On November 10, 2011, Barbosa, Antonio J. M.; Blomgren, Peter A.; Currie, Kevin S.; Krishnamoorthy, Ravi; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Ortwine, Daniel; Schmitt, Aaron C.; Wang, Xiaojing; Xu, Jianjun; Young, Wendy; Zhang, Honglu; Zhao, Zhongdong; Zhichkin, Pavel E. published a patent.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one The title of the patent was Preparation of pyridone and azapyridone compounds as Btk inhibitors for treating immune disorders, inflammation, cancer, and other Btk-mediated diseases. And the patent contained the following:
The invention is related to the preparation of pyridones and azapyridones I [R1 = H, D, F, CN, OH, etc.; R2-4 = independently alkyl, Cl, NH2, OEt, etc.; R5 = (un)substituted (hetero)aryl, carbocyclyl, etc.; X = (S)0-2, N, NR6, O, CH and derivatives; R6 = H, F, NH2, OH, (un)substituted alkyl; Y, Y’ = independently CR6, N; Z1-4 = independently C, CH and derivatives, N; Z5 = CO, CH2 and derivatives, CH:N and derivatives, NH and derivatives, etc.; one of Z1 and Z2 or X and Z1, where X is not (S)0-2, forms a 5-7 membered aryl, carbocyclyl, heterocyclyl, heteroaryl ring; where alkyl, aryl, carbocyclyl, heterocyclyl, heteroaryl are optionally substituted] their stereoisomers, tautomers, and pharmaceutically acceptable salts useful for inhibiting Btk kinase, and for treating immune disorders, inflammation, cancer, and other Btk-mediated diseases. Methods of using I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathol. conditions, are disclosed. Thus, a multi-step synthesis starting from 5-nitropyrazole-3-carboxylic acid via cyclization of 1-(2-Bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole to 5-Methyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine and cyclization of Et 1-(2-Aminoethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate to 3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one was given for II. II inhibited Btk kinase (IC50 = 0.002 μM). The experimental process involved the reaction of 3,5-Dibromo-1-methylpyrazin-2(1H)-one(cas: 87486-34-8).Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one
The Article related to pyridone azapyridone preparation btk inhibitor immune disease inflamation cancer, benzothienopyridinone pyrazinoindolone pyrazinobenzimidazolone methanopyrazinoindolone preparation rheumatoid arthritis and other aspects.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one