Broad spectrum antibiotics

A compound of Formula (I):

• wherein:
• E1 and E2 are each independently (C1-C6)alkyl, (C2-C7)alkenyl, (C2-C7)alkynyl, (C3-C7)cycloalkyl, heterocyclyl, heteroaryl, or aryl;
• L1 is a bond, —O—, —S—, —NR4—, —C(O)—, —CH2O—, —OCH2—, —CH2S—, —SCH2—, —CH2NR4—, —NR4CH2—, —NR4C(O)—, —C(O)NR4—, —NR4S(O)2—, —S(O)2NR4—, —NR4C(O)NR4—, —NR4C(O)O—, —OC(O)NR4—, or (C1-C4)alkylene optionally substituted with OH, CN, NO2, halogen, or (C1-C6)alkyl;
• L2 is a bond, or optionally substituted (C1-C6)alkylene;
• X is C(O)R20 or S(O)2R20;
• R20 is optionally substituted alkyl, optionally substituted alkoxy, or NR20aR20b, where R20a is H or SO2(C1-C6)alkyl;
• and
• R20b is H;
• or X is a group of formula
• wherein n4, n5, and n6 are each independently 1, 2 or 3;
• n7 is 0, 1 or 2;
• R21b and R22b are independently at each occurrence hydrogen, hydroxy, (C1-C6)alkyl, (C3-C7)cycloalkyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclyl, or (C6-C10) aryl, wherein any alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with 1 to 3 J;
• R25 is OH, ORC,
• or NR25aR25b where R25a and R25b are each independently H, SO2(C1-C6)alkyl, or optionally substituted alkyl;
• RB1 and RB2 are each independently H, (C1-C6) alkyl, (C3-C6) cycloalkyl, ORC, C(═O)N(RC)2, OC(═O)N(RC)2, C(═O)ORC, OC(═O)ORC, nitro, trifluoromethyl, trifluoromethoxy, (C1-C6)alkoxy, (C1-C6)thioalkoxy, N(RC)2, 5-7 membered heterocyclyl, 5-7 membered heteroaryl, or (C6-C10) aryl;
• RC is independently at each occurrence H or (C1-C6) alkyl, and a wavy line indicates a point of attachment of X to a carbon of formula (I) bearing X;
• or X is
• R1 comprises a group of formula (IID), (IIE), or (IIF):
• wherein each n1 is independently at each occurrence 0, 1, or 2;
• Y is (CH2)0-2H, (CH2)0-2OH, or (CH2)0-2OC(═O)(C1-C6)alkyl;
• RA6 is hydrogen, (C1-C6)alkyl, (C3-C7)cycloalkyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclyl, or (C6-C10) aryl, wherein any alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with 1 to 3 substituents, wherein each substituent is independently selected from the group consisting of halogen, amino, hydroxyl, aminocarbonyl, hydroxycarbonyl, nitro, cyano, trifluoromethyl, trifluoromethoxy, 5- to 7-membered heterocyclyl, (C1-C6)alkoxy, (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)-mono- or di-alkylamino, (C1-C6)alkoxycarbonyl, (C1-C6)alkylhydroxycarbonyl, (C1-C6)alkylaminocarbonyl, (C1-C6)alkylsulfonylamino, and (C6-C10)-arylsulfonylamino;
• and a wavy line indicates a point of attachment of R1 to an atom of formula (I) bearing R1;
• R5 is aryl, heteroaryl, or a linear or branched alkyl chain of about 1-22 carbon atoms, wherein R5 is bonded to the carbonyl carbon to which it is attached directly or by an O or NR4, to provide an amide, carbamate, or urea linkage, respectively;
• optionally comprising within the chain or at a chain terminus optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted
• wherein Z is a bond, O, S, NH, CH2 or C≡C;
• R2 and R3 are each independently nitro, halo, cyano, hydroxy, glycosyloxy, amino, (C1-C4)alkoxy, (C1-C4)acyloxy, (C1-C4)alkyl, or a group cleavable under physiological conditions to provide a compound of formula (I) wherein R2 or R3 respectively is hydroxy, wherein any carbon atom is optionally substituted with J;
• or wherein two R2 groups taken together, and/or two R3 groups taken together, optionally comprise fused cycloalkyl, aryl, heterocyclyl, or heteroaryl ring or rings, any of which is optionally substituted with 1 to 3 J;
• n2 and n3 are independently 0, 1, 2, 3 or 4;
• each m is independently 0, 1, or 2;
• R4, R4′, R4″ and R6 are each independently at every occurrence hydrogen, (C1-C6)alkyl, (C3-C7)cycloalkyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclyl, or (C6-C10) aryl, wherein any alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with 1 to 3 J;
• RA1, RA1′, RA2, RA3, RA3′, RA4, RA4′, RA5, RA5′, RA7, RA7′, RA8, RA8′, RA9, RA9′, RA10, and RA10′ are independently at each occurrence hydrogen, (C1-C6)alkyl, (C3-C7)cycloalkyl, 5- to 7-membered heteroaryl, 5- to 7-membered heterocyclyl, or (C6-C10) aryl, wherein any alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with 1 to 3 J;
• J is halogen, R′, OR′, CN, CF3, OCF3, (CH2)0-pN(R′)2, (CH2)0-pSR′, (CH2)0-pS(O)R′, (CH2)0-pS(O)2R′, (CH2)0-pS(O)2N(R′)2, (CH2)0-pSO3R′, (CH2)0-pC(O)R′, (CH2)0-pC(O)CH2C(O)R′, (CH2)0-pC(S)R′, (CH2)0-pC(O)OR′, (CH2)0-pOC(O)R′, (CH2)0-pC(O)N(R′)2, (CH2)0-pOC(O)N(R′)2, (CH2)0-pC(S)N(R′)2, (CH2)0-pNH—C(O)R′, (CH2)0-pN(R′)N(R′)C(O)R′, (CH2)0-pN(R′)N(R′)C(O)OR′, (CH2)0-pN(R′)N(R′)CON(R′)2, (CH2)0-pN(R)SO2R′, (CH2)0-pN(R′)SO2N(R′)2, (CH2)0-pN(R′)C(O)OR′, (CH2)0-pN(R′)C(O)R′, (CH2)0-pN(R′)C(S)R′, (CH2)0-pN(R′)C(O)N(R′)2, (CH2)0-pN(R′)C(S)N(R′)2, (CH2)0-pN(COR′)COR′, (CH2)0-pN(OR′)R′, (CH2)0-pC(═NH)N(R′)2, (CH2)0-pC(O)N(OR′)R′, or (CH2)0-pC(═NOR′)R′;
• wherein p is 4,
• each R′ is independently at each occurrence hydrogen, (C1-C6)-alkyl, (C2-C7)-alkenyl, (C2-C7)-alkynyl, (C3-C10)-cycloalkyl, (C3-C10)-cycloalkenyl, aryl, or heteroaryl wherein any alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heteroaryl is optionally substituted with F, Cl, Br, I, —CN, —NO2, —OH, —CF3, —OCF3, —OCH3, —NH2, —N((C1-C4)alkyl)2-, —NH(C1-C4)alkyl, C3-C8cycloalkyl, or C1-C6heteroalkyl;
• or, when two R′ are bound to a nitrogen atom or to two adjacent nitrogen atoms, the two R′ groups together with the nitrogen atom or atoms to which they are bound form a 3- to 8-membered monocyclic heterocyclic ring, or an 8- to 20-membered, bicyclic or tricyclic, heterocyclic ring system, wherein any ring or ring system further contains 1-3 additional heteroatoms selected from the group consisting of N, NR′, O, S, S(O) and S(O)2, wherein each ring is substituted with 0-3 substituents selected independently from F, Cl, Br, I, —CN, —NO2, —OH, —CF3, —OCF3, —OCH3, —NH2, —N((C1-C4)alkyl)2-, —NH(C1-C4)alkyl, C1-C6alkyl, C3-C8cycloalkyl, or C1-C6heteroalkyl;
• wherein, in any bicyclic or tricyclic ring system, each ring is linearly fused, bridged, or spirocyclic, wherein each ring is either aromatic or nonaromatic, wherein each ring is optionally fused to an aryl, heteroaryl, (C3-C10)cycloalkyl, or mono- or bicyclic 3-10 membered heterocyclyl;
• or a pharmaceutically acceptable salt, solvate, or prodrug thereof.