US 11,866,419 B2
Antibacterial compounds
Jérôme Émile Georges Guillemont, Andé (FR); Magali Madeleine Simone Motte, Louviers (FR); Pierre Jean-Marie Bernard Raboisson, Rosieres (BE); and Abdellah Tahri, Anderlecht (BE)
Assigned to Janssen Sciences Ireland Unlimited Company, County Cork (IE)
Filed by Janssen Sciences Ireland Unlimited Company, Little Island (IE)
Filed on Sep. 17, 2021, as Appl. No. 17/477,970.
Application 16/460,334 is a division of application No. 15/736,375, granted, now 10,364,232, issued on Jul. 30, 2019, previously published as PCT/EP2016/065499, filed on Jul. 1, 2016.
Application 17/477,970 is a continuation of application No. 16/848,337, filed on Apr. 14, 2020, granted, now 11,180,472.
Application 16/848,337 is a continuation of application No. 16/460,334, filed on Jul. 2, 2019, abandoned.
Claims priority of application No. 15174936 (EP), filed on Jul. 2, 2015; application No. 16174713 (EP), filed on Jun. 16, 2016; and application No. 16174718 (EP), filed on Jun. 16, 2016.
Prior Publication US 2023/0014173 A1, Jan. 19, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/12 (2006.01); A61K 31/06 (2006.01); C07D 403/12 (2006.01); C07D 401/14 (2006.01); C07D 487/04 (2006.01); C07D 487/10 (2006.01); C07D 513/04 (2006.01); C07D 519/00 (2006.01); A61K 45/06 (2006.01); A61K 31/404 (2006.01); A61K 31/429 (2006.01); A61K 31/437 (2006.01); A61K 31/438 (2006.01); A61K 31/444 (2006.01); A61K 31/4745 (2006.01); A61K 31/496 (2006.01); A61K 31/4985 (2006.01); A61K 31/519 (2006.01); C07D 471/04 (2006.01); A61P 31/04 (2006.01); A61K 31/4709 (2006.01); A61K 31/498 (2006.01); A61P 31/06 (2006.01)
CPC C07D 401/12 (2013.01) [A61K 31/404 (2013.01); A61K 31/429 (2013.01); A61K 31/437 (2013.01); A61K 31/438 (2013.01); A61K 31/444 (2013.01); A61K 31/4709 (2013.01); A61K 31/4745 (2013.01); A61K 31/496 (2013.01); A61K 31/498 (2013.01); A61K 31/4985 (2013.01); A61K 31/519 (2013.01); A61K 45/06 (2013.01); A61P 31/04 (2018.01); A61P 31/06 (2018.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01); C07D 487/10 (2013.01); C07D 513/04 (2013.01); C07D 519/00 (2013.01)] 18 Claims
 
1. A compound of formula (IA) for use in the treatment of tuberculosis

OG Complex Work Unit Chemistry
wherein
R1 represents C1-6 alkyl or hydrogen;
L1 represents a linker group —C(Ra)(Rb)—;
X1 represents an aromatic linker group that is phenylene (which linker group may itself be optionally substituted by one or more substituents selected from fluoro, —OH, —OC1-6 alkyl and C1-6 alkyl, wherein the latter two alkyl moieties are themselves optionally substituted by one or more fluoro atoms);
Ra and Rb independently represent hydrogen or C1-6 alkyl (optionally substituted by one or more fluoro atoms);
Xa represents CH or N;
Xb represents CH, N, O (in which case L2 is not present) or C═O (in which case L2 is also not present);
q1 represents —CH2—, —CH2—CH2—, —O—CH2—, or “—”;
q2 represents —CH2—, or —CH2—CH2—;
q3 represents —CH2—, or —CH2—CH2—;
q4 represents —CH2—, or —CH2—CH2—;
when Xb represents O or C═O, then L2 is not present;
when Xb represents C(Ra) or N, then L2 may represent hydrogen, halo, —ORf, —C(O)—Rg, C1-6 alkyl (optionally substituted by one or more halo), or an aromatic group (optionally substituted by one or more substituents selected from halo, C1-6 alkyl (itself optionally substituted by one or more substituents selected from fluoro, —CF3 and/or —SF5), —OC1-6alkyl (itself optionally substituted by one or more fluoro atoms), —O-phenyl (itself optionally substituted by halo, C1-6alkyl, C1-6fluoroalkyl and/or —OC1-6alkyl) or —SF5); or, when Xb is N, L2 represents —S(O)2—C1-6alkyl optionally substituted by one or more fluoro atoms;
Rf represents hydrogen, C1-6 alkyl (optionally substituted by one or more fluoro) or an aromatic group (itself optionally substituted by one or more substituents selected from halo, C1-6alkyl and —OC1-6alkyl, where the latter two alkyl moieties may themselves be optionally substituted by one or more fluoro atoms);
Rg represents hydrogen or C1-6alkyl (optionally substituted by one or more substituents selected from fluoro, or —OC1-3 alkyl, which latter moiety is also optionally substituted by one or more fluoro atoms) or an aromatic group (optionally substituted by one or more substituents selected from halo, C1-6 alkyl or —OC1-6alkyl);
wherein the combined ring systems, i.e. Ring A and Ring B may be represented as follows:

OG Complex Work Unit Chemistry
either ring A and/or ring B may be optionally substituted by one or more substituents selected from: halo, C1-6 alkyl (optionally substituted by one or more halo) and/or —OC1-6alkyl (itself optionally substituted by one or more fluoro atoms),
or a pharmaceutically-acceptable salt thereof.