1108745-30-7

Usage

Uses

Used in Pharmaceutical Industry:
5-(3,5-difluorobenzyl)-1H-indazol-3-amine is used as a potential drug candidate for the development of new therapeutic agents. Its unique structure with a 3,5-difluorobenzyl substituent at the 5-position may allow it to interact with specific enzymes or receptors in the body, making it a promising starting point for drug discovery and development.
5-(3,5-difluorobenzyl)-1H-indazol-3-amine is used as a research tool for investigating its biological activities and functions. Further research and investigation into the properties and potential applications of 5-(3,5-difluorobenzyl)-1H-indazol-3-amine are warranted to fully understand its pharmaceutical potential and explore its therapeutic uses in various diseases and conditions.

Upstream product

• 891864-98-5 C₈H₈BrN₃ 
• 156545-07-2 3,5-difluorophenylboronic acid 
• 218301-22-5 2-fluoro-5-formylbenzonitrile 
• 1108745-25-0 5-(3,5-difluorobenzyl)-2-fluorobenzonitrile 

Downstream Products

• 1108745-39-6 N-[5-(3,5-difluoro-benzyl)-1H-indazol-3-yl]-2,2,2-trifluoro-acetamide 
• 1108746-96-8 2,6-dichloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]pyridine-3-carboxamide 
• 1108746-70-8 methyl 4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-nitrobenzoate 
• 1108746-75-3 N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-nitro-4-(piperidin-1-ylmethyl)benzamide 
• 1108746-91-3 N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-nitro-2-[tetrahydro-2H-pyran-4-yl(trifluoroacetyl)amino]benzamide 
• 1108745-84-1 C₂₈H₃₀F₂N₆O₃ 
• 1108744-13-3 N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}-2-(tetrahydro-2H-pyran-4-ylamino)benzamide 
• 1108745-83-0 C₃₄H₃₆F₅N₇O₂ 
• 1108743-80-1 N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(piperazin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)amino) benzamide 

Relevant academic research and scientific papers

Preparation method of 5-benzyl-1H-indazole-3-amine compound

The invention discloses a method for preparing a 5-benzyl-1H-indazole-3-amine compound and a preparation method of the 5-benzyl-1H-indazole-3-amine compound. According to the method, 2-fluoro-5-formyl cyanophenyl, p-toluenesulfonhydrazide and arylboronic acid are taken as substrates and react in 1, 4-dioxane in the presence of alkali, and the 2-fluoro-5-benzyl cyanophenyl compound is obtained. The preparation method comprises the following steps: dissolving a 2-fluoro-5-benzyl cyanophenyl compound and hydrazine hydrate in tert-butyl alcohol, and reacting to obtain the 5-benzyl-1H-indazole-3-amine compound. The method provided by the invention has the following characteristics: (1) the reaction raw materials are common commercial raw materials, and the used alkali and solvent are cheap and easy to obtain; no noble metal catalyst is used, and the production cost is low; (2) the reaction is insensitive to air and moisture, and the open reaction has no influence on the yield; magnesium powder is not used as a Grignard reagent, water and oxygen removal operation is not needed, and the method is safe, efficient and suitable for industrial production; and (3) treatment and purification after reaction are simple and convenient, and pollution of solvents and silica gel to the environment is reduced.

Preparation method of entrectinib

The invention provides a preparation method of entrectinib. According to the invention, the route reaction steps are few, and the total yield of the reaction is increased; and the route is mature, the reaction condition is mild, extremely low temperature reaction is not needed, the post-treatment is simple and convenient, the synthesis of a large amount of target products is facilitated, the purity can reach 99.5% or above, and the industrial production of the product is facilitated.

TROPOMYOSIN RECEPTOR KINASE (TRK) DEGRADATION COMPOUNDS AND METHODS OF USE

This disclosure relates to bivalent compounds (e.g., bi-functional small molecule compounds), compositions comprising one or more of the bivalent compounds, and to methods of use the bivalent compounds for the treatment of certain disease in a subject in need thereof. The disclosure also relates to methods for identifying such bivalent compounds.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

TROPOMYOSIN RECEPTOR KINASE (TRK) DEGRADATION COMPOUNDS AND METHODS OF USE

Bivalent compounds, compositions comprising one or more of the bivalent compounds, and methods of use the bivalent compounds for the treatment of certain disease in a subject in need thereof are provided. Methods for identifying such bivalent compounds are provided, either.

Indazole compound for inhibiting kinase activity as well as composition and application thereof

The invention relates to an indazole compound for inhibiting kinase activity and relates to preparation and application of the indazole compound. Specifically, the invention discloses the indazole compound shown as a formula (I), or crystal forms, prodrugs, pharmaceutically acceptable salts, stereoisomers, tautomers, solvates or pharmaceutical compositions of hydrates of the indazole compound. Thecompound and the composition containing the compound, provided by the invention, have excellent inhibition performance on kinase protein, and also have better pharmacokinetics parameter characteristics at the same time; the medicine concentration of the compound in animals can be improved and the curative effect and safety of the medicine are improved. The formula (I) is shown in the description.

Discovery of Entrectinib: A New 3-Aminoindazole As a Potent Anaplastic Lymphoma Kinase (ALK), c-ros Oncogene 1 Kinase (ROS1), and Pan-Tropomyosin Receptor Kinases (Pan-TRKs) inhibitor

Anaplastic lymphoma kinase (ALK) is a receptor tyrosine kinase responsible for the development of different tumor types. Despite the remarkable clinical activity of crizotinib (Xalkori), the first ALK inhibitor approved in 2011, the emergence of resistance mutations and of brain metastases frequently causes relapse in patients. Within our ALK drug discovery program, we identified compound 1, a novel 3-aminoindazole active on ALK in biochemical and in cellular assays. Its optimization led to compound 2 (entrectinib), a potent orally available ALK inhibitor active on ALK-dependent cell lines, efficiently penetrant the blood-brain barrier (BBB) in different animal species and highly efficacious in in vivo xenograft models. Moreover, entrectinib resulted to be strictly potent on the closely related tyrosine kinases ROS1 and TRKs recently found constitutively activated in several tumor types. Entrectinib is currently undergoing phase I/II clinical trial for the treatment of patients affected by ALK-, ROS1-, and TRK-positive tumors.

SUBSTITUTED INDAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS

Substituted indazole derivatives of formula (I) and pharmaceutically acceptable salts thereof, as defined in the specification, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention may be useful in therapy in the treatment of diseases associated with a deregulated protein kinase activity, like cancer.

Highly efficient synthesis of 5-benzyl-3-aminoindazoles

A rapid and efficient procedure for the preparation of 5-benzyl-3-aminoindazoles 1 is reported. Key intermediates are fluoro-cyano diarylmethanes 2 which have been obtained by two different synthetic approaches. Benefits of these methods result from the u