WO1984003041A1 - Tetrahydro-1,3-thiazin-2,4-dione, son utilisation et agents de traitement cutane contenant ce compose - Google Patents

Tetrahydro-1,3-thiazin-2,4-dione, son utilisation et agents de traitement cutane contenant ce compose Download PDF

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Publication number
WO1984003041A1
WO1984003041A1 PCT/EP1984/000015 EP8400015W WO8403041A1 WO 1984003041 A1 WO1984003041 A1 WO 1984003041A1 EP 8400015 W EP8400015 W EP 8400015W WO 8403041 A1 WO8403041 A1 WO 8403041A1
Authority
WO
WIPO (PCT)
Prior art keywords
tetrahydro
aryl
dione
skin
thiazine
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.)
Ceased
Application number
PCT/EP1984/000015
Other languages
German (de)
English (en)
French (fr)
Inventor
Wolfgang Hanefeld
Rudi Roethlisberger
Friedrich Noser
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.)
Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
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 Wella GmbH filed Critical Wella GmbH
Priority to BR8405349A priority Critical patent/BR8405349A/pt
Publication of WO1984003041A1 publication Critical patent/WO1984003041A1/de
Priority to DK484484A priority patent/DK484484D0/da
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D279/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/041,3-Thiazines; Hydrogenated 1,3-thiazines
    • C07D279/061,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations

Definitions

  • the skin forms the boundary layer between the organism and its environment.
  • the most important task of the skin is therefore to protect the inside of the body against exogenous influences.
  • Our skin is in daily contact with substances that are foreign to the body, some of which are hostile to the body and especially hostile to the skin.
  • Particularly frequent contact of the unprotected skin with these substances which is often work-related (hairdressers, dentists, housewives), sooner or later leads to more or less severe skin damage.
  • two types of intervention have hitherto been used: protective skin protection and preservative skin care.
  • R 1 is one of the radicals H, alkyl, hydroxyalkyl, carboxyalkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, cycloalkyl, alkene nyl, alkynyl, arylalkyl, arylalkyl, aryl, alkyl, halogen, nitro, alkoxy, aryloxy, cyano-substituted aryl, pyridyl, thiazolyl, benzothiazolyl, thienyl, furyl, pyrazolyl, imidazolyl, pyridazinyl, thiadiazolyl substituted in the aryl part Represents pyrimidinyl and thiazinyl,
  • R 2 and R 3 are independently H, halogen, alkyl, cycloalkyl, carboxyl, arylalkyl, aryl, substituted aryl,
  • compositions containing physiologically compatible carriers and additives characterized by a content of at least one compound of the general formula I.
  • the total concentration of the compounds of the general formula I in the skin treatment compositions is about 0.1 to 5% by weight, preferably 0.5 to 3% by weight.
  • the compounds of the formula I can be present in the compositions on their own or in a mixture with one another.
  • composition of the skin treatment compositions is a mixture of the compounds of the formula I with the physiologically compatible constituents customary for such preparations, such as carriers and additives.
  • additives are, for example, cosmetic resins, dyes, perfume oils, propellants and preservatives crossing agents, such as B. p-hydroxybenzoic acid, sorbic acid, salicylic acid, formaldehyde and hexachlorophene.
  • the skin treatment agents are prepared in the manner customary for such preparations by mixing the compounds of the formula I which serve as active ingredients with the constituents which are used as carriers for the skin treatment agents and are then made up with the further constituents of the agents to give the finished end product.
  • the compounds of the general formula I contained as part of the skin treatment compositions described here cause the outermost skin layer, namely the dead horny layer, which is primarily responsible for natural skin protection. This thickening of the horny layer makes the skin more resistant to contact with all kinds of environmental noxious substances and thus provides optimal skin protection.
  • the skin protection agents according to the invention which contain compounds according to formula I do not have the disadvantages which are observed with conventional skin protection agents.
  • the skin treatment agents according to the invention can be applied to the skin surface irrespective of the contact with the foreign skin. You will never interfere with a work process because they are no longer on the surface of the skin at this point.
  • the skin protection can also not be removed (e.g. by washing), since it is achieved by the new condition of the skin (thickening).
  • the compounds of the general formula I enhance natural sun protection. This additional Sun protection is also achieved by thickening the horny layer, which is achieved after treatment with the skin treatment agent according to the invention.
  • a thickening of the horny layer causes an increased absorption of the light or sun rays.
  • This novel prophylactic sun protection has clear advantages over the effect that can be achieved with conventional sun protection products.
  • the usual sunscreens are applied to the surface of the skin, and their absorption capacity, ie their ability to protect against light, depends on the applied layer thickness. These preparations can interfere by e.g. B. too greasy and dirty clothes. You will e.g. B. rinsed again by bathing or showering and must therefore be reapplied constantly.
  • the agents according to the invention can be applied regardless of the exposure to the sun by, for. B. already 3 to 4 weeks before a summer vacation, repeated epicutaneous application, so that they then, thanks to the thickened horny layer, already offer long-lasting, non-washable protection against sunburn and other chronic light damage at vacation time.
  • the agents according to the invention are able, through their content of the tetrahydro-1,3-thiazine-2,4-diones of the formula I, to exposed and sensitive parts of the body, such as, B. on the face and hands, which are particularly exposed to bad weather conditions, to provide protection against the cold.
  • the agents are therefore particularly suitable for use by skiers and high mountain athletes, for example as preventive protection against extreme cold. Thanks to their horny layer thickening effect, the skin treatment agents according to the invention are able to offer effective protection against the cold, which in this case too does not skin-damaging and uncomfortable preparations remaining on the skin surface, because here too it is only a matter of enhancing the natural protection against the cold.
  • epidermis With age, the outer layer of the skin, the so-called epidermis, becomes thinner and thinner.
  • the thinning of the epidermis is responsible for the fact that the skin surface gets its typical parchment-like appearance with age and that sebaceous glands, retention cysts,
  • the agents according to the invention represent an effective means for the prophylactic treatment of skin aging.
  • the skin treatment agents according to the invention are expediently applied in such a way that they are applied to the corresponding skin areas, starting approximately 3 to 4 weeks before the thickening of the cornea or epidermis, and preferably once or twice a day .
  • R II , R III , R IV and R V independently of one another are H, alkyl, cycloalkyl, arylalkyl, aryl and substituted aryl,
  • the present application therefore also relates to new tetrahydro-1,3-thiazine2,4-diones of the general formula III which are particularly suitable for use in the skin treatment compositions according to the invention
  • Examples of compounds of the formula III according to the invention are: a) 3- (4-chlorobenzyl) tetrahydro-1,3-thiazine-2,4-dione b) 3- (4-chlorophenyl) -6-methyl-tetrahydro-1,3-thiazine-2,4-dione c) 3-benzyl-6-methyl-tetrahydro-1,3-thiazine-2,4-dione d) 6-methyl-3- (2-phenylethyl) tetrahydro-1,3-thiazine-2,4-dione e) 5, 5-diphenyl-tetrahydro-1,3-thiazine-2,4-dione f) 3-methyl-5,5-diphenyl-tetrahydro-1,3-thiazine-2,4-dione g) 6-pheny1-3- (4-methoxyphenyl) tetrahydro-1,3-thiazine-2,4dione
  • 2,4-dione 1 3,5,5-triphenyl-tetrahydro-1,3-thiazine-2,4-dione m) 3- (4-chlorobenzyl) -5,6-diphenyl-tetrahydro-1,3- thiazine2,4-dione n) 3-benzyl-5,5-dipheny1-tetrahydro-1,3-thiazine-2,4-dione o) 3-benzyl-5,5-di- (4-tolyl) tetrahydro- 1,3-thiazine-2,4-dione

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Cosmetics (AREA)
  • Steroid Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
PCT/EP1984/000015 1983-02-12 1984-01-19 Tetrahydro-1,3-thiazin-2,4-dione, son utilisation et agents de traitement cutane contenant ce compose Ceased WO1984003041A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
BR8405349A BR8405349A (pt) 1983-02-12 1984-01-19 Tetraidro-1,3-tiazino-2,4-dionas,seu emprego,bem como composicoes de tratamento de pele contendo esses compostos
DK484484A DK484484D0 (da) 1983-02-12 1984-10-10 Tetrahydro-1,3-thiazin-2,4-dioner, deres anvendelse samt hudbehandlingsmidler indeholdende disse forbindelser

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19833304871 DE3304871A1 (de) 1983-02-12 1983-02-12 Tetrahydro-1,3-thiazin-2,4-dione, ihre verwendung sowie diese verbindungen enthaltende hautbehandlungsmittel

Publications (1)

Publication Number Publication Date
WO1984003041A1 true WO1984003041A1 (fr) 1984-08-16

Family

ID=6190689

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1984/000015 Ceased WO1984003041A1 (fr) 1983-02-12 1984-01-19 Tetrahydro-1,3-thiazin-2,4-dione, son utilisation et agents de traitement cutane contenant ce compose

Country Status (14)

Country Link
US (2) US4746738A (https=)
EP (1) EP0116318B1 (https=)
JP (1) JPS60500414A (https=)
AT (1) ATE32659T1 (https=)
AU (1) AU565564B2 (https=)
BR (1) BR8405349A (https=)
DE (2) DE3304871A1 (https=)
DK (1) DK484484D0 (https=)
ES (1) ES8507125A1 (https=)
GR (1) GR81761B (https=)
IE (1) IE56765B1 (https=)
NZ (1) NZ207103A (https=)
WO (1) WO1984003041A1 (https=)
ZA (1) ZA841010B (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9114317D0 (en) * 1991-07-02 1991-08-21 Unilever Plc Cosmetic composition
RU2120272C1 (ru) * 1996-02-16 1998-10-20 Товарищество с ограниченной ответственностью "Биокосметическая фабрика" Зимний косметический крем для защиты кожи
CN114767701B (zh) * 2022-05-09 2023-10-20 黑龙江中医药大学 一种用于治疗痤疮的药物及其用途

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2938418A1 (de) * 1979-09-22 1981-04-09 Wella Ag Tetrahydro-1,3-thiazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende kosmetische mittel
US4352929A (en) * 1979-08-08 1982-10-05 The Upjohn Company 1,3-Thiazin-4-one

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2585064A (en) * 1952-02-12 Meta-thiazines
US2948657A (en) * 1957-10-09 1960-08-09 Siccama Nicholas Bernard Skin coloring compositions
GB1007587A (en) * 1963-06-12 1965-10-13 Lepetit Spa Thiazine dione derivatives and the preparation thereof
IT1020510B (it) * 1969-10-22 1977-12-30 Oreal Composizione cosmetica abbronzante
ZA814318B (en) * 1980-07-02 1982-07-28 Hoffmann La Roche Organo-aluminium compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4352929A (en) * 1979-08-08 1982-10-05 The Upjohn Company 1,3-Thiazin-4-one
DE2938418A1 (de) * 1979-09-22 1981-04-09 Wella Ag Tetrahydro-1,3-thiazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende kosmetische mittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Vol. 99, No. 11, 12 September 1983, Columbus, Ohio (US) W. Hanefeld: "Studies on 1.3-thiazines 22. Oxidation of thiourethanes 2. Oxidative desulfurization of 2-thioxo-tetrahydro-1.3-thiazin-4-ones to tetrahydro-1.3thiazine-2.4-diones with chromic acid anhydride", page 564, column 2, abstract 88131w; & Pharm. Ztg. 1983, 128 (23) 1242-5 *

Also Published As

Publication number Publication date
JPS60500414A (ja) 1985-03-28
US4883652A (en) 1989-11-28
EP0116318A1 (de) 1984-08-22
IE56765B1 (en) 1991-12-04
DE3469487D1 (en) 1988-04-07
ES529696A0 (es) 1985-08-16
DE3304871A1 (de) 1984-08-16
NZ207103A (en) 1987-04-30
AU2432984A (en) 1984-08-30
DK484484A (da) 1984-10-10
ZA841010B (en) 1985-02-27
ES8507125A1 (es) 1985-08-16
GR81761B (https=) 1984-12-12
AU565564B2 (en) 1987-09-17
DK484484D0 (da) 1984-10-10
BR8405349A (pt) 1985-02-12
ATE32659T1 (de) 1988-03-15
US4746738A (en) 1988-05-24
IE840308L (en) 1984-08-12
EP0116318B1 (de) 1988-03-02

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