27464-17-1

Usage

Chemical Properties

Off-white solid

InChI:InChI=1/C9H13ClN4/c1-13-4-6-14(7-5-13)9-3-2-8(10)11-12-9/h2-3H,4-7H2,1H3

Upstream product

• 64-18-6 formic acid 
• 56392-83-7 3-chloro-6-piperazin-1-yl-pyridazine 
• 109-01-3 1-methyl-piperazine 
• 141-30-0 3,6-dichlorpyridazine 

Downstream Products

• 1417455-07-2 3-(4-methylpiperazin-1-yl)-6-[3-(trifluoromethyl)phenyl]pyridazine 
• 1417455-15-2 3-(2-methoxyphenyl)-6-(4-methylpiperazin-1-yl)pyridazine 
• 1361941-30-1 5-tert-butyl-2-(2-(hydroxymethyl)-3-(1-methyl-5-(6-(4-methylpiperazin-1-yl)pyridazin-3-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one 

Relevant academic research and scientific papers

Selective mono-amination of dichlorodiazines

A mild, easy-to-perform, and versatile method for the formation of aminochlorodiazines from reaction of several types of dichlorodiazines (i.e., pyridazines, pyrimidines, and pyrazines) with primary or secondary amines in ethanol in the presence of trieth

Structure-activity relationship studies of SEN12333 analogues: Determination of the optimal requirements for binding affinities at α7 nAChRs through incorporation of known structural motifs

Alpha7 nicotinic acetylcholine receptors (nAChRs) have implications in the regulation of cognitive processes such as memory and attention and have been identified as a promising therapeutic target for the treatment of the cognitive deficits associated with schizophrenia and Alzheimer's disease (AD). Structure affinity relationship studies of the previously described α7 agonist SEN12333 (8), have resulted in the identification of compound 45, a potent and selective agonist of the α7 nAChR with enhanced affinity and improved physicochemical properties over the parent compound (SEN12333, 8).

An electrochemical nickel-catalyzed arylation of 3-amino-6- chloropyridazines

3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.

PYRIDINONES/PYRAZINONES, METHOD OF MAKING, AND METHOD OF USE THEREOF

Pyridone and pyrazinone compounds of Formula (I) 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.

BTK protein kinase inhibitors

This application discloses pyridine and pyrimidine compounds according to formula I wherein R1, R2, R3, R4, R5, X1 and A are as described herein which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are further useful to treat inflammatory and auto immune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions containing compounds of formula I and at least one carrier, diluent or excipient.

Optimization of a series of multi-isoform PI3 kinase inhibitors

Optimization of the cellular and pharmacological activity of a novel series of PI3 kinase inhibitors targeting multiple isoforms is described.

6-Chloropyridazin-3-yl derivatives active as nicotinic agents: Synthesis, binding, and modeling studies

3,8-Diazabicyclo[3.2.1]octane (1), 2,5-diazabicyclo[2.2.1]heptane (2), piperazine (3), and homopiperazine (4) derivatives, substituted at one nitrogen atom with the 6-chloro-3-pyridazinyl group while the other nitrogen atom was either unsubstituted or mono- or dimethylated, were synthesized and tested for their affinity toward the neuronal nicotinic acetylcholine receptors (nAChRs). All of the compounds had Ki values in the nanomolar range. A molecular modeling study allowed location of their preferred conformations, the energies of which were recalculated in water with a continuum solvent model. Some of the compounds showed, in their populated conformations, only pharmacophoric distances longer than the values taken into consideration by the Sheridan model for nAChRs receptors. Thus, this SAR study gives support to the hypothesis that these longer distances are still compatible with affinity for α4β2 receptors in the nanomolar range.