JP7040940B2 - ペプチド化合物、それらを含む組成物及び前記化合物の使用、特に化粧用途 - Google Patents
ペプチド化合物、それらを含む組成物及び前記化合物の使用、特に化粧用途 Download PDFInfo
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- JP7040940B2 JP7040940B2 JP2017532130A JP2017532130A JP7040940B2 JP 7040940 B2 JP7040940 B2 JP 7040940B2 JP 2017532130 A JP2017532130 A JP 2017532130A JP 2017532130 A JP2017532130 A JP 2017532130A JP 7040940 B2 JP7040940 B2 JP 7040940B2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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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
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
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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
-
- 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
-
- 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
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- 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
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Toxicology (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cosmetics (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
X-(AA)n-(AA)*-(AA)m-Z (I)
に応答し、(式中、
・(AA)*は、リジン(K*)、オルニチン(Orn*)、ジアミノプロピオン酸(Dap*)又はジアミノ酪酸(Dab*)又はこれらのアミノ酸のヒドロキシル化誘導体であり、その上のカルボン酸は、側鎖の窒素にペプチド結合によってグラフトされ、前記カルボン酸は、芳香族である又は芳香族でない、5つ、6つ又は7つの原子を有する少なくとも炭素環又は複素環を含み、前記環又は複素環は、-OH、-O-、-CO-、-S-、-N=、-NH-、-N=C-NH-官能基、並びに荷電窒素官能基を含むことができ;
・nは、0、1、2、3又は4であり;
・mは、0、1、2、3又は3であり;
・AAは、(AA)*、又はアラニン(A、Ala)、システイン(C、Cys)、アスパラギン酸(D、Asp)、グルタミン酸(E、Glu)、フェニルアラニン(F、Phe)、グリシン(G、Gly)、ヒスチジン(H、His)、イソロイシン(I、He)、リジン(K、Lys)、ロイシン(L、Leu)、メチオニン(M、Met)、アスパラギン(N、Asn)、プロリン(P、Pro)、グルタミン(Q、Gln)、アスパラギン(R、Arg)、セリン(S、Ser)、スレオニン(T、Thr)、バリン(V、Val)、トリプトファン(W、Trp)及びチロシン(Y、Tyr)、それらの誘導体又は類似体から選択されるアミノ酸であり;AAは、n+m>1である場合に、互いに独立して選択され;
・N末端で、Xは、H、-CO-R1及び-SO2-R1から選択され;
・C末端で、Zは、OH、OR1、NH2、NHR1及びNR1R2から選択され;及び
・R1及びR2は、互いに独立して、線状、分枝状、環状、多環式、不飽和、ヒドロキシル化、カルボニル化、リン酸化及び/又は硫酸化されていてもよいアルキル、アリール、アラルキル、アルキルアリール、アルコキシ及びアリールオキシ基から選択され、前記基は、その骨格中にヘテロ原子、特にO、S及び/又はNを含むことができる。
-コラーゲンの最も一般的なアミノ酸であるグリシン(G、Gly)、プロリン(P、Pro)又はリジン(K、Lys);
-ヒドロキシプロリン(Hyp)及びヒドロキシリジン(Hyl)のようなそれらのヒドロキシル化誘導体;
-セリン(S、Ser)、スレオニン(T、Thr)及びチロシン(Y、Tyr)などのアルコール機能を有するアミノ酸;そして
- 環を含む他の天然アミノ酸、すなわちヒスチジン(H、His)及びフェニルアラニン(F、Phe)。
式中、
(AA);X;Z;n、m及びpは、上記の通りであり;そして
φは、環又はポリ環であり、各環は5又は6個の炭素原子を有し、芳香族又は非芳香族であり、1つ以上の荷電Nヘテロ原子を含むか含まないかを問わない。
式中
(AA);X;Z;n、m及びpは、例えば、上記の通りであり;そして
φは、環又はポリ環であり、各環は5又は6個の炭素原子を有し、芳香族又は非芳香族であり、1つ以上の荷電Nヘテロ原子を含むか含まないかを問わない。
oK*=K(P):リジン(K、Lys)にグラフトされたプロリン(P、Pro);
oK*=K(Hyp):リジン(K、Lys)にグラフトされたヒドロキシプロリン(Hyp);及び
oK*=K(Pyr):リジン(K、Lys)にグラフトされたピログルタミン酸(Pyr)。
-R1及び/又はR2は、1~24個の炭素原子を含むアルキル鎖、好ましくは3~24個の炭素原子を含む親油性アルキル鎖であり;及び/又は
-Xは、CO-R1アシル基であり、Zは、OH、OMe、OEt及びNH2から選択され、好ましくはZは、OHであり;Xは、好ましくは、オクタノイル(C8)、デカノイル(C10)、ラウロイル(C12)、ミリストイル(C14)、パルミトイル(C16)、ステアロイル(C18)、ビオチノイル、エライドイル、オレオイル及びリポイルから選択される;より好ましくは、ラウロイル(C12)、ミリストイル(C14)及びパルミトイル(C16)から選択される;及び/又は
-Zは、OHであり、Xは、ミリストイル(C14)又はパルミトイル(C16)から選択される。
oX-K(P)-HG-Z、X-K(Pyr)-HG-Z、X-K(Hyp)-HG-Z、
oX-K(P)-GH-Z、X-K(Pyr)-GH-Z及びX-K(Hyp)-GH-Z。
oPal-K(P)-HG-OH、Pal-K(Pyr)-HG-OH、Pal-K(Hyp)-HG-OH、
oPal-K(P)-GH-OH、Pal-K(Pyr)-GH-OH、Pal-K(Hyp)-GH-OH。
X-KT-Z、
X-GHK-Z、
X-KPK-Z、
X-KFK-Z、
X-KAvaK-Z(Ava=5-アミノ吉草酸)、
X-KMO2K-Z(Matrixyl Synthe’6(商標))(MO2=二酸素化メチオニン)、
X-KTFK-Z(配列番号3)
X-KGHK-Z(Kollaren 6(商標)又はFolixyl(商標)又はChronoline(商標)(配列番号4)
X-KTTKS-Z(Matrixyl(商標))(配列番号1)、又は
X-GKTTKS-Z(配列番号5)
-広範囲の老化防止処置;及び/又は
-抗皺及び細かい線の処置(平滑な肌のリリーフ、詰まった皺);及び/又は
-皮膚の機械的特性を改善する処置:堅さ/トーン/弾力/柔軟性;及び/又は
-皮膚密度を高める処置(再構成効果);及び/又は
-皮膚のボリュームを増加させる処置(盛り上がり効果);及び/又は
-ストレッチマークの出現に対応するための処置;及び/又は
-保湿処置;及び/又は
-アンチスポット処置;及び/又は
-皮膚の均一性及び/又は輝きを改善するための処置;及び/又は
-皮膚の色素沈着に作用する処置。
-Pentapharmによって販売されているVialox(商標)(INCI名=ペンタペプチド-3(アラニン、アルギニン、イソロイシン、グリシン及びプロリンを含む合成ペプチド))、Syn-ake(商標)(β-Ala-Pro-Dab-NH-Bzl)又はSyn-Coll(商標)(Pal-Lys-Val-Lys-OH);
-Lipotecによって販売されているArgireline(商標)(Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2(INCIm名=アセチルヘキサペプチド-3)(配列番号16)、Leuphasyl(商標)(Tyr-D-Ala-Gly-Phe-Leu)(配列番号17)、Aldenine(商標)(Gly-His-Lys)、Trylagen(商標)(INCI名=Pseudoalteromonas Ferment抽出物、加水分解されたコムギタンパク質、加水分解された大豆タンパク質、トリペプチド-10シトルリン(シトルリンとトリペプチド-10(アスパラギン酸、イソロイシン及びリジンで構成される合成ペプチド)の反応生成物)、トリペプチド-1)、Eyeseryl(商標)(Ac-β-Ala-His-Ser-His)(配列番号18)、Serilesine(商標)(Ser-Ile-Lys-Val-Ala-Val)(配列番号19)、又はDecorinyl(商標)(INCI名:トリペプチド-10シトルリン=シトルリンとトリペプチド-10(アスパラギン酸、イソロイシン及びリジンで構成される合成ペプチド)の反応生成物));
-Vincienceによって販売されているCollaxyl(商標)(Gly-Pro-Gln-Gly-Pro-Gln(配列番号20))又はQuintescine(商標)(Cys-Gly);
-Les Laboratoires Serobiologiques/Cognisによって販売されているCytokinol(商標)LS(カゼイン加水分解物);
-l’lnstitut Europeen de Biologie Cellulaireによって販売されているKollaren(商標)(Gly-His-Lys)、IP2000(商標)(Pal-Val-Tyr-Val)又はMeliprene(商標)(INCI名=モノフルオロヘプタペプチド-1:酢酸と、アルギニン、グリシン、グルタミン酸、ヒスチジン、ノルロイシン、p-フルオロフェニルアラニン及びトリプトファンを含む合成ペプチドとの反応生成物);
-Innovationsによって販売されているNeutrazen(商標)(Pal-His-D-Phe-Arg-NH2);又は
-lnfinitec Activosによって販売されているBONT-L-Peptide(商標)(INCI名=パルミトイルヘキサペプチド-19:パルミチン酸とヘキサペプチド-19(アスパラギン、アスパラギン酸、リジン及びメチオニンからなる合成ペプチド)の反応生成物)、Timp-Peptide(商標)(INCI名=アセチルヘキサペプチド-20:ヘキサペプチド-20(アラニン、グリシン、リジン、バリン及びプロリンからなる合成ペプチド)のアセチル化によって得られた反応生成物))、又はECM Moduline(商標)(INCI名=パルミトイルトリペプチド-28:パルミチン酸とトリペプチド-28(アルギニン、リジン及びフェニルアラニンからなる合成ペプチド)の反応生成物))。
-広範囲の老化防止処置;及び/又は
-抗皺及び細かい線の処置(平滑な肌のリリーフ、詰まった皺);及び/又は
-皮膚の機械的特性を改善する処置:堅さ/トーン/弾力/柔軟性;及び/又は
-皮膚密度を高める処置(再構成効果);及び/又は
-皮膚のボリュームを増加させる処置(盛り上がり効果);及び/又は
-ストレッチマークの出現に対応するための処置;及び/又は
-保湿処置;及び/又は
-アンチスポット処置;及び/又は
-皮膚の均一性及び/又は輝きを改善するための処置;及び/又は
-皮膚の色素沈着に作用する処置。
以下の実施例は、本発明の特定の態様を開示し、説明する。開示を限定するものとみなされるべきではない。なぜなら、その理解と実施に有用な情報しか提供しないからである。
ペプチド化合物は、Fmocカップリング化学(アミン保護基(フルオレニルメトキシカルボニル))を用いて固相で合成され、次のアミノ酸をペプチドのN末端の方向に保護する。第1のFmoc-アミノ酸(250μM)を含む支持体をDMSOに懸濁させ、30分間、ピロリジン溶液(20%dans DMSO)で脱保護し、次いでDMSOで数回リンスする。N-メチルモルホリン(2M/DMSO)の存在下で2時間、HATU(0.5M/DMSO)(カルボン酸を活性エステルに変換するために使用される薬剤)を用いて、以下のFmoc-アミノ酸(200mM/DMSO)のカップリングを実現する。カップリングが完了したら、樹脂をDMSOを用いて数回リンスする。
開始製品:
-上記の合成方法に従って合成された純粋なペプチド性化合物;
-賦形剤:油性マトリックスを形成するために、例えば水を含まない化粧品組成物のさらなる製剤のための水を含まない組成物を形成するために選択される脂肪エステルの混合物。
操作様式:ペプチド化合物を賦形剤と混合し、可溶化及び完全な透明度になるまで穏やかに撹拌し、加熱する。
本発明のペプチド化合物は、以下に示す多くの顕著な効果を示す。上記A)に従って調製し、賦形剤に溶解した化合物をインビトロで試験し、以下に示す活性を示した。
1)ELISAアッセイ
プロトコール
培養中の正常ヒト線維芽細胞(NHF)を被験物質又はそれらの賦形剤(陰性対照)と72時間接触させる。接触後、培養上清を回収し、真皮巨大分子の合成をELISAによって推定する。細胞生存度の評価は、ヘキストアッセイによって行われ、得られたデータを重み付けするために使用される。
Pal-K(P)-HG-OH及び/又はPal-K(Pyr)-HG-OHを、同じELISAアッセイでPal-KHG-OHと比較する。
異なる処方を以下に記載する。本発明による有効成分の活性に任意で補助的に及び/又はそれに加えてもたらされる追加の化粧用有効成分は、それらの疎水性又は親水性に応じて正しい相に添加することができる。これらの成分は、それらの機能、適用部位(身体、顔、首、胸、手、髪、まつげ、眉毛、髪など)、所望の最終効果及び標的の消費者、例えば、例えば、抗酸化剤、保湿、栄養、保護、平滑化、リモデリング、ボリュームフィーリング(リポフィリング)、皮膚の輝きへの作用、スポット防止、目の周りのくま防止、抗糖化、スリミング、リラクシング、筋弛緩、赤味防止、抗ストレッチ跡などによる任意のカテゴリーのものであり得る。それらは、上記の説明において言及されている。
・CALMOSENSINE(商標):Tyr-Argリポジペプチドを含むSederma(WO1998/07744)により販売されている高感度の皮膚用の鎮静作用。不快感を軽減する。
・SEBULESS(商標):Sedermaから販売されているSyringa vulgaris抽出物を含む浄化セボレギュレーター成分。肌をマット化し、リフレッシュし、傷みをなくす。
・PRODIZIA(商標):SEDERMA(WO2013/046137)が販売する有効成分で、Albizia julibrissin抽出物を含み、皮膚の疲労と闘う:もの回りの熊、アイバッグの下、鈍い肌色及び描かれた特徴を、修復し、糖化及びグリコシド化の損傷によって引き起こされるものに対する。
・PACIFEEL(商標):Sedermaが販売する有効成分の活性成分であり、皮膚の不快感を緩和し、感受性の高い皮膚の赤みを消し、表皮を強化して水和させる、ペルーの驚異とも呼ばれるミラビリスジャラパ植物の天然抽出物を含む。
・AQUALANCE(商標):Sederma(WO2009/104118)が販売するオスモプロテクター保湿有効成分。ホアリン及びエリスリトールを含む。
・LEGANCE(商標):水溶性賦形剤中でCO2超臨界状態で得られ、ゼルンボン成分で滴定されたZingiber zerumbet Smith抽出物に対応する、Sederma(WO2013/105047)によって市販されているアンチエイジング活性物質。脚用の世界的なアンチエイジング成分である。水分保持を減らし、微小循環を改善し、脂肪組織を精製することによって、その外観及び快適性を改善する。
・BODYFIT(商標):Sederma(WO2004/024695)によって販売されているグロウシン(glaucine)を含むスリミング/パッキング有効成分。BODYFIT(商標)は、セルライトの出現を減らし、組織内の排水と水の分布を改善するのに役立つ。
・JUVINITY(商標):SEDERMAが販売している活性成分であり、顔やネックラインの老化の徴候を減らし、皺を滑らかにし、真皮を緻密化し、再構築する。
・VEGESOME MOIST 24(商標):SEDERMAが販売する、保湿パウダーメーキャップ用処方成分。保湿性を有するImperata cylindrica抽出物を装填した25ミクロンの中空粒子(Lycopodium clavatum exins)からなる粉末である。
・SUBLISKIN(商標):SEDERMA(WO2010/067327)によって市販している活性成分であり、皮膚に潤いを与え、皮膚を滑らかにし、外部侵襲に抵抗することを可能にする。
・VENUCEANE(商標):光老化(斑点、しわ、乾燥など)の目に見える兆候を防止し、UVによる損傷から細胞構造を保護し、皮膚強度を強くするThermus thermophilesバイオテクノロジー抽出物を含むSederma(WO2002/066668)活性剤。
・KOMBUCHKA(商標):SEDERMA(WO2004/012650)によって市販されている肌色に作用する有効成分。
・INTENSLIM(商標):Globularia cordifolia植物細胞培養物、zerumboneにおいて滴定されたZingiber zerumbet Smithによって得られた抽出物、及び超臨界CO2抽出によって得られた植物性カフェインの相乗的組み合わせに対応するSederma(WO2013/105048)によって市販されている減量有効成分。
Claims (8)
- 化粧品及び皮膚科学分野で使用することができるペプチド化合物であって、以下の一般式I:
X-(AA)n-(AA)*-(AA)m-Z (I)
(式中、
・(AA)*は、リジン(K*)であり、
前記リジン上に、カルボン酸が、側鎖の窒素にペプチド結合によってグラフトされ、
前記カルボン酸は、プロリン(P、Pro)、ヒドロキシプロリン(Hyp)、及びピログルタミン酸(Pyr)から選択され;
・nは、0であり;
・mは、2であり;
・AAは、グリシン(G、Gly)、及びヒスチジン(H、His)から選択されるアミノ酸であり、ここで、(AA) m は、GH又はHGであり;
・N末端で、Xは、ミリストイル(C14)、パルミトイル(C16)(Pal)、ステアロイル(C18)から選択されるアシルCO-R 1 ラジカルであり;及び
・C末端で、Zは、OHである)
を有する、ペプチド化合物。 - 前記ペプチド化合物が、Pal-K(P)-HG-OH、Pal-K(Pyr)-HG-OH、Pal-K(Hyp)-HG-OH、Pal-K(P)-GH-OH、Pal-K(Pyr)-GH-OH及びPal-K(Hyp)-GH-OHから選択される、請求項1に記載の化合物。
- 生理学的に許容される媒体中に請求項1又は2に記載の少なくとも1つのペプチド化合物を有効成分として含む化粧品又は皮膚医薬組成物。
- 皮膚及び/又はその附属部の全身状態を改善するための美容的な非治療的処置のための、請求項3に記載の組成物。
- 老化、並びに/又は皮膚及び/若しくはその附属部の欠陥に対処するための処置用の、請求項3又は4に記載の組成物。
- 局所処置のための、請求項3~5のいずれか一項に記載の組成物。
- 広範囲の老化防止処置;及び/又は
抗皺及び細線処置(平滑化された肌リリーフ;詰まった皺);及び/又は
皮膚の機械的特性:堅さ/トーン/弾性/柔軟性を改善する処置:及び/又は
皮膚密度を高める処置(再構成効果);及び/又は
皮膚の容積を増加させる処置(盛り上がり効果);及び/又は
ストレッチマークの出現と戦うための処置;及び/又は
保湿処置;及び/又は
アンチスポット処置;及び/又は
皮膚の均一性及び/又は輝きを改善するための処置;及び/又は
皮膚の色素沈着に作用する処置
のための、請求項3~6のいずれか1項に記載の組成物。 - 皮膚科学的局所処置のための、請求項1又は2に記載の化合物を含有する組成物。
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FR3077202B1 (fr) * | 2018-02-01 | 2020-01-10 | Sederma | Utilisation de cyclopeptides en cosmetique |
KR102208853B1 (ko) * | 2018-05-08 | 2021-01-28 | 오션펩 주식회사 | 주름개선 효능을 갖는 펩티드 |
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FR3101544B1 (fr) | 2019-10-07 | 2023-09-29 | Sederma Sa | Traitement cosmétique ou dermatologique a base de peptide(s) de la peau et de ses phanères |
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US11793746B2 (en) * | 2020-10-01 | 2023-10-24 | Chanda Zaveri | Intense skin hydration systems and methods |
FR3116273B1 (fr) | 2020-11-17 | 2023-10-27 | Sederma Sa | Tétrapeptides, compositions les comprenant et leur utilisation cosmétique |
FR3116275B1 (fr) | 2020-11-17 | 2022-09-30 | Sederma Sa | Tétrapeptide, composition le comprenant et son utilisation cosmétique |
FR3116274B1 (fr) | 2020-11-17 | 2023-12-08 | Sederma Sa | Tétrapeptides, compositions les comprenant et leur utilisation cosmétique |
CA3206148A1 (en) | 2021-01-24 | 2022-07-28 | Michael David FORREST | Therapeutic modifiers of the reverse mode of atp synthase |
CN113307851B (zh) * | 2021-06-11 | 2022-04-29 | 珠海医美企业管理有限公司 | 一种改善皮肤生理特性的活性肽与间充质干细胞外泌体在药品或化妆品中的应用 |
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BR112017012474B1 (pt) | 2021-05-11 |
JP2018500330A (ja) | 2018-01-11 |
EP3256102A1 (en) | 2017-12-20 |
KR20170086680A (ko) | 2017-07-26 |
FR3029782A1 (fr) | 2016-06-17 |
BR112017012474A2 (pt) | 2018-02-27 |
KR102655355B1 (ko) | 2024-04-05 |
CN113264984A (zh) | 2021-08-17 |
JP2022019764A (ja) | 2022-01-27 |
MX2017007819A (es) | 2017-10-02 |
FR3029782B1 (fr) | 2019-06-07 |
US20180000717A1 (en) | 2018-01-04 |
EP3256102B1 (en) | 2023-08-09 |
CN106999401B (zh) | 2021-05-28 |
WO2016097965A1 (en) | 2016-06-23 |
US11612556B2 (en) | 2023-03-28 |
CN106999401A (zh) | 2017-08-01 |
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