WO2009129857A1 - Hexapeptides et compositions de ces derniers - Google Patents

Hexapeptides et compositions de ces derniers Download PDF

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Publication number
WO2009129857A1
WO2009129857A1 PCT/EP2008/055011 EP2008055011W WO2009129857A1 WO 2009129857 A1 WO2009129857 A1 WO 2009129857A1 EP 2008055011 W EP2008055011 W EP 2008055011W WO 2009129857 A1 WO2009129857 A1 WO 2009129857A1
Authority
WO
WIPO (PCT)
Prior art keywords
seq
gly
phe
tyr
ala
Prior art date
Application number
PCT/EP2008/055011
Other languages
English (en)
Inventor
Igor Arturovic Petropavlov
Igor Anatolievich Pomytkin
Tamara Aleksandrovna Vitkalova
Original Assignee
United Technologies Ut Ag
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 United Technologies Ut Ag filed Critical United Technologies Ut Ag
Priority to PCT/EP2008/055011 priority Critical patent/WO2009129857A1/fr
Priority to EA201001598A priority patent/EA019154B1/ru
Publication of WO2009129857A1 publication Critical patent/WO2009129857A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • C07K14/70—Enkephalins
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • A61Q19/06—Preparations for care of the skin for countering cellulitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to hexapeptides and compositions thereof.
  • the present invention relates to skin care and dermatological compositions containing these hexapeptides.
  • the present invention provides a peptide of the general formula (I): wherein if Xi is GIy or L-AIa; X 2 is independently Leu, Met, lie, or VaI; and X 3 is independently Asp or GIu; wherein if Xi is D-AIa and X3 is Asp; X 2 is independently Leu, Met, lie, or VaI; and wherein if X 1 is D-AIa and X 3 is GIu; X 2 is independently Met, lie, or VaI.
  • peptide refers to an amino acid sequence of six amino acid length, wherein said amino acids may be in L- or D-form.
  • amino acids may be in L-form.
  • alanine may be in L- or D-form.
  • the peptide of the general formula (I) is selected from the group consisting of:
  • Tyr-Gly-Gly-Phe-lle-Asp (SEQ ID NO: 4) Tyr-Ala-Gly-Phe-lle-Asp (SEQ ID NO: 5)
  • Tyr-D-Ala-Gly-Phe-Met-Asp (SEQ ID NO: 9) Tyr-Gly-Gly-Phe-Val-Asp (SEQ ID NO: 10)
  • Tyr-D-Ala-Gly-Phe-Val-Asp (SEQ ID NO: 12) Tyr-Gly-Gly-Phe-Leu-Glu (SEQ ID NO: 13) Tyr-Ala-Gly-Phe-Leu-Glu (SEQ ID NO: 14) Tyr-Gly-Gly-Phe-lle-Glu (SEQ ID NO: 15) Tyr-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 16) Tyr-D-Ala-Gly-Phe-lle-Glu (SEQ ID NO: 17) Tyr-Gly-Gly-Phe-Met-Glu (SEQ ID NO: 18) Tyr-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 19) Tyr-D-Ala-Gly-Phe-Met-Glu (SEQ ID NO: 20) Tyr-Gly-Gly-Phe-Val-Glu (SEQ ID NO: 21 ) Tyr-Ala-Gly-Phe-Val-Glu (SEQ ID NO:
  • the present invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a peptide having an amino acid sequence selected from the group consisting of SEQ ID NO: 1 , SEQ ID NO: 2, SEQ ID NO: 3, SEQ ID NO: 4, SEQ ID NO: 5, SEQ ID NO: 6, SEQ ID NO: 7, SEQ ID NO: 8, SEQ ID NO: 9, SEQ ID NO: 10, SEQ ID NO: 11 , SEQ ID NO: 12, SEQ ID NO: 13, SEQ ID NO: 14, SEQ ID NO: 15, SEQ ID NO: 16, SEQ ID NO: 17, SEQ ID NO: 18, SEQ ID NO: 19, SEQ ID NO: 20, SEQ ID NO: 21 , SEQ ID NO: 22, or SEQ ID NO: 23; and a pharmaceutically acceptable carrier.
  • the present invention provides a skin care composition
  • a skin care composition comprising a peptide having an amino acid sequence selected from the group consisting of SEQ ID NO: 1 , SEQ ID NO: 2, SEQ ID NO: 3, SEQ ID NO: 4, SEQ ID NO: 5, SEQ ID NO: 6, SEQ ID NO: 7, SEQ ID NO: 8, SEQ ID NO: 9, SEQ ID NO: 10, SEQ ID NO: 11 , SEQ ID NO: 12, SEQ ID NO: 13, SEQ ID NO: 14, SEQ ID NO: 15, SEQ ID NO: 16, SEQ ID NO: 17, SEQ ID NO: 18, SEQ ID NO: 19, SEQ ID NO: 20, SEQ ID NO: 21 , SEQ ID NO: 22, or SEQ ID NO: 23; and a dermatologically acceptable carrier.
  • the present invention provides a dermatological composition
  • a dermatological composition comprising a peptide having an amino acid sequence selected from the group consisting of SEQ ID NO: 1 , SEQ ID NO: 2, SEQ ID NO: 3, SEQ ID NO: 4, SEQ ID NO: 5, SEQ ID NO: 6, SEQ ID NO: 7, SEQ ID NO: 8, SEQ ID NO: 9, SEQ ID NO: 10, SEQ ID NO: 11 , SEQ ID NO: 12, SEQ ID NO: 13, SEQ ID NO: 14, SEQ ID NO: 15, SEQ ID NO: 16, SEQ ID NO: 17, SEQ ID NO: 18, SEQ ID NO: 19, SEQ ID NO: 20, SEQ ID NO: 21 , SEQ ID NO: 22, or SEQ ID NO: 23; and a dermatologically acceptable carrier.
  • skin care composition refers to a composition that is applied topically to the human skin to improve the appearance and health of the skin.
  • skin encompasses whole skin or any portion of the skin, including hair, nails, etc.
  • the term "dermatological composition” refers to a pharmaceutical composition formulated for cutaneous administration, such as formulated for the application to a portion of skin affected by a skin condition or a skin disorder.
  • disorders and conditions include reduced skin elasticity, decreased skin firmness, loss- of skin moisture, dry skin, pruritus, blotches, wrinkles, lentigines, age spots, melasmas, hyperpigmented skin, hyperkeratotic skin, skin atrophy, senile purpura, psoriasis, eczema, inflammatory dermatoses, spider veins, keratoses, and brittle hair or nails.
  • compositions of the present invention include those described in Freedberg et al., Fitzpatrick's Dermatology in General Medicine (6th Edition, 2003), Kerdel, et al., Dermatologic Therapeutics (2005), and Hardman et al., Goodman & Gilman's: The Pharmacological Basis of Therapeutics (1 Oth Edition, 2001 ).
  • the content of the peptide of the invention is in the range from 0.00001 to 10 %, preferably 0.0001 to 0.1 % by the weight of the composition of the invention.
  • the term "dermatologically acceptable carrier” refers to one or more liquid, semi-solid, or solid diluents, which are suitable for administration to any portion of the human skin, and are compatible with the peptides of the general formula (I) of the present invention and other active or optional ingredients of the present invention.
  • examples of such carriers include, but are not limited to, distilled or deionized water, propyleneglycol, glycerol, and oil.
  • compositions of the present invention are useful for regulating the skin condition, visible and/or tactile discontinuities in skin (especially the skin surface; such discontinuities are generally undesirable). Such discontinuities may be induced or caused by internal and/or external factors, and include the signs of skin aging described herein.
  • the term "regulating skin condition" includes prophylactically regulating and/or therapeutically regulating skin condition, including visible and/or tactile discontinuities in skin.
  • prophylactically regulating skin condition includes delaying, minimizing and/or preventing visible and/or tactile discontinuities in skin.
  • therapeutically regulating skin condition includes ameliorating, e.g., diminishing, minimizing and/or effacing, discontinuities in skin. Regulating skin condition involves improving skin appearance and/or feel.
  • the compositions of the present invention are particularly advantageous for treatment of acne and other skin disorders.
  • compositions of the present invention are particularly advantageous for regulating signs of skin aging, more especially visible and/or tactile discontinuities in skin texture associated with aging.
  • “Regulating the signs of skin aging” includes prophylactically regulating and/or therapeutically regulating one or more of such signs (similarly, regulating a given sign of skin aging, e.g., lines, wrinkles or pores, includes prophylactically regulating and/or therapeutically regulating that sign).
  • prophylactically regulating such signs includes delaying, minimizing and/or preventing signs of skin aging.
  • therapeutically regulating such signs includes ameliorating, e.g., diminishing, minimizing and/or effacing signs of skin aging.
  • Signs of skin aging include, but are not limited to, all outward visibly and tactilely perceptible manifestations as well as any other macro or micro effects due to skin aging. Such signs may be induced or caused by intrinsic factors or extrinsic factors, e.g., chronological aging and/or environmental damage.
  • These signs may result from processes which include, but are not limited to, the development of textural discontinuities such as wrinkles, including both fine superficial wrinkles and coarse deep wrinkles, skin lines, crevices, bumps, large pores (e.g., associated with adnexal structures such as sweat gland ducts, sebaceous glands, or hair follicles), scaliness, flakiness and/or other forms of skin unevenness or roughness, loss of skin elasticity (loss and/or inactivation of functional skin elastin), sagging (including puffiness in the eye area and jowls), loss of skin firmness, loss of skin tightness, loss of skin recoil from deformation, discoloration (including undereye circles), blotching, sallowness, hyperpigmented skin regions such as age spots and freckles, keratoses, abnormal differentiation, hyperkeratinization, elastosis, collagen breakdown, and other histological changes in the stratum corneum, dermis, epidermis,
  • compositions of the present invention can comprise optional ingredients.
  • optional ingredients generally are used individually at levels from about 0.0005% to about 10.0%, preferably from about 0.005% to about 1.0% by weight of the composition..
  • suitable optional ingredients include, but are not limited to, depigmentation agents; humectants; antimicrobial (e.g., antibacterial) agents; anti-acne agents; anti-aging agents; anti-wrinkling agents, antiseptics; local anesthetics; wound healing promoters; deodorants and antiperspirants; skin emollients and skin moisturizers; tanning agents; skin lightening agents; antifungals; depilating agents; external analgesics; counterirritants; anti-diaper rash agents; make-up preparations; vitamins and nutrients such as thiamin, riboflavin, niacin, pantothenates, pyridoxine, folic acid, cobalamin, biotin, choline
  • humectants include, but not limited to, water soluble liquid polyols selected from the group comprising glycerine, propylene glycol, hexylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, and mixtures thereof.
  • Suitable amino acid agents include amino acids derived from the hydrolysis of various proteins as well as the salts, esters, and acyl derivatives thereof.
  • Examples of such amino acid agents nonexclusively include amphoteric amino acids such as alkylamido alkylamines, i.e.
  • stearyl acetyl glutamate capryloyl silk amino acid, caprylol collagen amino acids; capryloyl kertain amino acids; capryloyl pea amino acids; cocodimonium hydroxypropyl silk amino acids; corn gluten amino acids; cysteine; glutamic acid; glycine; hair keratin amino acids; hair amino acids such as aspartic acid, threonine, serine, glutamic acid, glycine, alanine, half-cystine, valine, methionine, isoleucine, leucine, tyrosine, phenylalanine, cysteic acid, lysine, histidine, arginine, cysteine, tryptophan, citrulline; lysine; silk amino acids, wheat amino acids; and mixtures thereof
  • suitable proteins include, but not limited to, collagen, deoxyribonuclease, iodized corn protein; keratin; milk protein; protease; serum protein; silk; sweet almond protein; wheat germ protein; wheat protein; wheat protein, alpha and beta helix of keratin proteins; hair proteins, such as intermediate filament proteins, high-sulfur proteins, ultrahigh-sulfur proteins, intermediate filament-associated proteins, high- tyrosine proteins, high-glycine tyrosine proteins, tricohyalin, arginine-rich peptides like as oligoarginines (Arg) 8 , and mixtures thereof.
  • collagen deoxyribonuclease, iodized corn protein
  • keratin milk protein
  • protease serum protein
  • silk sweet almond protein
  • wheat germ protein wheat protein
  • wheat protein wheat protein, alpha and beta helix of keratin proteins
  • hair proteins such as intermediate filament proteins, high-sulfur proteins, ultrahigh-sul
  • Suitable antiperspirants and deodorants include, but not limited to, aluminium chlorohydrates, aluminium zirconium chlorohydrates, and mixtures thereof.
  • countehrhtants include, but not limited to, camphor, menthol, methyl salicylate, peppermint and clove oils, ichtammol, and mixtures thereof.
  • Suitable anti-aging agents include, but are not limited to, retinoids; vitamins such as vitamin C, vitamin B, and derivatives thereof; antioxidants including acid such as glycolic acid, citric acid, lactic acid, malic acid, mandelic acid, ascorbic acid, alpha-hydroxybutyhc acid, alpha- hydroxyisobutyric acid, alpha-hydroxyisocaproic acid, atrrolactic acid, alpha-hydroxyisovalehc acid, ethyl pyruvate, galacturonic acid, glucopehtonic acid, glucopheptono 1 ,4-lactone, gluconic acid, gluconolactone, glucuronic acid, glucurronolactone, glycolic acid, isopropyl pyruvate, methyl pyruvate, mucic acid, pyruvia acid, saccharic acid, saccaric acid 1 ,4-lactone, tartaric acid, and tartronic acid; succinic acid or
  • depigmentation agents include, but are not limited to, hydroquinone and it derivatives; vitamins such as niacin, vitamin C and its derivatives; extracts such as chamomile and green tea, and mixtures thereof.
  • Examples of skin lightening agents include, but not limited to, hydroquinone, catechol and its derivatives, ascorbic acid and its derivatives, and mixtures thereof.
  • compositions of the invention are prepared by well-known procedures. Such procedures include, but are not limited to, mixing the peptides of the present invention with other ingredients of the composition in conventional manner.
  • Guidance for the preparation of skin care or dermatological compositions of the invention can be found in " Remington: The science and practice of pharmacy” 20th ed. Mack Publishing, Easton PA, 2000 ISBN 0-912734-04-3 and " Encyclopaedia of Pharmaceutical Technology", edited by Swarbrick, J. & J. C. Boylan, Marcel Dekker, Inc., New York, 1988 ISBN 0-8247-2800-9 or a newer edition.
  • compositions of the present invention can be formulated in a variety of forms. Such forms include, but are not limited to, lotions, gels, creams, sprays, and solutions.
  • compositions of the present invention can be used for regeneration of damaged hair and stimulating hair growth in subjects in need thereof. Also, the compositions of the present invention are particularly advantageous to improve nail health and appearance, accelerate nail growth and regeneration, to make nails more strength and flexible, and eliminate nail problems such as changes in the shape and texture of nails, thickened nails, nail fragility, and brittle nails.
  • compositions of the present invention are particularly advantageous for regulating regional fat deposits including cellulite.
  • regional fat deposits means areas of excessive fat, of which cellulite is an example, and excess fatty tissue.
  • cellulite means deposits of fat, which generally do not respond to dieting and exercise. Cellulite is not the only cosmetic condition that concerns women. Stretch marks are another example of a cosmetic condition which affects not only women, but also men.
  • the present invention provides a method for the skin care comprising a step of applying an effective amount of the composition of the invention to the skin, hair or nail of a subject in need thereof.
  • an effective amount of the composition of the invention is topically applied to the skin, and is preferably left on the skin for a period of at least about 15 minutes, more preferably at least about 30 minutes, even more preferably at least about 1 hour, most preferably for at least several hours, e.g., up to about 12 hours.
  • This method can be reapplied from 1 to about 5, preferably from 1 to 3 times per day.
  • the effective amount of the composition is from about 1 gram to about 100 grams, preferably from about 1 gram to about 20 grams.
  • the present invention provides a method for the dermatologic treatment comprising a step of applying an effective amount of the composition of the invention to the skin of a subject in need thereof.
  • an effective amount of the composition of the invention is topically applied to the skin, and is preferably left on the skin for a period of at least about 15 minutes, more preferably at least about 30 minutes, even more preferably at least about 1 hour, most preferably for at least several hours, e.g., up to about 12 hours.
  • This method can be reapplied from 1 to about 5, preferably from 1 to 3 times per day.
  • the effective amount of the composition is from about 1 gram to about 100 grams, preferably from about 1 gram to about 20 grams.
  • compositions of the present invention are usually formulated to have a pH from about 4.5 to 9.5, more preferably from about 5 to about 8.5.
  • Peptides may be prepared using solid-phase synthesis (SPPS).
  • SPPS solid-phase synthesis
  • protected amino acids in organic solvents can be added one at a time to resin-bound peptide chain, resulting in the assembly of a target peptide having a specific sequence in fully protected resin-bound form.
  • the product peptide can then be released by deprotection and cleavage from the resin support.
  • Such synthesis may use manual or automatic techniques.
  • the peptides having an amino acid sequences of SEQ ID NO: 1 through 23 are prepared by solid-phase peptide synthesis (SPPS) technique using
  • Example 2 This example demonstrates the skin care composition of the invention in form of a gel.
  • the peptide is selected from the group consisting of
  • the gel preparation The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the gel for skin care.
  • the method of skin care with the use of the gel 1 g of above- mentioned gel is topically applied to the skin, and is preferably left on the skin for a period of at least about 15 minutes.
  • This example demonstrates the dermatological composition of the invention in form of a gel.
  • the peptide is selected from the group consisting of
  • the gel preparation The peptide is mixed with above-mentioned ingredients in the conventional manner to prepare the dermatological composition in form of a gel.
  • the method of dermatological treatment with the use of the gel 1 g of above-mentioned gel is topically applied to the skin, and is preferably left on the skin for a period of at least about 15 minutes.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Zoology (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Birds (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Toxicology (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Dermatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Cosmetics (AREA)

Abstract

L'invention porte sur des peptides de la formule générale (I): Tyr-X1-Gly-Phe-X2-X3 dans laquelle, si X1 est Gly ou L-Ala, X2 est indépendamment Leu, Met, Ile ou Val et X3 est indépendamment Asp ou Glu; dans laquelle, si X1 est D-Ala et X3 est Asp, X2 est indépendamment Leu, Met, Ile ou Val; et dans laquelle, si X1 est D-Ala et X3 est Glu, X2 est indépendamment Met, Ile ou Val; et sur des compositions de ces derniers.
PCT/EP2008/055011 2008-04-24 2008-04-24 Hexapeptides et compositions de ces derniers WO2009129857A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/EP2008/055011 WO2009129857A1 (fr) 2008-04-24 2008-04-24 Hexapeptides et compositions de ces derniers
EA201001598A EA019154B1 (ru) 2008-04-24 2008-04-24 Гексапептиды и композиции на их основе

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2008/055011 WO2009129857A1 (fr) 2008-04-24 2008-04-24 Hexapeptides et compositions de ces derniers

Publications (1)

Publication Number Publication Date
WO2009129857A1 true WO2009129857A1 (fr) 2009-10-29

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PCT/EP2008/055011 WO2009129857A1 (fr) 2008-04-24 2008-04-24 Hexapeptides et compositions de ces derniers

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EA (1) EA019154B1 (fr)
WO (1) WO2009129857A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110189126A1 (en) * 2008-11-07 2011-08-04 Igor Anatolievich Pomytkin Compositions containing interleukin-1 and peptides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1498113A1 (fr) * 2003-07-17 2005-01-19 L'oreal Utilisation de béta-endorphine et/ou d'agents exercant une activité béta-endorphine-like en cosmétique et dermatologie
EP1892247A1 (fr) * 2005-04-08 2008-02-27 Lipotec, S.A. Composition cosmetique ou dermopharmaceutique comprenant des peptides derives d'encephalines afin de reduire et/ou d'eliminer les rides faciales

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1498113A1 (fr) * 2003-07-17 2005-01-19 L'oreal Utilisation de béta-endorphine et/ou d'agents exercant une activité béta-endorphine-like en cosmétique et dermatologie
EP1892247A1 (fr) * 2005-04-08 2008-02-27 Lipotec, S.A. Composition cosmetique ou dermopharmaceutique comprenant des peptides derives d'encephalines afin de reduire et/ou d'eliminer les rides faciales

Non-Patent Citations (3)

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Title
BYULLETEN' EKSPERIMENTAL'NOI BIOLOGII I MEDITSINY, vol. 104, no. 7, 1987, pages 89 - 91, ISSN: 0365-9615 *
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1987, VINOGRADOV V A ET AL: "OPIOID ACTIVITY OF PEPTIDES AND SKIN WOUND HEALING", XP002509588, Database accession no. PREV198885090654 *
HOUGHTEN R A ET AL: "THE USE OF SYNTHETIC PEPTIDE COMBINATORIAL LIBRARIES FOR THE DETERMINATION OF PEPTIDE LIGANDS IN RADIO-RECEPTOR ASSAYS: OPIOID PEPTIDES", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 3, no. 3, 1 January 1993 (1993-01-01), pages 405 - 412, XP000579486, ISSN: 0960-894X *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110189126A1 (en) * 2008-11-07 2011-08-04 Igor Anatolievich Pomytkin Compositions containing interleukin-1 and peptides
US8298523B2 (en) * 2008-11-07 2012-10-30 United Technologies Ut Ag Compositions containing interleukin-1 and peptides

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EA019154B1 (ru) 2014-01-30
EA201001598A1 (ru) 2011-06-30

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