Antibacterial agents: O-alkyl-deuterated pyronins

A compound of formula Ia, Ib, Ic, or Id:

• or a salt thereof, wherein:
• W is sulfur, oxygen, or nitrogen;
• X, Y, and Z are individually carbon, sulfur, oxygen, or nitrogen, wherein at least two of X, Y, and Z are carbon;
• one of R1 and R2 is C1-C10 alkyl, C2-C10 alkenyl, C1-C10 alkoxy, aryloxy, heteroaryloxy, or NRaRb, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkoxy, tetrahydrofuranyl, or furanyl, and wherein any aryloxy or heteroaryloxy is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, C1-C5 alkoxy, aryl, or heteroaryl, wherein any C1-C5 alkyl, C1-C5 alkoxy, aryl, and heteroaryl is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, or C1-C5 alkoxy;
• or one of R1 and R2 is a 5-6-membered saturated, partially unsaturated, or aromatic heterocycle that is optionally substituted by at least one of halogen, hydroxy, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy;
• and the other of R1 and R2 is absent or is one of H, halogen, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy is optionally substituted by at least one of halogen, hydroxy, or C1-C5 alkoxy;
• R3 is absent, or is one of H, C1-C2 alkyl, or halogen-substituted C1-C2 alkyl;
• R4 is absent, or is one of H, halogen, C1-C2 alkyl, or halogen-substituted C1-C2 alkyl;
• V′, W′, X′, Y′, and Z′ are individually carbon or nitrogen;
• wherein at least three of V′, W′, X′, Y′, and Z′ are carbon;
• one of R1′ and R2′ is C1-C10 alkyl, C2-C10 alkenyl, C1-C10 alkoxy, aryloxy, heteroaryloxy, or NRaRb, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkoxy, tetrahydrofuranyl, or furanyl, and wherein any aryloxy or heteroaryloxy is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, C1-C5 alkoxy, aryl, or heteroaryl, wherein any C1-C5 alkyl, C1-C5 alkoxy, aryl, and heteroaryl is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, or C1-C5 alkoxy;
• or one of R1′ and R2′ is a 5-6-membered saturated, partially unsaturated, or aromatic heterocycle that is optionally substituted by at least one of halogen, hydroxy, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy;
• and the other of R1′ and R2′ is absent or is one of H, halogen, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy is optionally substituted by at least one of halogen, hydroxy, or C1-C5 alkoxy;
• R3′, R4′, and R5′ are each independently absent, H, halogen, C1-C2 alkyl, or halogen-substituted C1-C2 alkyl;
• W″ is sulfur, oxygen, or nitrogen;
• U″, V″, X″, Y″, and Z″ are individually carbon, sulfur, oxygen, or nitrogen, wherein at least three of U″, V″, X″, Y″, and Z″ are carbon;
• one of R1″ and R2″ is C1-C10 alkyl, C2-C10 alkenyl, C1-C10 alkoxy, aryloxy, heteroaryloxy, or NRaRb, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkoxy, tetrahydrofuranyl, or furanyl, and wherein any aryloxy or heteroaryloxy is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, C1-C5 alkoxy, aryl, or heteroaryl, wherein any C1-C5 alkyl, C1-C5 alkoxy, aryl, and heteroaryl is optionally substituted by at least one of halogen, hydroxy, C1-C5 alkyl, or C1-C5 alkoxy;
• or one of R1″ and R2″ is a 5-6-membered saturated, partially unsaturated, or aromatic heterocycle that is optionally substituted by at least one of halogen, hydroxy, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy;
• and the other of R1″ and R2″ is absent or is one of H, halogen, C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy, wherein any C1-C10 alkyl, C2-C10 alkenyl, or C1-C10 alkoxy is optionally substituted by at least one of halogen, hydroxy, or C1-C5 alkoxy;
• R3″ is absent or is one of H, C1-C2 alkyl, or halogen-substituted C1-C2 alkyl;
• R4″, R5″, and R6″ are each independently absent, H, halogen, C1-C2 alkyl, or halogen-substituted C1-C2 alkyl;
• R5 is H or M+, where M+ is a pharmaceutically acceptable cation;
• R6 is H, halogen, or methyl that is optionally substituted with halogen;
• R9 is C1-C10 alkyl or C2-C10 alkenyl, wherein any C1-C10 alkyl or C2-C10 alkenyl is optionally substituted by at least one of halogen, hydroxy, alkoxy, or NRaRb;
• R10 is methyl that is substituted with 1, 2, or 3 deuterium atoms;
• one of R12 and R13 s hydrogen or C1-C4 straight alkyl, and the other of R12 and R13 is C1-C10 straight or branched alkyl, C2-C12 straight or branched hydroxyalkyl, C2-C12 straight or branched alkenyl, C2-C12 straight or branched hydroxyalkenyl, phenyl, C7-C12 aralkyl, C7-C12 (aryl)hydroxyalkyl, C6-C12 heteroaralkyl, C6-C12 (heteroaryl)hydroxyalkyl, or R12 and R13 are taken together with their intervening atom to form a 4-6 membered ring having 0-1 ring heteroatoms selected from nitrogen, oxygen or sulfur, said ring optionally substituted by one or two C1-C6 alkyl, C2-C6 alkenyl or hydroxyalkyl groups, wherein an alkyl, aryl or heteroaryl moiety of R12 and R13 optionally is substituted with 1-3 groups independently selected from halo, —C1-C6 hydroxyalkyl, —C1-C4 alkoxy, —C1-C4 trifluoroalkoxy, —CN, —C1-C4 alkoxycarbonyl, —C1-C4 alkylcarbonyl, —S(C1-C4 alkyl), and —SO2(C1-C4 alkyl);
• each Ra is C1-C10 alkyl that is optionally substituted by at least one of halogen, hydroxy, or C1-C5 alkoxy;
• and
• each Rb is H or C1-C10 alkyl that is optionally substituted by at least one of halogen, hydroxy, or C1-C5 alkoxy.