Carbon monoxide-releasing molecules for therapeutic applications and methods of making and using thereof

A compound according to Formula IX:

• or a pharmaceutically acceptable salt thereof, wherein:
• each R4, R5, and R6 is independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, hydroxyl, —N(Ra)2, —SRa, —S(O)Ra, —S(O)2Ra, —OS(O)ORa, —OS(O)2ORa, —OP(ORa)2, —OP(O)HORa, —OP(O)(ORa)2, —OP(O)(Ra)2, —P(O)(ORa)2, —ONO, —ONO2, —NO2, —(C═O)R7, —(C═O)OR8, —(C═O)NR9R10, a protecting moiety RP, a linking moiety RL, a targeting moiety RT, and a solubility-enhancing moiety RS;
• R3 is selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;
• R1 and R2 are independently selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl,
• or, alternatively, R1 and R2 are independently selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, and are taken together to form a fused tricyclic moiety which is optionally substituted with one or more R11 moieties, wherein
• each R11 is independently selected from the group consisting of halogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, hydroxyl, —N(Ra)2, —SRa, —S(O)Ra, —S(O)2Ra, —OS(O)ORa, —OS(O)2ORa, —OP(ORa)2, —OP(O)HORa, —OP(O)(ORa)2, —OP(O)(Ra)2, —P(O)(ORa)2, —ONO, —ONO2, —NO2, —(C═O)R5, —(C═O)OR6, —(C═O) NR7R8, a linking moiety RL, a targeting moiety RT, and a solubility-enhancing moiety RS;
• Ra is selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heteroaryl;
• each R7, R8, R9, and R10 is independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;
• X is CR12R13, S, O, or NR14, wherein each R12 and R13 is defined as for R1, and R14 is defined as for R7;
• each R15 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, and heteroaryl,
• or, alternatively two OR15 are taken together to form an oxo moiety;
• and
• subscript n is 1, 2 or 3.

A compound having a structure according to Formula XIV:

• or a pharmaceutically acceptable salt thereof, wherein:
• each R1, R2, R3, R4, R5, and R6 is independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, hydroxyl, —N(Ra)2, —SRa, —S(O)Ra, —S(O)2Ra, —OS(O)ORa, —OS(O)2ORa, —OP(ORa)2, —OP(O)HORa, —OP(O)(ORa)2, —OP(O)(Ra)2, —P(O)(ORa)2, —ONO, —ONO2, —NO2, —(C═O)R7, —(C═O)OR8, —(C═O)NR9R10, a protecting moiety RP, a linking moiety RL, a targeting moiety RT, and a solubility-enhancing moiety RS;
• or, alternatively, R1 and R2 are independently selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, and are taken together to form a fused tricyclic moiety which is optionally substituted with one or more R11 moieties, wherein each R11 is selected from the group consisting of hydrogen, halogen, alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, alkoxy, aryloxy, hydroxyl, —N(Ra)2, —SRa, —S(O)Ra, —S(O)2Ra, —OS(O)ORa, —OS(O)2ORa, —OP(ORa)2, —OP(O)HORa, —OP(O)(ORa)2, —OP(O)(Ra)2, —P(O)(ORa)2, —ONO, —ONO2, —NO2, —(C═O)R5, —(C═O)OR6, —(C═O)NR7R8, a linking moiety RL;
• Ra is selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heteroaryl;
• each R7, R8, R9, and R10 is independently selected from the group consisting of hydrogen, alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;
• X is CR12R13, S, O, or NR14, wherein each R12 and R13 is defined as for R1, and R14 is defined as for R7;
• “A” is selected from the group consisting of cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;
• and
• subscript m is 1, 2 or 3, provided that only one of X is S or O when m is 2 or 3.