Diaryl amidine compound, its production, medicinal composition and use

A diaryl amidine compound technology, applied in the field of new diaryl amidine compounds, can solve the problem of hysteresis of onset of action

Inactive Publication Date: 2007-09-05
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still serious deficiencies in the above-mentioned several drugs, and it is necessary to further improve the curative effect, reduce the incidence of toxic and side effects and drug withdrawal rate, especially to solve the problem of onset lag

Method used

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  • Diaryl amidine compound, its production, medicinal composition and use
  • Diaryl amidine compound, its production, medicinal composition and use
  • Diaryl amidine compound, its production, medicinal composition and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143] Preparation of 1-(N-phenylaminobenzyl)piperazine (compound 001)

[0144] Add 1.0 g (5.1 mmol) of N-phenylbenzamide and 2 ml of benzene into the reaction flask, heat at 50°C for 30 minutes, then add 1.1 g (5.3 mmol) of phosphorus pentachloride in batches, and stir at 90°C for 2 hours , the solid is completely dissolved. Benzene and phosphorus oxychloride were evaporated under reduced pressure, and the residue was cooled to room temperature. A solution of 0.9 g (10.5 mmol) of anhydrous piperazine dissolved in 20 ml of benzene was added in one portion, and stirred at room temperature for 2 hours. Leave overnight at room temperature. After filtering, the solid was washed with acetone, and the filtrate and washings were combined and concentrated under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel chromatography, eluted with petroleum ether / ethyl acetate / triethylamine (100:50:1), detected by thin-layer silica gel, and...

Embodiment 2

[0148] Preparation of 1-[N-(4'-trifluoromethylphenyl)aminobenzyl]piperazine (Compound 002)

[0149] a) Preparation of N-(4-trifluoromethylphenyl) benzamide

[0150] Add 12ml of 4-trifluoromethylaniline (15.4 grams, 0.099mol) in the reaction flask, cool in an ice bath, add dropwise 10ml of benzoyl chloride (12.1 grams, 0.086mol) and 60ml of 10% aqueous sodium hydroxide solution while stirring, always Keep the reaction solution alkaline. After the addition was complete, stirring was continued at room temperature for 1 hour. The precipitated solid was collected by filtration and recrystallized from ethanol to obtain 19 g of white crystals (83% yield), mp 203-204°C.

[0151] b) Preparation of 1-[N-(4'-trifluoromethylphenyl)iminobenzyl]piperazine (compound 002) Add a) obtained N-(4-trifluoromethylphenyl)benzene into the reaction flask 1.0 g (3.8 mmol) of formamide and 2 ml of benzene were heated at 50°C for 30 minutes, then 0.85 g (4.0 mmol) of phosphorus pentachloride was added...

Embodiment 3

[0155] Preparation of 1-[N-(3'-methylphenyl)iminobenzyl]piperazine hydrochloride (compound 003)

[0156] a) Preparation of N-(3-methylphenyl)benzamide

[0157] Add 5.0 grams (46.7 mmol) of 3-methylaniline and 12 ml of dichloromethane to the reaction flask, cool in an ice bath, and add dropwise a solution of 5.4 ml (6.6 grams, 46.7 mmol) of benzoyl chloride dissolved in 20 ml of dichloromethane while stirring. and 30ml of 10% sodium hydroxide aqueous solution, and keep the reaction liquid alkaline all the time. After the addition is complete, continue to stir and react at room temperature for 1 hour. The precipitated solid was collected by filtration, washed with saturated aqueous sodium bicarbonate and water, dried, and recrystallized from ethanol to obtain 8.02 g of white crystals, mp 122-124°C, yield 81.3%.

[0158] b) Preparation of 1-[N-(3'-methylphenyl)iminobenzyl]piperazine hydrochloride (compound 003)

[0159] Add 2.0 g (9.47 mmol) of N-(3-methylphenyl) benzamide obta...

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Abstract

Diaryl amidine compound, its production, medicinal composition and use are disclosed. The compound has serotonin reuptake inhibition activity and can be used to treat depressive disorders and other mental diseases.

Description

technical field [0001] The present invention relates to novel diarylamidine compounds, their preparation process, their pharmaceutical composition, and their use as medicine, especially as antidepressant medicine. Background technique [0002] Among the drugs currently clinically used to treat depression, serotonin reuptake inhibitors (SSRIs) are the most important and widely used drugs. Its representatives include fluoxetine [Fluoxetine, see USP 4018895 (1977), Ger.pat.2500110 (1975), USP 4314081 (1982)]; , USP 4007196 (1977)]; Sertraline [Sertraline, EP30081 (1981), USP 4536518 (1985)]; Citalopram [Citalopram, Ger.pat.2657013 (1977), USP 4136193 (1979)]; Voxamine [Fluvaxamine, Neth. pat. Apple 7503310 (1975), USP 4085225 (1978)]. 5-Hydroxytryptamine reuptake inhibitor antidepressants have positive therapeutic effect, less toxic and side effects, better safety and tolerance, and are used on a large scale all over the world. However, there are still serious deficiencies i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/125C07D241/04C07D213/53C07D213/78C07D207/335C07D207/416C07D333/22C07D333/38C07D307/68C07D307/52C07C257/10A61K31/495A61K31/496A61K9/00A61P25/24A61P25/00
Inventor 杨光中王小芳杜冠华张建军王娜沙时煜杨静王亚芳
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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