Peptidic compounds, compositions comprising them and uses of said compounds, in particular cosmetic uses

    公开(公告)号:US11612556B2

    公开(公告)日:2023-03-28

    申请号:US15535651

    申请日:2015-12-14

    申请人: SEDERMA

    IPC分类号: A61K8/65 A61Q19/08 C07K14/78

    摘要: The peptidic compound comprises at least an aminoacid which is lysine, ornithine, diaminopropionic acid or diaminobutyric acid or a derivative of these aminoacids, on which a carboxylic acid is grafted via a peptidic bound on the nitrogen of the lateral chain, said carboxylic acid comprising a (poly)cycle or (poly)heterocycle. Preferably, the grafted carboxylic acid is an aminoacid or a derivative, in particular selected from, a proline, a hydroxyproline or pyroglutamic acid.
    The peptidic compound can stimulate the synthesis of the main molecules constituting the extracellular matrix of the skin, especially collagen 1 and 4 and elastin. It can be used for topical cosmetic treatment such as a global anti-aging treatment, or for specific activities, including anti-wrinkles, moisturizing, to improve the mechanical properties of the skin, firmness/tone/elasticity/flexibility, to increase density and volume of the skin, improve skin radiance, for a restructuring effect and/or to fight stretch marks.

    PEPTIDE, COMPOSITION COMPRISING SAID PEPTIDE AND USES THEREOF, IN PARTICULAR COSMETIC USES

    公开(公告)号:US20190153030A1

    公开(公告)日:2019-05-23

    申请号:US16307548

    申请日:2017-06-13

    申请人: Sederma

    摘要: The peptide has from 3 to 10 amino acids comprising at least the sequence K*(Ac)GH or K*(Ac)HG and may further comprise an N-terminus modification, preferably an acylation, and/or a C-terminus modification; K* is selected from the group consisting of lysine, ornithine, diaminobutyric acid, diaminopropionic acid and a hydroxylated derivative thereof; K*(Ac) corresponds to a lysine, ornithine, diaminobutyric acid, diaminopropionic acid or a hydroxylated derivative thereof, acetylated on the amine of their lateral hydrocarbon chain. The two preferred peptides are Pal-K(Ac)GH and Pal-K(Ac)HG. This peptide can be used for a cosmetic treatment, in particular anti-aging, anti-wrinkle and fine lines, to improve the mechanical properties of the skin, firmness/tonicity/elasticity/flexibility, to increase the density and volume of the skin, for a restructuring, healing effect, and/or to fight stretch marks.

    Pro-pigmenting peptides
    3.
    发明授权

    公开(公告)号:US11324687B2

    公开(公告)日:2022-05-10

    申请号:US16848142

    申请日:2020-04-14

    申请人: Sederma

    摘要: Provided is at least one peptide of formula (I) and its use, where formula (I) is as follows: X-(Xaa1)n-Pro*-(Xaa2)m-Y (I). In formula (I), n=0 and m=1. At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1. At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independently selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom. Pro* corresponds to a Proline, an analogue or derivative thereof.

    Pro-pigmenting peptides
    4.
    发明授权

    公开(公告)号:US10660839B2

    公开(公告)日:2020-05-26

    申请号:US16259176

    申请日:2019-01-28

    申请人: Sederma

    摘要: The invention is directed to the use of at least one peptide of formula: X-(Xaa1)n-Pro*-(Xaa2)m-Y (I) With: —n=0, 1 or 2; —m=0 or 1 and if m=0 then n≠0 —Xaa1 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A polar aminoacid selected from Serine (Ser, S), Threonine (Thr, T), Tyrosine (Tyr, Y), Asparagine (Asn, N), Glutamine (Gln, Q) and analogues and derivatives thereof; —or Glycine (Gly, G); When n=2 the two aminoacids Xaa1 can be the same or different; —Xaa2 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A basic aminoacid selected from Arginine (Arg, R), Lysine (Lys, K) and Histidine (His, H) and analogues and derivatives thereof; —Glycine (Gly, G) or Serine (Ser, S); —At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; —At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom; —Pro* corresponding to a Proline, an analogue or derivative thereof; Excluding the peptides where X═H and Y═OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin. The invention also encompasses new tripeptides of formula (I) suitable for a non therapeutical cosmetic treatment of skin.

    Pro-pigmenting peptides
    5.
    发明授权

    公开(公告)号:US10231917B2

    公开(公告)日:2019-03-19

    申请号:US15361801

    申请日:2016-11-28

    申请人: Sederma

    摘要: The invention is directed to the use of at least one peptide of formula: X—(Xaa1)n-Pro*-(Xaa2)m-Y (I) With: —n=0, 1 or 2; —m=0 or 1 and if m=0 then n≠0-Xaai is: —An hydrophobic amino acid; —A polar amino acid; —or Glycine (Gly, G); When n=2 the two amino acids Xaa1 can be the same or different; —Xaa2 is: —An hydrophobic amino acid; —A basic amino acid Glycine (Gly, G) or Serine (Ser, S); —At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; —At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group; Excluding the peptides where X=H and Y=OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin.

    PRO-PIGMENTING PEPTIDES
    6.
    发明申请

    公开(公告)号:US20170071844A1

    公开(公告)日:2017-03-16

    申请号:US15361801

    申请日:2016-11-28

    申请人: Sederma

    摘要: The invention is directed to the use of at least one peptide of formula: X-(Xaa1)n-Pro*-(Xaa2)m-Y (I) With: —n=0, 1 or 2; -m=0 or 1 and if m=0 then n≠0-Xaa1 is: -An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A polar aminoacid selected from Serine (Ser, S), Threonine (Thr, T), Tyrosine (Tyr, Y), Asparagine (Asn, N), Glutamine (Gln, Q) and analogues and derivatives thereof; —or Glycine (Gly, G); When n=2 the two aminoacids Xaa1 can be the same or different; -Xaa2 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A basic aminoacid selected from Arginine (Arg, R), Lysine (Lys, K) and Histidine (His, H) and analogues and derivatives thereof; —Glycine (Gly, G) or Serine (Ser, S); —At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; —At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independantly from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom; -Pro* corresponding to a Proline, an analogue or derivative thereof; Excluding the peptides where X═H and Y═OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin. The invention also encompasses new tripeptides of formula (I) suitable for a non therapeutical cosmetic treatment of skin.

    Peptide, composition comprising said peptide and uses thereof, in particular cosmetic uses

    公开(公告)号:US11001607B2

    公开(公告)日:2021-05-11

    申请号:US16307548

    申请日:2017-06-13

    申请人: Sederma

    摘要: The peptide has from 3 to 10 amino acids comprising at least the sequence K*(Ac)GH or K*(Ac)HG and may further comprise an N-terminus modification, preferably an acylation, and/or a C-terminus modification; K* is selected from the group consisting of lysine, ornithine, diaminobutyric acid, diaminopropionic acid and a hydroxylated derivative thereof; K*(Ac) corresponds to a lysine, ornithine, diaminobutyric acid, diaminopropionic acid or a hydroxylated derivative thereof, acetylated on the amine of their lateral hydrocarbon chain. The two preferred peptides are Pal-K(Ac)GH and Pal-K(Ac)HG. This peptide can be used for a cosmetic treatment, in particular anti-aging, anti-wrinkle and fine lines, to improve the mechanical properties of the skin, firmness/tonicity/elasticity/flexibility, to increase the density and volume of the skin, for a restructuring, healing effect, and/or to fight stretch marks.

    Pro-Pigmenting Peptides
    8.
    发明申请

    公开(公告)号:US20200253852A1

    公开(公告)日:2020-08-13

    申请号:US16848142

    申请日:2020-04-14

    申请人: Sederma

    摘要: The invention is directed to the use of at least one peptide of formula: X-(Xaa1)n-Pro*-(Xaa2)m-Y (I) With: -n=0, 1 or 2; -m=0 or 1 and if m=0 then n≠0 -Xaa1 is: -An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; -A polar aminoacid selected from Serine (Ser, S), Threonine (Thr, T), Tyrosine (Tyr, Y), Asparagine (Asn, N), Glutamine (Gln, Q) and analogues and derivatives thereof; -or Glycine (Gly, G); When n=2 the two aminoacids Xaa1 can be the same or different; -Xaa2 is: -An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; -A basic aminoacid selected from Arginine (Arg, R), Lysine (Lys, K) and Histidine (His, H) and analogues and derivatives thereof; -Glycine (Gly, G) or Serine (Ser, S); -At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; -At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom; -Pro* corresponding to a Proline, an analogue or derivative thereof; Excluding the peptides where X=H and Y=OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin. The invention also encompasses new tripeptides of formula (I) suitable for a non therapeutical cosmetic treatment of skin.

    Peptides, compositions comprising them and uses in particular cosmetic uses

    公开(公告)号:US10668000B2

    公开(公告)日:2020-06-02

    申请号:US15312402

    申请日:2015-05-21

    申请人: SEDERMA

    摘要: The peptides have the general following formula: X-Pro*-Pro*-Xaa-Y in which: •Xaa is selected from Leucine (Leu, L), Arginine (Arg, R), Lysine (Lys, K), Alanine (Ala, A), Serine (Ser, S), and Aspartic acid (Asp, D); •At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; •At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 and NR1R2; •R1 and R2 are, independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulfured, and which skeletum can comprise an heteroatom, in particular an O, S and/or N atom; •Pro* correspond to a Proline, an analogue or derivative thereof; •if X is H then Y is selected from OR1, NH2, NHR1 and NR1R2, and if Y is OH then X is —CO— or —SO2—R1; and the peptide hypoxanthine-Pro-Pro-Arg being excluded. The invention provides the use of the peptides of above formula I to stimulate the synthesis of the molecules constituting the dermal extracellular matrix, including collagen I and IV and elastin. A cosmetic treatment according to the invention includes anti-aging, anti-wrinkles, improving mechanical properties of the skin, firmness/tone/elasticity/suppleness/flexibility, increasing density and volume of the skin, restructuring effect, fighting stretch marks, improving skin barrier and/or skin hydration.

    PRO-PIGMENTING PEPTIDES
    10.
    发明申请

    公开(公告)号:US20190142723A1

    公开(公告)日:2019-05-16

    申请号:US16259176

    申请日:2019-01-28

    申请人: Sederma

    摘要: The invention is directed to the use of at least one peptide of formula: X-(Xaa1)n-Pro*-(Xaa2)m-Y (I) With: —n=0, 1 or 2; —m=0 or 1 and if m=0 then n≠0 —Xaa1 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A polar aminoacid selected from Serine (Ser, S), Threonine (Thr, T), Tyrosine (Tyr, Y), Asparagine (Asn, N), Glutamine (Gln, Q) and analogues and derivatives thereof; —or Glycine (Gly, G); When n=2 the two aminoacids Xaa1 can be the same or different; —Xaa2 is: —An hydrophobic aminoacid selected from Alanine (Ala, A), Valine (Val, V), Methionine (Met, M), Leucine (Leu, L), Isoleucine (Ile, I), Phenylalanine (Phe, F), Proline (Pro, P) and analogues and derivatives thereof; —A basic aminoacid selected from Arginine (Arg, R), Lysine (Lys, K) and Histidine (His, H) and analogues and derivatives thereof; —Glycine (Gly, G) or Serine (Ser, S); —At the N terminal end of the peptide, X is selected from H, —CO—R1 and —SO2—R1; —At the C terminal end of the peptide, Y is selected from OH, OR1, NH2, NHR1 or NR1R2, R1 and R2 being independently from each other, selected from an alkyle, aryle, aralkyle, alkylaryl, alkoxy and aryloxy group, that can be linear, branched, cyclic, poly-cyclic, non-saturated, hydroxylated, carbonylated, phosphorylated and/or sulphured, with the possibility to have in said group skeleton a O, S and/or N heteroatom; —Pro* corresponding to a Proline, an analogue or derivative thereof; Excluding the peptides where X=H and Y=OH, for a non therapeutical cosmetic pro-pigmenting treatment of skin. The invention also encompasses new tripeptides of formula (I) suitable for a non therapeutical cosmetic treatment of skin.