US 9,809,602 B2
Compounds for treating viral infections
Marc P. Windisch, Datteln (DE); Hee-Young Kim, Gyeonggi-do (KR); Jaewon Yang, Gyeonggi-do (KR); Jong Yeon Hwang, Jeollabuk-do (KR); Suyeon Jo, Gyeonggi-do (KR); Jeongjin Kwon, Gyeonggi-do (KR); Dongsik Park, Gyeonggi-do (KR); Jihyun Choi, Seoul (KR); and Jaeheon Lee, Seoul (KR)
Assigned to Institut Pasteur Korea, Seongnam-si (KR)
Appl. No. 15/304,612
Filed by INSTITUT PASTEUR KOREA, Gyeonggi-do (KR)
PCT Filed Apr. 17, 2015, PCT No. PCT/EP2015/058421
§ 371(c)(1), (2) Date Oct. 17, 2016,
PCT Pub. No. WO2015/158908, PCT Pub. Date Oct. 22, 2015.
Claims priority of provisional application 61/980,940, filed on Apr. 17, 2014.
Prior Publication US 2017/0044181 A1, Feb. 16, 2017
Int. Cl. C07D 495/04 (2006.01); A61K 45/06 (2006.01); A61K 31/4365 (2006.01); C07D 333/68 (2006.01); C07D 211/44 (2006.01); C07D 295/12 (2006.01); C07D 211/58 (2006.01); C07D 409/14 (2006.01); C07D 401/04 (2006.01); C07D 407/12 (2006.01); C07D 211/14 (2006.01); C07D 487/04 (2006.01); C07D 401/06 (2006.01); C07D 401/12 (2006.01); C07D 409/12 (2006.01)
CPC C07D 495/04 (2013.01) [A61K 31/4365 (2013.01); A61K 45/06 (2013.01); C07D 211/14 (2013.01); C07D 211/44 (2013.01); C07D 211/58 (2013.01); C07D 295/12 (2013.01); C07D 333/68 (2013.01); C07D 401/04 (2013.01); C07D 401/06 (2013.01); C07D 401/12 (2013.01); C07D 407/12 (2013.01); C07D 409/12 (2013.01); C07D 409/14 (2013.01); C07D 487/04 (2013.01)] 17 Claims
 
1. A compound having Formula (If):

OG Complex Work Unit Drawing
wherein
RD is selected from the group consisting of halo; cyano; C1-C5 alkyl; C3-C6 cycloalkyl; C1-C3 alkoxy; C1-C3 haloalkyl; C1-C3 sulfanyl; phenyl; aryl; heteroaryl; —NRGRH; —C(O)NRaRb; —C(O)Rc; —C(O)ORc; sulfonyl; sulfoxide;
RO and RP are each independently at each occurrence selected from the group consisting of H, C1-C5 alkyl, C1-C5 alkenyl, C1-C5 alkynyl, C3-C6 cycloalkyl; heterocycloalkyl; heteroaryl; phenyl; with either the proviso that, when one of RO or RP is H, then the other one of RO or RP is not methyl; or with the proviso that the compound is not;

OG Complex Work Unit Drawing
RO and RP are joined together, forming a cycloalkyl group, cycloalkenyl group, or heterocycloalkyl group optionally substituted with one to four RI groups; wherein RI is selected from the group consisting of H; halo; cyano; C1-C5 alkyl; C1-C3 sulfanyl; C1-C4 alkoxy; C1-C3 haloalkyl; hydroxyl; oxo; —NRaRb; —C(O)NRaRb; —C(O)Rc; —C(O)ORc; sulfonyl; sulfoxide; (CH2)pOH; (CH2)pORa; (CH2)pNRGRH; (CH2)pOC(O)NRaRb; (CH2)pC(O)NRaRb; C3-C6 cycloalkyl; heterocycloalkyl; aryl; heteroaryl; phenyl;
RG is selected from the group consisting of H; C1-C6 alkyl; C1-C6 alkoxy; C3-C6 cycloalkyl; heterocycloalkyl; heteroaryl; phenyl;
RH is selected from the group consisting of H; C1-C6 alkyl; C1-C6 alkoxy; C3-C6 cycloalkyl; heterocycloalkyl; heteroaryl; phenyl; or
RG and RH, together with the nitrogen atom to which they are bonded, form a 4- to 10-membered saturated or unsaturated heterocyclic ring which is optionally substituted with one or more C1-C3 alkyl, benzyl, phenyl, C1-C3 alkoxy or halogen;
RC is selected from C1-C10 alkyl, C1-C10 alkenyl, C1-C10 alkynyl, C3-C10 cycloalkyl, C1-C3 haloalkyl, aryl, heteroaryl, heterocycloalkyl, wherein each of the aforementioned alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl and heterocycloalkyl may be substituted with one or more of hydroxyl, halo, alkoxy, oxo, sulfonyl, sulfoxide, aryl, heteroaryl or —NRaRb;
RM is selected from the group consisting of H; C1-C6 alkyl, C3-C6 cycloalkyl, C1-C3 haloalkyl, phenyl; aryl; heteroaryl; —NRGRH; —C(O)NRaRb; —C(O)Rc; —C(O)ORc; sulfonyl; sulfoxide; C1-C6 alkyl substituted with hydroxyl, alkoxy, —NRaRb, phenyl, —NRGRH, —C(O)NRaRb, —C(O)Rc, —C(O)ORc; sulfonyl, or sulfoxide;
RQ and RR represents a substituent which is at each occurrence independently selected from the group consisting of H; halo; cyano; C1-C5 alkyl; C3-C6 cycloalkyl; C1-C3 alkoxy; C1-C3 haloalkyl; C1-C3 sulfanyl; phenyl; aryl; heteroaryl; —NRGRH; —C(O)NRaRb; —C(O)Rc; —C(O)ORc; sulfonyl; sulfoxide; (CH2)pOH; (CH2)pORa; (CH2)pNRGRH; (CH2)pOC(O)NRaRb; (CH2)pC(O)NRaRb;
Ra and Rb are each independently at each occurrence selected from the group consisting of hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C6-C14 alkyl chain containing one or several of —O—, —C(O)NH—, —NHC(O)—, —N—, or —NHC(O)O— optionally with a terminal —NH2 or —NH-Boc; C1-C6 alkenyl, substituted C1-C6 alkenyl, C1-C6 alkynyl, substituted C1-C6 alkynyl, C3-C7 cycloalkyl, substituted C3-C7 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl; or
Ra and Rb, together with the nitrogen atom to which they are bonded, form a 4- to 10-membered saturated or unsaturated heterocyclic ring which is optionally substituted with one or more C1-C3 alkyl, benzyl, phenyl, C1-C3 alkoxy or halogen;
Rc is selected from the group consisting of hydrogen, C1-C10, C1-C10 alkenyl, C1-C10 alkynyl, C3-C10 cycloalkyl, C1-C3 haloalkyl, aryl, heteroaryl, heterocycloalkyl,
wherein each of the aforementioned alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl and heterocycloalkyl may be substituted with one or more of hydroxyl, halo, alkoxy, oxo, sulfonyl, sulfoxide, aryl, heteroaryl or —NRaRb;
m is an integer from 0 to 2;
k is an integer from 0 to 2;
p is an integer from 0 to 5;
q is an integer from 1 to 3; and
r is an integer from 1 to 3,
and pharmaceutically acceptable salts thereof.