US 12,325,699 B2
Antibacterial compounds
Min Teng, San Diego, CA (US); Baskar Nammalwar, San Diego, CA (US); Xiaoming Li, San Diego, CA (US); Christian Perez, San Diego, CA (US); Ian Yule, Abingdon (GB); Adele Faulkner, Abingdon (GB); Holly Atton, Abingdon (GB); Alastair Parkes, Abingdon (GB); Serge Convers-Reignier, Abingdon (GB); Michelle Southey, Abingdon (GB); and David T. Puerta, San Diego, CA (US)
Assigned to BLACKSMITH MEDICINES, INC., San Diego, CA (US)
Filed by Blacksmith Medicines, Inc., San Diego, CA (US)
Filed on Jun. 9, 2022, as Appl. No. 17/836,255.
Application 17/836,255 is a division of application No. 17/205,750, filed on Mar. 18, 2021, granted, now 11,407,740.
Application 17/205,750 is a continuation of application No. PCT/US2019/052021, filed on Sep. 19, 2019.
Claims priority of provisional application 62/767,313, filed on Nov. 14, 2018.
Claims priority of provisional application 62/734,173, filed on Sep. 20, 2018.
Prior Publication US 2022/0324846 A1, Oct. 13, 2022
Int. Cl. C07D 403/14 (2006.01); A61P 31/04 (2006.01); C07D 239/54 (2006.01); C07D 401/06 (2006.01); C07D 401/10 (2006.01); C07D 401/12 (2006.01); C07D 403/10 (2006.01); C07D 405/12 (2006.01); C07D 405/14 (2006.01); C07D 409/12 (2006.01); C07D 413/14 (2006.01); C07D 487/04 (2006.01); C07D 491/048 (2006.01); C07D 491/107 (2006.01)
CPC C07D 403/14 (2013.01) [A61P 31/04 (2018.01); C07D 239/54 (2013.01); C07D 401/06 (2013.01); C07D 401/10 (2013.01); C07D 401/12 (2013.01); C07D 403/10 (2013.01); C07D 405/12 (2013.01); C07D 405/14 (2013.01); C07D 409/12 (2013.01); C07D 413/14 (2013.01); C07D 487/04 (2013.01); C07D 491/048 (2013.01); C07D 491/107 (2013.01)] 18 Claims
 
1. A compound having the structure of Formula (II):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, or solvate thereof, wherein,
n is 0-4;
m is 0-4;
A1 is OH or SH;
A2 is O or S;
R1 and R2 are each independently H or optionally substituted alkyl;
or R1 and R2 are taken together with the carbon to which they are attached to form ═C(R11)2, ═NR11, ═O, or ═S;
or R1 and R2 are taken together with the carbon to which they are attached to form an optionally substituted 3- to 6-membered carbocyclyl or optionally substituted 4- to 7-membered heterocyclyl containing 1 or 2 heteroatoms selected from O, N, and S;
R3 is optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted carbocyclylalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, optionally substituted heteroaralkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted (C0-C4 alkylene)-COR11, optionally substituted (C0-C4 alkylene)-CO2R11, optionally substituted (C0-C4 alkylene)-CON(R11)2, optionally substituted (C0-C4 alkylene)-CN, optionally substituted (C0-C4 alkylene)-OR11, optionally substituted (C0-C4 alkylene)-N(R11)2, optionally substituted (C0-C4 alkylene)-N(R12)—COR11, optionally substituted (C0-C4 alkylene)-N(R12)—CO2R11, optionally substituted (C0-C4 alkylene)-N(R12)—CON(R11)2, optionally substituted (C0-C4 alkylene)-N(R12)—SO2N(R11)2, optionally substituted (C0-C4 alkylene)-O—SO2N(R11)2, optionally substituted (C0-C4 alkylene)-N(R11)—PO (optionally substituted C1-C4 alkyl)2, optionally substituted (C0-C4 alkylene)-SO2R11, optionally substituted (C0-C4 alkylene)-O—SO2R11, optionally substituted (C0-C4 alkylene)-N(R12)—SO2R11, optionally substituted (C0-C4 alkylene)-C(═N—OR11)(R11), or optionally substituted (C0-C4 alkylene)-OP(═O)(OR11)2;
R4 is H or optionally substituted alkyl;
or R3 and R4 are taken together with the carbon to which they are attached to form ═C(R11)2, ═NR11, ═O, or ═S;
or R3 and R4 are taken together with the carbon to which they are attached to form an optionally substituted 3- to 6-membered carbocyclyl or optionally substituted 4- to 7-membered heterocyclyl containing 1 or 2 heteroatoms selected from O, N, and S;
R5 is H, halogen, optionally substituted alkyl, hydroxyl, alkoxyl, cyano, amino, or nitro;
each X and Y is independently H, optionally substituted alkyl, halo, fluoroalkyl, cyano, nitro, —N(R13)2, or —OR13;
or R3 and one X are taken together with the intervening atoms to form an optionally substituted 5- to 7-membered carbocyclyl or optionally substituted 5- to 7-membered heterocyclyl containing 1 or 2 heteroatoms selected from O, N, and S;
Z is H, halo, nitro, or -L-G;
L is a bond or optionally substituted C1-C4 alkylene;
G is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, —CN, —N(R13)2, —OR13, —COR13, —CO2R13, —CON(R13)2, —N(R14)—COR13, —SO2R13—, —SO2N(R13)2, —N(R14)—SO2R13, —N(R14)—CON(R13)2, —N(R14)—CO2R13, —O—CON(R13)2—, —N(R14)—SO2N(R13)2, —O—SO2N(R13)2, —N(R14)—SO2—OR13, or —C(═N—OR14)(R13);
each R11 is independently H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted carbocyclylalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, or optionally substituted heteroarylalkyl;
or two R11 on the same nitrogen atom are taken together with the nitrogen to which they are attached to form an optionally substituted N-heterocyclyl;
each R12 is independently H, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted carbocyclylalkyl, optionally substituted heterocyclyl, or optionally substituted heterocyclylalkyl;
each R13 is H, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted carbocyclylalkyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heterocyclyl, optionally substituted heterocyclylalkyl, optionally substituted heteroaryl, or optionally substituted heteroarylalkyl; and
each R14 is independently H, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted carbocyclylalkyl, optionally substituted heterocyclyl, or optionally substituted heterocyclylalkyl;
wherein
each carbocyclyl is a stable non-aromatic monocyclic, fused polycyclic, or bridged polycyclic hydrocarbon ring comprising from three to ten carbon atoms;
each heterocyclyl is a stable 3- to 18-membered non-aromatic monocyclic, fused bicyclic, bridged bicyclic, or spirocyclic bicyclic ring system comprising from two to twelve carbon atoms and from one to six heteroatoms selected from nitrogen, oxygen, and sulfur which is optionally oxidized; and
each heterocyclylalkyl is a —Rc— heterocyclyl, where Rc is a C1-C8 alkylene.