Benzofuran and benzothiophene psychoplastogens and uses thereof

A compound of Formula (I), or a pharmaceutically acceptable salt or solvate thereof:

• wherein:
• one of A, B and D is NR5 and the remaining two of A, B and D are CH2;
• X is O or S(═O)x;
• x is 0, 1, or 2;
• each of R1, R2, R3 and R4 is independently hydrogen, halogen, —ORa, alkyl, heteroalkyl, aryl, arylalkyl, haloalkyl, hydroxyalkyl, aminoalkyl, or cycloalkyl, wherein each alkyl, heteroalkyl, aryl, arylalkyl, haloalkyl, hydroxyalkyl, aminoalkyl, or cycloalkyl is optionally substituted;
• or any of R1 and R2, R2 and R3, or R3 and R4 are taken together with the carbon atoms to which they are attached to form an optionally substituted 5- or 6-membered ring;
• R5 is hydrogen, alkyl, haloalkyl, cycloalkyl, or heterocycloalkyl, wherein each alkyl, haloalkyl, cycloalkyl, or heterocycloalkyl is optionally substituted;
• and
• Ra is hydrogen, alkyl, haloalkyl, heteroalkyl, aryl, arylalkyl, cycloalkyl, or heterocycloalkyl, wherein each alkyl, haloalkyl, heteroalkyl, cycloalkyl, aryl, arylalkyl, or heterocycloalkyl is optionally substituted;
• provided that when R5 is hydrogen or methyl, then at least one of R2-R4 is not hydrogen;
• when X is O or S, A and D are each CH2, B is NR5 wherein R5 is hydrogen or C1-C3 alkyl, and R2-R4 are each hydrogen, then R1 is not hydrogen, bromo, or methoxy;
• when X is O, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R1, R3, and R4 are each hydrogen, then R2 is not hydrogen, hydroxyl, fluoro, bromo, or methoxy;
• when X is O, R5 is —C(O)CF3, and R1, R3, and R4 are each hydrogen, then R2 is not hydrogen, hydroxy, fluoro, or bromo;
• when X is S, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R1, R3, and R4 are each hydrogen, then R2 is not hydrogen, hydroxyl, methoxy, fluoro, or trifluoromethyl;
• when X is O, B and D are each CH2, A is NR5 wherein R5 is hydrogen or methyl, and R1, R3, and R4 are each hydrogen, then R2 is not hydrogen, hydroxyl, or fluoro;
• when X is O, A and B are each CH2, D is NR5 wherein R5 is hydrogen or methyl, and R1, R3, and R4 are each hydrogen, then R2 is not hydrogen, hydroxyl, or methoxy;
• when X is O or S, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R2, and R4 are each hydrogen, then R1 and R3 are not hydroxyl or fluoro;
• when X is O, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R1, R2, and R4 are each hydrogen, then R3 is not hydrogen, bromo, or methoxy;
• when X is S, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R1, R2 and R4 are each hydrogen, then R3 is not hydrogen, fluoro, hydroxyl, or methoxy;
• and
• when X is O, A and D are each CH2, B is NR5 wherein R5 is hydrogen or methyl, and R1, R2, and R3 are each hydrogen, then R4 is not hydrogen, bromo, or methoxy.