Perylenequinone derivatives and uses thereof

A process for preparing a compound of formula IIIa or IIIb or stereoisomer or atropisomer thereof:

• wherein
• T is a —CH2—;
• R4 and R5 are independently hydrogen, deuterium, hydroxy, oxygen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl, C1-C12 heteroaryl, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2, —C(O)NH(R1), —C(O)NH2 or an amino suitable protecting group,
• said C1-C4 alkylenyl, C2-C4 alkenylenyl, C1-C4 heteroalkylenyl, C2-C4 heteroalkenylenyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl, and C1-C12 heteroaryl being unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom, hydroxy, carboxy, thiol, azide, nitro, C1-C8 deuterated alkyl group comprising at least one deuterated atom, —COH, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2, —C(O)NH(R1), —C(O)NH2, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl and C1-C12 heteroaryl;
• R1 is a hydrogen atom, C1-C8 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aralkyl, or C1-C12 heterocyclyl;
• each R2 is independently a hydrogen atom, C1-C8 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aralkyl, or C1-C12 heterocyclyl;
• p has a value of 4 so that ring A is a six-membered ring;
• R6 is hydrogen;
• and
• R7 is hydrogen;
• said process comprising:
• a) reacting a compound of formula (IVa) or (IVb):
• wherein
• R2 is as previously defined,
• with a compound of formula (VI):
• wherein
• T, R4, R5, and p are as previously defined,
• wherein compounds of formula (IVa) and (IVb) when reacted with compound (VI) result in compound (IIIa) and (IIIb), respectively.

A process for preparing a mixture of the compound of formula IIIa and IIIb or a stereoisomer or atropisomer thereof:

• wherein
• T is a —CH2;
• R4 and R5 are independently hydrogen, deuterium, hydroxy, oxygen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl, C1-C12 heteroaryl, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2, —C(O)NH(R1), —C(O)NH2 or an amino suitable protecting group,
• said C1-C4 alkylenyl, C2-C4 alkenylenyl, C1-C4 heteroalkylenyl, C2-C4 heteroalkenylenyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl, and C1-C12 heteroaryl being unsubstituted or substituted with at least one substituent selected from the group consisting of a halogen atom, hydroxy, carboxy, thiol, azide, nitro, C1-C8 deuterated alkyl group comprising at least one deuterated atom, —COH, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2, —C(O)NH(R1), —C(O)NH2, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl and C1-C12 heteroaryl;
• R1 is a hydrogen atom, C1-C8 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aralkyl, or C1-C12 heterocyclyl;
• each R2 is independently a hydrogen atom, C1-C8 alkyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aralkyl, or C1-C12 heterocyclyl;
• p has a value of 4 so that ring A is a six-membered ring;
• R6 is hydrogen;
• and
• R7 is hydrogen;
• said process comprising:
• a) reacting a compound of formula (IVa) and (IVb):
• wherein
• R2 is as previously defined, with a compound of formula (VI):
• wherein
• T, R4, R5, and p are as previously defined.