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

Description

6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester is an organic compound with the molecular formula C10H7ClN2O2. It is a derivative of imidazo[1,2-b]pyridazine, featuring a chloro substituent at the 6th position and an ethyl ester group at the 3rd position. 6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester is characterized by its potential reactivity and structural diversity, making it a valuable building block in the synthesis of various pharmaceuticals and bioactive molecules.

Uses

Used in Pharmaceutical Industry:
6-Chloro-iMidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester is used as a pharmaceutical intermediate for the development of novel drugs targeting a wide range of therapeutic areas. Its unique chemical structure allows for further functionalization and modification, enabling the creation of new drug candidates with improved pharmacological properties.
As a key intermediate, it can be employed in the synthesis of various drug classes, including but not limited to:
1. Anticancer agents: The compound can be used to develop new chemotherapeutic drugs that target specific cancer cell signaling pathways, potentially leading to more effective treatments with fewer side effects.
2. Anti-inflammatory drugs: By incorporating this intermediate into the molecular structure of anti-inflammatory medications, it may be possible to enhance their efficacy and reduce the risk of adverse effects.
3. Antimicrobial agents: The compound can be utilized in the development of new antibiotics or antifungal drugs, addressing the growing concern of drug resistance in the medical field.
4. Central nervous system (CNS) drugs: The compound may be used to design drugs targeting neurological disorders, such as Alzheimer's disease, Parkinson's disease, or epilepsy, by modulating specific neurotransmitter systems.

Upstream product

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

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 
• 1365212-65-2 6-(2-(3-fluorophenyl)pyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxamide 
• 1365214-08-9 ethyl 6-[2-(3-fluorophenyl)piperidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylate 
• 1365214-17-0 ethyl 6-[(2R,4S)-4-fluoro-2-(3-fluorophenyl)pyrrolidin-1-yl]imidazo[1,2-b]pyridazine-3-carboxylate 
• 1365214-66-9 ethyl 6-((3S)-2-(3-fluorophenyl)-3-hydroxypyrrolidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxylate 
• 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 

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.

Imidazopyridazine IRAK4 inhibitor, and preparation method and application thereof

The invention belongs to the field of medicines, and especially relates to an imidazopyridazine compound or a pharmaceutically acceptable salt thereof, a preparation method thereof, and an applicationof a medicinal composition of the compound or the salt in the treatment of tumors, inflammations, immunity and other diseases. The imidazopyridazine compound is a novel protein kinase IRAK4 inhibitor, and can selectively inhibit IRAK4 and downstream signaling pathways thereof. The compound has the structural formula I.