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Phenylpropionic acid compounds chained by nitrogen-containing heterocyclic rings, pharmaceutical composition, preparation method, and application thereof

A technology of phenylpropionic acids and compounds, applied in the field of pharmaceuticals, can solve the problems of insufficient insulin secretion function of pancreatic beta cells, collapse of compensatory mechanisms, and elevated blood sugar levels.

Inactive Publication Date: 2014-10-22
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as the course of the disease progresses, the insulin secretion function of the pancreatic β cells is insufficient, and the patient's compensatory mechanism collapses, resulting in an abnormal increase in the body's blood sugar level, which in turn leads to the disorder of glucose and lipid metabolism in the body and the occurrence of type Ⅱ diabetes

Method used

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  • Phenylpropionic acid compounds chained by nitrogen-containing heterocyclic rings, pharmaceutical composition, preparation method, and application thereof
  • Phenylpropionic acid compounds chained by nitrogen-containing heterocyclic rings, pharmaceutical composition, preparation method, and application thereof
  • Phenylpropionic acid compounds chained by nitrogen-containing heterocyclic rings, pharmaceutical composition, preparation method, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Embodiment 1: the preparation of 3-(4-bromomethylphenyl) ethyl propionate

[0082]

[0083] Weigh 4-bromobenzyl alcohol 1a (purchased from Shaoyuan Chemical Technology (Shanghai) Co., Ltd., 10.50 g, 56.0 mmol,) and dissolve it in 100 mL of triethylamine, add 20.0 mL of ethyl acrylate 2, palladium acetate (0.50 g, 2.2mmol), triphenylphosphine (0.50g, 1.9mmol). The reaction system was replaced with nitrogen three times, then placed in an oil bath at 95°C for 72 hours, the reaction solution was cooled to room temperature, filtered, and the filtrate was concentrated, then separated by silica gel column chromatography (petroleum ether / ethyl acetate=4 / 1) to obtain a white Solid 3a 10.8 g, 93% yield. 1 H NMR (300MHz, CDCl 3 ): δ=7.67(d,J=16.0Hz,1H),7.51(d,J=8.1Hz,2H),7.38(d,J=8.1Hz,2H),6.42(d,J=16.0Hz,1H ), 4.72(d, J=5.4Hz, 2H), 4.26(q, J=7.2Hz, 2H), 1.33(t, J=7.1Hz, 3H).

[0084] Dissolve 10.8g of intermediate 3a in 100mL of ethyl acetate, add 200mg of 10% palladium ca...

Embodiment 2

[0086] Embodiment 2: Preparation of 3-(4-bromomethyl-2-fluorophenyl) ethyl propionate

[0087]

[0088] Compound 3-(4-bromomethyl-2-fluorophenyl) ethyl propionate (compound 5b) was prepared according to a method similar to that shown in Example 1, substituting compound 1b for compound 1a. 1 H NMR (300MHz, CDCl 3 )δ7.19(t,J=7.8Hz,1H),7.11–7.03(m,2H),4.43(s,2H),4.12(q,J=7.1Hz,2H),2.96(t,J=7.6 Hz,2H),2.61(t,J=7.6Hz,2H),1.23(t,J=7.1Hz,3H).

Embodiment 3

[0089] Embodiment 3: Preparation of ethyl 3-(4-(((6-bromopyridin-2-yl)oxy)methylene)phenyl)propionate

[0090]

[0091] Weigh 2.50g of compound 6a, 3.90g of compound 5a, and 4.0g of potassium carbonate into a 100mL round bottom flask, add 50mL of anhydrous acetonitrile, and react at 50°C for 5 hours. The reaction solution was lowered to room temperature, filtered, and the filtrate was concentrated and separated by silica gel column chromatography (ethyl acetate / petroleum ether=1 / 10) to obtain 3.63 g of white solid compound 7a with a yield of 69%. 1 H NMR (300MHz, CDCl 3 ): δ=7.41(dd,J=15.1,7.5Hz,3H),7.22(d,J=8.0Hz,2H),7.07(d,J=7.4Hz,1H),6.72(d,J=8.2Hz ,1H),5.31(s,2H),4.13(q,J=7.1Hz,2H),2.96(t,J=7.8Hz,2H),2.62(t,J=7.8Hz,2H),1.23(dd ,J=8.3,6.0Hz,3H).

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Abstract

Provided are a phenylalanine compound having a nitrogen heterocyclic link that can substantially lower blood sugar and regulate glycolipid metabolic activity, pharmaceutically acceptable salts or stereoisomers thereof, pharmaceutical compositions having the compound, and the use of the compound in preparing medicines for diabetics and glycolipid metabolic disorders, in particular, the use thereof in preparing medicines for treating type II diabetes. The compound has a structure as presented in formula I.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to a phenylpropionic acid compound with a nitrogen-containing heterocyclic link, its pharmaceutically acceptable salt, stereoisomer or its prodrug molecule, its pharmaceutical composition, and its preparation method. And its use in the preparation of medicines for treating diabetes and glucose and lipid metabolism disorders, especially the use in the preparation of medicines for treating type II diabetes. The above-mentioned compound has obvious functions of lowering blood sugar and regulating glucose and lipid metabolism activity. Background technique [0002] As we all know, diabetes is the third chronic disease that seriously threatens human health after tumors and cardiovascular and cerebrovascular diseases. According to the World Health Organization report in 2011, 366 million people worldwide suffer from diabetes. In my country, the total number of diabetic patients has ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64C07D409/12C07D405/12C07D401/12A61K31/5377A61K31/4418A61K31/4436A61K31/4433A61K31/4439A61K31/4545A61K31/496A61P3/10
CPCC07D213/64C07D405/12C07D405/14C07D409/12C07D409/14A61P3/10
Inventor 胡有洪冷颖李德文宁萌萌
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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