Antimicrobial compounds and methods of making and using the same

A compound of formula (AA):

• or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer, wherein:
• J is selected from
• X is selected from a 5- or 6-membered heterocyclyl ring and phenyl, wherein each of the 5- or 6-membered heterocyclyl ring and phenyl is optionally substituted with one or more Rx;
• Z is selected from
• R1 is selected from H, C1-3 alkyl, and C2-4 alkenyl;
• R2 is selected from H and C1-3 alkyl;
• R3 is selected from H and C1-3 alkyl;
• or R2 and R3 together with the nitrogen atoms to which they are attached and the carbon atom connecting the two nitrogen atoms form a 5- or 6-membered ring;
• or R1 and R3 together with the nitrogen and sulfur atom to which they are attached and the carbon atom connecting the two nitrogen atoms form a 5- or 6-membered ring;
• R4 is selected from H and C1-3 alkyl;
• R5 is selected from H and C1-6 alkyl;
• R6 is selected from H, C1-6 alkyl, C2-6 alkenyl, and C3-6 cycloalkyl, wherein the C1-6 alkyl is optionally substituted with one or more substituents selected from the group consisting of halogen, ORa, SRa, —C(O)ORa, —SC(NH)NH2, C3-6 cycloalkyl, and 3-6 membered heterocyclyl;
• R7 is selected from H and C1-6 alkyl;
• or R6 and R7 together with the carbon and nitrogen atoms to which they are attached form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted with one or more OH;
• or R5 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting the two carbon atoms form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with OH;
• Q is selected from C1-2 alkylene or —C(O)—;
• R21 is selected from H, C1-6 alkyl optionally substituted with 1-3 halo;
• R8 is selected from H and halogen;
• each RX is independently selected from halogen, C1-6 alkyl, C1-4 haloalkyl, ORc, N(Rc)2, —C(O)ORc, —C(O)Rc, C3-6 cycloalkyl, and aryl, wherein the C1-6 alkyl is optionally substituted with one or more Rb;
• or two adjacent Rx come together with the atoms to which they are attached to form a 5- or 6-membered ring;
• each Ra is independently selected from H and C1-6 alkyl;
• each Rb is independently selected from C2-6 alkenyl, ORc, N(Rc)2, —C(O)ORc, C3-6 cycloalkyl, OC(NH)NH2, and aryl;
• each Rc is independently selected from H, C1-6 alkyl, aryl, —C(O)aryl, and —(CH2)aryl, wherein the C1-6 alkyl and the aryl are each optionally substituted with one or more Rd;
• and
• each Rd is independently selected from C1-3 alkyl, OH, O(C1-3 alkyl), NO2, NH2, NH(C1-3 alkyl), and N(C1-3 alkyl)2;
• or
• a compound of Formula (A):
• or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer, wherein:
• X is selected from a 5- or 6-membered heterocyclyl ring and phenyl, wherein each of the 5- or 6-membered heterocyclyl ring and phenyl is optionally substituted with one or more Rx,
• Z is selected from
• R1 is selected from H and C1-3 alkyl;
• R2 is selected from H and C1-3 alkyl;
• R3 is selected from H and C1-3 alkyl;
• or R2 and R3 together with the nitrogen atoms to which they are attached and the carbon atom connecting the two nitrogen atoms form a 5- or 6-membered ring;
• R4 is selected from H and C1-3 alkyl;
• R5 is selected from H and C1-6 alkyl;
• R6 is selected from H, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with one or more substituents selected from the group consisting of halogen, ORa, SRa, —C(O)ORa, —SC(NH)NH2, C3-6 cycloalkyl, and 3-6 membered heterocyclyl;
• R7 is selected from H and C1-6 alkyl;
• or R6 and R7 together with the carbon and nitrogen atoms to which they are attached form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted with one or more OH;
• or R5 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting the two carbon atoms form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with OH;
• Q is selected from C1-2 alkylene or —C(O)—;
• R21 is selected from H, C1-6 alkyl optionally substituted with 1-3 halo;
• R8 is selected from H and halogen;
• each Rx is independently selected from halogen, C1-6 alkyl, C1-4 haloalkyl, ORc, N(Rc)2, —C(O)ORc, —C(O)Rc, C3-6 cycloalkyl, and aryl, wherein the C1-6 alkyl is optionally substituted with one or more Rb;
• or two adjacent Rx come together with the atoms to which they are attached to form a 5- or 6-membered ring;
• each Ra is independently selected from H and C1-6 alkyl;
• each Rb is independently selected from C2-6 alkenyl, ORc, N(Rc)2, —C(O)ORc, C3-6 cycloalkyl, and aryl;
• each Rc is independently selected from H, C1-6 alkyl, aryl, —C(O)aryl, and —(CH2)aryl, wherein the C1-6 alkyl and the aryl are each optionally substituted with one or more Rd;
• and
• each Rd is independently selected from C1-3 alkyl, OH, O(C1-3 alkyl), NO2, NH2, NH(C1-3 alkyl), and N(C1-3 alkyl)2;
• or a compound of Formula (I)
• or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer, wherein:
• X is selected from a 5- or 6-membered heterocyclyl ring and phenyl, wherein each of the 5- or 6-membered heterocyclyl ring and phenyl is optionally substituted with one or more Rx,
• R1 is selected from H and C1-3 alkyl;
• R2 is selected from H and C1-3 alkyl;
• R3 is selected from H and C1-3 alkyl;
• or R2 and R3 together with the nitrogen atoms to which they are attached and the carbon atom connecting the two nitrogen atoms form a 5- or 6-membered ring;
• R4 is selected from H and C1-3 alkyl;
• R5 is selected from H and C1-6 alkyl;
• R6 is selected from H, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with one or more substituents selected from the group consisting of halogen, ORa, SRa, —C(O)ORa, —SC(NH)NH2, C3-6 cycloalkyl, and 3-6 membered heterocyclyl;
• R7 is selected from H and C1-6 alkyl;
• or R6 and R7 together with the carbon and nitrogen atoms to which they are attached form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with C1-6 alkyl,
• wherein the C1-6 alkyl is optionally substituted with one or more OH;
• or R5 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting the two carbon atoms form a ring having one of the formulas:
• wherein the ring is optionally substituted on a ring carbon atom with OH;
• R8 is selected from H and halogen;
• each Rx is independently selected from halogen, C1-6 alkyl, C1-4 haloalkyl, ORc, N(Rc)2, —C(O)ORc, —C(O)Rc, C3-6 cycloalkyl, and aryl, wherein the C1-6 alkyl is optionally substituted with one or more Rb;
• or two adjacent Rx come together with the atoms to which they are attached to form a 5- or 6-membered ring;
• each Ra is independently selected from H and C1-6 alkyl;
• each Rb is independently selected from C2-6 alkenyl, ORc, N(Rc)2, —C(O)ORc, C3-6 cycloalkyl, and aryl;
• each Rc is independently selected from H, C1-6 alkyl, aryl, —C(O)aryl, and —(CH2)aryl, wherein the C1-6 alkyl and the aryl are each optionally substituted with one or more Rd;
• and
• each Rd is independently selected from C1-3 alkyl, OH, O(C1-3 alkyl), NO2, NH2, NH(C1-3 alkyl), and N(C1-3 alkyl)2.