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Alpha 1-adrenalin receptor antagonist, and preparation and medical use thereof

A receptor antagonist, epinephrine technology, applied in the direction of pharmaceutical formulations, drug combinations, medical preparations containing active ingredients, etc., can solve the problems of not obtaining subtype selectivity prediction ability, not having α1B drugs on the market, etc., and achieving excellent Treatment of benign prostatic hyperplasia, long survival time, good reproducibility

Inactive Publication Date: 2013-02-27
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Numerous structure-activity relationship studies [3,4，5] different α 1B -AR subtype selectivity model, but no model with good predictive ability for subtype selectivity has been obtained, and the α 1B -AR subtype-selective compounds are still relatively small, and there is no α 1B -AR subtype-selective drug launch

Method used

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  • Alpha 1-adrenalin receptor antagonist, and preparation and medical use thereof
  • Alpha 1-adrenalin receptor antagonist, and preparation and medical use thereof
  • Alpha 1-adrenalin receptor antagonist, and preparation and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] XBMI: 1-(2,6-Dimethyl-4-bromophenoxy)-2-(3-methoxy-4-hydroxy)propane hydrochloride

[0062] Dissolve 1.5mmol of 4-bromo-2,6-dimethylphenoxyacetone and 1.6mmo of 3-methoxy-4-hydroxyphenethylamine in 5ml of methanol, add a small amount of p-toluenesulfonic acid as a catalyst, and reflux 3h, lowered to room temperature, added 0.2g KBH in batches 4 , so that the temperature of the reaction solution does not exceed 30°C, and react at room temperature for 3h. The methanol was evaporated under reduced pressure, extracted with a small amount of ethyl acetate, the insoluble matter was filtered off, the ethyl acetate was evaporated, the residue was dissolved in absolute ether, and dry HCl gas was introduced. A white solid was obtained, mp 149.8-152.4°C, yield 35%.

[0063] IR (KBr, cm -1 ): 3420, 2926, 1605, 1524, 1279, 1207, 1032.

[0064] 1 HNMR (DMSO-D 6 )δ: 1.43(d, 3H, J=6.47Hz, CH CH 3 ), 2.26(s, 6H, 2×ArCH 3 ), 2.94 (m, 2H, ArCH 2 ), 3.21 (m, 2H, NCH 2 ), 3.63(m,...

Embodiment 2

[0068] XBM Ⅱ: 1-(2,4,6-trimethylphenoxy)-2-(3-methoxy-4-hydroxy)propane hydrochloride

[0069] The reaction conditions were the same as XBMI, and a white solid was obtained, mp 164-166°C, yield 36%.

[0070] IR (KBr, cm -1 ): 3427, 2934, 1610, 1524, 1269, 1217, 1034.

[0071] 1 HNMR (DMSO-D 6 )δ: 1.43 (d, J=6.70Hz, 3H, CH CH 3 ), 2.19 (s, 3H, ArCH 3 ), 2.22(s, 6H, 2×ArCH 3 ), 2.97 (m, 2H, ArCH 2 ), 3.21 (m, 2H, NCH 2 ), 3.63(m, 1H, CHN), 3.73~3.76(2s, 6H, 2×ArOCH 3 ), 3.91 (m, 2H, OCH 2 ), 6.29~6.93(m, 5H, ArH), 9.06(d, 2H, J=37.35Hz, NH 2 + ).

[0072] Molecular formula: C 21 h 29 NO 3 .HCl.

[0073] HRMS: [M+H] + Meas. Mass, 344.22145; Calc. Mass, 344.22202.

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Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to an Alpha1-adrenergic receptor antagonist in the structural formula I, wherein, X represents Br or methyl. The compound of formula I has relatively strong Alpha1-adrenergic receptor antagonistic function and remarkable effect on treating benign prostatic hyperplasia and hypertension. The invention also discloses a preparation method thereof.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of α 1 - Adrenergic receptor antagonist, the invention also discloses its preparation method and medical application. Background technique [0002] alpha 1 - Adrenergic receptors (α 1 -adrenoceptor referred to as α 1 -AR) belongs to the family of guanylate-binding protein (G-protein)-coupled (GPCRs) membrane surface receptors, which triggers signal transduction processes by activating G-proteins after stimulation. alpha 1 - There are multiple subtypes of AR, and it is currently possible to identify α 1 - AR has at least α 1A , α 1B and alpha 1D Three subtypes. three kinds of alpha 1 -AR subtypes have similar structural characteristics, all are single polypeptide chains, each subtype has seven transmembrane domains (TMDs), and the TMDs of the three subtypes have 65%-75% homology. alpha 1 -AR is widely distributed in various tissues and organs, and all three s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/60A61K31/138A61P13/08A61P9/12
Inventor 习保民倪沛洲江振洲王涛
Owner CHINA PHARM UNIV
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