Patent ID: 11878019
Assignee: DANA-FARBER CANCER INSTITUTE, INC.
Field: Pharmaceuticals (Chemistry)
Classification: CPC A | IPC A

Claim 1:
2. A method of increasing the appearance of skin pigmentation in a subject, the method comprising administering topically to the subject's skin an effective amount of a compound of Formula (I):, or a pharmaceutically acceptable salt, solvate, hydrate, polymorph, co-crystal, tautomer, stereoisomer, isotopically labeled derivative, or prodrug thereof, or a pharmaceutical composition thereof, wherein:
Ring A is a phenyl ring, or a monocyclic, 5- to 6-membered heteroaryl ring, wherein one, two, three, or four atoms in the heteroaryl ring system are independently nitrogen, oxygen, or sulfur;
each instance of RA is independently halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORA1, —N(RA1)2, —SRA1, —CN, —SCN, —C(═NRA1)RA1, —C(═NRA1)ORA1, —C(═NRA1)N(RA1)2, —C(═O)RA1, —C(═O)ORA1, —C(═O)N(RA1)2, —NO2, —NRA1C(═O)RA1, —NRA1C(═O)ORA1, —NRA1C(═O)N(RA1)2, —OC(═O)RA1, —OC(═O)ORA1, or —OC(═O)N(RA1)2, wherein each instance of RA1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two RA1 groups are joined to form a substituted or unsubstituted heterocyclic or substituted or unsubstituted heteroaryl ring;
k is 0, 1, 2, 3, or 4;
L is a substituted or unsubstituted, saturated or unsaturated C3-10 hydrocarbon chain, optionally wherein one or more chain atoms of the hydrocarbon chain are independently replaced with —O—, —S—, —NRN—, —N═, or ═N—, wherein each instance of RN is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C1-6 alkyl, or a nitrogen protecting group;
RB is hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C1-6 alkyl, or a nitrogen protecting group;
each of XA, XB, and XC is independently N or CRX, wherein RX is hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORX1, —N(RX1)2, —SRX1, —CN, —SCN, —C(═NRX1)RX1, —C(═NRX1)OR, —C(═NRX1)N(RX1)2, —C(═O)RX1, —C(═O)ORX1, —C(═O)N(RX1)2, —NO2, —NRC(═O)RX1, —NRC(═)OR, —NRX1C(═O)N(RX1)2, —OC(═O)RX1, —OC(═O)ORX1, or —OC(═O)N(RX1)2, wherein each instance of RX1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two RX1 groups are joined to form a substituted or unsubstituted heterocyclic or substituted or unsubstituted heteroaryl ring;
Y is —O— or —NRY—, wherein RY is hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C1-6 alkyl, or a nitrogen protecting group;
or when Y is —NR— and XA is CRX, RY and RX of XA are joined to form a substituted or unsubstituted, monocyclic, 5- to 7-membered heterocyclic ring that is fused with Ring B;
each instance of RC is independently halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORC1, —N(RC1)2, —SRC1, —CN, —SCN, —C(═NRC1)RC1, —C(═NRC1)ORC1, —C(═NRC1)N(RC1)2, —C(═O)RC1, —C(═O)ORC1, —C(═O)N(RC1)2, —NO2, —NRC1C(═O)RC1, —NRC1C(═O)ORC1, —NRC1C(═O)N(RC1)2—OC(═O)RC1, —OC(═O)ORC1, or —OC(═O)N(RC1)2, wherein each instance of RC1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two RC1 groups are joined to form a substituted or unsubstituted heterocyclic or substituted or unsubstituted heteroaryl ring;
m is 0, 1, 2, 3, 4, or 5; and
RD is hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —ORD1, —N(RD1)2, —SRD1, —CN, —SCN, —C(═NRD1)RD1, —C(═NRD1)ORD1, —C(═NRD1)N(RD1)2, —C(═O)RD1, —C(═O)ORD1, —C(═O)N(RD1)2, —NO2, —NRD1C(═O)RD1, —NRD1C(═O)ORD1, —NRD1C(═O)N(RD1)2, —OC(═O)RD1, —OC(═O)ORD1, or —OC(═O)N(RD1)2, wherein each instance of RD1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of RD1 are joined to form a substituted or unsubstituted heterocyclic or substituted or unsubstituted heteroaryl ring;

wherein the subject does not suffer from psoriasis, scleroderma, pemphigus, inflammatory dermatoses, and poison ivy dermatitis.