1150566-27-0

Basic information

• Product Name: 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester
• Synonyms: 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester;Ethyl 6-chloroiMidazo[1,2...;ethyl 6-chloroiMidazo[1,2-b]pyridazne-3-carboxylate;6-chloroimidazo[1,2-a]pyrazine-3-carboxylic acid
• CAS NO: 1150566-27-0
• Molecular Formula: C₉H₈ClN₃O₂
• Molecular Weight: 225.63172
• Mol File: 1150566-27-0.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 0.88±0.30(Predicted)
• CAS DataBase Reference: 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester(1150566-27-0)
• EPA Substance Registry System: 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester(1150566-27-0)

Safety Data

• Hazardous Substances Data: 1150566-27-0(Hazardous Substances Data)

Usage

Uses

6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester is mainly used as pharmaceutical intermediates.

Upstream product

• 1150566-26-9 3-chloro-6-(dimethylamino-methyleneamino)-1-ethoxycarbonylmethyl-pyridazin-1-ium bromide 
• 5469-69-2 6-chloro-pyridazin-3-ylamine 
• 38362-95-7 ethyl (Z)-2-chloro-3-hydroxyacrylate 
• 105-36-2 ethyl bromoacetate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 141-78-6 ethyl acetate 
• 35053-55-5 N'-(6-chloropyridazin-3-yl)-N,N-dimethylmethanimidamide 
• 5941-55-9 ethyl 3-ethoxyacrylate 
• 33142-21-1 ethyl 2-chloro-3-oxopropanoate 

Downstream Products

• 1150566-28-1 6-(4-fluoro-benzylamino)-imidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester 
• 1150566-63-4 6-chloro-imidazo[1,2-b]pyridazine-3-carboxylic acid phenylamide 
• 1150566-32-7 6-(3,4-dichloro-benzylamino)-imidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester 
• 1150566-83-8 6-(3,4-dichloro-benzylamino)-imidazo[1,2-b]pyridazine-3-carboxylic acid 3,4-dichlorobenzylamide 
• 1150566-31-6 6-(4-sulfamoyl-benzylamino)-imidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester 
• 1365213-94-0 N-ethoxy-6-[(2R,4S)-4-fluoro-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxamide 
• 1365214-71-6 (R)-(6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazin-3-yl)methanol 
• 1365214-10-3 ethyl 6-[(2R)-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylate 
• 1365214-11-4 ethyl 6-[2-(3-fluorophenyl)-3-oxopyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylate 
• 1431653-83-6 6-(3-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazine-3-carboxylic acid 
• 1431654-38-4 benzyl 6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-ylcarbamate 
• 1431654-39-5 6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-amine 
• 1431644-92-6 5-methyl-N-(6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-yl)pyrazine-2-carboxamide 
• 1431649-87-4 6-hydroxy-N-(6-(2-(trifluoromethyl)phenyl)imidazo[1,2-b]pyridazin-3-yl)pyrimidine-4-carboxamide 

Relevant articles and documents

Design, synthesis and biological activity of bicyclic carboxamide derivatives as TRK inhibitors

‘precision medicine’ is characterized by the selection of targeted drugs based on genetic characteristics of tumor from patients, and no longer selected basis on the type of cancer tissue. Among them, clinical trials on neurotrophin receptor tyrosine kinase genes (NTRK) have proven that great anti-cancer effects can be achieved in different cancer patients. In this paper, a novel total of twenty compounds in two categories have been designed and synthesized. Results of Kinase activity tests showed that I-9 (TRKA IC50 = 1.3 nM, TRKAG595R IC50 = 6.1 nM), and I-10 (TRKA IC50 = 1.1 nM, TRKAG595R IC50 = 5.3 nM) have significant inhibitory activity, and results of cell viability tests showed that I-9 and I-10 can maintain a great inhibitory effect in the Ba/F3-LMNA-NTRK1 cell line(IC50 = 81.1 nM and 41.7 nM, respectively), and in Ba/F3-LMNA-NTRK1-G595R cell line, I-9 and I-10 have better cell activity (IC50 was 495.3 nM, 336.6 nM, respectively) compared with the positive control drug LOXO-101. These results indicate that I-9 and I-10 are potential TRK inhibitors that can overcome drug resistance for further investigation.

Design and synthesis of Imidazo[1,2-b]pyridazine IRAK4 inhibitors for the treatment of mutant MYD88 L265P diffuse large B-cell lymphoma

Harboring MYD88 L265P mutation triggers tumors growth through the activation of NF-κB by interleukin-1 receptor associated kinase 4 (IRAK4) in diffuse large B-cell lymphoma (DLBCL), highlighting IRAK4 as a therapeutic target for tumors driven by aberrant MYD88 signaling. Herein, we report the design, synthesis, and structure?activity relationships of imidazo[1,2-b]pyridazines as potent IRAK4 inhibitors. The representative compound 5 exhibited excellent IRAK4 potency (IRAK4 IC50 = 1.3 nM) and favorable kinase selectivity profile. It demonstrated cellular selectivity for activated B cell–like (ABC) subtype DLBCL with MYD88 L265P mutation in cytotoxicity assay. The kinase inhibitory efficiency of compound 5 was further validated by Western blot analysis of phosphorylation of IRAK4 and downstream signaling in OCI-LY10 and TMD8 cells. Besides, combination of compound 5 and BTK inhibitor ibrutinib synergistically reduced the viability of TMD8 cells. These results indicated that compound 5 could be a promising IRAK4 inhibitor for the treatment of mutant MYD88 DLBCL.

Convenient two-step one-pot synthesis of 3-substituted imidazo[1,2-a]pyridines and imidazo[1,2-b]pyridazines

Abstract: A convenient and novel two-step one-pot method for the synthesis of 3-substituted imidazo[1,2-a]pyridines and 3-substituted imidazo[1,2-b]pyridazines was developed through the reaction of heterocyclic amines and N,?N-dimethylformamide dimethyl a