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US 8,747,811 B2Granted
Perylenequinone derivatives and uses thereof
AssigneeQuest Pharmatech Inc.
InventorsSanjay K. Sharma, Thomas Woo, Selvaraj Naicker
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds which are perylenequinone derivatives, their stereoisomers and atropisomers. These compounds can be particularly useful as photosensitizers or sononsensitizers in photodynamic or sonodynamic therapy. The invention also relates to various methods for using these compounds in photodynamic and/or sonodynamic therapy. The compounds also are useful as therapeutic agents for treating various hyperproliferative disorders.
Claims30
A method for carrying out a therapy on a subject in need thereof comprising:
- a) administering to the subject a compound of formula (Ia) or (Ib) or 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,
- or a pharmaceutically acceptable salt thereof;
- and,
- b) activating a target area in the subject with a light having a wavelength suitable for activating said compound or an ultrasound suitable to activate said compound.
11 more elements
A method for detecting the presence of a target in a subject comprising:
- a) administering to the subject a compound of formula (Ia) or (Ib) or 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,
- or a pharmaceutically acceptable salt thereof;
- and,
- b) visualizing the compound within the subject.
11 more elements
Dependencies are inferred from the claim text.