US 11,053,196 B2
Substituted indoline derivatives as dengue viral replication inhibitors
Jean-François Bonfanti, Issy-les-Moulineaux (FR); Bart Rudolf Romanie Kesteleyn, Beerse (BE); Dorothée Alice Marie-Eve Bardiot, Leuven (BE); Arnaud Didier M Marchand, Leuven (BE); Erwin Coesemans, Beerse (BE); Benoît Christian Albert Ghislain De Boeck, Beerse (BE); and Pierre Jean-Marie Bernard Raboisson, Beerse (BE)
Assigned to Janssen Pharmaceuticals, Inc., Titusville, NJ (US); and Kathalieke Universiteif Leuven, Leuven (BE)
Appl. No. 16/614,715
Filed by JANSSEN PHARMACEUTICALS, INC., Titusville, NJ (US); and KATHOLIEKE UNIVERSITEIT LEUVEN, Leuven (BE)
PCT Filed May 18, 2018, PCT No. PCT/EP2018/063029
§ 371(c)(1), (2) Date Nov. 18, 2019,
PCT Pub. No. WO2018/215316, PCT Pub. Date Nov. 29, 2018.
Claims priority of application No. 17172247 (EP), filed on May 22, 2017.
Prior Publication US 2020/0181083 A1, Jun. 11, 2020
Int. Cl. C07D 209/04 (2006.01); A61P 31/14 (2006.01); C07D 495/04 (2006.01); A61K 45/06 (2006.01)
CPC C07D 209/04 (2013.01) [A61P 31/14 (2018.01); C07D 495/04 (2013.01); A61K 45/06 (2013.01); C07B 2200/07 (2013.01)] 25 Claims
 
1. A compound of formula (I), including any stereochemically isomeric form thereof,

OG Complex Work Unit Chemistry
wherein
A is

OG Complex Work Unit Chemistry
wherein
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is pentafluorosulfanyl, R5 is hydrogen, Z is carbon, and R6 is hydrogen; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethyl, R5 is hydrogen, Z is carbon, and R6 is methyl; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethyl, R5 is fluoro, Z is carbon, and R6 is hydrogen; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethoxy, R5 is hydrogen, Z is carbon, and R6 is methyl; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethoxy, R5 is fluoro, Z is carbon, and R6 is hydrogen; or
R1 is chloro, R2 is hydrogen, R3 is deuterium, A is (a-1), R4 is trifluoromethoxy, R5 is hydrogen, Z is carbon, and R6 is hydrogen; or
R1 is chloro, R2 is —OCH2CH2OH, R3 is hydrogen, A is (a-1), R4 is trifluoromethoxy, R5 is hydrogen, Z is carbon, and R6 is hydrogen; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethyl, R5 is methoxy, Z is nitrogen, and R6 is absent; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-2), and R4 is trifluoromethyl; or
R1 is chloro, R2 is hydrogen, R3 is hydrogen, A is (a-1), R4 is trifluoromethylthio, R5 is hydrogen, Z is carbon, and R6 is hydrogen;
or a pharmaceutically acceptable salt, solvate or polymorph thereof.