US 12,202,825 B2
Pyrimidine compounds and use thereof
Jang-Yang Chang, Taipei (TW); Meng-Ru Shen, Tainan (TW); Kak-Shan Shia, Taipei (TW); and Chien-Huang Wu, New Taipei (TW)
Assigned to National Health Research Institutes, Miaoli County (TW); and National Cheng Kung University, Tainan (TW)
Filed by National Health Research Institutes, Miaoli County (TW); and National Cheng Kung University, Tainan (TW)
Filed on Jul. 29, 2022, as Appl. No. 17/877,163.
Claims priority of provisional application 63/228,586, filed on Aug. 2, 2021.
Prior Publication US 2023/0085362 A1, Mar. 16, 2023
Int. Cl. C07D 413/14 (2006.01); A61P 23/00 (2006.01); A61P 25/02 (2006.01); C07D 403/14 (2006.01)
CPC C07D 413/14 (2013.01) [A61P 25/02 (2018.01); C07D 403/14 (2013.01)] 20 Claims
 
1. A compound of formula (I):

OG Complex Work Unit Chemistry
in which
R1 is H, halo, nitro, cyano, amino, C1-6 alkyl, C1-6 alkoxy, C3-10 cycloalkyl, C1-10 heterocycloalkyl, aryl, or heteroaryl;
W1 is C1-10 heterocycloalkyl or NH—CH2—Ar1-(CH2)m-A1;
one of W2 and W3 is NRaRb; and
the other of W2 and W3 is NH—CH2—Ar2-(CH2)n-A2,
wherein
each of Ar1 and Ar2, independently, is five-membered heteroaryl;
each of A1 and A2, independently, is H, OH, SH, CO2Rc, PO3RcRd, NH2, benzylamino, isopropylamino, ethanolamino, carbamido, guanidinyl, C1-6 alkoxy, C3-10 cycloalkyl, C3-10 cycloalkyloxy, C1-10 heterocycloalkyl, C1-10 heterocycloalkyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, or NCORc;
each of Ra and Rb, independently, is H, C1-6 alkyl, C3-10 cycloalkyl, C1-10 hetero-cycloalkyl, or Ra and Rb, together with the nitrogen atom to which they are bonded, are C1-10 heterocycloalkyl;
each of Rc and Rd, independently, is H, C1-6 alkyl, C3-10 cycloalkyl, C1-10 hetero-cycloalkyl, aryl, or heteroaryl;
each of C1-6 alkyl, C1-6 alkoxy, C3-10 cycloalkyl, C3-10 cycloalkyloxy, C1-10 hetero-cycloalkyl, C1-10 heterocycloalkyloxy, aryl, heteroaryl, aryloxy, heteroaryloxy, ethanolamino, benzylamino, and carbamido, is optionally substituted with hydroxyl, halo, nitro, cyano, amino, C1-6 alkyl, arylalkyl, C1-6 alkoxyl, C1-6 carboxyalkyl, aryl, heteroaryl, PO3ReRf, NCORe, NC(O)ORe, C(O)ORe, CORe, (CH2)x—PO3ReRf, (CH2)x—NCORe, or (CH2)x—C(O)ORe;
each of Re and Rf, independently, is H, C1-6 alkyl, C3-10 cycloalkyl, C1-10 hetero-cycloalkyl, aryl, or heteroaryl;
each of m and n, independently, is 0, 1, 2, 3, 4, or 5; and
x is 1, 2, 3, or 4.