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New amine compounds and their use in the treatment of depression

A technology of compounds, drugs, applied in the field of medicine

Active Publication Date: 2020-12-04
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, duloxetine has clear liver toxicity, so the development of SNRIs with high efficiency and low toxicity is still an important direction for the development of antidepressant drugs

Method used

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  • New amine compounds and their use in the treatment of depression
  • New amine compounds and their use in the treatment of depression
  • New amine compounds and their use in the treatment of depression

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1 5-(3-Methylamino-1-thiophen-2-yl)-propyl-benzo[1,3]dioxa-4-ol hydrochloride (I 1 ) preparation

[0070]

[0071] 1.1 Preparation of 3-dimethylamino-1-(thiophen-2-yl)-propyl-1-one hydrochloride

[0072] Place 20.0g (0.16mol) of 2-acetylthiophene, 16.8g (0.21mol) of dimethylamine hydrochloride, 9.5g (0.32mol) of paraformaldehyde and 50mL of absolute ethanol in a 150mL three-necked flask, and add concentrated Hydrochloric acid to pH 3-4, heated to reflux for 8h. Stop the reaction, cool to room temperature naturally, refrigerate overnight, filter with suction, wash the filter cake with cold absolute ethanol until white, and obtain 31.2 g of white crystals, with a yield of 89.6%. MS(m / e): 184.3(M+1 + ).

[0073] 1.2 Preparation of 3-dimethylamino-1-(thiophen-2-yl)-propanol

[0074] Dissolve 30.8g (0.14mol) of 3-dimethylamino-1-(2-thienyl)-propyl-1-one hydrochloride in 150mL distilled water, add dropwise 2.5M sodium hydroxide aqueous solution until the pH ...

Embodiment 2

[0082] Example 2 7-(3-Methylamino-1-thiophene-2-propyl)-benzo[1,3]dioxol-4-ol hydrochloride (II 1 ) of the preparation of the preparation

[0083]

[0084] Add 2 g (6.85 mmol) of N-methyl-3-(benzo[1,3]dioxol-4-oxyl)-3-(thiophen-2-yl)-propylamine to 40 mL of ethyl acetate , add 0.8g concentrated hydrochloric acid under stirring condition, stir at room temperature for 1h, heat the system to 45°C, continue the reaction for 1h, distill off the solvent under reduced pressure, separate by column chromatography, and separate by silica gel column chromatography to obtain a light yellow solid 7-(3-formazan Amino-1-thiophene-2-propyl)-benzo[1,3]dioxol-4-phenol hydrochloride (Ⅱ 1 ) 0.35g, yield 17.5%. MS (m / e): 292.2 (M+H + ). 1 H-NMRδ (ppm, DMSO-d 6 ): 9.27(br s,3H); 7.32-7.35(m,1H); 6.97-6.99(m,2H); 6.43-6.48(d,,1H); 6.33-6.38(d,1H); (m, 2H); 4.52-4.65(t, 1H); 2.73-2.77(m, 2H); 2.43(s, 3H); 2.31-2.33(m, 2H).

Embodiment 3

[0085] Example 3 5-(3-Ethylamino-1-thiophene-2-propyl)-benzo[1,3]dioxol-4-phenol hydrochloride (I 2 ) preparation

[0086]

[0087] Operation is the same as in Example 1, with N-ethyl-3-(benzo[1,3]dioxacyclo-4-oxyl group)-3-(thiophen-2-yl)-propylamine (see Chinese patent for preparation method) ZL200810127171.5) as the starting material to obtain light yellow solid 5-(3-ethylamino-1-thiophene-2-propyl)-benzo[1,3]dioxol-4-phenol hydrochloride ( I 2 )0.24g, yield 33.5%. MS (m / e): 306.2 (M+H + ). 1 H-NMRδ (ppm, DMSO-d 6 ): 9.01(br s,3H); 7.33-7.37(m,1H); 7.25-7.26(dd,1H); 6.97-6.98(d,1H); 6.63-6.65(d,,1H); 6.47-6.49 (d,2H);5.95-5.97(m,2H);4.58-4.62(t,1H);2.34-2.54(m,3H);2.06-2.12(m,1H);1.86-1.92(m,1H) ;0.80-0.84(t,3H).

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Abstract

The invention relates to a new amine compound and a use thereof in the treatment of depression, and concretely relates to a compound represented by formula I, optical isomers, solvates or pharmaceutically acceptable salts thereof, and a use thereof in the preparation of antidepressant drugs. Preclinical pharmacological studies show that the compound is comparable to and even better than first-line antidepressants (such as duloxetine).

Description

technical field [0001] The invention relates to the field of medicine, in particular to a novel amine compound and its application for treating depression. Background technique [0002] Depression is an affective mental illness, a syndrome characterized by significant and persistent low mood. Depression has complex symptoms and diverse clinical manifestations, mainly including depression, loss of energy, slow movement, lack of interest, sleep disturbance, cognitive dysfunction and loss of appetite, etc. Suicidal behavior may occur in severe cases. The World Health Organization predicts that by 2020, depression will rank second in the "global burden of disease". Depression is attracting great attention all over the world due to its high incidence, high recurrence rate, high disability rate and high suicide rate. In my country, about 20% of people have depressive symptoms, and 7% of people suffer from severe depression. The incidence of depression is increasing year by year....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/06C07D409/06A61K31/381A61K31/36A61K31/357A61P25/24
CPCC07D407/06C07D409/06
Inventor 张有志仲伯华薛瑞樊士勇何新华李云峰范琼尹张亭亭
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A