Perylenequinone derivatives and uses thereof

A process for preparing a compound of formula (Ia) or (Ib) or a stereoisomer or atropisomer thereof:

• wherein
• X and Y are independently hydrogen, 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), or —C(O)NH2, said 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;
• Z is —CH2—, —CHR3—, —CH2—CH═CH—, —CHR3—CH═CH—, or —CH2—CH═CR3—;
• 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;
• R3 is halogen atom, hydroxy, sulphydral(—SH), an amino acid residue, carboxy, thiol, azide, nitro, SO3H, —COH, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2—C(O)NH(R1), —C(O)NH2, —HNC(O)R1, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl or C1-C12 heteroaryl;
• n is an integer having a value of 1 to 13;
• and
• m is an integer having a value of 1 to 13
• said process comprising:
• a) reacting a compound of formula (IVa) or (IVb):
• wherein
• R2 is as previously defined,
• with a compound of formula (V):
• wherein
• X, Y, Z, R1 and n are as previously defined;
• and
• (b) purifying the compound of the formula (Ia) or (Ib).

A process for preparing a mixture of the compound of formula (Ia) and or (Ib) and respectively, or a stereoisomer or atropisomer thereof:

• wherein
• X and Y are independently hydrogen, 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), or —C(O)NH2,
• said 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;
• Z is —CH2—, —CHR3—, —CH2—CH═CH—, —CHR3—CH═CH—, or —CH2—CH═CR3—;
• 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;
• R3 is halogen atom, hydroxy, sulphydral(—SH), an amino acid residue, carboxy, thiol, azide, nitro, SO3H, —COH, —COR1, —(CH2)mOR1, —CO2H, —CO2R1, —C(O)N(R1)2—C(O)NH(R1), —C(O)NH2, —HNC(O)R1, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C4-C10 cycloalkenyl, C6-C12 aryl, C6-C12 aralkyl, C1-C12 heterocyclyl or C1-C12 heteroaryl;
• n is an integer having a value of 1 to 13;
• and
• m is an integer having a value of 1 to 13
• said process comprising:
• a) reacting a compound of formula (IVa) or (IVb):
• wherein
• R2 is as previously defined,
• with a compound of formula (V):
• wherein
• X, Y, Z, R1 and n are as previously defined.