On July 6, 2021, Yu, Hongtao; Hu, Qi; Huang, Jing; Wang, Tingliang; Hou, Ningke; Zhang, Lijing; Zhang, Wenyi; Tan, Qiaozhu published a patent.Synthetic Route of 1378839-26-9 The title of the patent was Preparation of heterocyclic derivatives as 3C like protease inhibitors. And the patent contained the following:
The invention relates to the preparation of heterocyclic derivatives with general formula I as 3C like protease inhibitors, where Ar = Ph or 6-membered heteroaryl; ring A = 9 or 10-membered heteroaryl, wherein: V1 , V2, V3, and V4 = not present, CH or N; and at most one of V1, V2, V3, and V4 may not exist; when one of W1, W2, W3, and W4 does not exist, then V1, V2, V3, and None of V4 can be absent; W1, W2, W3, and W4 = not present, CH or N; at most one of W1, W2, W3, and W4 can be absent; at least one of W1, W2, W3, and W4 must be N; X = absent, NRa or NRa(CRbRc)a; Y = absent, C3-C12 carbocyclyl, 3-12 membered heterocyclic group, or 5-10 membered heteroaryl; Z = absent, NRd, (CReRf)bNRd or C(=O)NRd(CRgRh)c; Ra and Rd = hydrogen or C1-C4 alkyl; Rb, Rc, Re and Rf = hydrogen or substituted C1-C4 alkyl; Rg and Rh = hydrogen or substituted C1-C4 alkyl; Ri and Rj = hydrogen or C1-C4 alkyl; a, b and c = 1, 2, 3 or 4; R1, R2. And R3 = halogen, cyano, C1-C6 alkane Group, C2-C6 alkenyl, C1-C6 alkoxy, C(=O)(C1-C6 alkyl), C(=O)NRpRq, NRpRq, NRpC(=O)Rs, NRpC(=O)ORs , NRpC(=O)NRqRr, NRpS(=O)wRs, NO2, NO2+, NH(=O)OH, ORs, OC(=O)Rs, OC(=O)ORs, OC(=O)NRpRq, S(=O)wRs, S(=O)wNRpRq, SO3, C3-C12 carbocyclic group, 3-12 membered heterocyclic group, Ph, 5-10 membered heteroaryl; Rp, Rq and Rr = hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl; Rs = hydrogen, C1-C4 alkyl or C3-C6 cycloalkyl; m = 0 For example, 5-bromo-2-((1-(5-hydroxyisoquinoline-4-carbonyl)piperidin-3-yl)amino)-N-methyl-3-nitrobenzamide was prepared by a multi-step reaction. The title compounds have good inhibitory effect on 3C like protease and can be used to treat SARS-COV-2 infection. The experimental process involved the reaction of 7-Hydroxyisoquinoline-4-carboxylic acid(cas: 1378839-26-9).Synthetic Route of 1378839-26-9
The Article related to amidation coupling hydrolysis preparation piperazine isoquinoline treatment human coronavirus, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Synthetic Route of 1378839-26-9
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem