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Agomelatine and medicine composition thereof

A technology of agomelatine and composition, applied in the field of medicinal chemical synthesis, can solve problems such as weight change, sexual dysfunction, drug withdrawal syndrome, etc., and achieve the effects of facilitating absorption, good solubility and high quality

Active Publication Date: 2010-07-21
TIPR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its unique mechanism of action is completely different from commonly used antidepressants such as selective serotonin reuptake inhibitors (SSRI) and serotonin-norepinephrine reuptake inhibitors (SNRI): SSRI and SNRI Antidepressants achieve antidepressant efficacy by increasing the concentration of serotonin, but this also brings many side effects, such as weight change, sexual dysfunction, withdrawal syndrome, etc.

Method used

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  • Agomelatine and medicine composition thereof
  • Agomelatine and medicine composition thereof
  • Agomelatine and medicine composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0058] Preparation of (7-methoxy-1-naphthyl)-ethyl acetate

[0059] Add 17.6g elemental sulfur and 90g (7-methoxy-1,2,3,4-tetrahydro-1-naphthenyl)-ethyl acetate to the reaction flask, stir and heat to 215°C, and react for 10 hours . After the reaction was completed, it was naturally cooled to 60°C, 500ml of ethyl acetate was added, and the mixture was stirred for 30min. Filter, wash the filter cake with 100 ml of ethyl acetate, combine the filtrates, and evaporate to dryness under reduced pressure to obtain 92 g of brown oil with a content of 82.4% (HPLC) and a pure yield of 85%.

Embodiment 3

[0061] Preparation of 7-methoxy-1-naphthylacetic acid

[0062] Dissolve 40g of sodium hydroxide in 1000ml of water, add 1000ml of 95% ethanol, and mix well. Then 50 g of (7-methoxy-1-naphthyl)-ethyl acetate was added to the above mixed solution, and stirred at room temperature for 3 hours. The reaction was stopped, and the ethanol was evaporated under reduced pressure to obtain a brown-red liquid. After washing with 300ml of ethyl acetate × 2, 30ml of 95% ethanol was added to the water layer, and under rapid stirring, concentrated hydrochloric acid was added dropwise to adjust the pH to 2, and a large amount of shallow brown solid. Filtrate and dry to obtain 32g of the product, mp154-156°C, the content determined by HPLC is 98.48%, and the yield is 72%.

[0063] Reference Example 4:

[0064] Preparation of 7-methoxy-1-naphthylacetamide

[0065] Add 50g of 7-methoxy-1-naphthyl acetic acid into 750ml of dichloromethane, heat to dissolve, and slowly add thionyl chloride dropw...

Embodiment 7

[0074] Preparation of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide (agomelatine)

[0075] Dissolve 40g of 2-(7-methoxy-1-naphthyl)ethylamine in 250ml of pyridine and heat to 40°C to completely dissolve. Under cooling and stirring in an ice bath, 21.9 g of acetyl chloride was slowly added dropwise. After dropping, remove the ice bath and stir at room temperature for 30 minutes. Then the reaction solution was poured into 300ml of ice water, while stirring vigorously, a large amount of white precipitate was separated out, and the stirring was continued for 1 hour, filtered, and the filter cake was washed with 200ml×2 water to obtain 48g of crude product (for the following preparation examples).

[0076] 1 H NMR (400MHZ, CDCl 3 ): δ7.77-7.15(m 6H,); δ5.61(s, 1H,); δ3.99(s, 3H,); δ3.62(m, 2H,); δ3.25(t, 2H ,); δ1.95(s, 3H,) is consistent with the literature report (J.Med.Chem, 1994, 37(20), 3231-3239.

[0077] Preparation Example

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Abstract

The invention discloses a medicine of Agomelatine for treating depression, in particular an Agomelatine crystal and a medicine composition thereof. The Agomelatine crystal is irradiated by using Cu-K alpha; and an X-ray powder diffraction spectrum expressed by the degree of 2theta of the Agomelatine crystal has characteristic diffraction peaks at positions of 12.84, 13.84, 16.14, 14.18, 18.56, 19.12, 20.86, 21.20 and 23.84, and an infrared absorption spectrum of the Agomelatine crystal has characteristic diffraction peaks approximately at position of 3234, 3060, 2940, 1638, 1511, 1436, 1249, 1215, 1184, 1032, 908, 828, 755 and 588cm-1. The DSP heat absorption transition is 97.6 DEG C. The invention further discloses application of the medicine composition containing the Agomelatine crystal as an active effective component to the preparation of medicines for treating the depression.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical chemical synthesis, and relates to agomelatine crystals and a preparation method thereof, as well as the application of agomelatine crystals as active ingredients in the preparation of drugs for treating depression. Background technique [0002] With the development of social economy and the acceleration of the pace of life, people's pressure and emotional impact have increased, resulting in an increase in the incidence of depression year by year. Depression, the main type of mood disorders, is a syndrome characterized by significant and persistent low mood. The main manifestations are depression, loss of interest, pessimism, slow thinking, lack of initiative, self-blame, poor diet and sleep, worry that you have various diseases, and feel multiple discomforts throughout the body. In severe cases, suicidal thoughts and behaviors may occur . Clinically, the treatment of depression mainly re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/18C07C231/24A61K31/165A61P25/24
CPCA61K31/165C07C231/24C07B2200/13C07C233/18A61P25/24
Inventor 朱建强田青松赵健
Owner TIPR PHARM CO LTD
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