933190-51-3

Basic information

• Product Name: 8-BROMO-6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE
• Synonyms: 8-BROMO-6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE;8-broMo-6-chloroiMidazo[1;IMidazo[1,2-b]pyridazine, 8-broMo-6-chloro-
• CAS NO: 933190-51-3
• Molecular Formula: C₆H₃BrClN₃
• Molecular Weight: 232.468
• Mol File: 933190-51-3.mol

Chemical Properties

• Appearance: /
• Density: 2.03 g/cm³
• Refractive Index: 1.767
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 0.73±0.30(Predicted)
• CAS DataBase Reference: 8-BROMO-6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BROMO-6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE(933190-51-3)
• EPA Substance Registry System: 8-BROMO-6-CHLOROIMIDAZO[1,2-B]PYRIDAZINE(933190-51-3)

Safety Data

• Hazardous Substances Data: 933190-51-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
8-Bromo-6-chloroimidazo[1,2-b]pyridazine is used as a building block for the synthesis of various biologically active molecules. Its unique structure and reactivity contribute to the development of new drug candidates with potential therapeutic benefits.
Used in Organic Synthesis:
8-Bromo-6-chloroimidazo[1,2-b]pyridazine is used as a reagent in organic synthesis, particularly in the preparation of heterocyclic compounds. Its presence in the synthesis process can enhance the properties and applications of the resulting compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 8-Bromo-6-chloroimidazo[1,2-b]pyridazine has potential applications in the discovery of new drug candidates. Its unique structural features and reactivity make it a promising candidate for the development of innovative therapeutic agents.

InChI:InChI=1/C6H3BrClN3/c7-4-3-5(8)10-11-2-1-9-6(4)11/h1-3H

Upstream product

• 446273-59-2 4-bromo-6-chloro-3-pyridazineamine 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 107-20-0 2-chloroethanal 

Downstream Products

• 1345842-98-9 3-(2-methoxyphenyl)-8-(4-methylpyridin-3-yl)imidazo[1,2-b]pyridazine 
• 1345843-23-3 4-(3-(2-chloro-4-fluorophenyl)imidazo[1,2-b]pyridazin-8-yl)isoquinoline 
• 1345843-26-6 3-(2,4-dichlorophenyl)-8-(4-methylpyridin-3-yl)imidazo[1,2-b]pyridazine 
• 1345843-49-3 3-(4-fluorophenyl)-8-(4-methoxypyridin-3-yl)imidazo[1,2-b]pyridazine 
• 1345843-62-0 8-bromo-6-chloro-3-(4-fluorophenyl)imidazo[1,2-b]pyridazine 
• 1415314-14-5 ethyl 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl) benzoate 
• 1415314-15-6 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid 
• 1415314-16-7 tert-butyl 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate 
• 1415314-03-2 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoic acid 
• 1415380-82-3 6-phenyl-N-(6-(piperidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine 
• 1365244-33-2 4-[6-bromo-8-(methylsulfonyl)imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropyl-2-methylbenzamide 

Relevant articles and documents

Design, synthesis, and biological evaluation of imidazo[1,2-b]pyridazine derivatives as mTOR inhibitors

ATP-competitive mTOR inhibitors have been studied as potential antitumor agents. Based on the structure-activity relationship of known mTOR inhibitors, a series of novel imidazo[1,2-b]pyridazine derivatives were synthesized and characterized. The anti-proliferative activities of these compounds were evaluated by SRB assay against six human cancer cell lines. Imidazo[1,2-b]pyridazine diaryl urea derivatives A15?A24 exhibited significant anti-proliferative activity especially against non-small cell lung cancer A549 and H460 with IC50values ranging from 0.02?μM to 20.7?μM. Among them, compounds A17 and A18 showed mTOR inhibitory activity with IC50of 0.067?μM and 0.062?μM, respectively. A more detailed analysis of compounds A17 and A18 showed that they induced G1-phase cell cycle arrest and suppressed the phosphorylation of AKT and S6 at cellular level. Moreover, obvious anticancer effect of A17 in?vivo was observed in established nude mice A549 xenograft model.

HPK1 ANTAGONISTS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

Binding to an Unusual Inactive Kinase Conformation by Highly Selective Inhibitors of Inositol-Requiring Enzyme 1α Kinase-Endoribonuclease

A series of imidazo[1,2-b]pyridazin-8-amine kinase inhibitors were discovered to allosterically inhibit the endoribonuclease function of the dual kinase-endoribonuclease inositol-requiring enzyme 1α (IRE1α), a key component of the unfolded protein response in mammalian cells and a potential drug target in multiple human diseases. Inhibitor optimization gave compounds with high kinome selectivity that prevented endoplasmic reticulum stress-induced IRE1α oligomerization and phosphorylation, and inhibited endoribonuclease activity in human cells. X-ray crystallography showed the inhibitors to bind to a previously unreported and unusually disordered conformation of the IRE1α kinase domain that would be incompatible with back-to-back dimerization of the IRE1α protein and activation of the endoribonuclease function. These findings increase the repertoire of known IRE1α protein conformations and can guide the discovery of highly selective ligands for the IRE1α kinase site that allosterically inhibit the endoribonuclease.

CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS

A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

Synthesis method of 6-cholro-8-bromoimidazole[1,2-b]pyridazine

The invention relates to a synthesis method of 6-chloro-8-bromoimidazole[1,2-b]pyridazine. 3-amino-6-chloropyridazine, liquid bromine, and a chloroacetaldehyde water solution are taken as the raw materials, the ratio of amount of substance of 3-amino-6-chloropyridazine to liquid bromine is 1:1.0-4.5, the ratio of amount of substance of 3-amino-6-chloropyridazine to the chloroacetaldehyde water solution (40%) is 5:1.0-1:3.2; in a proper solvent, in the presence of alkali, raw materials carry out continuous reactions at a temperature of 50 to 100 DEG C to generate a coarse product of 6-cholro-8-bromoimidazole[1,2-b]pyridazine, and then the coarse product is purified to obtain purified product of 6-cholro-8-bromoimidazole[1,2-b]pyridazine. The provided synthesis method has the advantages that the raw materials are easily available, the prices are reasonable, at the same time, no heavy metal or corrosive gas is used in the preparation reactions, the reactions are mild, there is no special requirement on reaction equipment, the product can be produced by common corrosion resistant equipment, and the reaction conditions are moderate.

6-aryl substituted-imidazo-[ 1,2-b] pyridazine derivatives, their preparation and use

The invention discloses a 6-aryl-substituted-imidazole-[1,2-b]pyridazine derivative and a preparation method thereof and application of the derivative in inhibition of tumors. The 6-aryl-substituted-imidazole-[1,2-b]pyridazine derivative provided by the invention is represented by a general formula (I), and substituent groups in the general formula are specifically defined in the specification. The derivative can inhibit growth of tumor cells in the G1 phase, exerts inhibitory effects on a lung cancer, a breast cancer, glioma and melanoma and has an obvious inhibitory effect on transplanted human lung tumors in nude mice.

IMIDAZOPYRIDAZINE COMPOUNDS

The present invention relates to the use of novel compounds of formula I: wherein all variable substituents are defined as described herein, which are SYK inhibitors and are useful for the treatment of auto-immune and inflammatory diseases.

IMIDAZOPYRIDAZINE COMPOUNDS

The present invention relates to the use of novel compounds of formula (I): wherein all variable substituents are defined as described herein, which are SYK inhibitors and are useful for the treatment of auto-immune and inflammatory diseases.

TRICYCLIC HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

There is provided compounds of formula (I), wherein R1, R2, X, R3 and R4 have meanings given in the description (and which compounds are optionally substituted as indicated in the description), and pharmaceutica

BICYCLIC PIPERAZINE COMPOUNDS

Bicyclic piperazine compounds of Formula I are provided, including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk kinase, and for treating immune disorders such as inflammation mediated by Btk kinase. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.