Neuroplastogens and Non-Hallucinogenic Serotonin 5-HT2A Receptor Modulators

A compound of Formula I:

• wherein
• X is selected from C1-C8 alkyl and C2-C8 alkenyl;
• Y is selected from C2-C8 alkyl and C2-C8 alkenyl;
• W1 is selected from O, Se, Se(O), SeO2, S, S(O), NR1, and SO2;
• W2 is selected from —CD2-, —CHD-, —(CD2)2-, —CH2— and —(CH2)2—;
• Z4 is selected from N and CR4;
• Z5 is selected from N and CR5;
• Z6 is selected from N and CR6;
• Z7 is selected from N and CR7,
• wherein at least one of Z4, Z5, Z6 or Z7 is N;
• R2, R3, Rr, R6 and R7 are each independently selected from hydrogen, deuterium, —N(R9)2, —SR9, halo, optionally substituted C1-C8 alkyl, —C1-C8 alkoxy, and optionally substituted C2-C8 alkenyl, or Y is absent and R3 taken together with carbon to which it is attached and the nitrogen atom to which X is attached form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S(O), SO2, and NR9;
• R4 and R5 are each independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, halo, hydroxyl, —N(R9)2, —SR9, —C1-C8 alkoxy, —OC(O)R8, —OC(O)OR8, —OP(O)(OR9)2, and —OSO2R8;
• R1 is selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, —C(O)R8, —C(O)OR8, —P(O)(OR9)2, —C(O)N(R9)2, —SOR8, and —SO2R8;
• R8 is selected from optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
• R9 is independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
• and
• salts, solvates, hydrates, and prodrugs thereof.

A compound selected from the following formula:

• wherein
• X and Y are each independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, and optionally substituted C2-C8 alkenyl, or Y is taken together with X and the nitrogen atom therebetween to form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S(O), SO2, and NR9;
• W1 is selected from O, Se, Se(O), SeO2, S, S(O), NR1, and SO2;
• W2 is selected from —CD2-, —CHD-, —(CD2)2-, —CH2— and —(CH2)2—;
• Z4 is selected from N and CR4;
• Z5 is selected from N and CR5;
• Z6 is selected from N and CR6;
• Z7 is selected from N and CR7,
• wherein at least one of Z5, Z6 or Z7 is N;
• R2, R3, R3, R6 and R7 are each independently selected from hydrogen, deuterium, —N(R9)2, —SR9, halo, optionally substituted C1-C8 alkyl, —C1-C8 alkoxy, and optionally substituted C2-C8 alkenyl, or Y is absent and R3 taken together with carbon to which it is attached and the nitrogen atom to which X is attached form a 3- to 7-membered heterocyclic ring optionally including 1 to 2 additional ring heteromoieties selected from O, S, S(O), SO2, and NR9;
• R4 is —OC(O)OR8;
• R5 is selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, halo, hydroxyl, —N(R9)2, —SR9, —C1-C8 alkoxy, —OC(O)R8, —OC(O)OR8, —OP(O)(OR9)2, and —OSO2R8;
• R1 is selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, —C(O)R8, —C(O)OR8, —P(O)(OR9)2, —C(O)N(R9)2, —SOR8, and —SO2R8;
• R8 is selected from optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
• R9 is independently selected from hydrogen, deuterium, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, and optionally substituted aryl;
• and
• salts, solvates, hydrates, and prodrugs thereof.