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    • 1. 发明申请
    • NOVEL PEPTIDES, USE THEREOF IN COSMETIC AND COSMECEUTIC APPLICATIONS, AND COMPOSITIONS COMPRISING SAME
    • 新型肽,其在化妆品和成膜应用中的应用,以及包含其的组合物
    • WO2009003284A8
    • 2010-03-04
    • PCT/CA2008001227
    • 2008-06-30
    • INNOVACTIV INCHOCQUAUX MICHELLOING ESTELLEBEDOS PHILIPPE
    • HOCQUAUX MICHELLOING ESTELLEBEDOS PHILIPPE
    • C07K7/06A61K8/64A61K38/06A61K38/07A61K38/08A61P17/00A61P29/00A61Q19/10C07K5/083C07K5/11C07K5/117
    • C07K5/1019A61K8/64A61K38/00A61Q17/04A61Q19/08C07K5/0806Y02P20/55
    • A peptide of formula I (SEQ ID NO: 1): Lip-A-Gly-His-B-R (I) wherein: Lip is a lipoyl residue of R or S configuration; A is absent or is a lysine residue of configuration L or D; GIy is a glycine residue; His is a histidine residue of configuration L or D; B is a lysine residue of configuration L or D, or a lysine residue of configuration L or D in which the NH2 group of the side chain comprises a modification, wherein said modification is (i) a replacement with a hydrogen or (ii) a modification with a protecting group selected from the group consisting of acetyl, benzoyl, tosyl, sulfonyl benzene, benzyloxycarbonyle and palmitoyl; wherein R is O(Z) or N(Z')(Z'), and wherein Z, Z' and Z' are independently of each other a hydrogen or a protecting group selected from the group consisting of methyl, ethyl, propyl, phenyl, hexyl, decyl and hexadecyl, or a racemate, an enantiomer or a diastereomer thereof, or a mixture thereof, or a salt thereof. A peptide of formula Il (SEQ ID NO: 2): Lip-A-His-B-C-Trp-R (II) wherein: Lip is a lipoyl residue of configuration R or S; His is a histidine residue of configuration L; Trp is a tryptophane residue of configuration L; A is absent, is an amino acid residue of configuration L or D selected from the group consisting of a lysine residue, an alanine residue, a glutamic acid residue and a glycine residue, or is a spacer of formula : NH-(CH2)n-CO- wherein n is an integer comprised between 2 and 14; B is an aromatic amino acid residue of configuration D selected from the group consisting of a phenylalanine residue, a homophenylalanine residue, a tryptophane residue, a ß-(1-Naphthyl)-alanine residue, a ß-(2-Naphthyl)-alanine residue and a phenylglycine residue; C is a basic amino acid residue of configuration L selected from the group consisting of an arginine residue, a lysine residue, an ornithine residue and a homoarginine residue; wherein R is O(Z) or N(Z')(Z'), and wherein Z, Z' and Z' are independently of each other a hydrogen or a protecting group selected from the group consisting of methyl, ethyl, propyl, phenyl, hexyl, decyl and hexadecyl, or a racemate, an enantiomer or a diastereomer thereof, or a mixture thereof, or a salt thereof.
    • 式I的肽(SEQ ID NO:1):Lip-A-Gly-His-B-R(I)其中:Lip是R或S构型的脂酰基残基; A不存在或是L或D构型的赖氨酸残基; Gly是甘氨酸残基; His是构型L或D的组氨酸残基; B是构型L或D的赖氨酸残基或其中侧链的NH 2基团包含修饰的构型L或D的赖氨酸残基,其中所述修饰是(i)用氢取代或(ii) 用选自乙酰基,苯甲酰基,甲苯磺酰基,磺酰基苯,苄氧基羰基和棕榈酰基的保护基改性; 其中R是O(Z)或N(Z')(Z'),并且其中Z,Z'和Z'彼此独立地是氢或选自甲基,乙基,丙基, 苯基,己基,癸基和十六烷基,或其外消旋物,对映异构体或非对映体,或其混合物,或其盐。 式II(SEQ ID NO:2)的肽:Lip-A-His-B-C-Trp-R(II)其中:Lip是R或S构型的脂酰基残基; His是构型L的组氨酸残基; Trp是配置L的色氨酸残基; A不存在,是选自赖氨酸残基,丙氨酸残基,谷氨酸残基和甘氨酸残基的构型L或D的氨基酸残基,或者是下式的间隔基:NH-(CH 2)n -CO-,其中n是2至14之间的整数; B是配置D的芳族氨基酸残基,选自苯丙氨酸残基,高苯丙氨酸残基,色氨酸残基,β-(1-萘基) - 丙氨酸残基,β-(2-萘基) - 丙氨酸 残基和苯基甘氨酸残基; C是选自精氨酸残基,赖氨酸残基,鸟氨酸残基和高精氨酸残基的构型L的碱性氨基酸残基; 其中R是O(Z)或N(Z')(Z'),并且其中Z,Z'和Z'彼此独立地是氢或选自甲基,乙基,丙基, 苯基,己基,癸基和十六烷基,或其外消旋物,对映异构体或非对映体,或其混合物,或其盐。
    • 7. 发明申请
    • NOVEL PEPTIDES, USE THEREOF IN COSMETIC AND COSMECEUTIC APPLICATIONS, AND COMPOSITIONS COMPRISING SAME
    • 新型肽,其在化妆品和成膜应用中的应用,以及包含其的组合物
    • WO2009003284A1
    • 2009-01-08
    • PCT/CA2008/001227
    • 2008-06-30
    • LES BIOTECHNOLOGIES OCEANOVA INC.HOCQUAUX, MichelLOING, EstelleBEDOS, Philippe
    • HOCQUAUX, MichelLOING, EstelleBEDOS, Philippe
    • C07K7/06A61K38/06A61K38/07A61K38/08A61K8/64A61P17/00A61P29/00A61Q19/10C07K5/083C07K5/11C07K5/117
    • C07K5/1019A61K8/64A61K38/00A61Q17/04A61Q19/08C07K5/0806Y02P20/55
    • A peptide of formula I (SEQ ID NO: 1): Lip-A-Gly-His-B-R (I) wherein: Lip is a lipoyl residue of R or S configuration; A is absent or is a lysine residue of configuration L or D; GIy is a glycine residue; His is a histidine residue of configuration L or D; B is a lysine residue of configuration L or D, or a lysine residue of configuration L or D in which the NH2 group of the side chain comprises a modification, wherein said modification is (i) a replacement with a hydrogen or (ii) a modification with a protecting group selected from the group consisting of acetyl, benzoyl, tosyl, sulfonyl benzene, benzyloxycarbonyle and palmitoyl; wherein R is O(Z) or N(Z')(Z"), and wherein Z, Z' and Z" are independently of each other a hydrogen or a protecting group selected from the group consisting of methyl, ethyl, propyl, phenyl, hexyl, decyl and hexadecyl, or a racemate, an enantiomer or a diastereomer thereof, or a mixture thereof, or a salt thereof. A peptide of formula Il (SEQ ID NO: 2): Lip-A-His-B-C-Trp-R (II) wherein: Lip is a lipoyl residue of configuration R or S; His is a histidine residue of configuration L; Trp is a tryptophane residue of configuration L; A is absent, is an amino acid residue of configuration L or D selected from the group consisting of a lysine residue, an alanine residue, a glutamic acid residue and a glycine residue, or is a spacer of formula : NH-(CH2)n-CO- wherein n is an integer comprised between 2 and 14; B is an aromatic amino acid residue of configuration D selected from the group consisting of a phenylalanine residue, a homophenylalanine residue, a tryptophane residue, a β-(1-Naphthyl)-alanine residue, a β-(2-Naphthyl)-alanine residue and a phenylglycine residue; C is a basic amino acid residue of configuration L selected from the group consisting of an arginine residue, a lysine residue, an ornithine residue and a homoarginine residue; wherein R is O(Z) or N(Z')(Z"), and wherein Z, Z' and Z" are independently of each other a hydrogen or a protecting group selected from the group consisting of methyl, ethyl, propyl, phenyl, hexyl, decyl and hexadecyl, or a racemate, an enantiomer or a diastereomer thereof, or a mixture thereof, or a salt thereof.
    • 式I的肽(SEQ ID NO:1):Lip-A-Gly-His-B-R(I)其中:Lip是R或S构型的脂酰基残基; A不存在或是L或D构型的赖氨酸残基; Gly是甘氨酸残基; His是构型L或D的组氨酸残基; B是构型L或D的赖氨酸残基或其中侧链的NH 2基团包含修饰的构型L或D的赖氨酸残基,其中所述修饰是(i)用氢取代或(ii) 用选自乙酰基,苯甲酰基,甲苯磺酰基,磺酰基苯,苄氧基羰基和棕榈酰基的保护基改性; 其中R是O(Z)或N(Z')(Z“),并且其中Z,Z'和Z”彼此独立地是氢或选自甲基,乙基,丙基, 苯基,己基,癸基和十六烷基,或其外消旋物,对映异构体或非对映体,或其混合物,或其盐。 式II(SEQ ID NO:2)的肽:Lip-A-His-B-C-Trp-R(II)其中:Lip是R或S构型的脂酰基残基; His是构型L的组氨酸残基; Trp是配置L的色氨酸残基; A不存在,是选自赖氨酸残基,丙氨酸残基,谷氨酸残基和甘氨酸残基的构型L或D的氨基酸残基,或者是下式的间隔基:NH-(CH 2)n -CO-,其中n是2至14之间的整数; B是配置D的芳族氨基酸残基,选自苯丙氨酸残基,高苯丙氨酸残基,色氨酸残基,β-(1-萘基) - 丙氨酸残基,β-(2-萘基) - 丙氨酸 残基和苯基甘氨酸残基; C是选自精氨酸残基,赖氨酸残基,鸟氨酸残基和高精氨酸残基的构型L的碱性氨基酸残基; 其中R是O(Z)或N(Z')(Z“),并且其中Z,Z'和Z”彼此独立地是氢或选自甲基,乙基,丙基, 苯基,己基,癸基和十六烷基,或其外消旋物,对映异构体或非对映体,或其混合物,或其盐。