JP2008515858A - 下側の目の輪郭の下に形成される袋を低減又は除去する合成ペプチド及び化粧品又は皮膚薬剤組成物でのそれらの使用 - Google Patents
下側の目の輪郭の下に形成される袋を低減又は除去する合成ペプチド及び化粧品又は皮膚薬剤組成物でのそれらの使用 Download PDFInfo
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- JP2008515858A JP2008515858A JP2007535186A JP2007535186A JP2008515858A JP 2008515858 A JP2008515858 A JP 2008515858A JP 2007535186 A JP2007535186 A JP 2007535186A JP 2007535186 A JP2007535186 A JP 2007535186A JP 2008515858 A JP2008515858 A JP 2008515858A
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/14—Preparations for removing make-up
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
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- Cosmetics (AREA)
Abstract
【化1】
のペプチド、それらの立体異性体及びそれらのラセミ又は非ラセミ混合物、及びそれらの化粧品的又は皮膚薬剤的に許容可能である塩に関し、式中、Xはシステニル、セリル、トレオニル又はアミノブチリルであり、R1はH又はアルキル、アリール、アラルキル又はアシル基であり、及びR2はアミノ、ヒドロキシ又はチオールであり、それらの全ては脂肪族又は環状基で置換又は非置換である。本発明は、それらを有する化粧品又は皮膚薬剤組成物を得る方法、及び皮膚を処理するための、好ましくは、目の下に形成される袋を低減又は除去するためのそれらの使用にも関する。
【選択図】なし
Description
Xはシステニル、セリル、トレオニル又はアミノブチリルとすることができ、
R1はH又はアルキル、アリール、アラルキル又はアシル基とすることができ、及び、
R2はアミノ、ヒドロキシ又はチオールとすることができ、これらの全ては、脂肪族又は環状基で置換又は非置換である。
Xはセリル又はアミノブチリルとすることができ、
R1はH又は飽和又は不飽和、分岐又は環状、直鎖C2からC24アシルとすることができ、及び、
R2はアミノ又はヒドロキシとすることができ、飽和又は不飽和、分岐又は環状、直鎖、脂肪族C1からC24基で置換又は非置換である。
(化学合成)
全ての合成処理は、多孔質のポリエチレンディスクを備えたポリプロピレンシリンジで実行される。全ての試薬及び溶媒は合成用の品質であり、いかなる追加処理もなく使用される。Fmoc基の除去は、ピペリジン−DMF(2:8、v/v)(1×1分、1×5分、5mL/g樹脂)で実行される[ロイド−ウィリアムズ(Lloyd−Williams),P.,アルベリチオ(Albericio),F.とジラルト(Giralt),E.(1997)Chemical Approaches to the Synthesis of Peptides and Protein.CRC,ボーカラートン(フロリダ、米国)]。脱保護、カップリング、及び、再度、脱保護のステップの間の洗浄は、各回で、10mLの溶媒/g樹脂を使用して、DMF(3×1分)で実行された。カップリング反応は、3mLの溶媒/g樹脂で実行された。カップリングの制御は、ニンヒドリン試験によって実行される[カイザー(Kaiser),E.、コールスコット(Colescott) R.L.、ボッシンジャー(Bossinger) C.D.とクック(Cook) P.I.(1970) Color test for detection of free terminal amino groups in the solid−phase synthesis of peptides Anal. Biochem. 34,595−598]。全ての合成変換及び洗浄は、25℃で実行された。
アミノ酸に使用される略語は、Eur.J.Biochem.(1984)138,9−37及びJ.Biol.Chem.(1989)264,633−673で定められる生化学命名法においてIUPAC−IUB委員会の規則に従う。
(Ac−βAla−His−Cys−His−OHを得る)
1.3mLのDIEA(2.9mmol、0.33当量)が添加される55mLのDCMに溶解した5.5gのFmoc−L−His(Trt)−OH(8.9mmol、1当量)が2−クロロトリチル樹脂(5.5g、8.8mmol)を乾燥するために組み入れられた。それは5分間撹拌状態を維持し、その後に、2.5mLのDIEA(5.9mmol、0.67当量)が添加された。それは、40分間反応することができた。残った塩化物基は4.4mLのMeOHでの処理によってブロックされた。
(Palm−βAla−His−Ser−His−NH2の合成)
0.73mmol/g(0.5mmol)の官能基化を備えた0.685mgのFmoc−AM−MBHA樹脂は、ピペリジン−DMFとともに、説明される一般的な手順にしたがって、Fmoc基を除去する目的で、処理された。1.58gのFmoc−L−His(Trt)−OH(2.5mmol、5当量)は、DIPCDI(385μL、2.5mmol、5当量)及びHOBt(385mg、2.5mmol、5当量)の存在下で、溶媒としてDMFを使用して、1時間、樹脂に組み入れられた。
(Ac−βAla−His−Ser−His−NH−(CN2)9−CH3を得る)
500μLのDIEA(1.1mmol、0.33当量)が添加されている20mLのDCMに溶解された2.0gのFmoc−L−His(Trt)−OH(3.23mmol、1当量)は、乾燥2−クロロトリチル樹脂(2.0g、3.3mmol)に組み入れられた。それは、5分間、撹拌状態を維持し、その後に、1mLのDIEA(2.2mmol、0.67当量)が添加された。それは、40分間、反応することができた。残った塩化物基は、1.6mLのMeOHでの処理によってブロックされた。
(Ac−βAla−His−Ser−His−OHを得る)
実施例4のペプチドは、実施例1のように、同様の合成の手順にしたがって、得られるが、Fmoc−L−Ser(tBu)−OH(8.43g、22mmol)をFmoc−L−Cys(Trt)−OHの代わりに第2のアミノ酸として組み入れる。合成が完了すると、樹脂は、DMF(5×1分)、DCM(4×1分)、ジエチル・エーテル(4×1分)で洗浄され、そして、真空下で乾燥された。
(Ac−βAla−His−Ser−His−OHを含有する化粧品組成物の調整)
次の剤形は本発明で説明されるように調整された。
(Ac−βAla−His−Cys−His−OHを含有する化粧品組成物の調整)
次の剤形は本発明で説明されるように調整された。
目の下に形成された袋を持つ20人の被験者で実施された実施例5で説明された化粧品組成物の臨床研究では、組成物は、目の下に形成される袋の大きさを低減することができることを示した。被験者は、化粧品組成物を目の輪郭領域に、柔らかいマッサージで、1日に1度、2ヶ月間、適用するように支持された。コルネオメーター(Skinlab(登録商標))による皮膚の水分補給及びエラストメーターによる皮膚の弾力性の程度の客観的な計測は、時間0と、処理の開始後15、30及び60日とで実行され、そして、下側の目袋の大きさは皮膚科医によって観察もされた。
−Xは、システニル、セリン、トレオニル、及びアミノブチリルによって形成されるグループから選択され、
−R1は、H又はアルキル、アリール、アラルキル、及びアシル基によって形成されるグループから選択され、及び、
−R2は、アミノ、ヒドロキシ及びチオールによって形成されるグループから選択され、脂肪族又は環状基で置換又は非置換である。
Claims (19)
- R1は飽和又は不飽和、分岐又は環状、直鎖C2からC24アシルであることを特徴とする請求項1に記載されたペプチド。
- R2はアミノ又はヒドロキシであり、飽和又は不飽和、分岐又は環状、直鎖C1からC24脂肪族基で置換又は非置換であることを特徴とする請求項1に記載されたペプチド。
- XはL−Serであり、R1はHであり、及びR2はアミノであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- XはL−Serであり、R1はアセチルであり、及びR2はアミノであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- XはL−Serであり、R1はパルミトイルであり、及びR2はアミノであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- XはL−Serであり、R1はHであり、及びR2はヒドロキシであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- XはL−Serであり、R1はアセチルであり、及びR2はヒドロキシであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- XはL−Serであり、R1はパルミトイルであり、及びR2はヒドロキシであり、メチル又はエチル又はドデシル又はヘキサデシル基で置換又は非置換であることを特徴とする請求項1から3のいずれか1項に記載されたペプチド。
- 固相で実行されることを特徴とする請求項1から9のいずれか1項に記載された一般式(I)のペプチドを得る処理。
- Fmoc/tブチル、Fmoc/トリチル及びFmoc/アリルによって形成されるグループから選択される保護基を使用することを特徴とする請求項10に記載された一般式(I)のペプチドを得る処理。
- 化粧品的又は皮膚薬剤的に有効量の少なくとも1つの一般式(I)のペプチド及び少なくとも1つの化粧品的又は皮膚薬剤的に許容可能である賦形剤又はアジュバントを有することを特徴とする請求項1から9のいずれか1項に記載された化粧品又は皮膚薬剤組成物。
- リポソーム、ミリカプセル、マイクロカプセル、ナノカプセル、スポンジ、ミリスフェア、マイクロスフェア、ナノスフェア、ミリ粒子、マイクロ粒子及びナノ粒子によって形成されるグループから選択される化粧品的又は皮膚薬剤的に許容可能であるキャリアに組み入れられる少なくとも1つの一般式(I)のペプチドを有することを特徴とする請求項12に記載された化粧品又は皮膚薬剤組成物。
- 水中油型乳剤、油中水型乳剤、ミルク、化粧水、ジェル、軟膏、香油、泡、ボディオイル、石けん、棒、鉛筆、スプレー、クリーム、塗布剤、膏薬、美容液及びムースによって形成されるグループから選択される剤形を有することを特徴とする請求項12及び13のいずれか1項に記載された化粧品又は皮膚薬剤組成物。
- タオレット、ヒドロゲル、パッチ及びフェースマスクによって形成されるグループから選択される固体支持体に組み入れられる少なくとも1つの一般式(I)のペプチドを有することを特徴とする請求項12及び13のいずれか1項に記載された化粧品又は皮膚薬剤組成物。
- コンシーラー、化粧ファンデーション、化粧水、及び化粧除去化粧水によって形成されるグループから選択される化粧製品に組み入れられる少なくとも1つの一般式(I)のペプチドを有することを特徴とする請求項12及び13のいずれか1項に記載された化粧品又は皮膚薬剤組成物。
- 皮膚処理用化粧品又は皮膚薬剤組成物の製造における請求項1から9のいずれか1項に記載された式(I)のペプチドの使用。
- 顔面皮膚処理用化粧品又は皮膚薬剤組成物の製造における請求項17に記載された式(I)のペプチドの使用。
- 下側の目の輪郭の下に形成される袋を低減又は除去するための化粧品又は皮膚薬剤組成物の製造における請求項17及び18のいずれか1項に記載された式(I)のペプチドの使用。
Applications Claiming Priority (3)
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ES200402364A ES2261036B1 (es) | 2004-10-05 | 2004-10-05 | Peptidos sinteticos que disminuyen o eliminan las bolsas formadas bajo el contorno inferior de los ojos y su uso en composiciones cosmeticas o dermofarmaceuticas. |
ESP200402364 | 2004-10-05 | ||
PCT/ES2005/000514 WO2006040374A1 (es) | 2004-10-05 | 2005-09-22 | Péptidos sintéticos que disminuyen o eliminan las bolsas formadas bajo el contorno inferior de los ojos y su uso en composiciones cosméticas o dermofarmacéuticas |
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US (2) | US8114439B2 (ja) |
EP (1) | EP1798238B1 (ja) |
JP (1) | JP4977613B2 (ja) |
KR (1) | KR101261065B1 (ja) |
CN (1) | CN101061135A (ja) |
AT (1) | ATE459639T1 (ja) |
AU (1) | AU2005293529B2 (ja) |
BR (1) | BRPI0516466B8 (ja) |
CA (1) | CA2583670C (ja) |
DE (1) | DE602005019764D1 (ja) |
ES (2) | ES2261036B1 (ja) |
IL (1) | IL182358A (ja) |
MX (1) | MX2007004099A (ja) |
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ES2342754B1 (es) * | 2008-10-03 | 2011-05-11 | Lipotec, S.A. | Peptidos utiles en el tratamiento y/o cuidado de la piel, mucosas, cuero cabelludo y/o cabello y su uso en composiciones cosmeticas o farmaceuticas. |
FR2939040B1 (fr) * | 2008-12-03 | 2013-08-09 | Laboratoires Inneov Snc | Association de lycopene, polyphenol et vitamines pour le soin des matieres keratiniques |
JP6326601B2 (ja) * | 2013-03-13 | 2018-05-23 | アンティース ソシエテ アノニム | 皮膚更新のためのペプチド及び前記ペプチドを使用する方法 |
CN105813695A (zh) | 2013-11-01 | 2016-07-27 | 斯弗尤姆生物制药有限公司 | 用于透皮递送治疗剂和美容剂的包含体 |
CA2965525A1 (en) | 2014-10-31 | 2016-05-06 | Lubrizol Advanced Materials, Inc. | Thermoplastic polyurethane film for delivery of active agents to skin surfaces |
WO2017079248A1 (en) | 2015-11-05 | 2017-05-11 | Lubrizol Advanced Materials, Inc. | Thermoformable dual network hydrogel compositions |
US10493020B2 (en) | 2016-04-14 | 2019-12-03 | The Procter & Gamble Company | Method of improving the appearance of periorbital dyschromia |
Citations (1)
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WO1993004690A1 (en) * | 1991-09-09 | 1993-03-18 | Peptide Technology Limited | Method for the treatment of the complications and pathology of diabetes |
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WO1993004690A1 (en) * | 1991-09-09 | 1993-03-18 | Peptide Technology Limited | Method for the treatment of the complications and pathology of diabetes |
Also Published As
Publication number | Publication date |
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US20100098769A1 (en) | 2010-04-22 |
CA2583670C (en) | 2013-04-09 |
MX2007004099A (es) | 2007-06-15 |
RU2387666C2 (ru) | 2010-04-27 |
EP1798238B1 (en) | 2010-03-03 |
RU2007112479A (ru) | 2008-11-20 |
ATE459639T1 (de) | 2010-03-15 |
EP1798238A1 (en) | 2007-06-20 |
BRPI0516466B8 (pt) | 2021-05-25 |
USRE45610E1 (en) | 2015-07-14 |
DE602005019764D1 (de) | 2010-04-15 |
BRPI0516466B1 (pt) | 2018-01-09 |
CA2583670A1 (en) | 2006-04-20 |
JP4977613B2 (ja) | 2012-07-18 |
WO2006040374A1 (es) | 2006-04-20 |
BRPI0516466A (pt) | 2008-09-09 |
CN101061135A (zh) | 2007-10-24 |
US8114439B2 (en) | 2012-02-14 |
IL182358A (en) | 2012-01-31 |
PL1798238T3 (pl) | 2010-11-30 |
KR101261065B1 (ko) | 2013-05-06 |
AU2005293529B2 (en) | 2011-06-23 |
AU2005293529A1 (en) | 2006-04-20 |
ES2342307T3 (es) | 2010-07-05 |
ES2261036B1 (es) | 2007-12-16 |
KR20070099522A (ko) | 2007-10-09 |
IL182358A0 (en) | 2007-07-24 |
ES2261036A1 (es) | 2006-11-01 |
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