1227861-73-5

Basic information

• Product Name: 4-(benzylamino)-6-chloronicotinamide
• Synonyms: 4-(benzylamino)-6-chloronicotinamide
• CAS NO: 1227861-73-5
• Molecular Weight: 261.711
• Mol File: 1227861-73-5.mol

Chemical Properties

• CAS DataBase Reference: 4-(benzylamino)-6-chloronicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzylamino)-6-chloronicotinamide(1227861-73-5)
• EPA Substance Registry System: 4-(benzylamino)-6-chloronicotinamide(1227861-73-5)

Safety Data

• Hazardous Substances Data: 1227861-73-5(Hazardous Substances Data)

Upstream product

• 73027-79-9 4,6-dichloro-nicotinic acid 
• 1609530-95-1 4,6-dichloro-N-methylnicotinamide 
• 100-46-9 benzylamine 
• 40296-46-6 ethyl 4,6-dichloronicotinate 
• 1374215-05-0 methyl 4-(benzylamino)-6-chloronicotinate 
• 1374215-06-1 4-(benzylamino)-6-chloronicotinic acid 
• 65973-52-6 methyl 4,6-dichloropyridine-3-carboxylate 
• 70593-57-6 4,6-dichloro-nicotinamide 

Downstream Products

• 1227862-57-8 6-anilino-4-(benzylamino)nicotinamide 
• 1227866-36-5 4-benzylamino-6-(pyridin-4-ylamino)pyridine-3-carboxyamide 
• 1227865-71-5 4-(benzylamino)-6-{[4-(morpholinomethyl)phenyl]amino}pyridine-3-carboxyamide 
• 1227864-97-2 6-{[4-(4-acetylpiperazin-1-yl)phenyl]amino}-4-(benzylamino)pyridine-3-carboxyamide 
• 1227482-53-2 C₂₀H₁₉N₅O₂ 

Relevant articles and documents

Discovery and structure-based design of 4,6-diaminonicotinamides as potent and selective IRAK4 inhibitors

The identification of small molecule inhibitors of IRAK4 for the treatment of autoimmune diseases has been an area of intense research. We discovered novel 4,6-diaminonicotinamides which potently inhibit IRAK4. Optimization efforts were aided by X-ray crystal structures of inhibitors bound to IRAK4. Structure activity relationship (SAR) studies led to the identification of compound 29 which exhibited sub-micromolar potency in a LTA stimulated cellular assay.

Design, synthesis, and evaluation of 4,6-diaminonicotinamide derivatives as novel and potent immunomodulators targeting JAK3

In organ transplantation, T cell-mediated immune responses play a key role in the rejection of allografts. Janus kinase 3 (JAK3) is specifically expressed in hematopoietic cells and associated with regulation of T cell development via interleukin-2 signaling pathway. Here, we designed novel 4,6-diaminonicotinamide derivatives as immunomodulators targeting JAK3 for prevention of transplant rejection. Our optimization of C4- and C6-substituents and docking calculations to JAK3 protein confirmed that the 4,6-diaminonicotinamide scaffold resulted in potent inhibition of JAK3. We also investigated avoidance of human ether-a-go-go related gene (hERG) inhibitory activity. Selected compound 28 in combination with tacrolimus prevented allograft rejection in a rat heterotopic cardiac transplantation model.

NICOTINAMIDES AS JAK KINASE MODULATORS

The present invention is directed to compounds of formula I and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of JAK kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition JAK kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by JAK kinase activity, such as undesired thrombosis and Non Hodgkin's Lymphoma.

PYRIDINE-3-CARBOXYAMIDE DERIVATIVE

To provide a novel JAK3 inhibitor that is useful as a preventive and/or therapeutic agent for rejection and graft versus host disease (GvHD) in organ transplantation, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, Sj?gren syndrome, Behcet's disease, type I diabetes mellitus, autoimmune thyroiditis, idiopathic thrombocytopenic purpura, ulcerative colitis, Crohn's disease, asthma, allergic rhinitis, atopic dermatitis, contact dermatitis, urticaria, eczema, psoriasis, allergic conjunctivitis, uveitis, cancer, leukemia and the like. The pyridine-3-carboxyamide derivative represented by the general formula (1): or its salt or a solvate thereof.