyclic structure has mostly been discontinued due to toxic liver damage, anti-M choline effect, especially cardiotoxicity and other side effects, and the new antidepressant with less side effects There are few drugs to choose from, and most of them have the problem of slow onset of action, so there is an urgent need to develop new antidepressant drugs

Method used

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  • Compound with antidepressant activity and preparation method thereof
  • Compound with antidepressant activity and preparation method thereof
  • Compound with antidepressant activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0031] Example: such as Figure 1-2 As shown, there is an antidepressant active compound, and its molecular formula is: C 13 h 17 NO 2 Cl, molecular weight: 252.5, melting point: 207°C; its structural formula is:

[0032]

[0033] The structure data is: 1 H NMR (DMSO) δ: 2.984, 3.125, 3.347 (m, 4H, morpholine ring-H), 3.525, 3.605, 3.753 (m, 4H, morpholine ring-H), 6.385(s, 1H, nitrogen heterocycle -H), 7.210, 7.224 (d, 1H, nitrogen heterocycle-H), 7.415, 7.428, 7.542, 7.629 (m, 3H, benzene ring-H), 8.367 (s, 1H, nitrogen heterocycle-NH), 11.408 (br, 1H, HCl); IR (KBr), ν, cm-1: 3191, 2924, 2754, 1427, 1373, 1310, 1258, 1193, 1117, 1058, 1002, 817, 673; ESI-MS, m / z : 254.24(M+1).

[0034] from figure 1 As can be seen from the mass spectrum shown, the molecular weight of the compound is 254.24 (M+1) when the abundance is close to 100.

[0035] Such as image 3 Shown, have the preparation method of antidepressant active compound, its concrete steps are as follows:

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Abstract

The present invention provides compounds with antidepressant activity and a preparation method thereof. The molecular formula of the compound is C13H17NO2Cl, the molecular weight is 252.5, the meltingpoint is 207 DEG C, and the structural formula is shown in the specification. The preparation method comprises the following steps: adding 3-methyl-4-nitrobenzoic acid and thionyl chloride into a first reaction container, stirring, dissolving and uniformly mixing the mixture, and condensing and refluxing the mixture at the temperature of 80 +/-3 DEG C to obtain acyl chloride A1; dropwise adding the acyl chloride A1, cooled to 0 DEG C, into a second reaction container to obtain an intermediate product A2; dissolving A2 in DMF, and adding the solution into a third reaction container to obtain an intermediate product A3; adding the obtained intermediate product A3 into a fourth reaction container to obtain a crude product, and treating the crude product in a chromatographic column to obtainan intermediate product A4; and adding the obtained intermediate product A4 into a sixth reaction container to obtain a powdery solid A5, which is the compound with the antidepressant activity.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a compound with antidepressant activity and a preparation method thereof. Background technique [0002] Depression is a kind of mental disease, which can lead to suicide in severe cases. It not only brings huge mental pressure to patients, but also adds a heavy burden to patients' families and society. The global economic loss caused by depression exceeds 2,000 yuan every year. One hundred million U.S. dollars. The World Health Organization predicts that depression will become the main killer of human beings in the 21st century. Depression ranks fourth in all disease burdens in my country, and currently ranks second in the disease burden among young and middle-aged adults. Depression has become a serious global problem. [0003] The antidepressant drug promazine hydrochloride (Imipramine hydrochloride) with traditional tricyclic structure has mostly been ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08A61P25/24
Inventor 肖新荣黄卓贤苗青黄超杨迎春
Owner NANHUA UNIV
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