On January 7, 2010, Dewdney, Nolan James; Lou, Yan; Sjogren, Eric Brian; Soth, Michael; Sweeney, Zachary Kevin published a patent.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one The title of the patent was Phenylpyrazinones derivatives as kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of inflammation and autoimmune diseases. And the patent contained the following:
The invention provides 5-phenyl-1H-pyrazin-2-one derivatives of formula I 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 autoimmune diseases associated with aberrant B-cell proliferation such as rheumatoid arthritis. Also disclosed are compositions comprising compounds of formula I and at least one carrier, diluent or excipient. Compounds of formula I wherein the dotted bond is either a single or a double bond; R is H, R1, -R1-R2-R3, -R1-R3 and -R2-R3; R1 is (un)substituted (hetero)aryl and (un)substituted (hetero)cycloalkyl; R2 is CO, COO, (CH2)1-3-COO, CONH2 and derivatives, (CH2)1-3, O(CH2)1-3, etc.; R3 is H, (un)substituted lower (hetero)alkyl, (un)substituted lower alkoxy, amino, (un)substituted (hetero)aryl, (un)substituted arylalkyl, etc.; A is (un)substituted CH2, NH and N; B is CH and N; D is -C(O)- and -S(O2)-; Q is (un)substituted CH2 and NH; Y1 is H and lower alkyl; Y2 is H, halo and (un)substituted lower alkyl; n is 0-3; each Y21 is independently halo, (un)substituted lower alkyl, OH, lower alkoxy and amino; each Y3 is independently halo and (un)substituted lower alkyl; m is 0-1; Y4 is H, halo, (un)substituted lower alkyl, (un)substituted lower cycloalkyl, amino and derivatives; and their pharmaceutically acceptable salts thereof, are claimed. All the invention compounds were evaluated for their kinase inhibitory activity. From the assay, it was determined that example compound II exhibited the IC50 value of 0.01 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 phenylpyrazinones derivative preparation kinase inhibitor treatment inflammation autoimmune disease, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Reference of 3,5-Dibromo-1-methylpyrazin-2(1H)-one