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Aminotriazolopyridines and their use as kinase inhibitors

A technology of alkyl and aryl groups, applied in the field of aminotriazolopyridine and its use as a kinase inhibitor, can solve problems such as hindering the production of neuronal products

Inactive Publication Date: 2011-09-28
SIGNAL PHARMA LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, Syk inhibitors hinder the production of neuronogenic products

Method used

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  • Aminotriazolopyridines and their use as kinase inhibitors
  • Aminotriazolopyridines and their use as kinase inhibitors
  • Aminotriazolopyridines and their use as kinase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1426] Example 1: N,5-diphenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

[1427]

[1428] A. 2-(3-Ethoxycarbonyl-2-thioureido)-6-bromopyridine. To a solution of 2-amino-6-bromopyridine (8 g, 46.5 mmol) in dioxane (160 mL) was added dropwise ethoxycarbonyl isothiocyanate (6.09 g, 46.5 mmol) at room temperature under nitrogen. ), the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was monitored by TLC (petroleum ether:ethyl acetate=5:1). When the starting material was consumed, the dioxane was removed under reduced pressure to give crude 2-(3-ethoxycarbonyl-2-thioureido)-6-bromopyridine (14.81 g) as a solid. 1 HNMR (300MHz, DMSO-d 6 )δ (ppm) 12.16 (br s, 1H), 11.65 (br s, 1H), 8.65 (d, J=8.1Hz, 1H), 7.84 (dd, J 1 =8.1,J 2 =7.2Hz, 1H), 7.49(d, J=7.2Hz, 1H), 4.24(q, J=7.2Hz, 2H), 1.27(t, J=7.2Hz, 3H); MS(ESI): m / z 303.9[M+1] + .

[1429]B. 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine. To hydroxylamine hydrochloride (16.16g, 232.5mmol) and ...

Embodiment 2

[1432] Example 2: N-(4-morpholinylphenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

[1433]

[1434] A. N-(4-Morpholinylphenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. In 5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (100 mg, 0.47 mmol), 4-(4-bromo-phenyl)-morpholine ( 137mg, 0.57mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (27mg, 0.047mmol) and potassium tert-butoxide (105mg, 0.94mmol) in dioxane After degassing the mixture in (6 mL), tris(dibenzylideneacetone)dipalladium(0) (21.6 mg, 0.024 mmol) was added under nitrogen and the reaction mixture was heated at 80° C. overnight with stirring under nitrogen. The reaction mixture was quenched by adding water, and the mixture was extracted with ethyl acetate (15 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by preparative TLC (eluting with 25% ethyl acetate in petroleum ether) to give N-(4-morpholinophenyl)-5-phenyl-[...

Embodiment 3

[1435] Example 3: 5-(furan-3-yl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

[1436]

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Abstract

Provided herein are Heteroaryl Compounds of formula (I): wherein R1 and R2 are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing inflammatory conditions or cancer, and conditions treatable or preventable by inhibition of a kinase or a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a subject in need thereof.

Description

[0001] This application claims the benefit of US Provisional Application No. 61 / 095,217, filed September 8, 2008, and US Provisional Application No. 61 / 230,479, filed July 31, 2009, the entire contents of which are hereby incorporated by reference. 1. Technical field [0002] The present invention provides certain heteroaryl compounds, compositions containing an effective amount of one or more of said compounds, and therapeutic or curable compounds for the treatment or prevention of cancer, inflammatory diseases, immune diseases, metabolic diseases and by inhibiting kinases or kinase pathways. A method of preventing a disease comprising administering to a subject in need thereof an effective amount of a heteroaryl compound. 2. Background technology [0003] The link between abnormal protein phosphorylation and the cause or consequence of disease has been known for more than 20 years. Therefore, protein kinases have become a very important group of drug targets. See Cohen, N...

Claims

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Application Information

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IPC IPC(8): A61P35/00A61P19/00A61K31/437A61P25/00C07D471/04A61P29/00A61P9/00A61P5/00
CPCC07D519/00C07D471/04A61P1/00A61P1/04A61P1/16A61P11/00A61P11/02A61P11/06A61P17/00A61P17/02A61P17/06A61P17/10A61P19/00A61P19/02A61P19/06A61P19/08A61P21/00A61P21/04A61P25/00A61P25/02A61P25/14A61P25/28A61P27/14A61P29/00A61P3/00A61P3/04A61P31/00A61P31/04A61P31/12A61P35/00A61P35/02A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P5/00A61P7/02A61P7/04A61P7/06A61P9/00A61P9/10A61P3/10A61K31/437C07D519/04C07D519/06
Inventor 索哥利·巴曼亚R·J·贝茨凯特·布利兹安德鲁·安东尼·卡拉布雷斯托马斯·奥兰·丹尼尔默西迪丝·迪尔加多简·埃尔斯纳保罗·厄尔德曼布鲁斯·法尔格雷戈里·弗格森布兰登·李利萨·纳多尔尼加里克·帕卡德帕特里克·帕佩薇罗尼卡·普朗特维-克拉尼斯基詹尼弗·里格斯帕特丽夏·罗汉萨比塔·桑卡尔约翰·塞派泽佐藤喜孝维克托·斯隆兰德尔·史蒂文斯琳达·泰赫拉尼杰雅诗丽·蒂克赫艾杜亚度·托里斯安德鲁·华莱士布兰登·韦德·怀特菲尔德晶晶·赵
Owner SIGNAL PHARMA LLC
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