5334-41-8Relevant academic research and scientific papers
Preparation method and applications of azimsulfuron key intermediate
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Paragraph 0063; 0064; 0065; 0066, (2016/10/10)
The present invention provides a preparation method of 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)1H-pyrazole-5-sulfamide. The preparation method comprises that trimethyl orthoformate and malononitrile are adopted as starting raw materials, a three-step reaction is performed to obtain 1-methyl-5-amino-4-(tetrazole-5-yl)pyrazole, the 1-methyl-5-amino-4-(tetrazole-5-yl)pyrazole reacts with dimethylsulfate in the presence of an acid-binding agent to obtain 2-methyl-5-(1-methyl-5-amino-1H-pyrazole-4-yl)-2H-tetrazole, the 2-methyl-5-(1-methyl-5-amino-1H-pyrazole-4-yl)-2H-tetrazole is subjected to a sodium nitrite diazo-reaction under an acid condition, the obtained material reacts with a sodium sulfite-copper chloride-acetic acid mixture, and finally hydrolysis with ammonia is performed to obtain the target product. The present invention further provides a preparation method of azimsulfuron prepared from the 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)1H-pyrazole-5-sulfamide. The preparation method of the present invention has characteristics of short reaction route, environmental protection raw materials, and high yield.
A Michael Equilibration Model to Control Site Selectivity in the Condensation toward Aminopyrazoles
Fandrick, Daniel R.,Sanyal, Sanjit,Kaloko, Joseph,Mulder, Jason A.,Wang, Yuwen,Wu, Ling,Lee, Heewon,Roschangar, Frank,Hoffmann, Matthias,Senanayake, Chris H.
supporting information, p. 2964 - 2967 (2015/06/30)
A Michael equilibration model is presented to provide for site-selective pyrazole condensations between alkoxyacrylonitriles and hydrazines. Both pyrazole isomers were accessed with high selectivity by employment of kinetically or thermodynamically controlled conditions. Substrate scope and identification of Michael intermediates, as well as competitive pathways, support the presented mechanistic proposal. Sandmeyer derivatization provided site-selective access to fully substituted pyrazoles.
PROCESS OF PREPARATION OF AZIMSULFURON
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Paragraph 0210, (2015/04/28)
The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.
HETEROCYCLIC PYRIDONE COMPOUND, AND INTERMEDIATE, PREPARATION METHOD AND USE THEREOF
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Paragraph 0279; 0280, (2014/08/06)
The present invention relates to a heterocyclic pyridone compound represented by General Formula (I), where the heterocyclic pyridone compound is used as a tyrosine kinase inhibitor, and particularly a c-Met inhibitor. The present invention also relates to intermediates for preparing heterocyclic pyridone compound and a preparation method. The present invention further relates to a pharmaceutical composition containing the heterocyclic pyridone compound as an active ingredient, and a use of the pharmaceutical composition in treatment of diseases associated with tyrosine kinase c-Met, especially cancer associated with c-Met, as a medicament.
SUBSTITUTED TETRAZOLE COMPOUNDS AND PROCESS THEREOF
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Page/Page column 96; 97, (2014/01/17)
The present disclosure provides a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, useful as intermediates in preparation of sulfonamide or sulfonyl urea growth regulators or herbicides. Formula I The present disclosure further provides a process for preparing compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.
PROCESS OF PREPARATION OF AZIMSULFURON
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Page/Page column 38, (2014/01/17)
The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, (Formula I should be inserted here.) with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.
SUBSTITUTUED PYRAZOLE COMPOUNDS AND PROCESS FOR PREPARATION THEREOF.
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Page/Page column 79; 80, (2014/01/17)
The present disclosure provides a compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof, useful as intermediates in preparation of sulfonamide or sulfonyl urea growth regulators or herbicides. Formula I The present disclosure further provides a process for preparing compound of formula I, its derivatives, salts, stereo-isomers, or regio-isomers thereof.
PF-04859989 as a template for structure-based drug design: Identification of new pyrazole series of irreversible KAT II inhibitors with improved lipophilic efficiency
Dounay, Amy B.,Anderson, Marie,Bechle, Bruce M.,Evrard, Edelweiss,Gan, Xinmin,Kim, Ji-Young,McAllister, Laura A.,Pandit, Jayvardhan,Rong, Suobao,Salafia, Michelle A.,Tuttle, Jamison B.,Zawadzke, Laura E.,Verhoest, Patrick R.
, p. 1961 - 1966 (2013/04/23)
The structure-based design, synthesis, and biological evaluation of a new pyrazole series of irreversible KAT II inhibitors are described herein. The modification of the inhibitor scaffold of 1 and 2 from a dihydroquinolinone core to a tetrahydropyrazolopyridinone core led to discovery of a new series of potent KAT II inhibitors with excellent physicochemical properties. Compound 20 is the most potent and lipophilically efficient of these new pyrazole analogs, with a kinact/Ki value of 112,000 M-1 s -1 and lipophilic efficiency (LipE) of 8.53. The X-ray crystal structure of 20 with KAT II demonstrates key features that contribute to this remarkable potency and binding efficiency.
Organoruthenium antagonists of human A3 adenosine receptors
Paira, Priyankar,Chow, Mun Juinn,Venkatesan, Gopalakrishnan,Kosaraju, Vamsi Krishna,Cheong, Siew Lee,Klotz, Karl-Norbert,Ang, Wee Han,Pastorin, Giorgia
, p. 8321 - 8330 (2013/07/27)
Human A3 adenosine receptor (hA3AR) is a membrane-bound G protein-coupled receptor implicated in a number of severe pathological conditions, including cancer, in which it acts as a potential therapeutic target. To derive structure-activity relationships on pyrazolo-triazolo-pyrimidine (PTP)-based A3AR antagonists, we developed a new class of organometallic inhibitors through replacement of the triazolo moiety with an organoruthenium fragment. The objective was to introduce by design structural diversity into the PTP scaffold in order to tune their binding efficacy toward the target receptor. These novel organoruthenium antagonists displayed good aquatic stability and moderate binding affinity toward the hA3 receptor in the low micromolar range. The assembly of these complexes through a template-driven approach with selective ligand replacement at the metal center to control their steric and receptor-binding properties is discussed. Scaffold design: A novel class of ruthenium(II)-arene complexes containing chelating N,N-pyrazolo-pyrimidine ligands was rationally developed to be selective antagonists of human A3 adenosine receptors based on the proven pyrazolo-triazolo-pyrimidine design (see figure). Copyright
PYRAZOLOPYRIMIDINE PI3K INHIBITOR COMPOUNDS AND METHODS OF USE
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Page/Page column 64, (2009/09/05)
Compounds of Formula I, and including stereoisomers, geometric isomers, tautomers, solvates, metabolites and pharmaceutically acceptable salts thereof, are useful for inhibiting lipid kinases including p110 alpha and other isoforms of PI3K, and for treating disorders such as cancer mediated by lipid kinases. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed. [Fomula I]
