US 11,655,225 B2
Antimycobacterial heterocyclic amides
Joshua Day, Boulder, CO (US); James Graham, Boulder, CO (US); Thale Jarvis, Boulder, CO (US); Elizabeth Mcfaddin, Nederland, CO (US); Urs Ochsner, Boulder, CO (US); Xicheng Sun, Boulder, CO (US); and Christina Wong, Boulder, CO (US)
Assigned to CRESTONE, INC., Boulder, CO (US)
Appl. No. 16/976,743
Filed by Crestone, Inc., Boulder, CO (US)
PCT Filed Feb. 28, 2019, PCT No. PCT/US2019/020095
§ 371(c)(1), (2) Date Aug. 28, 2020,
PCT Pub. No. WO2019/169158, PCT Pub. Date Jun. 9, 2019.
Claims priority of provisional application 62/636,328, filed on Feb. 28, 2018.
Prior Publication US 2021/0002239 A1, Jan. 7, 2021
Int. Cl. C07D 277/82 (2006.01); C07D 235/30 (2006.01); C07D 263/58 (2006.01); C07D 277/68 (2006.01); C07D 333/72 (2006.01); A61P 31/04 (2006.01); A61P 31/06 (2006.01)
CPC C07D 277/82 (2013.01) [A61P 31/04 (2018.01)] 8 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
in which:
X is selected from C or N,
Y is selected from N, O or S,
n=1-6
R1, R2, R3, R4 are independently selected from the group consisting of H, halogens, small alkyl (C1-C6), small alkyloxy (C1-C6), halogenated small alkyl (C1-C6), halogenated small alkyloxy (C1-C6), and carboxylates,
when X is carbon, R5 is selected from the group consisting of H, alkyl, halogens, and cyano, when X is nitrogen, R5 is null,
when Y is nitrogen, R6 is selected from the group consisting of H, alkyl, and substituted alkyl, when Y is O or S, R6 is null,
R7 is selected from the group consisting of H, small alkyl (C1-C6), halogenated small alkyl (C1-C6), R7 can not be H when n<3,
each R8 is independently selected from the group consisting of H, small alkyl (C1-C6), halogenated small alkyl (C1-C6), m is 1-6,
R7 and R8 can link together to form rings when they are alkyl or halogenated alkyl with proviso that

OG Complex Work Unit Chemistry
 does not include: 4-propylcyclohexane-1-carbonyl, 1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexane-1-carbonyl, 4-methylcyclohexane-1-carbonyl, 4-butylcyclohexane-1-carbonyl, cyclohexanecarbonyl, cyclopentanecarbonyl, cyclobutanecarbonyl, cycloheptanecarbonyl, 3-(trifluoromethyl)cyclohexane-1-carbonyl, 4,4-difluorocyclohexane-1-carbonyl, bicyclo[3.1.0]hexane-3-carbonyl, 1-methylcyclopentane-1-carbonyl, bicyclo[2.2.1]heptane-2-carbonyl, adamantane-1-carbonyl, 3-bromoadamantane-1-carbonyl, 3-chloroadamantane-1-carbonyl, 3,5-dimethyladamantane-1-carbonyl, 3-methyladamantane-1-carbonyl, 5,5,6-trifluoro-6-(trifluoromethyl)bicyclo[2.2.1]heptane-2-carbonyl, adamantane-2-carbonyl.