Tyrosinase inhibitors
AssigneeAvon Products, Inc.
InventorsHong Hu, Sunghan Yim, Uma Santhanam, John W. Lyga
Life of this patent
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Abstract
The compositions and methods of described herein comprise novel ingredients effective to reduce unwanted pigmentation, such as skin discoloration, freckles, age spots, liver spots, sun damage, tans, pigmented acne marks, scars, pigmented birthmarks, hyperpigmentation, post-inflammatory hyperpigmentation, post-injury hyperpigmentation, melasma, cholasma, after-burn scar, nail stain, yellowing of skin, dark circles under eyes, and the like. The composition may include additional ingredients accordingly for a colored cosmetic, moisturizer, cleanser, toner, and the like.
Claims47
A cosmetic composition for improving the aesthetic appearance of human skin comprising a cosmetically acceptable vehicle, and an effective amount of a compound according to formula I(a):
- wherein,
- R1 and R2 are independently selected from hydrogen, aliphatic C1-C12 hydrocarbon radicals;
- aromatic C1-C12 hydrocarbon radicals;
- aliphatic C1-C12 heterocycles, aromatic C1-C12 heterocycles, or combinations thereof;
- each of the foregoing optionally containing from 1-8 heteroatoms selected from halogen, O, N, and S and being optionally substituted with one or more groups R, and wherein R1 and R2 may together form a three- to six-membered ring, with the proviso that one of R1 and R2 are not hydrogen;
- R3 and R4 are independently selected from hydrogen, aliphatic C1-C12 hydrocarbon radicals;
- aromatic C1-C12 hydrocarbon radicals;
- aliphatic C1-C12 heterocycles, aromatic C1-C12 heterocycles, or combinations thereof;
- each of the foregoing optionally containing from 1-8 heteroatoms selected from halogen, O, N, and S and being optionally substituted with one or more groups R, and wherein R3 and R4 may together form a three- to six-membered heterocyclic ring, with the proviso that one of R3 and R4 are not hydrogen;
- R is selected, independently at each occurrence, from hydrogen, —F;
- —Cl;
- —Br;
- —I;
- ═O, —OH, —OR*;
- —NH2;
- —NHR*;
- —N(R*)2;
- —N(R*)3;
- —N(R*)—OH;
- —N(—O)(R*)2;
- —O—N(R*)2;
- —N(R*)—O—R*;
- —N(R*)—N(R*)2;
- —C═N—R*;
- —N═C(R*)2;
- —C═N—N(R*)2;
- —C(═NR*)—N(R*)2;
- —SH;
- —SR*;
- —CN;
- —NC;
- —(C═O)—R*;
- —CHO;
- —CO2H;
- —CO2−;
- —CO2R*;
- —(C═O)—S—R*;
- —O—(C═O)—H;
- —O—(C═O)—R*;
- —S—(C═O)—R*;
- —(C═O)—NH2;
- —(C═O)—N(R*)2;
- —(C═O)—NHNH2;
- —O—(C═O)—NHNH2;
- —(C═S)—NH2;
- —(C═S)—N(R*)2;
- —N(R*)—CHO;
- —N(R*)—(C═O)—R*;
- —(C═NR)—O—R*;
- —O—(C═NR*)—R*, —SCN;
- —NCS;
- —NSO;
- —SSR*;
- —N(R*)—C(═O)—N(R*)2;
- —N(R*)—C(═S)—N(R*)2;
- —SO2—R*;
- —O—S(═O)2—R*;
- —S(═O)2—OR*;
- —N(R*)—SO2—R*;
- —SO2—N(R*)2;
- —O—SO3;
- —O—S(═O)2—OR*;
- —O—S(═O)—OR*;
- —O—S(═O)—R*;
- —S(═O)—OR*;
- —S(═O)—R*;
- —NO;
- —NO2;
- —NO3;
- —O—NO;
- —O—NO2;
- —N3;
- —N2—R*;
- —N(C2H4);
- —Si(R*)3;
- —CF3;
- —O—CF3;
- —PR*2;
- —O—P(═O)(OR*)2;
- —P(═O)(OR*)2;
- C1-C8 perfluoroalkyl;
- an aliphatic C1-C8 hydrocarbon radical;
- a C1-C8 aromatic hydrocarbon radical;
- or a C1-C8 heteroaryl radical;
- where R* is independently at each occurrence hydrogen or a straight chained, branched, or cyclic C1-C20 hydrocarbon radical, which may be saturated, partially saturated, or aromatic, each of which may be optionally substituted with one or more groups R, or optionally substituted with 1-6 heteroatoms selected from nitrogen, oxygen, sulfur, or halogen;
- and cosmetically acceptable salts thereof.
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A cosmetic composition for improving the aesthetic appearance of human skin comprising a cosmetically acceptable vehicle, and an effective amount of a compound according to formula II(a):
- wherein,
- R1 is selected from hydrogen, aliphatic C1-C12 hydrocarbon radicals;
- aromatic C1-C12 hydrocarbon radicals;
- aliphatic C1-C12 heterocycles, aromatic C1-C12 heterocycles, or combinations thereof;
- each of the foregoing optionally containing from 1-8 heteroatoms selected from halogen, O, N, and S and being optionally substituted with one or more groups R;
- R2 is either a bond (i.e., it is absent) or a methylene group —CH2—;
- R3 and R4 are independently selected from hydrogen, aliphatic C1-C12 hydrocarbon radicals;
- aromatic C1-C12 hydrocarbon radicals;
- aliphatic C1-C12 heterocycles, aromatic C1-C12 heterocycles, or combinations thereof;
- each of the foregoing optionally containing from 1-8 heteroatoms selected from halogen, O, N, and S and being optionally substituted with one or more groups R, and wherein R3 and R4 may together form a three- to six-membered heterocyclic ring, with the proviso that one of R3 and R4 are not hydrogen;
- R is selected, independently at each occurrence, from hydrogen, —F;
- —Cl;
- —Br;
- —I;
- ═O, —OH, —OR*;
- —NH2;
- —NHR*;
- —N(R*)2;
- —N(R*)3;
- —N(R*)—OH;
- —N(—O)(R*)2;
- —O—N(R*)2;
- —N(R*)—O—R*;
- —N(R*)—N(R*)2;
- —C═N—R*;
- —N═C(R*)2;
- —C═N—N(R*)2;
- —C(═NR*)—N(R*)2;
- —SH;
- —SR*;
- —CN;
- —NC;
- —(C═O)—R*;
- —CHO;
- —CO2H;
- —CO2−;
- —CO2R*;
- —(C═O)—S—R*;
- —O—(C═O)—H;
- —O—(C═O)—R*;
- —S—(C═O)—R*;
- —(C═O)—NH2;
- —(C═O)—N(R*)2;
- —(C═O)—NHNH2;
- —O—(C═O)—NHNH2;
- —(C═S)—NH2;
- —(C═S)—N(R*)2;
- —N(R*)—CHO;
- —N(R*)—(C═O)—R*;
- —(C═NR)—O—R*;
- —O—(C═NR*)—R*, —SCN;
- —NCS;
- —NSO;
- —SSR*;
- —N(R*)—C(═O)—N(R*)2;
- —N(R*)—C(═S)—N(R*)2;
- —SO2—R*;
- —O—S(═O)2—R*;
- —S(═O)2—OR*;
- —N(R*)—SO2—R*;
- —SO2—N(R*)2;
- —O—SO3;
- —O—S(═O)2—OR*;
- —O—S(═O)—OR*;
- —O—S(═O)—R*;
- —S(═O)—OR*;
- —S(═O)—R*;
- —NO;
- —NO2;
- —NO3;
- —O—NO;
- —O—NO2;
- —N3;
- —N2—R*;
- —N(C2H4);
- —Si(R*)3;
- —CF3;
- —O—CF3;
- —PR*2;
- —O—P(═O)(OR*)2;
- —P(═O)(OR*)2;
- C1-C8 perfluoroalkyl;
- an aliphatic C1-C8 hydrocarbon radical;
- a C1-C8 aromatic hydrocarbon radical;
- or a C1-C8 heteroaryl radical;
- where R* is independently at each occurrence hydrogen or a straight chained, branched, or cyclic C1-C20 hydrocarbon radical, which may be saturated, partially saturated, or aromatic, each of which may be optionally substituted with one or more groups R, or optionally substituted with 1-6 heteroatoms selected from nitrogen, oxygen, sulfur, or halogen;
- and cosmetically acceptable salts thereof.
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Dependencies are inferred from the claim text.