Patent ID: 11905306
Assignee: THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL
Field: Organic fine chemistry (Chemistry)
Classification: CPC C | IPC C

Claim 15:
16. A pharmaceutical composition comprising a therapeutically effective amount of a compound having a structure represented by a formula:, wherein A is selected from —NR10C(O)— and —C(O)NR11;
wherein each of R10, when present, and R11, when present, is selected from hydrogen and C1-C4 alkyl;

wherein each of Z1 and Z2 is independently selected from —N═ and —C(R13)═;
wherein each occurrence of R13, when present, is independently selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;

wherein each of R1a, R1b, R1c, and R1d is independently selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein each of R2a and R2b is independently selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein R3 is selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 hydroxyhaloalkyl, —NR14C(O)R15, —C(O)NR16aR16b, —OSO2NR16aR16b, —NR17SO2R18, —P(O)(OR19)2, —CO2(C1-C4 alkyl), —CO2Cy1, —CO2(C1-C4 alkyl)Cy1, Cy1, and —CH2Cy5;
wherein R14, when present, is selected from hydrogen and C1-C4 alkyl;
wherein R15, when present, is selected from C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 aminoalkyl, —OR20, —NR21aR21b, —CH2NR21aR21b, and Cy2;
wherein R20, when present, is selected from hydrogen and C1-C4 alkyl;
wherein each of R21a and R21b, when present, is independently selected from hydrogen and C1-C4 alkyl;
or wherein R21a and R21b, when present, are covalently bonded, and, together with the intermediate atoms, comprise an unsubstituted 4- to 6-membered heterocycloalkyl;
wherein Cy2, when present, is selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, C6-C14 aryl, and C2-C10 heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;

or wherein R14 and R15, when present, are covalently bonded, and, together with the intermediate atoms, comprise a 4- to 9-membered heterocycloalkyl ring substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
or wherein R15, when present, and R2b are covalently bonded, and, together with the intermediate atoms, comprise a 5- to 7-membered heterocycloalkyl ring substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein each of R16a and R16b, when present, is independently selected from hydrogen, C1-C4 alkyl, and Cy3;
wherein Cy3, when present, is a C3-C6 cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;

wherein R17, when present, is selected from hydrogen and C1-C4 alkyl;
wherein R18, when present is a C1-C4 alkyl;
or wherein R17 and R18, when present, are covalently bonded, and together with the intermediate atoms, comprise an unsubstituted 5- to 7-membered heterocycloalkyl;
wherein each occurrence of R19, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein Cy1, when present, is a C3-C6 cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl; and
wherein Cy5, when present, is a C3-C6 heterocycloalkyl substituted with at least one ═O group, and substituted with 0, 1, or 2 additional groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;

or wherein R2a is selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl,
and wherein R2b and R3 are covalently bonded, and, together with the intermediate atoms, comprise a 5- or 6-membered heteroaryl, and are substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl;
wherein R4 is selected from hydrogen, halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, C1-C4 aminoalkyl, Cy4, and —O(C1-C4 alkyl)Cy4; and
wherein Cy4, when present, is a C3-C6 cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —CN, —NH2, —OH, —NO2, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and C1-C4 aminoalkyl,

or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.