Cysteine derivative

Patent metadata

Field	Value
Publication number	US-10144717-B2
Application number	US-201514934596-A
Country	US
Kind code	B2
Filing date	Nov 6, 2015
Priority date	May 28, 2010
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

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.

First claim

The invention claimed is:

1. A cysteine compound represented by formula (I):

wherein
X and Y are each independently OR 1 or NHR 2 wherein R 1 and R 2 are each independently a hydrogen atom or a C 1-22 alkyl group or X and Y together are —O—;
Z is a hydrogen or C 1-22 alkyl group;
provided that when Z is a hydrogen atom, at least one of (i) and (ii) is satisfied;
(i) X is not methoxy, or
(ii) Y is not hydroxy; and
W is a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 alkylamino group,
or a salt thereof;
and provided that said compound or a salt thereof is not:
N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid or a salt thereof,
N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid anhydride or a salt thereof, or
N-acetyl-2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester or a salt thereof.

2. A cysteine compound or salt thereof according to claim 1 , which is in the trans form.

3. The cysteine compound or salt thereof according to claim 1 , wherein Z is a C 1-22 alkyl group.

4. The cysteine compound or salt thereof according to claim 1 , wherein Z is a hydrogen atom.

5. The cysteine compound or salt thereof according to claim 4 , wherein X is not methoxy.

6. The cysteine compound or salt thereof according to claim 4 , wherein Y is not hydroxy.

7. The cysteine compound or salt thereof according to claim 4 , wherein X is not methoxy and Y is not hydroxy.

8. A method of producing a cysteine compound according to claim 1 ,
said method comprising:
reacting a compound represented by formula (IV):

wherein each symbol is as defined in claim 1 ,
with:
(a) a compound represented by formula (V):

wherein
A is a halogen atom; and
W is as defined in claim 1 , or
(b) a compound represented by formula (V′):

wherein W is as defined in claim 1 .

9. A method of selectively producing a trans form of a cysteine compound according to claim 1 , represented by formula (I′):

wherein
Y″ is a C 1-22 alkoxy group;
Z″ is a C 1-22 alkyl group; and
W is a C 1-22 alkyl group, a C 1-22 alkoxy group or a C 1-22 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.

Assignees

• Ajinomoto Kk

Inventors

• Amino Yusuke
• Takino Yoshinobu
• Kuroda Shinji
• Iwasaki Keiji
• Kaneko Megumi
• Okura Fumie

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61Q17/00

  Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings · CPC title

• C07D277/06 Primary

  with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• C07D513/08

  Bridged systems · CPC title

• A61Q15/00

  Anti-perspirants or body deodorants (deodorisation of air A61L9/00) · CPC title