EP4362904A1 - Kosmetische, nicht-therapeutische verwendungen von peptiden - Google Patents

Kosmetische, nicht-therapeutische verwendungen von peptiden

Info

Publication number
EP4362904A1
EP4362904A1 EP22748069.6A EP22748069A EP4362904A1 EP 4362904 A1 EP4362904 A1 EP 4362904A1 EP 22748069 A EP22748069 A EP 22748069A EP 4362904 A1 EP4362904 A1 EP 4362904A1
Authority
EP
European Patent Office
Prior art keywords
group
arg
glu
asp
gin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22748069.6A
Other languages
English (en)
French (fr)
Inventor
Garcia CONSUELO
Xiang-hua QU
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Advanced Materials Inc
Original Assignee
Lubrizol Advanced Materials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lubrizol Advanced Materials Inc filed Critical Lubrizol Advanced Materials Inc
Publication of EP4362904A1 publication Critical patent/EP4362904A1/de
Pending legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • 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

Definitions

  • the invention relates to the cosmetic treatment and/or care of the skin.
  • the invention relates to the use of compounds that are effective in increasing the energy of skin cells and to the use of the compounds for promoting skin radiance and/or as antiskin fatigue agents.
  • Skin cells like all the other cells of the body, are the site of bioenergetic metabolic processes.
  • the energy necessary for all cell functions can be derived from ATP, the classic intracellular energy source, or it can be derived from an exterior source.
  • Skin has a high energy requirement in order to support its metabolic needs, constant tissue regeneration and the repair that is necessary for normal tissue maintenance.
  • UV irradiation exposure to the skin and other external factors that generate ROS (reactive oxidative species) cause harmful changes to (mitochondrial) DNA, cellular membranes, catalytic and structural proteins (e.g. collagen).
  • Human skin cells that are directly exposed to environmental factors such as sunlight, are highly dependent on large amounts of energy in order to combat cellular deregulation and/or damage. Deficiencies in cutaneous energy capacity are closely related to striking alterations in the structure of human skin. If the skin's repair mechanisms cannot keep pace, detrimental changes in skin structure can occur, leading to a skin looking dull and less healthy.
  • Mitochondria are the batteries for energy production in the cells and play a vital role in the skin. While the energy requirement may not be as great as other organs, such as skeletal muscle, energy is still integral for processes such as cell signaling, wound healing, pigmentation and vasculature homeostasis [Stout, S. and Birch-Machin,M ‘Mitochondria’s Role in Skin Ageing’, Biology (Basel). 2019 Jun; 8(2): 29] Data shows that human skin cells that are energetically balanced, are metabolically reactivated and thus markedly protected against structural changes of human skin [Blatt T, et al. ‘Stimulation of skin's energy metabolism provides multiple benefits for mature human skin’. Biofactors. 2005;25(1-4):179-85].
  • W02019008452A1 discloses the use of specific peptides for energizing the skin and preventing the symptoms of skin fatigue. However, there is a need for alternative or improved ways to the provide these cosmetic effects to the skin. There is a need for other compounds that are active in this respect.
  • the invention provides the use of a compound of formula (I) Ri- AA1-AA2-AA3-AA4-AA5-AA6-R2 (I), a stereoisomer and/or cosmetically acceptable salt thereof, wherein:
  • AAi is Arg or Lys
  • AA2 is Arg or Lys
  • AA 3 is Gin, Glu, Asn or Asp
  • AA4 is Met or Leu
  • AA 5 is Glu, Asp or Gin
  • AAb is Glu, Asp or Gin
  • Ri is selected from the group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, wherein l3 ⁇ 4 is selected from the group consisting of H, a non- cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl;
  • R2 is selected from the group consisting of-NRsRi, -OR 3 , -SRB, wherein R3 and R4 are independently selected from a group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; and Ri and R2 are not amino acids, for the cosmetic non-therapeutic treatment and/or care of the skin, wherein said cosmetic non-therapeutic treatment and/or care is: increasing the energy metabolism and/or energy production in skin cells; improving and/or increasing skin radiance; and/or reducing and/or preventing skin fatigue.
  • the compounds of formula (I) are effective at energising skin cells, improving skin radiance and/or as anti-skin fatigue agents.
  • the compounds are relatively small (6 amino acids) and therefore can be prepared more efficiently than other cosmetically active agents.
  • the invention provides a method of cosmetic, non- therapeutic treatment and/or care of the skin of a subject comprising administering a cosmetically effective amount of a compound of formula (I)
  • AAi is Arg or Lys
  • AA 2 is Arg or Lys
  • AA3 is Gin, Glu, Asn or Asp
  • AA4 is Met or Leu
  • AA 5 is Glu, Asp or Gin
  • AA 6 is Glu, Asp or Gin
  • Ri is selected from the group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, wherein Rs is selected from the group consisting of H, a non- cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl;
  • R 2 is selected from the group consisting of-NReRi, -OR 3 .-SR 3 , wherein R 3 and R 4 are independently selected from a group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; and Ri and R2 are not amino acids, to the subject, wherein the cosmetic, non-therapeutic treatment and/or care is: increasing the energy metabolism and/or energy production in skin cells; improving and/or increasing skin radiance; and/or reducing and/or preventing skin fatigue.
  • skin is understood to be the layers which comprise it, from the uppermost layer or stratum corneumtothe lowermost layer or hypodermis, both inclusive. These layers are composed of different types of cells such as keratinocytes, fibroblasts, melanocytes, mast cells, neurones and/or adipocytes among others.
  • the term “skin” also comprises the scalp.
  • skin includes the skin of mammals and includes human skin. In the context of this invention, skin includes the skin of the whole body including the skin of the face (including skin around the eyes), neckline, neck, decolletage, arms, hands, legs, feet, thighs, hips, buttocks, stomach and torso.
  • cosmetic, non-therapeutic treatment and “care” as used herein has the aim of improving or maintaining the aesthetic appearance of the skin.
  • the treatment can have the aim of improving cosmetic properties of the skin.
  • care in the context of this specification refers to the maintenance of properties of the skin. Said properties are subject to being improved or maintained by cosmetic treatment and/or care of the skin both in healthy subjects as well as in those which present diseases and/or disorders of the skin.
  • Gly represents NH2-CH2-COOH
  • Gly- represents NH2-CH2- CO-
  • -Gly represents -NH-CH2-COOH
  • -Gly- represents -NH-CH2-CO-.
  • the hyphen which represents the peptide bond, eliminates the OH in the 1 -carboxyl group of the amino acid (represented here in the conventional non-ionized form) when situated to the right of the symbol, and eliminates the H of the 2-amino group of the amino acid when situated to the left of the symbol; both modifications can be applied to the same symbol (see Table 1).
  • non-cyclic aliphatic group includes linear (i.e. straight and unbranched) or branched, saturated or unsaturated hydrocarbyl groups such as alkyl, alkenyl and alkynyl.
  • the non-cyclic aliphatic group may be substituted (mono- or poly- ) or unsubstituted.
  • alkyl includes both saturated linear and branched alkyl groups, which may be substituted (mono- or poly-) or unsubstituted.
  • the alkyl group is bound to the rest of the molecule by a single bond.
  • the alkyl group has from 1 to 24, preferably from 1 to 16, more preferably from 1 to 14, even more preferably from 1 to 12, yet more preferably 1 , 2, 3, 4, 5 or 6 carbon atoms.
  • alkyl includes, for example, methyl, ethyl, isopropyl, isobutyl, tert- butyl, 2-methylbutyl, heptyl, 5-methylhexyl, 2-ethylhexyl, octyl, decyl, dodecyl, lauryl, hexadecyl, octadecyl and amyl.
  • alkenyl refers to a group containing one or more double carbon-carbon bonds and which may be linear or branched and substituted (mono- or poly-) or unsubstituted. Preferably it has 1 , 2 or 3 double carbon-carbon bonds. If more than one double carbon-carbon bond is present, the double bonds may be conjugated or not conjugated.
  • the alkenyl group has from 2 to 24, preferably from 2 to 16, more preferably from 2 to 14, even more preferably from 2 to 12, yet more preferably 2, 3, 4, 5 or 6 carbon atoms.
  • the alkenyl group is bound to the rest of the molecule by a single bond.
  • alkynyl refers to a group containing one or more triple carbon-carbon bonds and which may be linear or branched, and substituted (mono- or poly-) or unsubstituted.
  • the alkynyl group has 1 , 2 or 3 triple carbon-carbon bonds.
  • the triple bonds may be conjugated or not conjugated
  • the alkynyl group has from 2 to 24, preferably from 2 to 16, more preferably from 2 to 14, even more preferably from 2 to 12, yet more preferably 2, 3, 4, 5 or 6 carbon atoms.
  • the alkynyl group is bound to the rest of the molecule by a single bond.
  • alkynyl includes, for example and not restricted to, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, pentynyl, such as
  • alkynyl group can also contain one or more double carbon- carbon bonds, and alkynyl groups include, for example and not restricted to, but-1-en-3- ynyl and pent-4-en-1-ynyl groups, and similar.
  • alicyclyl is used herein to cover, for example and not restricted to, aliphatic cyclic (alicyclic) groups such as cycloalkyl or cycloalkenyl or cycloalkynyl groups.
  • alicyclyl refers to a monoradical that contains one or more rings of carbon atoms, the rings may be saturated (e.g., cyclohexyl) or unsaturated (e.g., cyclohexenyl) provided that they are not aromatic. More specifically alicylic groups contain three or more, from 3 to 24, from 3 to 12, or from 6 to 12, ring carbon atoms.
  • the alicyclic group may be a monocyclic, bicyclic, or tricyclic ring system and the rings may be, for example, fused or linked by a single bond or a linking group such as a methylene or other alkylene group.
  • the alicyclic group may be substituted (mono- or poly-) or unsubstituted.
  • the alicyclyl group is a 6 to 12 membered ring system which consists of carbon atoms and optionally contains one or two double bonds.
  • cycloalkyl refers to a saturated mono- or polycyclic alkyl group which may be substituted (mono- or poly-) or unsubstituted.
  • the cycloalkyl group has from 3 to 24, preferably from 3 to 16, more preferably from 3 to 14, even more preferably from 3 to 12, yet even more preferably 3, 4, 5 or 6 carbon atoms.
  • the cycloalkyl group is bound to the rest of the molecule by a single bond.
  • Cycloalkyl groups include, for example and not restricted to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, methyl cyclohexyl, dimethyl cyclohexyl, octahydroindene, decahydronaphthalene, dodecahydrophenalene and similar.
  • cycloalkenyl refers to a non-aromatic mono- or polycyclic alkenyl group which may be substituted (mono- or poly-) or unsubstituted.
  • the cycloalkenyl group has from 5 to 24, preferably from 5 to 16, more preferably from 5 to 14, even more preferably from 5 to 12, yet more preferably 5 or 6 carbon atoms.
  • the cycloalkenyl group is bound to the rest of the molecule by a single bond.
  • the cycloalkenyl group contains 1 ,
  • Cycloalkenyl groups include, for example and not restricted to, the cyclopent-1-en-1-yl group and similar.
  • cycloalkynyl refers to a non-aromatic mono- or polycyclic alkynyl group which may be substituted (mono- or poly-) or unsubstituted.
  • the cycloalkynyl group has from 8 to 24, preferably from 8 to 16, more preferably from 8 to 14, even more preferably from 8 to 12, yet even more preferably 8 or 9 carbon atoms and is bound to the rest of the molecule by a single bond.
  • the cycloalkynyl group contains 1, 2 or 3 triple carbon-carbon bonds, conjugated or not conjugated.
  • Cycloalkynyl groups include, for example and not restricted to, the cyclooct-2-yn-1 -yl group and similar. Cycloalkynyl groups can also contain one or more double carbon-carbon bonds, including, for example and not restricted to, the cyclooct-4-en-2-ynyl group and similar.
  • heterocyclyl refers to a hydrocarbon ring system of 3 to 10 members, wherein one or more of the atoms in the ring or rings is a heteroatom (i.e. not a carbon atom).
  • heterocyclyl or “heterocyclic” refers a cyclic group in which the ring atoms consist of carbon and one or more heteroatoms.
  • the heteroatom may be bonded to H or substituent groups. Preferably from 1 , 2 or 3 of the ring carbon atoms are heteroatoms.
  • Each heteroatom can be independently selected from the group consisting of O, N, S, P and B, or the group consisting of O, N, and S.
  • the heterocyclyl group may be substituted (mono- or poly-) or unsubstituted.
  • the heterocyclyl group may be a monocyclic, bicyclic, or tricyclic ring system and the rings may be, for example, fused or linked by a single bond or a linking group such as a methylene or other alkylene group.
  • Nitrogen, carbon or sulfur atoms present in the heterocyclyl radical may be optionally oxidized and the nitrogen atom may be optionally quaternized.
  • the heterocyclyl radical may be unsaturated or partially or fully saturated.
  • the heterocyclyl radical may be aliphatic or aromatic.
  • the heterocyclyl is aliphatic (also known as heteroalicyclyl) and is a 3 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4, or 1 , 2 or 3 heteroatoms.
  • the heterocyclyl group is a 6 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4 heteroatoms and where the ring system optionally contains one or two double bonds.
  • the heterocyclyl is aromatic (also known as heteroaryl) and is a 6 to 10 membered ring system where the atoms of the ring or rings consist of carbon atoms and from 1 to 4, or 1 , 2 or 3 heteroatoms.
  • the greatest preference is for the term heterocyclyl to refer to a ring of 5 or 6 members.
  • saturated heteroalicyclyl groups are dioxane, piperidine, piperazine, pyrrolidine, morpholine and thiomorpholine.
  • aromatic heterocyclyl groups are pyridine, pyrrol, furan, thiophene, benzofuran, imidazoline, quinolein, quinoline, pyridazine and naphthyridine.
  • aryl group refers to an aromatic group which has from 6 to 30, preferably from 6 to 18, more preferably between 6 and 10, yet even more preferably 6 or 10 carbon atoms.
  • the aryl group can comprise 1 , 2, 3 or 4 aromatic rings, which may be linked by a carbon-carbon bond or fused together and includes, for example and not restricted to, phenyl, naphthyl, diphenyl, indenyl, phenanthryl or antranyl among others.
  • the aryl group may be substituted (mono- or poly-) or unsubstituted.
  • aralkyl group refers to an alkyl group substituted by an aromatic group, with from 7 to 24 carbon atoms and including, for example and not restricted to, -(CH2)i-6-phenyl, -(CH 2 )I- 6 -(1 -naphthyl), -(CH 2 )i- 6 -(2-naphthyl), -(CH2)i-6-CH(phenyl)2 and similar.
  • heteroarylalkyl refers to an alkyl group substituted by a heteroaryl (also known as aromatic heterocyclic) group as defined above, the alkyl group having from 1 to 6 carbon atoms and the heteroaryl group having from 2 to 24 carbon atoms and from 1 to 3 heteroatoms.
  • Heteroarylalkyl groups include, for example and not restricted to, -(CH2)i-6-imidazolyl, -(CH2)i-6-triazolyl, -(CH2)i-6-thienyl, -(CH2)i-6-furyl, -(CH2)i-6-pyrr olidinyl and similar.
  • substituted groups (radicals) referred to above are groups (or radicals) which are substituted in one or more positions available by one or more substituents. Preferably substitution is in the 1 , 2 or 3 positions, more preferably in the 1 or 2 positions, yet even more preferably in the 1 position.
  • This invention is based on the finding of surprising cosmetic, non-therapeutic properties of compounds of formula (I).
  • Compounds of formula (I), including all the embodiments of formula (I) disclosed herein, are also referred to herein as compounds of the invention. It has been discovered that compounds of formula (I) are able to increase the energy of skin cells. In particular, it has been found that compounds of formula (I) are able to increase the mitochondrial potential of human dermal fibroblasts skin cells. It is believed that, as a result, compounds of formula (I) are able to cause a higher production of energy in skin cells.
  • the terms “increase in the energy”, “increase of energy metabolism” and/or “increase of energy production in skin cells” as used herein refer to an increase in the supply of energy to skin (i.e. cutaneous) cells.
  • the compounds of formula (I) can enable an increase in the energy supply to the cells through an increase of the mitochondrial membrane potential.
  • An increase of the energy metabolism of the skin cells improves skin function.
  • the compounds of formula (I) promote a healthy appearance of the skin.
  • the invention relates to the use of compounds of formula (I) for the cosmetic, non- therapeutic treatment and/or care of the skin, wherein said cosmetic, non-therapeutic treatment and/or care is the increase of energy metabolism and/or energy production in skin cells.
  • the compounds of formula (I) can be used to improve and/or increase skin radiance.
  • Skin radiance is a vibrant look associated with healthy, well- rested skin. Skin radiance is the ability of the skin to reflect light and is referred to in terms of “gloss” of the skin. Skin with high gloss reflects more light and and thus has better or more radiance that skin of low gloss.
  • improving and/or increasing skin radiance means an improvement of the physical appearance of the skin by an improvement in the natural gloss of the skin.
  • the invention relates to the use of compounds of formula (I) for the cosmetic, non-therapeutic treatment and/or care of the skin, wherein said cosmetic, non-therapeutic treatment and/or care is the improvement and/or increase of skin radiance.
  • the compounds of formula (I) can be used as anti-skin fatigue agents.
  • the compounds of formula (I) can be used for reducing and/or preventing skin fatigue.
  • Skin fatigue is also known as “skin tiredness” Skin tiredness can be measured by determining the “tiring effects” of the skin, for instance by determining the standard R9 parameter with a Cutometer® MPA 580 from Courage+Khazaka electronic GmbH , where R9 represents the tiring effects of the skin after repeated sucking. The smaller the R9 value, the smaller the tiring effects and thus the lower skin fatigue.
  • the compounds of formula (I) can be used for reducing and/or preventing tiring effects of the skin.
  • the invention relates to the use of compounds of formula (I) for the cosmetic, non- therapeutic treatment and/or care of the skin, wherein said cosmetic, non-therapeutic treatment and/or care is the reduction and/or prevention skin fatigue.
  • the invention relates to cosmetic, non-therapeutic uses of and methods of treatment and/or care employing a compound of formula (I)
  • AAi is Arg or Lys
  • AA2 is Arg or Lys
  • AA 3 is Gin, Glu, Asn or Asp
  • AA4 is Met or Leu
  • AA 5 is Glu, Asp or Gin
  • AAe is Glu, Asp or Gin
  • Ri is selected from the group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl, aralkyl and R5-CO-, wherein Rs is selected from the group consisting of H, a non- cyclic aliphatic group, alicyclyl, aryl, aralkyl, heterocyclyl and heteroarylalkyl;
  • R2 is selected from the group consisting of-NRjRi, -OR3.-SR3, wherein R3 and R4 are independently selected from a group consisting of H, a polymer derived from polyethylene glycol, a non-cyclic aliphatic group, alicyclyl, heterocyclyl, heteroarylalkyl, aryl and aralkyl; and Ri and R2 are not amino acids.
  • Ri is bound to the amino terminal end (N-terminal) of the peptide and F3 ⁇ 4 is bound to the carboxy-terminal end (C-terminal) of the peptide.
  • Ri can be selected from the group consisting of H, a polymer derived from polyethylene glycol with a molecular weight comprised between 200 and 35000 Daltons and R5-CO-, wherein R 5 is selected from the group consisting of C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C30 aryl, C7-C24 aralkyl, 3-10 membered heterocyclyl ring, and a heteroarylalkyl containing from 2 to 24 carbon atoms and from 1 to 3 heteroatoms, wherein the alkyl group has 1 to 6 carbon atoms.
  • R 5 is selected from the group consisting of C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C
  • Ri can be selected from the group consisting of H and R5-CO-, wherein R 5 is selected from the group consisting of C1-C18 alkyl, C2-C24 alkenyl, C3-C24 cycloalkyl or the group consisting of C1-C16 alkyl, C2-C18 alkenyl, C3-C7 cycloalkyl.
  • the R5-CO- group includes alkanoyl groups such as acetyl (CH3-CO-, which is abbreviated herein as “Ac-”), myristoyl (CH 3 -(CH 2 )i2-CO-, which is abbreviated herein as “Myr-“) and palmitoyl (CH3-(CH )i4-CO-, which is abbreviated herein as “Palm-”).
  • alkanoyl groups such as acetyl (CH3-CO-, which is abbreviated herein as “Ac-”), myristoyl (CH 3 -(CH 2 )i2-CO-, which is abbreviated herein as “Myr-“) and palmitoyl (CH3-(CH )i4-CO-, which is abbreviated herein as “Palm-”).
  • Ri can be selected from the group consisting of H and acetyl, ferf-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl and linoleoyl.
  • Ri can be selected from the group consisting of H and R5-CO-, wherein R 5 is selected from the group consisting of C1-C16 alkyl or C2-C18 alkenyl.
  • Ri can be selected from the group consisting of H and R5-CO-, wherein Rs is C1-C15 alkyl.
  • Ri can be selected from the group consisting of H, acetyl and palmitoyl.
  • R2 can be selected from the group consisting of -NR3R4, -OR3, -SR3, wherein R3 and R4 are independently selected from the group formed by H, a polymer derived from polyethylene glycol, C1-C24 alkyl, C2-C24 alkenyl, C2-C24 alkynyl, C3-C24 cycloalkyl, C5-C24 cycloalkenyl, C8-C24 cycloalkynyl, C6-C3oaryl, C7-C24 aralkyl, 3-10 membered heterocyclyl ring, and heteroarylalkyl containing from 2 to 24 carbon atoms and from 1 to 3 heteroatoms, wherein the alkyl group has 1 to 6 carbon atoms.
  • R3 and R4 can be joined by a saturated or unsaturated carbon-carbon bond, forming a ring with the nitrogen atom.
  • R3 and R4 can be independently selected from the group consisting of H, a polymer derived from polyethylene glycol with a molecular weight comprised between 200 and 35000 Daltons, methyl, ethyl, hexyl, dodecyl and hexadecyl.
  • R3 and R can be independently selected from the group consisting of H and C1-C16 alkyl.
  • R2 is not OR3 where R3 is a methyl group, i.e. R2 is not OCH3.
  • R3 is H and R4 is selected from the group formed by H and C1-C16 alkyl, including methyl, ethyl, hexyl, dodecyl and hexadecyl.
  • R2 can be selected from the group consisting of -OH, -NH2and -NHR4 where R* is C1-C16 alkyl or C1-C3 alkyl or C1-C2 alkyl.
  • R2 can be -OH or -NH2.
  • Ri can be selected from the group consisting of H and R5-CO-, wherein R5 is selected from the group consisting of C1-C18 alkyl, C2-C24 alkenyl, C3-C24 cycloalkyl; and R2 is -NR3R4 or -OR3 wherein R3 and R4 are independently selected from the group consisting of H and Ci-Ci6alkyl.
  • R3 can be H and R4 can be selected from the group formed by H, C1-C16 alkyl, C1-C3 alkyl and C1-C2 alkyl; for example, R2 can be selected from the group consisting of -OH and -NH2.
  • Ri can be selected from the group consisting of H and acetyl, ferf-butanoyl, prenyl, hexanoyl, 2-methylhexanoyl, cyclohexanecarboxyl, octanoyl, decanoyl, lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl and linoleoyl; and R2 is -NR3R4 or -OR3 wherein R3 and R4 are independently selected from the group consisting of H and C1-C16 alkyl.
  • R3 can be H and R4 can selected from the group formed by H, C1-C16 alkyl, C1-C3 alkyl and C1-C2 alkyl; for example, R2 can be selected from the group consisting of -OH and -NH2.
  • Ri can be selected from the group consisting of H and R5-CO-, wherein R5 is selected from the group consisting of C1-C16 alkyl or C2-C18 alkenyl; and R2 is -NR3R4 or -OR3 wherein R3 and R4 are independently selected from the group consisting of H and C1-C16 alkyl.
  • R3 can be H and i can be selected from the group formed by H, C 1 -C 16 alkyl, C 1 -C 3 alkyl and C 1 -C 2 alkyl; for example, F3 ⁇ 4 can be selected from the group consisting of -OH and -NH2.
  • Ri can be selected from the group consisting of H, acetyl, myristoyl or palmitoyl; and F3 ⁇ 4 is -NR 3 R 4 or -OR 3 wherein R 3 and R 4 are independently selected from the group consisting of H and CrCi 6 alkyl.
  • R 3 can be H and R 4 can be selected from the group formed by H, C 1 -C 16 alkyl, C 1 -C 3 alkyl and C 1 -C 2 alkyl; for example, R 2 can be selected from the group consisting of -OH and -NH 2 .
  • Ri can be selected from the group consisting of H and R 5 -CO-, wherein R 5 is C 1 -C 15 alkyl and R 2 is -NR 3 R 4 or -OR 3 wherein l3 ⁇ 4 and l3 ⁇ 4 are independently selected from the group consisting of H and Ci-Ci 6 alkyl.
  • R 3 can be H and R 4 can be selected from the group formed by H, C 1 -C 16 alkyl, C 1 -C 3 alkyl and C 1 -C 2 alkyl; for example, R 2 can be selected from the group consisting of -OH and -NH 2 .
  • Ri can be selected from the group consisting of H, acetyl and palmitoyl and R 2 is -NR 3 R 4 or -OR 3 wherein R 3 and R 4 are independently selected from the group consisting of H and C 1 -C 16 alkyl.
  • R 3 can be H and R 4 can be selected from the group formed by H, C 1 -C 16 alkyl, C 1 -C 3 alkyl and C 1 -C 2 alkyl; for example, R 2 can be selected from the group consisting of -OH and -NH 2 .
  • Ri can be selected from the group consisting of a substituted non-cyclic aliphatic group, substituted alicyclyl, substituted heterocyclyl, substituted heteroarylalkyl, substituted aryl, substituted aralkyl and R 5 -CO-, wherein R 5 is selected from the group consisting of a substituted non-cyclic aliphatic group, substituted alicyclyl, substituted aryl, substituted aralkyl, substituted heterocyclyl and substituted heteroarylalkyl; and/or R 2 is -NR 3 R 4 , wherein at least one of R3 and R4 is selected from the group consisting of a substituted non-cyclic aliphatic group, substituted alicyclyl, substituted heterocyclyl, substituted heteroarylalkyl, substituted aryl and substituted aralkyl, or R is -OR 3 , or -SR 3 , wherein R3 is selected from the group consisting of a substituted non-cyclic
  • the most preferred structures of the polymer derived from polyethylene glycol are the group (-CH 2 -CH 2 -0)rH in which r is a number comprised between 4 and 795 and the group where s is a number comprised between 1 and 125.
  • the compound of formula (I) can be such that at least one of: Ri is not H; and F3 ⁇ 4 is not OH. That is, the compound of formula (I) can be such that Ri is not H and/or R2 is not OH.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA3 is selected from the group consisting of Gin and Asp; AA4 is selected from the group consisting of Met and Leu; AA5 is selected from the group consisting of Glu and Asp; and AAb is selected from the group consisting of Glu and Gin.
  • AAi is Arg and/or AA 2 is Arg.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA3 is Gin; AA4 is Met; AA5 is selected from the group consisting of Glu and Asp; and AAb is selected from the group consisting of Glu and Gin.
  • AAi is Arg and/or AA2 is Arg.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA3 is selected from the group consisting of Gin and Asp; AA4 is selected from the group consisting of Met and Leu; AA 5 is selected from the group consisting of Glu, Asp and Gin; and AAe is selected from the group consisting of Glu, Gin and Asp.
  • AAi is Arg and/or AA2 is Arg.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA 3 is selected from the group consisting of Gin and Glu; AA4 is selected from the group consisting of Met and Leu; AA 5 is selected from the group consisting of Glu, Asp and Gin; and AAb is selected from the group consisting of Glu, Gin and Asp.
  • AAi is Arg and/or AA2 is Arg.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA3 is selected from the group consisting of Gin, Glu, Asn and Asp or the group consisting of Gin and Asp; AA * is selected from the group consisting of Met and Leu; AA5 is selected from the group consisting of Glu and Gin; and AAe is is selected from the group consisting of Glu and Gin.
  • AAi is Arg and/or AA2 is Arg.
  • the compound of formula (I) can be such that: AAi is Arg; AA2 is selected from the group consisting of Arg and Lys; AA 3 is selected from the group consisting of Gin and Asp; AA4 is selected from the group consisting of Met and Leu; AA 5 is Glu; and AAb is Glu.
  • AA2 is Arg.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is Arg; AA3 is Gin; AA* is Met; AA5 is selected from the group consisting of Glu and Asp; and AAb is selected from the group consisting of Glu and Gin.
  • AAi is Arg.
  • the compound of formula (I) can be such that: AAi is Arg; AA 2 is Arg; AA3 is Gin; AA is Met; AA5 is Glu; and AAe is Glu; and 0, 1, 2, 3 or 4 of AAi, AA2, AA3, AA4, AA5 and AAe are replaced providing that: when AA ⁇ is replaced, it is replaced by Lys; when AA2 is replaced, it is replaced by Lys; when AA3 is replaced, it is replaced by Glu, Asn or Asp; when AA4 is replaced, it is replaced by Leu; when AAs is replaced, it is replaced by Asp or Gin; and when AAe is replaced, it is replaced by Asp or Gin.
  • AAi, AA2, AA3, AA 4 , AA 5 and AAe are replaced.
  • 0 (none) of AAi, AA2, AA3, AA 4 , AA5 and AAb is replaced.
  • one of AAi, AA2, AA3, AA4, AA5 and AAb is replaced.
  • two of AAi, AA2, AA3, AAt, AA5 and AAb are replaced.
  • three of AAi, AA2, AA3, AA , AAs and AAb are replaced.
  • the compound of formula (I) can be such that: AAi is Arg; AA2 is Arg; AA3 is Gin; AA 4 is Met; AAs is Glu; and AAe is Glu; and 0, 1, 2, 3 or 4 of AAi, AA2, AAB, AA*, AAs and AA b are replaced providing that: when AAi is replaced, it is replaced by Lys; when AA2 is replaced, it is replaced by Lys; when AA3 is replaced, it is replaced by Glu; when AA 4 is replaced, it is replaced by Leu; when AA5 is replaced, it is replaced by Asp; and when AAe is replaced, it is replaced by Gin.
  • AAi, AA2, AA3, AA*, AAs and AAb are replaced.
  • 0 (none) of AAi, AA2, AA3, AA 4 , AAs and AAe is replaced.
  • one of AAi, AA2, AA3, AA4, AA5 and AAe is replaced.
  • two of AAi, AA2, AA3, AA4, AA 5 and AAe are replaced.
  • three of AAi, AA2, AA3, AA4, AA5 and AAe are replaced.
  • the compound of formula (I) can be as described above, wherein each of AAi, AA2, AA 3 , AA4, AA5 and AAb in formula (I) is an L-amino acid.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA2 is L-Arg; AA3 is L-Gln; AA4 is L-Met; AAs is L-Glu; and AAe is L-Glu.
  • the compound of formula (I) can be such that at least one of AAi, AA , AA3, AA4, AA5 and AAe in formula (I) is a D-amino acid.
  • This embodiment includes a compound of formula (I), wherein 1 , 2 or 3 of AAi, AA2, AA3, AA4, AAs and AAe in formula (I) is a D- amino acid and the remaining of AAi, AA2, AA3, AA4, AA 5 and AAe are L-amino acids.
  • a compound of formula (I) where 1, 2, or 3 of AA3, AA* and AA5 are D- amino acids and the other amino acids, i.e.
  • AAi to AAe are L-amino acids.
  • This embodiment includes where 1 or 2 of AA3, AA4 and AA5 are D-amino acids and the other amino acids, i.e the remaining of AAi to AAe, are L-amino acids.
  • This embodiment includes, for example, a compound of formula (I), where AA* is a D-amino acid and each of AAi, AA ⁇ , AA3, AAs and AAe is an L-amino acid.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of Arg and Lys; AA2 is selected from the group consisting of Arg and Lys; AA3 is selected from the group consisting of Gin and Asp; AA4 is selected from the group consisting of Met and Leu; AAs is selected from the group consisting of Glu and Asp; and AAb is selected from the group consisting of Glu and Gin, and 1, 2, or 3 of AA 3 , AA4and AAs are D-amino acids and the other amino acids, i.e. the remaining of AAi to AAb, are L-amino acids.
  • This embodiment includes where 1 or2 of AA3, AA4and AAs are D-amino acids and the other amino acids, i.e. the remaining of AAi to AAe, are L-amino acids.
  • This embodiment includes where AA* is a D-amino acid and each of AAi, AA2, AA3, AAs and AAe is an L-amino acid.
  • the compound of formula (I) can be such that: AAi is Arg; AA2 is Arg; AAB is Gin; AA4 is Met; AAs is Glu; and AAs is Glu; and 0, 1, 2, 3 or 4 of AAi, AA 2 , AA3, AA4, AAs and AAs are replaced providing that: when AAi is replaced, it is replaced by Lys; when AA2 is replaced, it is replaced by Lys; when AA 3 is replaced, it is replaced by Glu, Asn or Asp; when AA4 is replaced, it is replaced by Leu; when AA5 is replaced, it is replaced by Asp or Gin; and when AA is replaced, it is replaced by Asp or Gin, and 1 , 2, or 3 of AA3, AA4 and AA5 are D-amino acids and the other amino acids, i.e.
  • AAi to AAb are L-amino acids.
  • This embodiment includes where 1 or 2 of AA3, AAiand AA5 are D- amino acids and the other amino acids, i.e the remaining of AAi to AAe, are L-amino acids.
  • This embodiment includes where AA is a D-amino acid and each of AAi, AA3 ⁇ 4 AA3, AA5 and AA is an L-amino acid.
  • 0, 1 , 2 or 3 of AAi, AA2, AA3, AA4, AA5 and AA can be replaced.
  • 0 (none) of AAi, AA 2 , AA 3 , AA4, AA5 and AA 6 can be replaced.
  • AAi, AA 2 , AAB, AA4, AA5 and AA 6 can be replaced.
  • Two of AAi, AA 2 , AA 3 , AA4, AA5 and AAe can be replaced.
  • Three of AAi, AA2, AA 3 , AA4, AAs and AAb can be replaced.
  • the compound of formula (I) can be such that: AAi is Arg; AA2 is Arg; AA is Gin; AA4 is Met; AA5 is Glu; and AA is Glu; and 0, 1, 2, 3 or 4 of AAi, AA , AAs, AA4, AA5 and AA are replaced providing that: when AAi is replaced, it is replaced by Lys; when AA2 is replaced, it is replaced by Lys; when AAs is replaced, it is replaced by Glu; when AA4 is replaced, it is replaced by Leu; when AA5 is replaced, it is replaced by Asp; and when AAQ is replaced, it is replaced by Gin, and 1 , 2, or 3 of AAs, AAiand AAs are D-amino acids and the other amino acids, i.e.
  • AAi to AA are L-amino acids.
  • This embodiment includes where 1 or 2 of AA, AAand AA 5 are D-amino acids and the other amino acids, i.e the remaining of AAi to AAs, are L-amino acids.
  • This embodiment includes where AA4 is a D-amino acid and each of AAi, AA2, AA3, AAs and AAs is an L- amino acid.
  • 0, 1 , 2 or 3 of AAi, AA2, AAs, AA t , AAs and AA 6 can be replaced.
  • 0 (none) of AAi, AA 2 , AA 3I AA4, AAs and AA 6 can be replaced.
  • AAi, AA 2 , AA3, AA t , AAs and AAb can be replaced.
  • Two of AAi, AA 2 , AAs, AA, AA 5 and AA 6 can be replaced.
  • Three of AAi, AA, AA, AA, AA 5 and AA can be replaced.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of L-Arg and L-Lys; AA is selected from the group consisting of L-Arg and L-Lys; AA3 is selected from the group consisting of D-Gln, D-Glu, D-Asn and D-Asp or from the group consisting of D-Gln and D-Asp; AA is selected from the group consisting of L-Met and L-Leu; A is selected from the group consisting of L-Glu, L-Asp and L-Gln; and AA is selected from the group consisting of L-Glu, L-Gln and L-Asp.
  • AAi is L-Arg and AA is L-Arg.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA 2 is L-Arg; AA3 is D-Gln; AA4 is L-Met; AAsis L-Glu; and AAs is L-Glu.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of L-Arg and L-Lys; AA 2 is selected from the group consisting of L-Arg and L-Lys; AA 3 is selected from the group consisting of L-Gln, L-Glu, L-Asn and L-Asp or from the group consisting of L-Gln and L-Asp; AA4 is selected from the group consisting of D-Met and D-Leu; AAs is selected from the group consisting of L-Glu, L-Asp and L-Gln; and AAb is selected from the group consisting of L-Glu, L-Gln and L-Asp.
  • AAi is L-Arg and AA 2 is L-Arg.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA 2 is L-Arg; AA3 is L-Gln; AA4 is D-Met; AAsis L-Glu; and AAe is L-Glu.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of L-Arg and L-Lys; AA 2 is selected from the group consisting of L-Arg and L-Lys; AA3 is selected from the group consisting of L-Gln, L-Glu, L-Asn and L-Asp or from the group consisting of L-Gln and L-Asp; AA* is selected from the group consisting of L-Met and L- Leu; AA5 is selected from the group consisting of D-Glu, D-Asp and D-Gln; and AAe is selected from the group consisting of L-Glu, L-Gln and L-Asp.
  • AAi is L-Arg and AA 2 is L-Arg.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA 2 is L-Arg; AA3 is L-Gln; AA4 is L-Met; AA 5 is D-Glu; and AAb is L-Glu.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of L-Arg and L-Lys; AA2 is selected from the group consisting of L-Arg and L-Lys; AA3 is selected from the group consisting of L-Gln, L-Glu, L-Asn and L-Asp or from the group consisting of L-Gln and L-Asp; AA4 is selected from the group consisting of D-Met and D-Leu; AA5 is selected from the group consisting of D-Glu, D-Asp and D-Gln; and AA 6 is selected from the group consisting of L-Glu, L-Gln and L-Asp.
  • AAi is L-Arg and AA 2 is L-Arg.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA 2 is L-Arg; AA3 is L-Gln; AA4 is D-Met; AAs is D-Glu; and AAb is L-Glu.
  • the compound of formula (I) can be such that: AAi is selected from the group consisting of L-Arg and L-Lys; AA 2 is selected from the group consisting of L-Arg and L-Lys; AA3 is selected from the group consisting of D-Gln, D-Glu, D-Asn and D-Asp or from the group consisting of D-Gln and D-Asp; AA4 is selected from the group consisting of D-Met and D-Leu; AA5 is selected from the group consisting of L-Glu, L-Asp and L-Gln; and AAb is selected from the group consisting of L-Glu, L-Gln and L-Asp.
  • AAi is L-Arg and AA2 is L-Arg.
  • This embodiment includes a compound of formula (I) wherein: AAi is L-Arg; AA2 is L-Arg; AA3 is D-Gln; AA4 is D-Met; AA5 is L-Glu; and AAe is L-Glu.
  • Compounds of formula (I) include those selected from the group of amino acid sequences listed in Table 2, in which their sequence identifier is detailed, their stereoisomers, and/or their cosmetically or pharmaceutically acceptable salts.
  • Arg-Arg-Asp-D-Met-Asp-Gln SEQ ID NO. 15 Arg-Arg-Asp-D-Leu-Asp-Gln SEQ ID NO. 16 L-Arg-L-Arg-L-GIn-L-Met-L-Glu-L-Glu SEQ ID NO. 17 L-Arg-L-Arg-L-Gln-D-Met-L-Glu-L-Glu SEQ ID NO. 18 L-Arg-L-Arg-L-Asp-D-Met-L-Glu-L-Glu SEQ ID NO. 19 L-Arg-L-Arg-L-Gln-D-Met-L-Asp-L-Glu SEQ ID NO.
  • Compounds of formula (I) include each of the sequences of Table 2 in which one of amino acids AAi to AAb is replaced by a replacement amino acid, wherein the replacement amino acid is selected from the alternative amino acids listed for the amino acid being replaced in formula (I) above.
  • the replacement amino acid is different from the amino acid that is being replaced.
  • the invention provides for each of the sequences of Table 2 in which one of amino acids AAi to AAb is replaced by an amino acid, wherein: when an AAi amino acid in one of the sequences in Table 2 is replaced it is replaced by Arg or Lys, with the proviso that if the AAi amino acid is Arg it is replaced by Lys and if the AAi amino acid is Lys it is replaced by Arg; when an AA2 amino acid in one of the sequences in Table 2 is replaced it is replaced by Arg or Lys, with the proviso that if the AA2 amino acid is Arg it is replaced by Lys and if the AA2 amino acid is Lys it is replaced by Arg; when an AA3 amino acid in one of the sequences in Table 2 is replaced it is replaced by Gin, Glu, Asn or Asp, with the proviso that if the AA3 amino acid is Gin it is replaced by Glu, Asn or Asp, if the AA3 amino acid is Glu it is replaced by Gin, As
  • Ri and f3 ⁇ 4 are H and OH, respectively.
  • Compounds of formula (I) include each of the sequences of Table 2 with their N- and C- terminals modified by the other Ri and R2 groups, respectively, as defined herein for formula (1 ).
  • compounds of formula (I) include each of the sequences of Table 2 in which the N-terminal amino acid residue terminates with Ri as defined above for formula (1) where Ri is not H, and, alternatively or additionally, where the C-terminal amino acid residue optionally terminates with R2 as defined above for formula (1) where R2 is not OH.
  • the compound according to formula (i) can be an amino acid sequence selected from SEQ ID NO.s 1, 2, 11, 13, 17, 18, 19, 20, 21 , 25, 26, 27, 28, 29 and 30, or from SEQ ID NO.s 1, 2, 11, 13, 17, 18, 27 and 30, and its stereoisomers, and/or its cosmetically or pharmaceutically acceptable salts, wherein optionally, said sequence has its N-terminal amino acid modified by Ri as defined above for formula (1), where Ri is not H, and, alternatively or additionally, said sequence has its C-terminal amino acid modified by R2 as defined above for formula (1) where R2 is not OH.
  • the amino acid sequence can be SEQ ID NO.s 17, 18, 19, 20, 21, 25, 26, 27, 28, 29 and 30.
  • the amino acid sequence can be SEQ ID NO.s 17, 18, 27 and 30.
  • the amino acid sequence can be SEQ ID NO. 17.
  • the amino acid sequence can be SEQ ID NO. 27.
  • the amino acid sequence can be SEQ ID NO. 18.
  • the amino acid sequence can be SEQ ID NO. 30.
  • the compounds of formula (I) can exist as stereoisomers or mixtures of stereoisomers; for example, the amino acids which comprise them can have the configuration L-, D-, or be racemic independently of each other. Therefore, it is possible to obtain isomeric mixtures as well as racemic mixtures or diastereomeric mixtures, or pure diastereomers or enantiomers, depending on the number of asymmetric carbons and on which isomers or isomeric mixtures are present.
  • the preferred structures of the compounds of formula (I) are pure isomers, i.e., enantiomers or diastereomers.
  • AA2 can be Arg
  • AA2 is selected from L-Arg, D-Arg or mixtures of both, racemic or non-racemic.
  • the preparation procedures described in this document enable the person skilled in the art to obtain each of the stereoisomers of the compound by choosing the amino acid with the right configuration.
  • amino acids includes the amino acids encoded by the genetic code as well as non-encoded amino acids, whether they are natural or not.
  • non-encoded amino acids are, without restriction, citrulline, ornithine, sarcosine, desmosine, norvaline, 4-aminobutyric acid, 2-aminobutyric acid, 2-aminoisobutyric acid, 6-aminohexanoyc acid, 1-naphthylalanine, 2-naphthylalanine, 2-aminobenzoic acid, 4-aminobenzoic acid, 4-chlorophenylalanine, 2,3- diaminopropionic acid, 2,4-diaminobutyric acid, cycloserine, carnitine, cystine, penicillamine, pyroglutamic acid, thienylalanine, hydroxyproline, allo-isoleucine, allo- threonine,
  • the compound of formula (I) can be selected from the group of compounds listed in Tables 3, their stereoisomers, and/or their cosmetically acceptable salts.
  • Compounds of the formula (I) include each of the compounds of Table 3 in which one of amino acids AAi to AAe is replaced by a replacement amino acid, wherein the replacement amino acid is selected from the alternative amino acids listed for the amino acid being replaced in formula (I) above.
  • the replacement amino acid is different from the amino acid that is being replaced.
  • the compounds of formula (I) include the compounds of Table 3, in which one of amino acids AAi to AAe is replaced by an amino acid, wherein: when an AAi amino acid in one of the sequences in Table 3 is replaced it is replaced by Arg or Lys, with the proviso that if the AAi amino acid is Arg it is replaced by Lys and if the AAi amino acid is Lys it is replaced by Arg; when an AA2 amino acid in one of the sequences in Table 3 is replaced it is replaced by Arg or Lys, with the proviso that if the AA2 amino acid is Arg it is replaced by Lys and if the AA2 amino acid is Lys it is replaced by Arg; when an AA3 amino acid in one of the sequences in Table 3 is replaced it is replaced by Gin, Glu, Asn or Asp, with the proviso that if the AA3 amino acid is Gin it is replaced by Glu, Asn or Asp, if the AA3 amino acid is Glu it is replaced by Gin
  • the compound according to formula (I) can beselected those in Table 3 and, in particular can be selected from PEP1, PEP2, PEP3, PEP4, PEP21, PEP22, PEP23, PEP24, PEP26, PEP27, PEP30, PEP31, PEP35, PEP36, PEP37 and PEP41 or from PEP1, PEP2, PEP3, PEP4, PEP21, PEP22, PEP23, and PEP24, and its stereoisomers, and/or its cosmetically or pharmaceutically acceptable salts.
  • the compound can be PEP21, PEP22, PEP23, PEP24, PEP26, PEP27, PEP30, PEP31, PEP35, PEP36, PEP37 and PEP41.
  • the compound can be PEP21 , PEP22, PEP23 or PEP24.
  • the compound can be PEP21.
  • the compound can be PEP22.
  • the compound can be PEP23.
  • the compound can be PEP24.
  • cosmetically or pharmaceutically acceptable salts of the compounds of formula (I) are also found within the field of this invention.
  • the term “cosmetically or pharmaceutically acceptable salt” means a salt recognized for its use in animals, for example, in mammals, and more specifically in human beings, and includes salts used to form base addition salts, either they are inorganic, for example and not restricted to, lithium, sodium, potassium, calcium, magnesium, manganese, copper, zinc or aluminium among others, or they are organic, for example and not restricted to, ethylamine, diethylamine, ethylenediamine, ethanolamine, diethanolamine, arginine, lysine, histidine or piperazine among others, or acid addition salts, either they are organic, for example and not restricted to, acetate, citrate, lactate, malonate, maleate, tartrate, fumarate, benzoate, aspartate, glutamate, succinate, oleate, trifluoroacetate, oxalate, pamoate or
  • the nature of the salt is not critical, provided that it is cosmetically or pharmaceutically acceptable.
  • the cosmetically or pharmaceutically acceptable salts of the compounds of the invention can be obtained by the conventional methods, well known in the prior art [Berge S.M. et al., "Pharmaceutical Salts", (1977), J. Pharm. Sci., 66, 1-19].
  • Synthesis of the compounds of formula (I), their stereoisomers, mixtures thereof and/or their cosmetically or pharmaceutically acceptable salts can be carried out according to conventional methods, known in the prior art, such as solid phase peptide synthesis methods [Stewart J.M. and Young J.D., “Solid Phase Peptide Synthesis, 2nd edition”, (1984), Pierce Chemical Company, Rockford, Illinois; Bodanzsky M. and Bodanzsky A., “The practice of Peptide Synthesis”, (1994), Springer Verlag, Beriin; Lloyd-Williams P.
  • W02020031146A1 discloses the use of the peptides defined therein in the treatment and/or prevention of skin aging and wrinkle reduction. W02020031146A1 is silent regarding the use of these peptides for energizing the skin or preventing skin fatigue.
  • the invention also extends to the use of the compounds of formula (I) in combination with a Botulinum toxin, Ac-Glu-Glu-Met-Gln-Arg-Arg-Nhk, or H-Tyr-D-Ala-Gly-Phe-Leu- OH or H-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2 or combinations thereof.
  • the invention extends to the use of the compounds of formula (I) in combination with H-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-Nhfe.
  • the invention provides a method of cosmetic, non-therapeutic treatment and/or care of the skin, of a subject comprising administering an effective amount of a compound of formula (I), a stereoisomer and/or cosmetically or pharmaceutically acceptable salt thereof or a composition comprising a cosmetically effective amount of a compound of formula (I), a stereoisomer and/or a cosmetically or pharmaceutically acceptable salt thereof, to the subject, wherein said cosmetic, non- therapeutic treatment and/or care is: the increase of energy metabolism and/or energy production in skin cells; the improvement and/or increase skin radiance; and/or the reduction and/or prevention of skin fatigue.
  • the invention also extends to the above-described methods of treatment and/or care of the skin wherein the compound of formula (I) is administered in combination with a Botulinum toxin, Ac-Glu-Glu-Met-Gln-Arg-Arg-Nhfe, H-Tyr-D-Ala-Gly-Phe-Leu-OH or H- Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-Nhh or combinations thereof.
  • Botulinum toxin, Ac-Glu-Glu-Met-Gln-Ang-Arg-NH 2 , or H-Tyr-D-Ala-Gly-Phe-Leu-OH or H-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2 or combinations thereof and the compound of formula (I) can be administered simultaneously (at the same time) or administered one after the other.
  • the Botulinum toxin, Ac-Glu-Glu-Met-GIn-Arg- Arg-Nhfe, or H-Tyr-D-Ala-Gly-Phe-Leu-OH or H-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro- NH 2 or combinations thereof, and the compound or composition comprising an effective amount of a compound of formula (I) are administered at the same time, they can be administered as a separate dosage forms or as a part of a single composition. When the products are administered in separate dosage forms, the dosage forms can be in the same or different containers.
  • the methods of treatment and/or care of the skin described herein can comprise the topical administration of the compound of formula (I) or a composition comprising a compound of formula (I).
  • topical ortransdermal application can be carried out by iontophoresis, sonophoresis, electroporation, mechanical pressure, osmotic pressure gradient, occlusive cure, microinjections, by needle-free injections by means of pressure, by microelectric patches, face masks or any combination thereof.
  • the frequency of application or administration can vary greatly, depending on the needs of each subject, with a recommendation of an application from once a month to ten times a day, preferably from once a week to four times a day, more preferably from three times a week to twice a day, even more preferably once a day.
  • the frequency of the administration according to the method of treatment and/or care of the skin of a subject comprising administering a combination of the compound of formula (I), a stereoisomer and/or cosmetically or pharmaceutically acceptable salt thereof with a Botulinum toxin, Ac-Glu- Glu-Met-Gln-Arg-Arg-Nhfe, or H-Tyr-D-Ala-Gly-Phe-Leu-OH or H-Phe-Trp-Met-Lys-Arg- Lys-Arg-Val-Pro-NH 2 or combinations thereof, to the subject, can vary widely, depending on the need of each subject.
  • method of the invention comprises the administration of Botulinum toxin, followed by the administration of the compound of formula (I) or composition comprising a compound of formula (I).
  • the compound of formula (I) or compositions comprising a compound of formula (I) are administered at least once a day for at least one week. More particularly, the compound of formula (I) or composition comprising a compound of formula (I) are administered at least once a day until the next administration of Botulinum toxin.
  • Cosmetic compositions comprising a compound according to formula (I), a stereoisomer and/or a cosmetically acceptable salt thereof, together with at least one cosmetically acceptable excipient or adjuvant can be prepared by conventional means known to persons skilled in the art [“Harry’s Cosmeticology”, Seventh edition, (1982), Wilkinson J.B., Moore R.J., ed. Longman House, Essex, GB].
  • the compounds of formula (I) have variable solubility in water, according to the nature of their amino acid sequence or any possible modifications in the N-terminal and/or C-terminal ends. Therefore, the compounds of formula (I) can be incorporated into the compositions by aqueous solution, and those which are not soluble in water can be solubilized in cosmetically or pharmaceutically acceptable conventional solvents such as and not restricted to, ethanol, propanol, isopropanol, propylene glycol, glycerin, butylene glycol or polyethylene glycol or any combination thereof.
  • the cosmetically effective amount of the compounds of formula (I) which should be administered, as well as their dosage, will depend on numerous factors, including age, state of the patient, the nature or severity of the condition, disorder or disease to be treated and/or cared for, the route and frequency of administration and of the particular nature of the compounds to be used.
  • cosmetically effective amount and “pharmaceutically effective amount” are understood to mean a non-toxic but sufficient amount of the compound or compounds of the invention to provide the desired effect.
  • pharmaceutically effective and “therapeutically effective” are used interchangeably herein.
  • the compounds of the invention are used in the cosmetic or pharmaceutical compositions of this invention at cosmetically or pharmaceutically effective concentrations to achieve the desired effect; for example in amounts with respect to the total weight of the composition of: from 0.00000001% (in weight) to 20% (in weight); from 0.000001% (in weight) to 15% (in weight), from 0.00001% (in weight) to 10% (in weight); or from 0.0001% (in weight) to 5% (in weight).
  • the compounds of formula (I), their stereoisomers, mixtures thereof and/or their cosmetic or pharmaceutically acceptable salts, can also be incorporated into cosmetic or pharmaceutical delivery systems and/or sustained release systems.
  • the term “delivery system” relates to a diluent, adjuvant, excipient or carrier with which the compound of the invention is administered.
  • These cosmetic or pharmaceutical carriers can be liquids, such as water, oils or surfactants, including those of petroleum, animal, plant or synthetic origin, for example and not restricted to, peanut oil, soybean oil, mineral oil, sesame oil, castor oil, polysorbates, sorbitan esters, ether sulfates, sulfates, betaines, glycosides, maltosides, fatty alcohols, nonoxynols, poloxamers, polyoxyethylenes, polyethylene glycols, dextrose, glycerol, digitonin and similar.
  • a person skilled in the art knows the diluents, adjuvants or excipients which can be used in the different delivery systems in which the compound of the invention can be administered.
  • sustained release is used in a conventional sense relating to a delivery system of a compound which provides the gradual release of this compound during a period of time and preferably, although not necessarily, with relatively constant compound release levels over a period of time.
  • Examples of delivery or sustained release systems include, without restriction, liposomes, mixed liposomes, oleosomes, niosomes, ethosomes, milliparticles, microparticles, nanoparticles and solid lipid nanoparticles, nanostructured lipid carriers, sponges, cyclodextrins, vesicles, micelles, mixed micelles of surfactants, surfactant- phospholipid mixed micelles, millispheres, microspheres and nanospheres, lipospheres, millicapsules, microcapsules and nanocapsules, as well as in microemulsions and nanoemulsions, which can be added to achieve a greater penetration of the active principle and/or improve its pharmacokinetic and pharmacodynamic properties.
  • Preferred delivery or sustained release systems are liposomes, surfactant-phospholipid mixed micelles, microemulsions, more preferably water-in-oil microemulsions with an internal structure of reverse micelle and nanocapsules containing microemulsions.
  • the cosmetic composition comprising a compound of formula (I) and a cosmetically or pharmaceutically acceptable carrier are selected from the group consisting of creams, emulsions, gels, liposomes, nanoparticles and ointments.
  • the sustained release systems can be prepared by methods known in the prior art, and the compositions which contain them can be administered, for example, by topical or transdermal administration, including adhesive patches, non-adhesive patches, occlusive patches and microelectric patches, or by systemic administration, for example and not restricted to, oral or parenteral route, including nasal, rectal or subcutaneous implantation or injection, or direct implantation or injection into a specific body part, and preferably should release a relatively constant quantity of the compounds of formula (I).
  • the amount of compound contained in the sustained release system will depend, for example, on where the composition is to be administered, the kinetics and duration of the release of the compound of formula (I), as well as the nature of the condition, disorder and/or disease to be treated and/or cared for.
  • the compounds of formula (I) can also be adsorbed on solid organic polymers or solid mineral supports such as and not restricted to, talc, bentonite, silica, starch or maltodextrin among others.
  • compositions which contain the compounds of formula (I), their stereoisomers, mixtures thereof and/or their cosmetically or pharmaceutically acceptable salts can also be incorporated into fabrics, non-woven fabrics and medical devices which are in direct contact with the skin, thus releasing the compounds of the invention whether by biodegradation of the binding system to the fabric, non-woven fabric or medical device, or by friction between them and the body, due to bodily moisture, the skin’s pH or body temperature.
  • the compounds of the invention can be incorporated into the fabrics and non-woven fabrics used to make garments that are in direct contact with the body.
  • the preferred fabrics, non-woven fabrics, garments and medical devices are bandages, gauzes, t-shirts, socks, tights, underwear, girdles, gloves, diapers, sanitary napkins, dressings, bedspreads, wipes, adhesive patches, nonadhesive patches, occlusive patches, microelectric patches and/or face masks.
  • compositions which contain the compounds of formula (I), their stereoisomers, mixtures thereof and/or their cosmetically acceptable salts, can be used in different types of compositions for topical or transdermal application which optionally include cosmetically or pharmaceutically acceptable excipients necessary for formulating the desired administration form.
  • compositions for topical or transdermal application can be produced in any solid, liquid or semisolid formulation, such as and not restricted to, creams, multiple emulsions such as and not restricted to, oil and/or silicone in water emulsions, water-in-oil and/or silicone emulsions, water/oil/water or water/silicone/water type emulsions and oil/water/oil or silicone/water/silicone type emulsions, anhydrous compositions, aqueous dispersions, oils, milks, balsams, foams, lotions, gels, cream gels, hydroalcoholic solutions, hydroglycolic solutions, hydrogels, liniments, soaps, shampoos, conditioners, serums, polysaccharide films, ointments, mousses, pomades, powders, bars, pencils and sprays or aerosols (sprays), including leave-on and rinse-off formulations.
  • creams such as and not restricted to, creams, multiple emul
  • topical or transdermal application formulations can be incorporated using techniques known by the person skilled in the art into different types of solid accessories for example and not restricted to, bandages, gauzes, t-shirts, socks, tights, underwear, girdles, gloves, diapers, sanitary napkins, dressings, bedspreads, wipes, adhesive patches, nonadhesive patches, occlusive patches, microelectric patches or face masks, or they can be incorporated into different make-up products such as make-up foundation, such as fluid foundations and compact foundations, make-up removal lotions, make-up removal milks, under-eye concealers, eye shadows, lipsticks, lip protectors, lip gloss and powders among others.
  • the cosmetic compositions may include agents which increase the percutaneous absorption of the compounds of the invention, for example and not restricted to, dimethylsulfoxide, dimethylacetamide, dimethylformamide, surfactants, azone (1- dodecylazacycloheptane-2-one), alcohol, urea, ethoxydiglycol, acetone, propylene glycol or polyethylene glycol, among others.
  • agents which increase the percutaneous absorption of the compounds of the invention for example and not restricted to, dimethylsulfoxide, dimethylacetamide, dimethylformamide, surfactants, azone (1- dodecylazacycloheptane-2-one), alcohol, urea, ethoxydiglycol, acetone, propylene glycol or polyethylene glycol, among others.
  • the cosmetic compositions can be applied to local areas to be treated by means of iontophoresis, sonophoresis, electroporation, microelectric patches, mechanical pressure, osmotic pressure gradient, occlusive cure, microinjections or needle-free injections by means of pressure, such as injections by oxygen pressure, or any combination thereof, to achieve a greater penetration of the peptide of the invention.
  • the application area will be determined by the nature of the condition, disorder and/or disease to be treated and/or cared for.
  • cosmetically acceptable adjuvants contained in the cosmetic compositions described herein are additional ingredients commonly used in cosmetic or pharmaceutical compositions, for example and not restricted to anti-wrinkle agents, botox-like agents and/or anti-aging agents; (ii) firming agents, skin elasticity agents and/or restructuring agents; moisturizing agents; (iv) anti-photoaging agents, and/or blue-light protector agents; DNA protecting agents, DNA repair agents, and/or stem cell protecting agents; free radical scavengers and/or anti-glycation agents, detoxifying agents, antioxidant and/or anti-pollution agents; anti-perspirant agents; melanin synthesis stimulating or inhibiting agents; whitening or depigmenting agents; propigmenting agents; self-tanning agents; lipolytic agents or agents stimulating lipolysis, adipogenic agents, etc. Additional examples can be found in CTFA International Cosmetic Ingredient Dictionary & Handbook, 12th Edition (2008).
  • the cosmetic compositions described herein can comprise a compound of formula (I) and a cosmetically effective amount of an adjuvant selected from the group consisting of: (i) anti-wrinkle-agent, botox-like agent and/or anti-aging agent; (ii) firming agent, skin elasticity agent and/or restructuring agent; (iii) moisturizing agent; (iv) anti-photoaging agent, and/or blue-light protector agent; (v) DNA protecting agent, DNA repair agent, and/or stem cell protecting agent; (vi)free radical scavengers and/or anti-glycation agent, detoxifying agent, antioxidant and/or anti-pollution agents; and/or combinations thereof.
  • adjuvants are known in the art and examples are given in W02019008452A1, for example.
  • Mitochondria are intracellular organelles that play a vital role in cellular metabolism, including heme, fatty acid, and steroid synthesis; oxidative phosphorylation; Ca2+ homeostasis; and apoptosis. Mitochondria are enclosed within an outer and inner membrane.
  • the inner membrane is more complex in structure, and contains the electron transport chain (ETC) complex and the complex for ATP synthesis through oxidative phosphorylation.
  • ETC electron transport chain
  • This process consists of a series of redox reactions in which electrons are transferred from electron donors to electron acceptors.
  • the energy released by electrons flowing through the ETC transports protons across the inner membrane, creating an electrochemical gradient.
  • the electrochemical gradient consists of two parts, the electric potential and the proton gradient.
  • MMP mitochondrial membrane potential
  • Dyih mitochondrial membrane potential
  • Measuring the MMP is useful for evaluating mitochondrial function as it is a direct biomarker of adenosine triphosphate (ATP) synthesis, the main source of energy in the cell. For this reason, products with the ability to increase MMP can increase energy in cells and improve skin functions.
  • ATP adenosine triphosphate
  • the main objective of this experiment was to evaluate the capacity of peptides to increase mitochondrial membrane potential in human dermal fibroblasts.
  • Human Dermal Fibroblasts from adult are seeded at a density of 6,000 cells/well (3 wells per treatment) in 96-well plates. Cells are seeded in culture medium M106 with Low Serum Growth Supplement (Life Technologies) during 24 hours at 37°C in 5% C0 2 humidified air. Then, culture medium is removed and cells are treated with the peptide or peptide combinations set out above dissolved in Dulbecco’s Modified Eagle Medium (Life Technologies) supplemented with 10% (volume/volume) of fetal bovine serum (FBS, Cultek) for 16 hours at 37°C in 5% C0 2 humidified air. Non-treated cells incubated with medium alone are used as basal conditions.
  • FCCP carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone
  • JC-1 mitochondrial membrane potential assay kit (Abeam) according to the manufacturer’s protocol. Briefly, cells are incubated with a JC-1 working solution prepared with Supplemented Dilution Buffer in the presence of the treatment with the peptide (each treatment is always present during the assay) at 37 ° C in 5% C0 2 for 30 minutes.
  • the JC-1 dye fluoresces red or green, respectively, when it aggregates in healthy mitochondria with high membrane potentials (hyperpolarization; energized cells) or exists as a monomer in mitochondria with diminished membrane potential (depolarization; non-energized cells).
  • Cells are imaged and mitochondrial membrane potential is measured using Operetta ® High Content Imaging System (PerkinElmer, Inc). In energized cells, red aggregates appear, and the dye emits at 560-630 nm when excited at 520-550 nm. In depolarized cells, the dye emits at 500-550 nm when excited at 460-490 nm. Cell number is quantified by using Hoechst 33342 (ThermoFisher Scientific) staining, a cell- permeant nuclear counterstain that emits blue fluorescence at 460nm when bound to dsDNA and is excited at 350nm. For each image, intensity fluorescence from energized and depolarized cells is quantified and normalized against the number of nuclei. The mean of the percentage of mitochondrial membrane potential after the treatment of cells with peptide or peptide combinations relative to basal conditions is summarized in Table 4. These values represent the values for at least three independent assays.
  • PEP23 was able to increase the mitochondrial potential of HDFa cells, which demonstrates the capacity of the peptide to increase the cell energy metabolism.
  • PEP23 is relatively small (6 amino acids) compared with H-Phe-Trp- Met-Lys-Arg-Lys-Arg-Val-Pro-NH2 (9 amino acids) and therefore can be prepared more efficiently.
  • a cosmetic copostion was prepared by the following process:
  • Phase A Dissolving phase A in an adequate vessel and adding Carbopol® Ultrez 21 Polymer (from the Lubrizol Corporation) (Phase A1). complete dispersion.
  • phase B in a separate vessel, then additing to phase A while mixing with a turbine.
  • phase C while mixing with overhead stirrer with a dispersion blade.
  • phase D to adjust pH to 6-6.5.
  • PHASE INGREDIENTS % A Water (Aqua) q.s.p. 100
  • Subjects with skin disorders on the test area - Subjects with pharmacological treatment (both locally or systemically) that may interfere with the test execution.
  • the skin radiance is the ability of the skin to reflect the light and it is measured using the gloss parameter (taken using the spectrophotometer/colorimeter CM-700D (Konica-Minolta).
  • the gloss value is used in the management of the brilliance of the color.
  • Fatigue effect (or tiring effect) was determined by a Cutometer® MPA 580 (Courage+ Khazaka electronic GmbH) by determining the R9 value, wherein smaller values represent smaller tiring effect.
  • the results show that the Active Cream significantly increases skin radiance compared to the Placebo Cream.
  • the Active Cream significantly reduced skin tiredess which can be correlated with a reduction of skin fatigue.

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EP22748069.6A 2021-07-02 2022-06-30 Kosmetische, nicht-therapeutische verwendungen von peptiden Pending EP4362904A1 (de)

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