50593-24-3

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-1H-INDAZOL-5-AMINE is used as a key intermediate compound in the synthesis of Hydrazone compounds with a (hetero)aryl group at the terminal amine group. These Hydrazone compounds are utilized for treating tau protein-associated diseases, which are a group of neurodegenerative disorders characterized by the abnormal accumulation of tau protein in the brain.
1-METHYL-1H-INDAZOL-5-AMINE is also used in the preparation of Dihydroisoindole-1H-pyrazolo[3,4-d]pyrimidinone compounds, which serve as Wee1 inhibitors. Wee1 is a protein kinase that plays a crucial role in regulating the cell cycle, and its inhibition has been shown to have potential therapeutic benefits in the treatment of kinase-related diseases, which are a class of disorders caused by the abnormal activity of protein kinases.

InChI:InChI=1/C8H9N3/c1-11-8-3-2-7(9)4-6(8)5-10-11/h2-5H,9H2,1H3

Upstream product

• 5228-49-9 1-methyl-5-nitro-1H-indazole 
• 64-17-5 ethanol 
• 679839-39-5 4-bromo-2-fluoro-5-nitro-benzaldehyde 
• 57848-46-1 4-bromo-2-fluorobenzaldehyde 
• 5401-94-5 5-nitroindazole 

Downstream Products

• 1097730-93-2 1-methyl-1H-indazole-5-sulfonyl chloride 
• 945928-65-4 benzyl (1-methyl-1H-indazol-5-yl)carbamate 
• 852660-74-3 N-(1-methyl-indazol-5-yl)-phenylcarbamate 
• 1122710-39-7 2-chloro-N-(1-methyl-1H-indazol-5-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1046454-31-2 5-(3-benzyl-thioureido)-1-methyl-1H-indazole 
• 128056-50-8 2-(4-Chloro-phenyl)-8-methyl-5,8-dihydro-2H-1,2,5,8,9-pentaaza-dicyclopenta[a,h]naphthalen-3-one 
• 132283-39-7 2-(1-Methyl-1H-indazol-5-ylamino)-benzoic acid 

Relevant academic research and scientific papers

SnCl2/EtOH-mediated Synthesis of Novel 4-Ethoxy-and 4-Chloroindazoles Bearing Sulfonamide Moieties

The treatment of N-alkyl-5-nitroindazole with stannous chloride in ethanol, aftercoupling of the obtained amines with arylsulfonyl chloride in pyridine, gave the new 4-ethoxy-and 4-chloroindazoles bearing sulfonamide in moderate to good yields. Chlorinati

Discovery of 1-(1H-indazol-4-yl)-3-((1-phenyl-1H-pyrazol-5-yl)methyl) ureas as potent and thermoneutral TRPV1 antagonists

A series of 1-indazol-3-(1-phenylpyrazol-5-yl)methyl ureas were investigated as hTRPV1 antagonists. The structure–activity relationship study was conducted systematically for both the indazole A-region and the 3-trifluoromethyl/t-butyl pyrazole C-region to optimize the antagonism toward the activation by capsaicin. Among them, the antagonists 26, 50 and 51 displayed highly potent antagonism with Ki(CAP) = 0.4–0.5 nM. Further, in vivo studies in mice indicated that these derivatives both antagonized capsaicin induced hypothermia, consistent with their in vitro activity, and themselves did not induce hyperthermia. In the formalin model, 51 showed anti-nociceptive activity in a dose-dependent manner.

An Alternative Indazole Synthesis for Merestinib

A new synthesis of a key indazole-containing building block for the MET kinase inhibitor merestinib was designed and demonstrated. Crucial to the successful construction of the challenging indazole is an SNAr reaction, which forges the heterocy

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.

THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.

THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases

CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

3' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential

Several novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their 6-alkyl and 8-alkyl derivatives have been synthesised in high overall yields starting from 5-nitro and 6-nitroindazoles in a three-step route involving the regioselective cyclisation of thioureidoindazoles and indazolyl dithiocarbamates as the key steps. Some assorted thiazoloindazoles have been screened for anticancer properties, which demonstrated the anticancer potential of at least one product, justifying its further follow-up.