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Aminotriazolopyridines and their use as kinase inhibitors
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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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In addition, Syk inhibitors hinder the production of neuronogenic products
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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 (petroleumether: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 hydroxylaminehydrochloride (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 sodiumsulfate, and concentrated. The residue was purified by preparative TLC (eluting with 25% ethyl acetate in petroleumether) 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 proteinphosphorylation 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...
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