JP2019500367A - チオピリジノン化合物を使用してケラチン物質を脱色するための方法 - Google Patents
チオピリジノン化合物を使用してケラチン物質を脱色するための方法 Download PDFInfo
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- JP2019500367A JP2019500367A JP2018531196A JP2018531196A JP2019500367A JP 2019500367 A JP2019500367 A JP 2019500367A JP 2018531196 A JP2018531196 A JP 2018531196A JP 2018531196 A JP2018531196 A JP 2018531196A JP 2019500367 A JP2019500367 A JP 2019500367A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 17
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- 108010076876 Keratins Proteins 0.000 title claims abstract description 7
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- 239000002537 cosmetic Substances 0.000 claims abstract description 18
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 210000003491 skin Anatomy 0.000 claims description 22
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
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- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
Description
R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基、から選択される基を表す、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C10アルキル基;
c) 飽和分枝状C3〜C10アルキル基;
d) C1〜C6フェニルアルキル基、例えばベンジル、から選択される基を表す)
および、それらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物に対応する。
http://pubchem.ncbi.nlm.nih.gov/compound/47329290?from=summary#section=Top entry:2010−11−26
に開示されている。
(R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基および好ましくはメチル、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基;
c) 飽和分枝状C3〜C6アルキル基、から選択される基を表す)
およびさらに単独または混合物としての、それらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体を有する。
(R1は:
a) 水素原子;
b) メチル基、から選択される基を表す、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基、好ましくはエチル;
c) 飽和分枝状C3〜C4アルキル基、好ましくはイソプロピルおよびイソブチル、から選択される基を表す)
およびさらに単独または混合物としての、それらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体を有する。
本発明のまた別の主題は、式(II):
R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C10アルキル基;
c) 飽和分枝状C3〜C10アルキル基;
d) C1〜C6フェニルアルキル基、例えばベンジルから選択される基を表す)の新規な化合物、およびそれらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物としての化合物であるが、
ただし、下記の2種の化合物(a)および(b):
(R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基および好ましくはメチル、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基;
c) 飽和分枝状C3〜C6アルキル基、から選択される基を表す)
および、それらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物としての意味を有するが、
ただし、下記の化合物(a):
(R1は:
a) 水素原子;
b) メチル基、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基、好ましくはエチル;
c) 飽和分枝状C3〜C4アルキル基、好ましくはイソプロピルおよびイソブチル、から選択される基を表す)
および、それらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物として意味を有するが、
ただし、下記の化合物(a):
− 剥離を促進することにより落屑に直接的に作用できる任意の化合物、例えばβ−ヒドロキシ酸、特にサリチル酸およびその誘導体(5−n−オクタノイルサリチル酸を含む);α−ヒドロキシ酸、例えばグリコール酸、クエン酸、乳酸、酒石酸、リンゴ酸もしくはマンデル酸;尿素;ゲンチシン酸;オリゴフコース;ケイ皮酸;サフォラ・ジャポニカ(Saphora japonica)の抽出物;レスベラトロールなど;
− またはコルネオデスモゾーム、グリコシダーゼ、角質層キモトリプシン酵素(SCCE)もしくは他のプロテアーゼ(トリプシン、キモトリプシン様)の落屑もしくは分解に関係する酵素のいずれかに作用できる任意の化合物を意味することが意図されている。挙げることができるのは、無機塩キレート剤:EDTA;N−アシル−N,N’,N’−エチレンジアミン三酢酸;アミノスルホン酸化合物および特に(N−2−ヒドロキシエチルピペラジン−N−2−エタン)スルホン酸(HEPES);2−オキソチアゾリジン−4−カルボン酸(プロシステイン)誘導体;グリシン型のα−アミノ酸の誘導体(欧州特許第0852949号明細書に記載されている、およびさらにBASF社によって商標名Trilon Mの下で販売されている二酢酸グリシンメチルナトリウム);蜂蜜;糖誘導体、例えばO−オクタノイル−6−D−マルトースおよびN−アセチルグルコサミンである。
化合物3からN−[(2−チオキソ−1,2−ジヒドロピリジン−3−イル)カルボニル]グリシン
N−メチル−N−[(2−チオキソ−1,2−ジヒドロピリジン−3−イル)カルボニル]グリシン
皮膚の色素沈着の予防もしくは減少および/または皮膚の明色化の作用を評価するために、下記の方法で実施例を実施した。
下記(単位、g)を含む皮膚脱色組成物を調製した。
化合物番号4 2g
PEG 400 68g
エタノール 30g
下記(単位、重量%)を含む皮膚脱色ジェルを調製した。
化合物番号1 0.5%
カルボマー(Lubrizol社製のCarbopol 981) 1%
防腐剤 十分量
水 100%まで十分量
DMSO中の300μMの化合物1、2、3もしくは4を含む組成物を色素沈着再構成表皮のサンプルに塗布した(欧州特許第1878790号明細書を参照されたい)。コントロールは、DMSOであった。メラニンは、フォンタナ・マッソン染料を用いた染色後に組織学的切片上での画像分析によって定量した。色素沈着表皮の各サンプルは、顕微鏡に接続したカメラを使用してその全長にわたって撮影した。メラニンを閾値化し、自動画像解析ソフトウエアを使用して各視野においてメラニンのピクセル数を測定した。測定の有意性を決定するために、ノンパラメトリック統計学的試験(マン・ホイットニー試験)を実施した。
Claims (16)
- ケラチン物質を脱色、明色化および/または白色化するための非治療的な美容的方法であって、生理学的に許容される媒体中に、式(I):
R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基、から選択される基を表す、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C10アルキル基;
c) 飽和分枝状C3〜C10アルキル基;
d) C1〜C6フェニルアルキル基、例えばベンジル、から選択される基を表す)の化合物、およびそれらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の少なくとも1つを、単独または混合物として含む美容的組成物の適用を含む方法。 - R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基および好ましくはメチル、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基;
c) 飽和分枝状C3〜C6アルキル基、から選択される基を表す、請求項1に記載の方法。 - R1は:
a) 水素原子;
b) メチル基、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基、好ましくはエチル;
c) 飽和分枝状C3〜C4アルキル基、好ましくはイソプロピルおよびイソブチル、から選択される基を表す、請求項1または2に記載の方法。 - 式(I)の前記化合物が:
- 式(I)の前記化合物は、下記の化合物:
- 式(I)の前記化合物は、単独または混合物として、前記組成物中で、前記組成物の総重量に対して、0.01重量%〜10重量%、好ましくは0.1重量%〜5重量%および特に0.5重量%〜3重量%の量で存在する、請求項1〜5のいずれか一項に記載の方法。
- 前記組成物は、水;有機溶媒、特にC1〜C6アルコールおよびC2〜C10カルボン酸エステル;鉱物、動物および/または植物起源の炭素ベースの油および/またはシリコ−ン油;ワックス、顔料、フィラー、染料、界面活性剤、乳化剤、共乳化剤;化粧用もしくは皮膚科学活性剤、UV遮断剤、ポリマー、親水性もしくは親油性ゲル化剤、増粘剤、防腐剤、香料、殺菌剤、セラミド、悪臭吸収剤、酸化防止剤からなる群から選択される少なくとも1種のアジュバントを含む、請求項1〜6のいずれか一項に記載の方法。
- 前記組成物は:落屑剤;鎮静剤、有機もしくは無機光保護剤、保湿剤;脱色剤もしくは色素沈着促進剤;抗糖化剤;NOシンターゼ阻害剤;真皮もしくは表皮高分子の合成を刺激する、および/またはその分解を防止するための作用物質;線維芽細胞および/またはケラチン生成細胞の増殖を刺激するため、またはケラチン生成細胞分化を刺激するための作用物質;筋弛緩剤および/または皮膚収縮低減剤;伸張剤;汚染防止剤および/またはフリーラジカル捕捉剤;毛細血管循環に作用する作用物質;細胞のエネルギー代謝に作用する作用物質;およびそれらの混合物から選択される少なくとも1種の活性剤を含む、請求項1〜7のいずれか一項に記載の方法。
- ケラチン物質を白色化、明色化および/または脱色するための作用物質としての、請求項1〜6のいずれか一項に規定された式(I)の化合物の非治療的な美容的使用。
- 式(II):
R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基から選択される基を表す、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基;
c) 飽和分枝状C3〜C10アルキル基;
d) C1〜C6フェニルアルキル基、例えばベンジルから選択される基を表す)の化合物、およびそれらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物としての化合物であって、
ただし、下記の2種の化合物(a)および(b):
- 式(II)中、
R1は:
a) 水素原子;
b) 飽和直鎖状C1〜C4アルキル基および好ましくはメチル、から選択される基を表し、
R2は:
a) 水素原子;
b) 飽和直鎖状C1〜C6アルキル基;
c) 飽和分枝状C3〜C6アルキル基、から選択される基を表す化合物、およびそれらの互変異性体、それらの塩、それらの溶媒和物およびそれらの光学異性体ならびにそれらのラセミ体の、単独または混合物としての、請求項1〜10のいずれか一項に記載の化合物であって、
ただし、下記の2種の化合物(a):
-
- 請求項10〜12のいずれか一項に記載の式(II)の少なくとも1種の化合物を含む組成物、特に化粧用組成物。
- 前記式(II)の化合物は、前記組成物の前記総重量に対して、0.01重量%〜10重量%、好ましくは0.1重量%〜5重量%および特に0.5重量%〜3重量%の量で存在することを特徴とする、請求項13に記載の組成物。
- 下記のスキーム:
- 下記の工程:
(i)式(W):
ii)前記化合物(W)を式(V):
次に
iii)式(I)および(II)の化合物を形成できるように、例えば二亜硫酸ナトリウム、チオ尿素、チオ硫酸ナトリウムもしくはチオ酢酸などの試薬によって塩素と硫黄を交換する工程、次に任意選択により場合によっては
iv)R2基が水素を表す式(I)および(II)の化合物については、直接得るか、または無機塩基を使用して対応するエステルの鹸化とそれに続く酸性化の追加の工程によって得ることができる工程を含む、請求項15に記載の調製方法。
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FR3115207B1 (fr) | 2020-10-15 | 2022-10-07 | Oreal | Utilisation de composés thiopyridinones pour prévenir la formation des points noirs cutanés |
FR3118877B1 (fr) | 2021-01-18 | 2023-11-17 | Oreal | Stabilisation d’un composé de thiopyridinone et réduction du jaunissement de la composition le comprenant |
WO2022138471A1 (en) | 2020-12-22 | 2022-06-30 | L'oreal | Stabilization of thiopyridinone compound and yellowing reduction of composition comprising same |
FR3118871B1 (fr) | 2021-01-19 | 2024-03-01 | Oreal | stabilisation d’un composé de thiopyridinone dans une composition du type E/H |
EP4267097A1 (en) | 2020-12-22 | 2023-11-01 | L'oreal | Stabilization of thiopyridinone compound in w/o composition |
FR3138869A1 (fr) | 2022-08-22 | 2024-02-23 | L'oreal | Stabilisation de composé thiopyridinone et composition comprenant ce dernier |
FR3141624A1 (fr) | 2022-11-04 | 2024-05-10 | L'oreal | Composition comprenant un composé de type thiopyridinone et des émulsifiants à base de polyglycéryle |
WO2023249912A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Cosmetic composition comprising hydrophilic antioxidants and thiopyridinone compounds |
WO2023245462A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Stabilized composition comprising thiopyridinone compound |
FR3141623A1 (fr) | 2022-11-04 | 2024-05-10 | L'oreal | Composition cosmétique comprenant des antioxydants hydrophiles et des composés de thiopyridinone |
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FR3138036A1 (fr) | 2022-07-22 | 2024-01-26 | L'oreal | Stabilisation de composé de thiopyridinone et composition comprenant ledit composé |
WO2023249122A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Stabilization of thiopyridinone compound and composition comprising same |
WO2023245461A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Composition for delivery of active compound |
FR3138310A1 (fr) | 2022-07-26 | 2024-02-02 | L'oreal | Stabilisation de composé thiopyridinone et composition le comprenant |
JP2024000769A (ja) | 2022-06-21 | 2024-01-09 | ロレアル | チオピリジノン化合物及びチオピリジノン化合物を含む組成物の安定化 |
WO2023245459A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Anti-oxidizing composition comprising a thiopyridinone compound |
WO2023249121A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Stabilization of thiopyridinone compound and composition comprising same |
FR3139008A1 (fr) | 2022-08-24 | 2024-03-01 | L'oreal | Solubilisation de composé thiopyridinone et composition comprenant ce dernier |
WO2023249915A1 (en) | 2022-06-21 | 2023-12-28 | L'oreal | Cosmetic composition comprising natural emulsifiers and thiopyridinone compounds |
FR3141622A1 (fr) | 2022-11-04 | 2024-05-10 | L'oreal | Composition cosmétique comprenant des émulsifiants naturels et des composés de thiopyridinone |
WO2023248247A1 (en) | 2022-06-21 | 2023-12-28 | L'oréal | Stabilization of thiopyridinone compound and composition comprising same |
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WO2023248248A1 (en) | 2022-06-21 | 2023-12-28 | L'oréal | Solubilization of thiopyridinone compound and composition comprising same |
WO2023245463A1 (en) * | 2022-06-21 | 2023-12-28 | L'oreal | A stabilized composition comprising a thiopyridinone compound and chelating agent |
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2015
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- 2016-12-01 ES ES16809679T patent/ES2759554T3/es active Active
- 2016-12-01 EP EP16809679.0A patent/EP3390363B1/en active Active
- 2016-12-01 US US16/061,908 patent/US20190380937A1/en active Pending
- 2016-12-01 CN CN202210183416.6A patent/CN114533579A/zh active Pending
- 2016-12-01 KR KR1020187020640A patent/KR102110104B1/ko active IP Right Grant
- 2016-12-01 WO PCT/EP2016/079394 patent/WO2017102349A1/en active Application Filing
- 2016-12-01 JP JP2018531196A patent/JP6629451B2/ja active Active
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Also Published As
Publication number | Publication date |
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EP3390363A1 (en) | 2018-10-24 |
FR3045604B1 (fr) | 2018-01-26 |
JP6629451B2 (ja) | 2020-01-15 |
CN114533579A (zh) | 2022-05-27 |
KR20180096708A (ko) | 2018-08-29 |
CN108473432B (zh) | 2022-03-15 |
US20190380937A1 (en) | 2019-12-19 |
CN108473432A (zh) | 2018-08-31 |
FR3045604A1 (fr) | 2017-06-23 |
KR102110104B1 (ko) | 2020-05-13 |
ES2759554T3 (es) | 2020-05-11 |
WO2017102349A1 (en) | 2017-06-22 |
EP3390363B1 (en) | 2019-09-18 |
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