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Novel optical activity phenylethanolamine compounds and preparation method thereof

A compound, the technology of tert-butylaminoethanol, which is applied in the field of phenylethanolamine compounds, can solve the problem that there is no description of the optical activity of phenylethanolamine compounds.

Inactive Publication Date: 2008-01-09
SHENYANG PHARMA UNIV BENXI PHARMA SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no description of the optically active isomers of these phenylethanolamine compounds in this patent

Method used

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  • Novel optical activity phenylethanolamine compounds and preparation method thereof
  • Novel optical activity phenylethanolamine compounds and preparation method thereof
  • Novel optical activity phenylethanolamine compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (-)-2-(3-chloro-4-amino-5-trifluoromethylphenyl)-2-tert-butylaminoethanol hydrochloride and (+)-2-(3-chloro-4-amino-5 -Trifluoromethylphenyl)-2-tert-butylaminoethanol hydrochloride

[0037] a) (-)-2-(3-Chloro-4-amino-5-trifluoromethylphenyl)-2-tert-butylaminoethanol hydrochloride

[0038] Dissolve 4.45g (0.0143mol) of 2-(3-chloro-4-amino-5-trifluoromethylphenyl)-2-tert-butylaminoethanol in 53.4ml of absolute ethanol, drop 2.57g (0.00717mol) A solution prepared from dibenzoyl-D-tartaric acid and 25.7ml of absolute ethanol was added to 188ml of petroleum ether (bp.60-90°C), stirred for 1 hour, filtered, and dried to obtain 2-(3-chloro-4-amino -5-trifluoromethylphenyl)-2-tert-butylaminoethanol dibenzoyl-D-tartrate 2.9g, yield 82.6%.

[0039] Add 2.9g of 2-(3-chloro-4-amino-5-trifluoromethylphenyl)-2-tert-butylaminoethanol dibenzoyl-D-tartrate into 60ml of water, stir, and drop in 20% sodium hydroxide The solution was adjusted to pH=10, extracted with ether, and dried ov...

Embodiment 2

[0048] (-)-2-(3-trifluoromethyl-4-aminophenyl)-2-tert-butylaminoethanol hydrochloride and (+)-2-(3-trifluoromethyl-4-aminophenyl) -2-tert-butylaminoethanol hydrochloride

[0049] a) (-)-2-(3-trifluoromethyl-4-aminophenyl)-2-tert-butylaminoethanol hydrochloride

[0050] Dissolve 4.5g (0.0163mol) of 2-(3-trifluoromethyl-4-aminophenyl)-2-tert-butylaminoethanol in 65ml of isopropanol, add dropwise 1.23g (0.0082mol) of L-tartaric acid and 25ml The solution prepared in isopropanol was stirred for 2 hours, filtered, and dried to obtain 2.24 g of 2-(3-trifluoromethyl-4-aminophenyl)-2-tert-butylaminoethanol L-tartrate, with a yield of 78.1%.

[0051] Add 2.24g of 2-(3-trifluoromethyl-4-aminophenyl)-2-tert-butylaminoethanol L-tartrate into 50ml of water, stir, add dropwise 20% sodium hydroxide solution to pH=10, extract with ether, Dry over anhydrous sodium sulfate. Filtrate, evaporate ether under reduced pressure to obtain 1.67 g of (-)-2-(3-trifluoromethyl-4-aminophenyl)-2-tert-but...

Embodiment 3

[0058] (-)-2-(3-Chloro-4-amino-5-cyanophenyl)-2-tert-butylaminoethanol hydrochloride and d-2-(3-chloro-4-amino-5-cyanophenyl base)-2-tert-butylaminoethanol hydrochloride

[0059] a) (-)-2-(3-Chloro-4-amino-5-cyanophenyl)-2-tert-butylaminoethanol hydrochloride

[0060] Dissolve 2.5g (0.0093mol) of 2-(3-chloro-4-amino-5-cyanophenyl)-2-tert-butylaminoethanol in 50ml of absolute ethanol, and drop into 1.67g (0.0047mol) of diphenylmethane Acyl-D-tartaric acid and 16.7ml of absolute ethanol solution, add 200ml of anhydrous ether, stir for 1 hour, filter, and dry to obtain 2-(3-chloro-4-amino-5-cyanophenyl)- 1.58 g of 2-tert-butylaminoethanol dibenzoyl-D-tartrate, yield 75.6%.

[0061] Add 1.58g of 2-(3-chloro-4-amino-5-cyanophenyl)-2-tert-butylaminoethanol dibenzoyl-D-tartrate into 32ml of water, stir, and drop in 20% sodium hydroxide solution to pH=10, extracted with ether, dried over anhydrous sodium sulfate. Filtrate, evaporate ether under reduced pressure to obtain 0.9 g of ...

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Abstract

A Icompound with (-) or (+) structure or its medicinal salt, composition containing the compound and the production of the compound are disclosed. R 1 is H or halogen; R2 is CF3, CN or halogen; R3 is C1-6 straight chain or branched chain alkyl radical or C3-6 naphthene. It has beta-2 acceptor excitation function and can be used to treat asthma or bronchitis.

Description

technical field [0001] The present invention relates to having β 2 - New optically active phenylethanolamines for receptor stimulant, especially for the treatment of asthma or bronchitis. The present invention also relates to the preparation method of these compounds, the pharmaceutical composition containing these compounds, and the use of these compounds. Background technique [0002] Asthma or bronchitis is a common disease, the current treatment method mostly adopts antibiotic treatment, the curative effect is not good, and long-term use also has certain side effects. Some betas have been found to treat asthma 2 -receptor agonists, but these known compounds all have deficiencies in aspects such as drug efficacy and physicochemical properties. [0003] Chinese patent 01128234.7 discloses a new phenylethanolamine compound, which has better β 2 - Receptor stimulant. There is no description of the optically active isomers of these phenylethanolamines in this patent. C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/68C07C215/56A61K31/137A61P11/06
CPCC07C255/59C07B2200/07C07C215/72C07C215/68A61P11/04A61P11/06A61P11/08A61P29/00A61P43/00
Inventor 程卯生潘莉王东凯邢瑞娟陈旭曜赵冬梅
Owner SHENYANG PHARMA UNIV BENXI PHARMA SCI & TECH
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