Bacterial efflux pump inhibitors

A compound of formula I:

• wherein:
• R1 is:
• (a) (C1-C14)alkyl wherein the (C1-C14)alkyl is substituted with one or more —NRa1Rb1 groups, and wherein the (C1-C14)alkyl is substituted with one or more groups independently selected from the group consisting of —OH, —ORc, —CN, NO2, —B(OH)2, —SO2Rd, —CO2Re, —OC(═O)—NRa2Rb2, and —O(C═O)—(C1-C6)alkyl-NRa2Rb2, and wherein the (C1-C14)alkyl is optionally substituted independently with one or more halo, (C1-C4)alkyl or (C3-C7)carbocyclyl;
• or
• (b) 4-7 membered monocyclic heterocyclyl-(C1-C6)alkyl- wherein the 4-7 membered monocyclic heterocyclyl-(C1-C6)alkyl- is substituted independently with one or more Z1 or Z2, and wherein the 4-7 membered monocyclic heterocyclyl-(C1-C6)alkyl- is substituted independently with one or more oxo, Z3, or Z4, and wherein the 4-7 membered monocyclic heterocyclyl-(C1-C6)alkyl- is optionally substituted independently with one or more halo, (C1-C4)alkyl, or (C3-C7)carbocyclyl;
• R2 is hydrogen, (C1-C4)alkyl, or (C3-C7)carbocyclyl;
• R3 is hydrogen, halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, —OH, —X—(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl, wherein the —X—(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl is independently optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, —NO2, —CN, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, and (C1-C4)haloalkoxy;
• R4 is hydrogen, halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, —OH, X-aryl, —X-heterocyclyl, or —X-heteroaryl, wherein the —X—(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl is independently optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, —NO2, —CN, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C6)alkoxy, and (C1-C4)haloalkoxy;
• R5 is hydrogen, halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, —OH, X-aryl, —X-heterocyclyl, or —X-heteroaryl, wherein the —X—(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl is independently optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, —NO2, —CN, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, and (C1-C4)haloalkoxy;
• R6 is hydrogen, halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, —OH, X-aryl, —X-heterocyclyl, or —X-heteroaryl, wherein the —X—(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl is independently optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, —NO2, —CN, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, and (C1-C4)haloalkoxy;
• R7 is hydrogen, halo, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, —OH, X-aryl, —X-heterocyclyl, or —X-heteroaryl, wherein the ~X-(C3-C7)carbocyclyl, —X-aryl, —X-heterocyclyl, or —X-heteroaryl is independently optionally substituted with one or more groups independently selected from the group consisting of halo, —OH, —NO2, —CN, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, and (C1-C4)haloalkoxy;
• R8 is hydrogen, (C1-C4)alkyl, or (C3-C7)carbocyclyl;
• each X is independently absent, —(C1-C6)alkyl-, —O—, —S—, —S(═O)—, —S(═O)2, or —NRf—;
• Z1 is —NRd1Rb1,
• each Z2 is independently —(C1-C6)alkyl substituted with one or more Z1, wherein the —(C1-C6)alkyl is optionally substituted independently with one or more halo or (C3-C7)carbocyclyl;
• each Z3 is independently —OH, —ORE, —CN, NO2, —B(OH)2, —SO2Rd, —CO2Re, —OC(═O)—NRa2Rb2 and —O(C═O)—(C1-C6)alkyl-NRa2Rb2,
• each Z4 is independently —(C1-C6)alkyl substituted with one or more Z3, wherein the —(C1-C6)alkyl is optionally substituted independently with one or more halo or (C3-C7)carbocyclyl;
• each Ra1 and Rb1 is independently hydrogen, (C1-C6)alkyl or (C3-C7)carbocyclyl;
• each Ra2 and Rb2 is independently hydrogen, (C1-C6)alkyl, or (C3-C7)carbocyclyl;
• and
• each Ra3 and Rb3 is independently hydrogen, (C1-C6)alkyl, or (C3-C7)carbocyclyl;
• each Rc is independently (C1-C6)alkyl, wherein the (C1-C6)alkyl is optionally substituted independently with one or more —NRa3Rb3, OH, (C1-C6)alkoxy, or (C1-C6)haloalkoxy;
• each Rd is independently (C1-C6)alkyl or (C3-C7)carbocyclyl;
• each Re is independently hydrogen, (C1-C6)alkyl, or (C3-C7)carbocyclyl;
• and
• each Rf is independently hydrogen, (C1-C6)alkyl, or (C3-C7)carbocyclyl;
• or a salt thereof.