EP0617609A1 - Thioethers and dithioethers liposolubles contenus dans des preparations cosmetiques agissant contre le vieillissement de la peau chez l'homme - Google Patents

Thioethers and dithioethers liposolubles contenus dans des preparations cosmetiques agissant contre le vieillissement de la peau chez l'homme

Info

Publication number
EP0617609A1
EP0617609A1 EP93915617A EP93915617A EP0617609A1 EP 0617609 A1 EP0617609 A1 EP 0617609A1 EP 93915617 A EP93915617 A EP 93915617A EP 93915617 A EP93915617 A EP 93915617A EP 0617609 A1 EP0617609 A1 EP 0617609A1
Authority
EP
European Patent Office
Prior art keywords
skin
cosmetic
preparation according
acid
general formula
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.)
Withdrawn
Application number
EP93915617A
Other languages
German (de)
English (en)
Inventor
Günter Wolfgang Holzner
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.)
Beiersdorf AG
Original Assignee
Beiersdorf 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 Beiersdorf AG filed Critical Beiersdorf AG
Publication of EP0617609A1 publication Critical patent/EP0617609A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10—Sulfides; Sulfoxides; Sulfones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/145—Amines having sulfur, e.g. thiurams (>N—C(S)—S—C(S)—N< and >N—C(S)—S—S—C(S)—N<), Sulfinylamines (—N=SO), Sulfonylamines (—N=SO2)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/795—Polymers containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • Lipid-soluble thioethers and dithioethers in cosmetic preparations prevent the aging of human skin.
  • Occurring mutations affect the immune system and ultimately the vital processes in the cell (1).
  • Free radicals are molecules or fragments of molecules that have a free electron in their outer molecular orbital. This makes them very reactive and can initiate chain reactions that oxidize the membrane lipids, but also damage proteins and nucleic acids.
  • the well-known brown age spots of the skin from lipoprotein complexes are formed by cross-linking proteins with oxidation products of the membrane lipids.
  • free radicals and their secondary products either cause polymerisation of biomolecules (e.g. cross-linking of collagen) or their cleavage (e.g. oxidation of lipids, especially unsaturated fatty acids).
  • the attack of the free radicals on unsaturated fatty acids causes an addition of oxygen with subsequent formation of hydroperoxides which continue to react to cyclic peroxides and to cyclic endoperoxides.
  • These lipoperoxides can either disintegrate to form short-chain aldehydes (e.g. malondialdehyde) or they can form polymerization products (4).
  • lipoperoxides reduce the electrical resistance of biomembranes.
  • the bases in the nucleic acids can also form peroxide radicals (9).
  • the living cell has developed various protective mechanisms against the action of free radicals, especially oxygen radicals and lipoperoxides.
  • the most important of these are the enzymes superoxide dismutase, catalase and various peroxidases, the best known of which is glutathione peroxidase.
  • Cholesterol, uric acid, vitamins A, C, E and the vitamins of the B group are biological antioxidants that inactivate free radicals.
  • all living organisms are composed of substances that are thermodynamically unstable against activated oxygen. Proteins, lipids, polysaccharides and nucleic acids can react with oxygen and be inactivated. Aerobic metabolism is a balance between the oxidation required for energy generation and the antioxidation which protects the sensitive cell components (10).
  • the skin is exposed to a variety of physical, chemical and biological attacks that form free radicals and peroxides (light, air pollution, bacteria, immune reactions).
  • Antioxidants inactivate free radicals. They are used industrially in large quantities to stabilize plastics, rubber, food and also cosmetic preparations (perfume, creams, soaps).
  • Oxygen radicals (singlet oxygen * 02, super oxide anion O2-,
  • Hydroxyl radical HO hydroperoxyl radical HO 2
  • Plant extracts such as ginseng, ginko-biloba, wheat germ oil and coltsfoot whose effect is based at least in part on their antioxidant activity are used in cosmetic preparations. The same applies to vitamins A (as carotene, vitamin A acid or ester), E (tocopherol) and the water-soluble B vitamins.
  • Vitamin E synthetic alpha tocopherol or a natural mixture of different isomers
  • Vitamin E is particularly recommended as a radical scavenger for skin care products (13).
  • R * free radicals
  • Hydroperoxides are not inactivated by AH and can continue to react with biological substances in the cell. This is also the reason why primary antioxidants are only effective if they are added to the fresh substrate right from the start before a large amount of hydroperoxides is formed. Their effect is best if they are used before the cells are exposed to radical formers (16).
  • the present invention relates to the use of special substances in cosmetic preparations which are also effective at a later point in time against the lipid hydroperoxides.
  • the resulting sulfoxides are also active by inactivating the harmful hydroxyirical (HO * ) (17).
  • Free radicals and peroxides are known to cause sunburn, melanin formation, and probably melanin regression.
  • compositions of city air such as ozone and nitrogen oxides are known as initiators for radical reactions (27). They cause lipoperoxides to form on the skin. Creams containing RSR ideally protect the skin against this air pollution.
  • UV rays kill bacteria. Like the sun erythema of human skin, this effect is based on the formation of free radicals and subsequent peroxides.
  • hypophilic test substances were mixed in a ratio of 1: 4 with a solubilizer (Cremophor RH 60 from BASF or Lamacit 877 from Henkel). 1% of this mixture was dissolved homogeneously in the hot plate count agar. This was poured into petri dishes (9 cm in diameter) and infected with E. coli bacteria using the usual method. The petri dishes were then irradiated for 50 minutes in a Xenotest device (Heraeus, Hanau).
  • a solubilizer Cosmetic RH 60 from BASF or Lamacit 877 from Henkel
  • RSSR in test 3 protects practically all bacteria against the influence of the rays.
  • Alpinists used the W / O Creme Formula 1 during the day as the basis for a sunscreen and in the evening as a night cream. The result was a significant improvement in the skin stressed by wind and weather.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Emergency Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Chez l'homme, le vieillissement de la peau est essentiellement dû à l'action biochimique de radicaux libres, de peroxydes et des produits dérivés. Les thioéthers et les dithioéthers liposolubles contenus dans des préparations cosmétiques inactivent les peroxydes formés dans la peau et retardent de ce fait les effets du vieillissement.
EP93915617A 1992-08-06 1993-07-26 Thioethers and dithioethers liposolubles contenus dans des preparations cosmetiques agissant contre le vieillissement de la peau chez l'homme Withdrawn EP0617609A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH2462/92 1992-08-06
CH246292A CH686285A5 (fr) 1992-08-06 1992-08-06 Preparation cosmetique ou pharmaceutique servant a retarder le vieillissement de la peau humaine.
PCT/CH1993/000187 WO1994003149A2 (fr) 1992-08-06 1993-07-26 Thioethers and dithioethers liposolubles contenus dans des preparations cosmetiques agissant contre le vieillissement de la peau chez l'homme

Publications (1)

Publication Number Publication Date
EP0617609A1 true EP0617609A1 (fr) 1994-10-05

Family

ID=4234368

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93915617A Withdrawn EP0617609A1 (fr) 1992-08-06 1993-07-26 Thioethers and dithioethers liposolubles contenus dans des preparations cosmetiques agissant contre le vieillissement de la peau chez l'homme

Country Status (4)

Country Link
EP (1) EP0617609A1 (fr)
JP (1) JPH07500117A (fr)
CH (1) CH686285A5 (fr)
WO (1) WO1994003149A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2735977B1 (fr) * 1995-06-27 1997-07-25 Sederma Sa Nouvelles compositions cosmetiques et dermopharmaceutiques contenant des thioethers
FR2809007B1 (fr) * 2000-05-18 2003-01-31 Oreal Utilisation de composes contenant une fonction thio-ether, sulfoxyde ou sulfone comme agent cosmetique anti-pollution
US20040067245A1 (en) * 2000-12-20 2004-04-08 Harish Mahalingam Cosmetic compositions and methods for using same to improve the aesthetic appearance of skin
US20090092561A1 (en) * 2007-10-09 2009-04-09 Lupia Joseph A Body-care and household products and compositions comprising specific sulfur-containing compounds
EP2964334B1 (fr) * 2013-03-07 2021-04-07 Avon Products, Inc. Compositions et procédés pour le traitement de cheveux abîmés

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1426136A (fr) * 1964-06-29 1966-01-28 Expanscience Laboratoires D Ex Perfectionnement aux cosmétiques
FR2483915B1 (fr) * 1980-06-06 1987-11-13 Elf Aquitaine Nouveaux emulsionnants porteurs du groupe sulfoxy
DE3672846D1 (de) * 1985-02-04 1990-08-30 Searle & Co Bicycloalkyl-, tricycloalkyl-, azabicycloalkyl- und azatricycloalkyl-amide.
ZA885192B (en) * 1987-08-19 1989-04-26 Hoffmann La Roche Pharmaceutical preparations
FR2631339B1 (fr) * 1988-05-10 1990-11-16 Cird Nouveaux eicosanoides sulfures et leur application en pharmacie et en cosmetique
ZA894879B (en) * 1988-07-14 1991-03-27 Hoffmann La Roche Use of retinoids
ES2106770T3 (es) * 1990-09-05 1997-11-16 Ciba Geigy Ag Compuestos difenilicos como inhibidores del metabolismo del acido araquidonico y su empleo en composiciones farmaceuticas.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9403149A2 *

Also Published As

Publication number Publication date
JPH07500117A (ja) 1995-01-05
CH686285A5 (fr) 1996-02-29
WO1994003149A2 (fr) 1994-02-17
WO1994003149A3 (fr) 1994-06-23

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