Triazolium and imidazolium salts and uses thereof

A compound selected from a compound of Formula Ib, and pharmaceutically acceptable salts, solvates and prodrugs thereof:

• R1 and R1′ are independently selected from C1-20alkyl, C3-20cycloalkyl, C6-14aryl and C1-20alkylene-C6-14aryl, where each C1-20alkyl, C3-20cycloalkyl and C1-20alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR6, and each C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• R4 is selected from C10-20alkylene, (C6-10arylene)p, C1-10alkylene-(C6-10arylene)p, (C6-10arylene)p-C1-10alkylene, C1-10alkylene-(C6-10arylene)p-C1-10alkylene and (C6-10arylene)-C1-10alkylene-(C6-10arylene), wherein each C10-20alkylene and C1-10alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S and C(O)R5, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR6, and each C6-10arylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R5;
• R5 is selected from H, OH, SH, C1-6alkyl, C3-10cycloalkyl, C6-14aryl, OC1-6alkyl, SC1-6alkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, OC6-14aryl, SC6-14aryl, C1-4alkyleneC6-14aryl, NH2, NH(C1-6alkyl) and N(C1-6alkyl)(C1-6alkyl);
• R6 is selected from H and C1-4alkyl;
• p is 1 or 2;
• and
• Y− and Y′− are, independently, a counter anion.

A compound selected from a compound of Formula Ic, and pharmaceutically acceptable salts, solvates and prodrugs thereof:

• R1 and R1′ are independently selected from C1-20alkyl, C3-20cycloalkyl, C6-14aryl and C1-20alkylene-C6-14aryl, where each C1-20alkyl, C3-20cycloalkyl and C1-20alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR6, and each C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• R2 and R2′ are independently selected from H, C1-6alkyl, C3-10cycloalkyl and C6-14aryl, where C1-6alkyl, C3-10cycloalkyl and C6-14aryl are unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R5;
• R3 and R3′ are independently selected from H, OC1-6alkyl, SC1-6alkyl, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C3-10cycloalkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, C6-14aryl, C1-6alkyleneC6-14aryl, OC6-14aryl and SC6-14aryl, where each C1-6alkyl, C1-6alkylene, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5,
• or R1 and R3 and/or R1′ and R3′ are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• R4 is selected from biphenylene, CH2-biphenylene, biphenylene-CH2, CH2-biphenylene-CH2, wherein each biphenylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R5;
• R5 is selected from H, OH, SH, C1-6alkyl, C3-10cycloalkyl, C6-14aryl, OC1-6alkyl, SC1-6alkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, OC6-14aryl, SC6-14aryl, C1-4alkyleneC6-14aryl, NH2, NH(C1-6alkyl) and N(C1-6alkyl)(C1-6alkyl);
• R6 is selected from H and C1-4alkyl;
• p is 1 or 2;
• X is selected from C—R7 and N;
• X′ is selected from C—R7′ and N
• R7 and R7′ are independently selected from H, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C3-10cycloalkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, C6-14aryl, C1-6alkyleneC6-14aryl, OC6-14aryl and SC6-14aryl, where each C1-6alkyl, C1-6alkylene, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5,
• or
• R7 and R3 and/or R7′ and R3′ are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• and
• Y− and Y′− are, independently, a counter anion,
• with the proviso that, when R4 is CH2-biphenylene-CH2, R1 is not CH2Ph.

A compound selected from a compound of Formula IIa, and pharmaceutically acceptable salts, solvates and prodrugs thereof

• wherein:
• R9 is selected from H and phenyl,
• R10 is selected from C1-6alkyl;
• R11 and R15 are independently selected from C6-14aryl which is unsubstituted or substituted with one or more substituents, independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R12;
• R12 is selected from H, OH, SH, C1-6alkyl, C3-10cycloalkyl, C6-14aryl, OC1-6alkyl, SC1-6alkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, OC6-14aryl, SC6-14aryl, NH2, NH(C1-6alkyl) and N(C1-6alkyl)(C1-6alkyl);
• n is 0, 1, 2, 3 or 4;
• m is 1, 2, 3 or 4;
• X″ is selected from C—R14 and N;
• R14 is selected from H, C1-10alkyl, C3-10cycloalkyl and C6-10aryl, where each C1-6alkyl, C3-10cycloalkyl, and C6-14aryl are unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R12;
• and
• Y″− is a counter anion.

A method of treating or preventing an infection by a Plasmodium or Babesia parasite comprising administering to a subject in need thereof, an effective amount of a compound selected from a compound of Formula I, and pharmaceutically acceptable salts, solvates, and prodrugs thereof:

• wherein,
• R1 and R1′ are independently selected from C1-20alkyl, C3-20cycloalkyl, C6-14aryl and C1-20alkylene-C6-14aryl, where each C1-20alkyl, C3-20cycloalkyl and C1-20alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR6, and each C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• R2 and R2′ are independently selected from H, C1-6alkyl, C3-10cycloalkyl and C6-14aryl, where each C1-6alkyl, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R5;
• R3 and R3′ are independently selected from H, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C3-10cycloalkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, C6-14aryl, C1-6alkyleneC6-14aryl, OC6-14aryl and SC6-14aryl, where each C1-6alkyl, C1-6alkylene, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• or R1 and R3 and/or R1′ and R3′ are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5,
• R4 is selected from C10-20alkylene, (C6-10arylene)p, C1-10alkylene-(C6-10arylene)p, (C6-10arylene)p-C1-10alkylene, C1-10alkylene-(C6-10arylene)p-C1-10alkylene and (C6-10arylene)-C1-10alkylene-(C6-10arylene), wherein each C10-20alkylene and C1-10alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S and C(O)R5, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR6, and each C6-10arylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R5;
• R5 is selected from H, OH, SH, C1-6alkyl, C3-10cycloalkyl, C6-14aryl, OC1-6alkyl, SC1-6alkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, OC6-14aryl, SC6-14aryl, C1-4alkyleneC6-14aryl, NH2, NH(C1-6alkyl) and N(C1-6alkyl)(C1-6alkyl);
• R6 is selected from H and C1-4alkyl;
• p is 1 or 2;
• X is selected from C—R7 and N;
• X′ is selected from C—R7′ and N
• R7 and R7′ are independently selected from H, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C3-10cycloalkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, C6-14aryl, C1-6alkyleneC6-14aryl, OC6-14aryl and SC6-14aryl, where each C1-6alkyl, C1-6alkylene, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5,
• or
• R7 and R3 and/or R7′ and R3′ are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R5;
• and
• Y− and Y′− are, independently, a counter anion.

A method of treating or preventing an infection by a Plasmodium or Babesia parasite comprising administering to a subject in need thereof, an effective amount of a compound selected from a compound of Formula II, and pharmaceutically acceptable salts, solvates, and prodrugs thereof:

• wherein,
• R8 and R10 are independently selected from C1-20alkyl, C6-14aryl, C3-20cycloalkyl and C1-20alkylene-C6-14aryl, where each C1-20alkyl, C3-20cycloalkyl and C1-20alkylene is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, ═O, ═S, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12, and/or one or more carbon atoms are optionally replaced with a heteroatom independently selected from O, S and NR13, and each C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12;
• R9 is independently selected from H, C1-6alkyl, C3-10cycloalkyl and C6-14aryl, where C1-6alkyl, C3-10cycloalkyl and C6-14aryl are unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2 and C(O)R12;
• R11 is selected from H, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C3-10cycloalkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, C6-14aryl, C1-6alkyleneC6-14aryl, OC6-14aryl and SC6-14aryl, where each C1-6alkyl, C1-6alkylene, C3-10cycloalkyl or C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12,
• or R10 and R11 are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12;
• R12 is selected from H, OH, SH, C1-6alkyl, C3-10cycloalkyl, C6-14aryl, OC1-6alkyl, SC1-6alkyl, OC3-10cycloalkyl, SC3-10cycloalkyl, OC6-14aryl, SC6-14aryl, C1-4alkyleneC6-14aryl, NH2, NH(C1-6alkyl) and N(C1-6alkyl)(C1-6alkyl);
• R13 is selected from H and C1-4alkyl;
• X″ is selected from C—R14 and N;
• R14 is selected from H, C1-10alkyl, C3-10cycloalkyl and C6-10aryl, where each C1-6alkyl, C3-10cycloalkyl and C6-14aryl is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12,
• or R14 and R8 are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12,
• or R14 and R11 are joined to form, together with the atoms to which they are attached, a monocyclic or bicyclic ring, where the ring is saturated, unsaturated or aromatic and is unsubstituted or substituted with one or more substituents independently selected from halo, C1-6alkyl, OC1-6alkyl, SC1-6alkyl, fluoro-substituted C1-6alkyl, fluoro-substituted OC1-6alkyl, fluoro-substituted SC1-6alkyl, OH, SH, CN, NH2, NHC1-6alkyl, N(C1-6alkyl)(C1-6alkyl), NO2, C6-10aryl, C1-4alkyleneC6-10aryl and C(O)R12;
• and
• Y″− is a counter anion.