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Bicycloheteroaryl compounds as GPR Receptor stimulant, compositions and application thereof

A compound, heteroaryl technology, applied in the field of bicyclic heteroaryl compounds, can solve problems such as hypoglycemia, failure to achieve accurate standardization of blood glucose levels, etc.

Inactive Publication Date: 2012-08-01
CENTAURUS BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Neither method accurately normalizes blood glucose levels and both carry the risk of hypoglycemia

Method used

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  • Bicycloheteroaryl compounds as GPR Receptor stimulant, compositions and application thereof
  • Bicycloheteroaryl compounds as GPR Receptor stimulant, compositions and application thereof
  • Bicycloheteroaryl compounds as GPR Receptor stimulant, compositions and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] 1-(1-(5-Ethylpyrimidin-2-yl)piperidinyl-4-yl)-5-(4-(methylsulfonyl)phenyl)-1hydro-indole

[0150]

[0151] Step 1: 4-Hydroxy-(2-(5-ethylpyrimidinyl))piperidine

[0152]

[0153] To 4-hydroxypiperidine (2.55g, 25.2mmol) in acetonitrile (50mL) was added 2-chloro-5-ethylpyrimidine (3.00g, 21.0mmol) and N,N-diisopropylethylamine ( 3.00g, 21.0mmol). The reaction solution was heated at 80°C for 16 hours, and then diluted with water. The resulting mixture was extracted with ethyl acetate, and the organic phase was washed with saturated brine, then dried and concentrated in vacuo. The residue was separated by silica gel column chromatography (dichloromethane: ethyl acetate = 3:1 to 1:1) to obtain the desired product (3.69 g, 85%).

[0154] 1 H NMR(CDCl 3 ): δ8.16 (2H, s), 4.37-4.42 (2H, m), 3.92-3.94 (1H, m), 3.24-3.30 (2H, m), 2.45 (2H, q, J=7.6 Hz), 1.92-1.98 (2H, m), 1.69 (1H, brs), 1.48-1.53 ​​(2H, m), 1.19 (3H, t, J=7.6 Hz).

[0155] Step 2: (2-(5-Ethylpyrimidinyl)))piperidiny...

Embodiment 2

[0168] 6-(4-(1Hydroxy-tetrazol-1-yl)phenyl)-3-(1-(5-ethylpyrimidin-2-yl)piperidinyl)-3hydro-[1,2,3 ]Triazolo[4,5-b]pyridine

[0169]

[0170] Step 1: 1-(4-Bromophenyl)-1hydro-tetrazole

[0171]

[0172] Trimethyl orthoformate (1.14 g, 13.4 mmol) was added dropwise to a solution of 4-bromoaniline (2 g, 11.6 mmol) in acetic acid (12 mL) and stirred at room temperature for 1 hour. Then sodium azide was added and stirred at 80°C for 2 hours. After cooling, water and 6N (12 mL) hydrochloric acid (3.6 mL) were added, and a solution of sodium nitrite (0.64 g, 9.3 mmol) was added dropwise under an ice water bath. After stirring for 1 hour, it was filtered, washed with water, and dried to obtain the desired product (2.20 g, 98%).

[0173] 1 H NMR(CDCl 3 ): δ 8.98 (1H, s), 7.74 (2H, d, J=8.0 Hz), 7.61 (2H, d, J=8.0 Hz).

[0174] Step 2: 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1hydro-tetrazole

[0175]

[0176] To a solution of 1-(4-bromophenyl)-1hydro-tetrazole (1.0g, 4.44mm...

Embodiment 3

[0207] 5-(4-(1hydro-tetrazol-1-yl)phenyl)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-1hydro-indole

[0208]

[0209] In a method similar to that described in Example 2 step 7 from 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene Yl)-1hydro-tetrazole (Example 2 step 2) and 5-bromo-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-1hydro-indole (Example 1, Step 3) The title compound was synthesized.

[0210] 1 H NMR(CDCl 3 )δ9.02 (1H, s), 8.23 ​​(2H, s), 7.76-7.91 (5H, m), 7.49-7.56 (2H, m), 6.61-6.62 (1H, m), 5.00-5.04 (2H, m), 4.53-4.60 (1H, m), 3.05-3.14 (2H, m), 2.51 (2H, q, J=7.6 Hz), 2.21-2.25 (2H, m), 1.98-2.08 (2H, m) , 1.23 (3H, t, J=7.6 Hz).

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Abstract

The invention discloses bicycloheteroaryl compounds of formula (I), pharmaceutical compositions containing the compounds, application of the compounds in regulating the activity of GPR119 and preparing medicines for treating diseases associated with metabolism, and methods for treating diseases associated with metabolism.

Description

Technical field [0001] The present invention relates to a new class of bicyclic heteroaryl compounds, pharmaceutical compositions containing these compounds and their application in regulating the activity of GPR119 in the treatment of metabolic-related disorders and their complications. Background technique [0002] Diabetes is a serious disease that affects millions of people worldwide. The most common forms of diabetes are type I diabetes (also known as insulin-dependent diabetes) and type II diabetes (also known as non-insulin-dependent diabetes). Type II diabetes accounts for about 90% of all diabetes cases and is a serious progressive disease that causes microvascular complications (including retinopathy, neuropathy, and nephropathy) and macrovascular complications (including accelerated arteriosclerosis, coronary heart disease, and stroke). [0003] There is currently no cure for diabetes. Standard treatments for the disease are limited and focus on keeping blood sugar lev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D471/04C07D401/14C07D413/14A61K31/454A61K31/506A61P3/00A61P3/10A61P3/08A61P5/50A61P3/06A61P3/04
CPCC07D401/14C07D401/12C07D471/04C07D413/14C07D451/14C07D401/04A61P3/00A61P3/04A61P3/06A61P3/08A61P3/10A61P5/50A61P43/00A61K31/506
Inventor 校登明朱岩胡远东王虎庭刘昱良李继军孙德广王哲魏永恒王赞平唐国静荆禄涛
Owner CENTAURUS BIOPHARMA
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