On February 19, 2013, Chen, Wei; Loury, David J. published a patent.COA of Formula: C14H21BO3 The title of the patent was Preparation of pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine derivatives as Btk kinase inhibitors. And the patent contained the following:
The invention related to pyrazolo[3,4-d]pyrimidine derivatives of formula I, pharmaceutical composition comprising them, their preparations and use as Bruton’s tyrosine kinase (Btk) inhibitors thereof. Compounds of formula I wherein X is a bond; Y is (un)substituted (hetero)arylene; Z is CO, CS, S(O)1-2, NHCO and derivatives, and NHSO1-2 and derivatives; R1 and R2 are independently H, (un)substituted (hetero)aryl, heterocycloalkyl, C1-4 alkyl and C3-6 cycloalkyl; or R1R2 taken together form a heterocycloalkyl ring; each R3 is independently halo, C1-4 alkyl, CF3, CN, NO2, NH2, OH and OMe; m is 1 – 3; and their pharmaceutically acceptable salt, are claimed. Example compound II was prepared by amination of (R)-tert-Bu 3-hydroxy-1-pyrrolidinecarboxylate with 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine,the resulting substituted pyrazolopyrimidine underwent deprotection followed by N-acylation with 4-(dimethylamino)but-2-enoic acid to afford 2-(E)-1-((R)-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(dimethylamino)but-2-en-1-one, which underwent coupling reaction with 4-chlorophenylboronic acid to afford compound II. All the invention compounds were evaluated for their Btk inhibitory activity. From the assay, it was determined that example compound II exhibited IC50 value of < 100 nM. The experimental process involved the reaction of 2-(3-Methoxy-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 1417036-28-2).COA of Formula: C14H21BO3
The Article related to pyrazolopyrimidine preparation btk kinase inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrimidines and Quinazolines and other aspects.COA of Formula: C14H21BO3
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