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Naphthyl ethylamine derivative and preparation method thereof and application of naphthyl ethylamine derivative in preparing weight-reducing medicament

The technology of a derivative, naphthylethylamine, which is applied in the field of obesity medicine and pharmacy, can solve the problems of limited choice and insignificant curative effect, and achieve a good effect of weight loss and lipid reduction.

Active Publication Date: 2009-12-16
苏州凯达生物医药技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a new structural compound—naphthylethylamine derivatives, as a new drug for the treatment of obesity, which solves the defects of limited selection of drugs for the treatment of obesity and ineffective curative effect in the prior art

Method used

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  • Naphthyl ethylamine derivative and preparation method thereof and application of naphthyl ethylamine derivative in preparing weight-reducing medicament
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  • Naphthyl ethylamine derivative and preparation method thereof and application of naphthyl ethylamine derivative in preparing weight-reducing medicament

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Experimental program
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Effect test

Embodiment 1

[0048]The preparation of embodiment 1 pharmaceutical intermediate of the present invention

[0049] Synthesis of (7-methoxy-3,4-dihydro-1-naphthyl)acetonitrile:

[0050] 7-methoxytetralin-1-one (17.6g, 0.1mol), cyanoacetic acid (12.8g, 0.15mol), benzylamine (2.7g, 25mmol), heptanoic acid (3.3g, 25mmol) were dropped into toluene ( 160ml), refluxed and separated water for 24 hours, cooled to room temperature, the reaction solution was washed successively with 2mol / L sodium hydroxide solution (60ml), water (60ml) and saturated brine (60ml), dried with anhydrous sodium sulfate, filtered , the filtrate was distilled off toluene to obtain an oil (18.9 g, 95%).

[0051] Synthesis of (7-methoxyl-1-naphthyl)acetonitrile:

[0052] DDQ (25g, 0.11mol) was dropped into dry dichloromethane (200ml), and a dichloromethane solution (100ml) of the above-mentioned oil (20g, 0.1mol) was added dropwise at 20°C. Filter, the filtrate was washed successively with saturated sodium bicarbonate solut...

Embodiment 2

[0056] Embodiment 2 The preparation of [1-(7-methoxy-1-naphthyl) cyclobutyl] methylamine of the present invention

[0057] Add 1-(7-methoxynaphthyl)cyclobutyronitrile (9.5g, 0.04mol), nickel chloride hexahydrate (9.5g, 0.04mol), and 30ml of absolute ethanol into a 100ml eggplant-shaped bottle under an ice bath , sodium borohydride (4.6 g, 0.12 mol) was added in batches under vigorous stirring, the color of the solution turned black, and stirring was continued for 30 minutes after addition. Then slowly add 30ml of hydrochloric acid with a concentration of 4mol / L to the reaction solution, and the color of the solution gradually changes to light green. The solution was concentrated to remove ethanol, and then filtered to remove unreacted 1-(7-methoxynaphthyl)cyclobutyronitrile. The filtrate was adjusted to pH 9-10 with sodium hydroxide, the solution was extracted with ethyl acetate (20ml×3), the ethyl acetate was combined, washed with water (30ml) and saturated brine (30ml) resp...

Embodiment 3

[0059] Embodiment 3 Preparation of 1-[1-(7-methoxy-1-naphthyl)cyclobutyl]-N,N-dimethylmethylamine of the present invention

[0060] Get [1-(7-methoxy-1-naphthyl)cyclobutyl]methylamine (2.4g, 0.01mol) in a 50ml eggplant-shaped bottle, slowly mix 88% formic acid (15ml), 37% formaldehyde Solution (5ml) was added therein, refluxed for one hour, then 37% formaldehyde (5ml) was added dropwise, continued to reflux for 24h, cooled to room temperature, poured into 40ml ice water, adjusted pH to about 9-10 with 50% sodium hydroxide, Extracted three times with ethyl acetate (20ml×3), combined ethyl acetate was washed with water (30ml) and saturated brine (30ml) respectively. Dry over anhydrous sodium sulfate, filter, and evaporate the solvent from the filtrate to obtain an orange-red oil (2.15 g, 79.6%), which becomes a salt.

[0061] 1 H-NMR (δ, ppm, d-DMSO): 2.01(m, 2H) 2.26(s, 6H); 2.52~2.79(m, 4H) 2.63(s, 2H); 3.76(s, 3H); 7.10~ 7.75 (m, 6H)

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Abstract

The invention discloses a naphthyl ethylamine derivative and a preparation method thereof and application of the naphthyl ethylamine derivative in preparing medicaments for treating obesity. The naphthyl ethylamine derivative is characterized in that the composition exists in a form of alkali or pharmaceutical salt, and has the general structural formula shown in the formula (I), wherein R is halogen, halogenated methyl radical, nitryl or optionally-substituted C1 to C3 alkoxy; R1 and R2 are H, optionally-substituted C1 to C6 alkyl or a substituent group of which the structure is shown in general formula (II); in the formula (II), R4 is the H, aryl, or optional C1 to C6 alkyl or C1 to C3 alkoxy; and the R3 is the optionally-substituted C1 to C6 alkyl. Pharmacological tests prove that the composition has good function of treating the obesity.

Description

technical field [0001] The invention belongs to the technical field of medicine and pharmacy for obesity, and relates to a derivative of naphthylethylamine which has the function of reducing weight. The invention also relates to a preparation method of the derivative and an application in preparing a medicine for treating obesity. Background technique [0002] Obesity has become a common problem in various countries and populations all over the world. Studies have shown that obesity is closely related to hypertension, coronary heart disease, stroke, type II diabetes and other diseases, and can increase the morbidity and mortality of these diseases. Therefore, obesity has attracted more and more attention, and it is more and more important to develop safe, effective and easy-to-use drugs for the treatment of obesity. [0003] The current drugs for treating obesity include the following categories according to their mechanism of action. One is an appetite suppressant, which ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/56C07C213/02C07C233/25C07C231/02A61K31/137A61K31/165A61P3/04
Inventor 李飞孙旭钦瑞良陆军季兴殷晓佳
Owner 苏州凯达生物医药技术有限公司
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