On October 8, 2014, Xu, Yong; Wang, Xuehai; Li, Lie; Huang, Lu; Tian, Hua; Yang, Zhongwen; Xia, Qingfeng; Xiao, Qiang; Guo, Diliang; Tu, Ronghua; Yu, Yanping; Yu, Jing; Huang, Xiang; Fan, Zhaoze; He, Zhenyu; Zhang, Yi; Yang, Jing published a patent.Name: N-(3-Aminophenyl)acrylamide The title of the patent was Purine compounds as kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. And the patent contained the following:
The invention provides purine compounds of formula I and their preparing method and application. The inventive compounds can serve as Bruton’s tyrosine kinase (BTK) inhibitors. Compound of formula I wherein X is (un)substituted Ph, (un)substituted 3- to 7-membered saturated or unsaturated carbon ring, (un)substituted 8- to 10-membered saturated or unsaturated bicyclic ring or aryl ring, etc.; R1 is -R, halo, -OR, -O(CH2)aOR, -CN, -NO2, -SO2R, -SO2N(R)2, -SOR, -C(O)R, -CO2R, -C(O)N(R)2, -NRC(O)R, -NRC(O)NR2, -NRSO2R or -N(R)2; R2 is -R, halo, -OR, -O(CH2)aOR, -CN, -NO2, -SO2R, -SO2N(R)2, -SOR, -C(O)R, -CO2R, -C(O)N(R)2, -NRC(O)R, -NRC(O)NR2, -NRSO2R or -N(R)2; R is H, (un)substituted C1-6 alkyl, (un)substituted Ph, (un)substituted 4- to 7-membered heterocycle having 1-2 heteroatoms, (un)substituted 5- to 6-membered monocyclic heteroaryl ring including 1-4 heteroatoms, and the heteroatoms are selected from N, O, and S; and their stereoisomers, tautomers, pharmaceutically active metabolites, pharmaceutically acceptable salts, hydrates, solvates, or prodrugs as kinase inhibitors in the treatment of diseases thereof, are claimed. Compound of formula I were prepared via condensation of 2-chloro-9H-purin-6-amine with 4-hydroxypiperidine; the resulting 2-chloro-9-(4-piperidinyl)-9H-purin-6-amine underwent acylation with acryloyl chloride to give to give 2-chloro-6-(acryloylamino)-9-(1-acryloylamino-4-piperidinyl)-9H-purine, which underwent condensation with amines to give I. All the invention compounds were evaluated for their BTK inhibitory activity. From the assay, it was determined that two of the tested compounds exhibited the IC50 value of 0.016 μM. The experimental process involved the reaction of N-(3-Aminophenyl)acrylamide(cas: 16230-24-3).Name: N-(3-Aminophenyl)acrylamide
The Article related to purine preparation btk kinase inhibitor treatment disease, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Name: N-(3-Aminophenyl)acrylamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics