Antibacterial and antiparasitic quinoxaline-2,3-diamine derivatives

A method of treating a patient infected with parasites selected from schistosome, Fasciola, or Plasmodium parasites and/or a patient infected pathogenic bacteria selected from S. aureus, MRSA and Enterococcus faecalis, the method comprising administering to said patient a therapeutically effective amount of a compound of formula (III), or a pharmaceutically acceptable salt or solvate thereof;

• wherein R1 and R2 are independently selected from a C1-C8 alkyl, a C1-C8 alkenyl, an aryl group or an alkylaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, fluoro, chloro, CF3, CHF2 or CH2F groups;
• wherein Z is selected from —NR3R4 or —NR5 (CO) R6;
• wherein R3 and R4 are each independently selected from H, a C1-C6 alkyl, optionally forming a ring, a C1-C6 alkenyl, an aryl group, or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein R5 is selected from H, a C1-C6 alkyl or a C1-C6 alkenyl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein R6 is selected from a C1-C6 alkyl, a C1-C6 alkenyl, an aryl or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein R7 and R8 are each independently selected from a H or a C1-C4 alkyl;
• wherein R9, R10 and R11 are each independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, —(CO)WR12, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein W is a bond, N or O and wherein R12 is selected from C1-C6 alkyl, a C1-C6 alkenyl, an aryl or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups.

A method for disinfecting parasites selected from schistosome, Fasciola, or Plasmodium parasites and/or a patient infected pathogenic bacteria selected from S. aureus, MRSA and Enterococcus faecalis from a surface, the method comprising the step of applying, to a surface, a compound according to of formula (I), or a pharmaceutically acceptable salt or solvate thereof;

• wherein X and Y are each N;
• wherein R1 and R2 are each independently selected from a C1-C8 alkyl, a C1-C8 alkenyl, an aryl group, an alkylaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• or a (CO)OR13 or (CO)NHR13 group wherein R13 is selected from said groups;
• wherein Z is selected from —NO2, —NR3R4, or —NR5(CO)R6;
• wherein R3 and R4 are each independently selected from H, a C1-C6 alkyl, optionally forming a ring, a C1-C6 alkenyl, an aryl group, or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• or a (CO)OR14 or (CO) NHR14 group wherein R14 is selected from said groups;
• wherein R5 is selected from H, a C1-C6 alkyl or a C1-C6 alkenyl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein R6 is selected from a C1-C6 alkyl, a C1-C6 alkenyl, an aryl or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• or a (CO)OR15 or (CO) NHR15 group wherein R15 is selected from said groups;
• wherein R7 and R8, when present, are each independently selected from a H or a C1-C4 alkyl;
• wherein R9, R10 and R11 are each independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, —(CO)WR12, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups;
• wherein W is a bond, N or O and wherein R12 is selected from C1-C6 alkyl, a C1-C6 alkenyl, an aryl or a heteroaryl group, optionally substituted with one or more of C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylamino, C1-C4 alkylthio, hydroxy, amino, thiol, chloro, fluoro, CF3, CHF2 or CH2F groups.