US 10,889,566 B2
Derivatives and composition of quinoline and naphthyridine
Supanna Techasakul, Bangkok (TH); Arthit Makarasen, Bangkok (TH); Nanthawan Reuk-Ngam, Bangkok (TH); Panita Khlaychan, Bangkok (TH); Mayuso Kuno, Bangkok (TH); and Supa Hannongbua, Bangkok (TH)
Assigned to Chulabhorn Foundation, Bangkok (TH); Kasetsart University, Bangkok (TH); and Srinakharinwirot university, Bangkok (TH)
Appl. No. 16/638,330
Filed by CHULABHORN FOUNDATION, Bangkok (TH); KASETSART UNIVERSITY, Bangkok (TH); and SRINAKHARINWIROT UNIVERSITY, Bangkok (TH)
PCT Filed Aug. 29, 2017, PCT No. PCT/TH2017/000066
§ 371(c)(1), (2) Date Feb. 11, 2020,
PCT Pub. No. WO2019/045655, PCT Pub. Date Mar. 7, 2019.
Prior Publication US 2020/0223820 A1, Jul. 16, 2020
Int. Cl. C07D 215/44 (2006.01); A61K 31/47 (2006.01); C07D 401/12 (2006.01); A61P 31/18 (2006.01); A61P 35/02 (2006.01)
CPC C07D 401/12 (2013.01) [A61P 31/18 (2018.01); A61P 35/02 (2018.01)] 14 Claims
 
1. A compound of the formula (I):

OG Complex Work Unit Drawing
where
X and Y may be identical or different and represent O, NH, or S;
R1, R2, R3, R4, R5, R6, R7, R8, R9, and R10 may be identical or different and represent H, halogen, CN, NO2, (C1-4)alkyl, (C1-4)haloalkyl, (C2-4)alkenyl, OH, O(C1-4)alkyl, O(C1-4)haloalkyl, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, CHO, C2-4 alkenyl substituted with CN, C2-4 alkenyl substituted with COOH, C2-4 alkenyl substituted with CHO, or C2-4 alkenyl substituted with OH;
RA and RB may be identical or different and represent H, (C1-4)alkyl, (C1-4)haloalkyl, or (C2-4)alkenyl;
A1, A2, A3, and A4 may be identical or different and represent CH or N with the proviso that either A1 or A2 is N, A1 and A2 cannot both be N, and R5 and R10 are absent when A3 and A4 are N;
or a pharmaceutically acceptable salt thereof, stereoisomer thereof, or mixture comprising stereoisomers thereof.