Anti-infective and anti-inflammatory compounds

A compound, or salt thereof, comprising an Amphiphilic Lysosomally trapped Compound (ALC), wherein the ALC is a compound of Formula 6:

• or a salt thereof, wherein:
• each R″ is independently
• —H;
• —NO(y) wherein y is 2;
• —C(═O)OR3, or —C(═O)R3;
• R1 and R2 are independently of each other H, OH, OR4, —C1-C10 alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, or alkylheteroaryl;
• wherein alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl and alkylheteroaryl groups are optionally modified with one to five substituents selected independently from:
• (C2-C9)heterocycloalkyl, nitro (—NO2), R4C(═O)O—, and —XNO(y) wherein X is O, and y is 2;
• or N(R1R2) is an aziridine, azetidine, pyrrolidine, piperidine, azepane, azocane, 1-substituted piperazine, or morpholine moiety;
• R3 is —C1-C10 alkyl, alkynyl, aryl, heteroaryl, alkylaryl, or alkylheteroaryl;
• wherein alkyl, alkynyl, aryl, heteroaryl, alkylaryl and alkylheteroaryl groups are optionally modified with one to five substituents selected independently from:
• (C2-C9)heterocycloalkyl nitro (—NO2), R6C(═O)O—, and —XNO(y) wherein X is O, and y is 2;
• R4 and R6 are each independently:
• —H;
• —(C1-C12)alkyl;
• —(C2-C12)alkenyl;
• —(C2-C12)alkynyl;
• —(C1-C8)[(C1-C4)alkoxy]alkyl;
• —(C2-C8)[(C1-C4)alkoxy]alkenyl;
• —(C6-C10)aryl-(C1-C5)alkyl;
• or
• —(C2-C9)heteroaryl-(C1-C5)alkyl;
• wherein alkyl, alkenyl, and alkynyl are optionally modified with one to five substituents selected independently from (C2-C9)heterocycloalkyl, nitro (—NO2), and —XNOy wherein X is O, and y is 2;
• Mac is a macrolide ring or macrolide ring system of the formula:
• wherein
• X′ is —N(CH3)—CH2—;
• —CH2—N[(CH2)n—CH3]— wherein n is 0-4;
• —C(═O)—;
• —C(═NOR8′)—;
• or
• —C(═NR12′)—;
• R3′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)OR7′, or —C(═O)R7′;
• if Z′ is O, R4′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)OR7′, or —C(═O)R7′;
• R5′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)OR7′, or —C(═O)R7′;
• or Z′ is O or NR9′ and the R4′ and R5′ bearing atoms are connected via —C(═O)—;
• or the R4′ and R5′ bearing atoms are connected via W′;
• W′ is:
• —(−)CH—(C1-C12)alkyl;
• —(−)CH—(C3-C12)alkenyl;
• —(−)CH—(C3-C12)alkynyl;
• —(−)CH—(C1-C8)[(C1-C4)alkoxy]alkyl;
• or
• —(−)CH—(C2-C8)[(C1-C4)alkoxy]alkenyl;
• wherein alkyl, alkenyl, alkynyl are optionally modified with one to five substituents selected independently from (C2-C6)heterocycloalkyl, nitro (—NO2), R14′C(═O)O— and —XNO2;
• wherein X is O;
• R6′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)OR7′, or —C(═O)R7′;
• each R7′ is independently:
• —H;
• -ferrocene;
• —C1-C10 alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl, or alkylheteroaryl
• wherein alkyl, alkenyl, alkynyl, aryl, heteroaryl, alkylaryl and alkylheteroaryl groups are optionally modified with one to five substituents selected independently from:
• (C2-C6)heterocycloalkyl, nitro (—NO2), R14′C(═O)O—, and —XNO(y);
• wherein X is O;
• and y is 2;
• R8′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)—R7′;
• —(C1-C12)alkyl;
• —(C2-C12)alkenyl;
• —(C2-C12)alkynyl;
• —(C1-C8)[(C1-C4)alkoxy]alkyl;
• —(C2-C8)[(C1-C4)alkoxy]alkenyl;
• —(C6-C10)aryl-(C1-C5)alkyl;
• or
• —(C2-C9)heteroaryl-(C1-C5)alkyl;
• R9′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)—R7′;
• —(C1-C12)alkyl;
• —(C2-C12)alkenyl;
• —(C2-C12)alkynyl;
• —(C1-C8)[(C1-C4)alkoxy]alkyl;
• —(C2-C8)[(C1-C4)alkoxy]alkenyl;
• —(C6-C10)aryl-(C1-C5)alkyl;
• or
• —(C2-C9)heteroaryl-(C1-C5)alkyl;
• R12′ is:
• —H;
• —NO(y) wherein y is 2;
• —C(═O)—R7′;
• —(C1-C12)alkyl;
• —(C2-C12)alkenyl;
• —(C2-C12)alkynyl;
• —(C1-C8)[(C1-C4)alkoxy]alkyl;
• —(C2-C8)[(C1-C4)alkoxy]alkenyl;
• —(C6-C10)aryl-(C1-C5)alkyl;
• or
• —(C2-C9)heteroaryl-(C1-C5)alkyl;
• R14′ is each independently:
• —H;
• —(C1-C12)alkyl;
• —(C2-C12)alkenyl;
• —(C2-C12)alkynyl;
• —(C1-C8)[(C1-C4)alkoxy]alkyl;
• —(C2-C8)[(C1-C4)alkoxy]alkenyl;
• —(C6-C10)aryl-(C1-C5)alkyl;
• or
• —(C2-C9)heteroaryl-(C1-C5)alkyl;
• wherein alkyl, alkenyl, alkynyl, aryl and heteroaryl are optionally modified with one to five substituents selected independently from (C2-C6)heterocycloalkyl, nitro (—NO2), and —XNOy;
• wherein X is O;
• and y is 2;
• wherein the compound comprises at least one moiety consisting of —ONO2 or —NNO2.