Cysteine derivative
AssigneeAjinomoto Co., Inc.
InventorsYusuke AMINO, Yoshinobu TAKINO, Shinji KURODA, Keiji IWASAKI, Megumi KANEKO, Fumie OKURA
Life of this patent
Estimating the term…
Abstract
Cysteine compounds represented by the following formula wherein each symbol is as defined in the specification, and salts thereof, are superior in stability, have less odor, exhibit an eumelanin production suppressive effect, and are useful as cosmetic agents.
Claims24
A cosmetic composition, comprising at least one cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A cosmetic composition, comprising at least one cysteine compound represented by formula (IX):
- wherein
- X′ is OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue;
- D is
- (1) an aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of:
- (i) a hydroxyl group, and
- (ii) a C1-6 alkyl group optionally substituted by one or more hydroxyl groups, or
- (2) a C1-22 alkyl group optionally substituted by one or more hydroxyl groups;
- Z′ is a hydrogen atom or a C1-22 alkyl group;
- and
- W′ is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A whitening composition, comprising at least one cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A whitening agent, comprising at least one cysteine compound represented by formula (IX):
- wherein
- X′ is OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue;
- D is
- (1) an aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of:
- (i) a hydroxyl group, and
- (ii) a C1-6 alkyl group optionally substituted by one or more hydroxyl groups, or
- (2) a C1-22 alkyl group optionally substituted by one or more hydroxyl groups;
- Z′ is a hydrogen atom or a C1-22 alkyl group;
- and
- W′ is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof,
- provided that said compound is not:
- N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, or
- N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid anhydride.
A cysteine compound represented by formula (IX):
- wherein
- X′ is OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue;
- D is
- (1) an aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of:
- (i) a hydroxyl group, and
- (ii) a C1-6 alkyl group optionally substituted by one or more hydroxyl groups, or
- (2) a C1-22 alkyl group optionally substituted by one or more hydroxyl groups;
- Z′ is a hydrogen atom or a C1-22 alkyl group;
- and
- W′ is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
Trans N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, or a salt thereof.
Trans N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester, or a salt thereof.
A method of producing a cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- provided that said compound is not:
- N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid, or
- N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid anhydride
- said method comprising:
- reacting a compound represented by formula (IV):
- wherein each symbol is as defined above,
- with:
- (a) a compound represented by formula (V):
- wherein
- A is a halogen atom;
- and
- W is as defined above, or
- (b) a compound represented by formula (V′):
- wherein W is as defined above.
A method of selectively producing a trans form of a cysteine compound represented by formula (I′):
- wherein
- Y″ is a C1-22 alkoxy group;
- Z″ is a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof,
- said method comprising:
- reacting a compound represented by formula (IV′):
- wherein each symbol is as defined above,
- with:
- (a) a compound represented by formula (V):
- wherein
- A is a halogen atom;
- and
- W is as defined above,
- in the presence of an organic base, or
- (b) a compound represented by formula (V′):
- wherein W is as defined above,
- in the absence of a base.
A method for suppressing eumelanin production, comprising applying to skin an effective amount of a cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A method for improving or treating skin fleck, comprising applying to skin an effective amount of a cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
A method for whitening skin, comprising applying to skin an effective amount of a cysteine compound represented by formula (I):
- wherein
- X and Y are each independently OR1 or NHR2 wherein R1 and R2 are each independently a hydrogen atom or a C1-22 alkyl group, or an optionally modified amino acid residue, or X and Y together are —O—;
- Z is a hydrogen atom or a C1-22 alkyl group;
- and
- W is a C1-22 alkyl group, a C1-22 alkoxy group or a C1-22 alkylamino group,
- or a salt thereof.
Dependencies are inferred from the claim text.