74906-19-7

Upstream product

• 2392-68-9 3-chlorophenyl-isothiocyanate 
• 109-77-3 malononitrile 
• 74-88-4 methyl iodide 
• 108-42-9 3-chloro-aniline 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 

Downstream Products

• 183739-47-1 5-amino-1-benzyl-3-(3-chloro-phenylamino)-4-cyano-pyrazole 
• 196505-08-5 [1-Benzyl-4-(3-chloro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-(3-chloro-phenyl)-amine 
• 183739-51-7 1-benzyl-3,4-di(3-chloro-phenylamino)pyrazolo[3,4-d]pyrimidine 
• 183739-52-8 1-benzyl-4-(3-bromo-phenylamino)-3-(3-chloro-phenylamino)-pyrazolo[3,4-d]pyrimidine 
• 183739-53-9 1-benzyl-3-(3-chloro-phenylamino)-4-(3-methyl-phenylamino)-pyrazolo[3,4-d]pyrimidine 
• 183739-50-6 1-benzyl-3-(3-chloro-phenylamino)-4-phenylamino-pyrazolo[3,4-d]pyrimidine 
• 196505-02-9 1-Benzyl-N³-(3-chloro-phenyl)-1H-pyrazolo[3,4-d]pyrimidine-3,4,6-triamine 
• 183739-49-3 (1-Benzyl-4-chloro-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-(3-chloro-phenyl)-amine 
• 183739-48-2 1-benzyl-3-(3-chloro-phenylamino)-4-hydroxy-pyrazolo[3,4-d]pyrimidine 

Relevant academic research and scientific papers

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation

A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

3,5-DIAMINOPYRAZOLE KINASE INHIBITORS

Provided herein are 3,5-diaminopyrazoles, for example, compounds of Formula IA, that are useful for modulating regulated-in-COPD kinase activity, and pharmaceutical compositions thereof. Also provided herein are methods of their use for treating, preventi

Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(Phenylamino)pyrazolo[3,4-d]pyrimidines

In the course of the random screening of a pool of CIBA chemicals, the two pyrazolopyrimidines 1 and 2 have been identified as fairly potent inhibitors of the EGF-R tyrosine kinase. Using a pharmacophore model for ATP- competitive inhibitors interacting w