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Indolines compounds, preparation method and pharmaceutical application thereof

A compound, indoline technology, applied in the field of indoline compounds, which can solve problems such as cardiovascular side effects

Inactive Publication Date: 2009-04-29
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, α 1 -AR antagonists are fast, safe, and highly effective. These drugs mainly include: prazosin, terazosin, alfuzosin, doxazosin, etc., because of their effect on the cardiovascular system α 1 -AR lacks selectivity, so there are certain cardiovascular side effects

Method used

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  • Indolines compounds, preparation method and pharmaceutical application thereof
  • Indolines compounds, preparation method and pharmaceutical application thereof
  • Indolines compounds, preparation method and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Example 1: 1-Acetyl-5-(2-bromopropionyl)indoline (VIa)

[0137] CH 2 Cl 2 90ml, anhydrous AlCl 3 100g (0.75mol), 37.5ml (0.36mol) of 2-bromopropionyl bromide were mixed and stirred, and 36.0g (0.22mol) of 1-acetylindoline (V) and CH 2 Cl 2 100ml of the prepared solution was added and reacted at room temperature for 6 hours. The reaction solution was poured into 1.0L ice water, with CH 2 Cl 2 250ml×3 extraction, combined with CH 2 Cl 2 layer, washed with water, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to obtain 54.0 g of light yellow solid, yield 82.6%, mp 138-141°C.

Embodiment 2

[0138] Example 2: 1-acetyl-5-(2-bromoacetyl)indoline (VIb)

[0139] V5.0g (0.03mol), 2-bromoacetyl bromide 10.0g (0.05mol), anhydrous AlCl 3 27.0g (0.20mol) and CH 2 Cl 2 40ml was prepared in a similar manner to VIa to obtain 8.0g of light yellow solid, yield 91.8%, mp 103-105.5°C.

Embodiment 3

[0140] Example 3: 1-acetyl-5-(2-bromopropyl)indoline (VIIa)

[0141] Add 50.0 g (0.17 mol) of VIa into 100 ml of TFA, stir at room temperature to dissolve, add 60 ml (0.38 mol) of triethylsilane dropwise, and react at room temperature for 12 hours. The reaction solution was distilled under reduced pressure, and the residual liquid was added to CH 2 Cl 2 150ml×3 extraction, combined organic layer, washed with water, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate under reduced pressure to obtain 45.5 g of off-white solid, yield 95.5%, mp 145-147°C.

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Abstract

The invention relates to the field of pharmaceutical chemistry, in particular to an alpha 1-AR antagonist indoline compound (I), wherein the definitions of R1, R2, R3 and m see the instruction. The invention also discloses a method for preparing the compound (I), a medical composition containing the compound (I), and application of the compound (I) in treating prostatoplasia and cardiovascular system diseases and adjusting the intraocular pressure.

Description

technical field [0001] The invention relates to an indoline compound, a preparation method thereof, a pharmaceutical composition containing the compound and the application of the compound in medicine. Background technique [0002] Benign prostatic hyperplasia is a common and frequently-occurring disease in middle-aged and elderly men. At present, there are two main types of drugs used clinically to treat benign prostatic hyperplasia: 1 - Adrenergic receptors (α 1 - AR) antagonists and 5α-reductase inhibitors. Among them, α 1 -AR antagonists are fast, safe, and highly effective. These drugs mainly include: prazosin, terazosin, alfuzosin, doxazosin, etc., because of their effect on the cardiovascular system α 1 -AR lacks selectivity, so there are certain cardiovascular side effects. [0003] In 2006, Kissei successfully developed and listed Silodosin (Silodosin, Fig. 1) (LA Sorbera, J Silvestre, JCastaner. KMD-3213 Treatment of BPH, α 1-A drenoceptor antaonist. Drugs Fu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08A61K31/496A61P9/00A61P27/02A61P13/08
Inventor 陈国华罗小川张江波
Owner CHINA PHARM UNIV
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