CH495750A - Treatment of seborrhea - Google Patents

Treatment of seborrhea

Info

Publication number
CH495750A
CH495750A CH119365A CH119365A CH495750A CH 495750 A CH495750 A CH 495750A CH 119365 A CH119365 A CH 119365A CH 119365 A CH119365 A CH 119365A CH 495750 A CH495750 A CH 495750A
Authority
CH
Switzerland
Prior art keywords
product according
active compound
cysteine
hydrochloride
methyl
Prior art date
Application number
CH119365A
Other languages
French (fr)
Inventor
Kalopissis Gregoire
Original Assignee
Oreal
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 Oreal filed Critical Oreal
Publication of CH495750A publication Critical patent/CH495750A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • 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
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/447Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/006Antidandruff preparations

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Prepns. (II) containing cpds. of general formula I, salts or functional derivs. of I. R - S - CH2 - H - COOH (I) R = (C6H5)3 - C-, (C6H5)2-CH, C6H5-CH2- or HOOC - (CH2)n- where n is = 4 Treatment of seborrhea. Prepns. containing 0.5-5.0% I, tog. with perfumes, dyes, penetrating agent etc., and may cont. several I and other active cpds. Experiments with rats demonstrated that II caused a reduction in size of the sebaceous glands, and fat prodn., together with a closer and more rapid growth of hair.

Description

  

  
 



  Produit capillaire
 On sait qu'une sécrétion excessive des glandes sébacées confère à la chevelure un aspect graisseux jugé généralement peu esthétique.



   On a déjà utilisé un certain nombre de composés de synthèse, notamment des composés à base de soufre, pour lutter contre la séborrhée. Cependant, la plupart des composés utilisés jusqu'à ce jour n'ont pu donner entière satisfaction, soit qu'après avoir manifesté une action antiséborrhéique durant leur application ils provoquent, lorsqu'on cesse de les utiliser, une recrudescence de la séborrhée, soit encore du fait qu'ils présentent une instabilité notable en fonction du temps, de sorte que les préparations cosmétiques à base de tels composés ne possèdent plus au moment de leur application sur le cuir chevelu l'activité antiséborrhéique qu'elles pouvaient présenter lors de leur fabrication.



   La présente invention concerne un nouveau produit capillaire doué de propriétés antiséborrhéiques, qui se conserve parfaitement pendant le temps nécessaire à sa commercialisation et qui ne présente pas les inconvénients de la plupart des produits antiséborrhéiques connus jusqu'à ce jour.



   Le produit selon l'invention consiste en un mélange qui contient au moins un composé actif correspondant à la formule générale suivante:
EMI1.1     
 formule dans laquelle:
 R représente soit le radical   (cas5)3      - C -,    soit le radical   (C6H5)2-CH-,    soit le radical   c6H5 - CH2 -,    soit enfin le radical   HOOC-(CH2)n-,    n étant un nombre entier inférieur ou égal à 4, de préférence égal à 1 ou à 2.



   Les produits capillaires antiséborrhéiques selon l'invention peuvent se présenter sous forme de dispersions du composé actif dans de l'eau, dans une huile, dans une crème ou dans un gel par exemple.



   Il est possible, pour exécuter l'invention, d'utiliser les composés actifs indiqués plus haut sous forme de leurs sels obtenus avec des acides minéraux ou organiques, et plus particulièrement sous forme de leurs chlorhydrates, ce qui permet d'augmenter leur solubilité dans l'eau, lorsque cela est jugé nécessaire.



     I1    est également possible d'estérifier les composés actifs précités de manière à accroître leur liposolubilité.



   Parmi les composés actifs définis ci-dessus, la titulaire a remarqué que des résultats particulièrement bons peuvent être obtenus en utilisant la S-trityl-l cystéine de formule:
EMI1.2     
 ou le S-trityl-l cystéine, chlorhydrate de formule:
EMI1.3     
 ou la   S-(2carboxyéthyl)-l    cystéine de formule:
EMI1.4     
 ou le S-(2-carboxyéthyl)-l cystéine, chlorhydrate de formule:
EMI1.5     
 ou la S-(carboxyméthyl)-l cystéine de formule:
EMI1.6     
  ou le S-(carboxyméthyl)-l cystéine, chlorhydrate de formule:
EMI2.1     
 ou le S-(méthoxy carbonyl méthyl)-l cystéinate de méthyle de formule:
EMI2.2     
 ou encore le chlorhydrate de S-(méthoxy carbonyl méthyl)-l cystéinate de méthyle de formule:

  :
EMI2.3     

 Les produits antiséborrhéiques selon l'invention ont de préférence une concentration en produits actifs tels que définis ci-dessus, qui est comprise entre 0,5 et   5 oxo    et plus particulièrement de l'ordre de 1,5 à   2 O/o.   



   Dans le produit selon l'invention, les composés actifs précédemment définis par leur formule générale, peuvent être soit seuls, soit en mélanges entre eux, soit encore en mélanges avec d'autres composés déjà connus pour leur activité antiséborrhéique.



   Par ailleurs, il va de soi que   l'on    peut incorporer aux produits capillaires selon l'invention, des ingrédients tels que des agents de pénétration, des colorants, ou des parfums, qui sont généralement utilisés en cosmétique.



   L'invention est illustrée par les exemples suivants.



   Exemple I
 On obtient un produit antiséborrhéique selon l'invention en créant une suspension très fine de   1,50/o    de
S-trityl-l cystéine dans de l'huile d'olive à laquelle on ajoute 0,1   o/o    de parfum. Cette suspension peut facilement être obtenue à l'aide d'un homogénéiseur du type Serval ou Virtis.



   Exemple 2
 On prépare un produit capillaire selon l'invention en mélangeant:
 S-trityl-l cystéine, chlorhydrate . 1,5 g
 Alcool éthylique à 500 q.s.p. 100   cc   
 Parfum   0,lg   
 Colorant   0,lg   
 Exemple 3
 On prépare un produit capillaire selon l'invention en mélangeant:
 S-(2-carboxyéthyl)-l cystéine, chlorhydrate 2g
 Alcool éthylique à 700 q.s.p.   .    100 cc
 Exemple 4
 On obtient un produit antiséborrhéique selon l'invention en dissolvant 2g de chlorhydrate de S-diphényl méthyl-l cystéinate de méthyle dans 100 cc d'alcool éthylique à 600 et en y ajoutant 0,1   o/o    de colorant.



   Exemple 5
 On prépare une solution de stéarate de magnésium à la concentration de   5 oxo    dans le myristate d'isopropyle à la température de 120-1300. Par la suite et à cette même température, on ajoute 2    /0    de S-trityl-l cystéine et on refroidit brusquement à la température ambiante. On obtient ainsi un gel opaque qui peut être appliqué comme produit antiséborrhéique selon l'invention.



   Exemple 6
 On obtient une lotion antiséborrhéique selon l'invention en dissolvant 0,75 g de chlorhydrate de S-(carboxyméthyl)-l cystéine dans 100   cc    d'alcool éthylique à 500 contenant également 0,1   o/o    de colorant et   0,1 0/o    de parfum.

 

   Exemple 7
 On prépare une solution antiséborrhéique selon l'invention, qui a la composition suivante:
 Chlorhydrate de S-(méthoxy carbonyl
 méthyl)-l cystéinate de méthyle 0,75 g
 Alcool éthylique à 500 q.s.p.   .    100 cc
 Parfum 0,1    /o   
 Les produits capillaires décrits dans ces exemples ont été appliqués sur le cuir chevelu d'un nombre important de personnes présentant chacune un état séborrhéique plus ou moins marqué et   l'on    a relevé dans la quasitotalité des cas une régression notable et persistante de la séborrhée ainsi que pour de nombreuses personnes un arrêt de la chute des cheveux qui, comme chacun sait, est généralement liée à la présence d'un état séborrhéique. 



  
 



  Hair product
 It is known that excessive secretion from the sebaceous glands gives the hair a greasy appearance which is generally considered unattractive.



   A certain number of synthetic compounds have already been used, in particular sulfur-based compounds, to combat seborrhea. However, most of the compounds used to date have not been entirely satisfactory, either after having manifested an antiseborrheic action during their application they cause, when they cease to use them, an upsurge of seborrhea, or again due to the fact that they exhibit a notable instability as a function of time, so that the cosmetic preparations based on such compounds no longer possess, at the time of their application to the scalp, the antiseborrheic activity which they could exhibit during their manufacturing.



   The present invention relates to a new hair product endowed with antiseborrheic properties, which keeps perfectly for the time necessary for its marketing and which does not have the drawbacks of most of the antiseborrheic products known to date.



   The product according to the invention consists of a mixture which contains at least one active compound corresponding to the following general formula:
EMI1.1
 formula in which:
 R represents either the radical (cas5) 3 - C -, or the radical (C6H5) 2-CH-, or the radical c6H5 - CH2 -, or finally the radical HOOC- (CH2) n-, n being a lower whole number or equal to 4, preferably equal to 1 or to 2.



   The antiseborrheic hair products according to the invention may be in the form of dispersions of the active compound in water, in an oil, in a cream or in a gel, for example.



   It is possible, to carry out the invention, to use the active compounds indicated above in the form of their salts obtained with mineral or organic acids, and more particularly in the form of their hydrochlorides, which makes it possible to increase their solubility in water, when deemed necessary.



     It is also possible to esterify the aforementioned active compounds so as to increase their liposolubility.



   Among the active compounds defined above, the licensee has noticed that particularly good results can be obtained by using S-trityl-1 cysteine of formula:
EMI1.2
 or S-trityl-1 cysteine, hydrochloride of the formula:
EMI1.3
 or S- (2carboxyethyl) -l cysteine of formula:
EMI1.4
 or S- (2-carboxyethyl) -l cysteine, hydrochloride of formula:
EMI1.5
 or S- (carboxymethyl) -l cysteine of the formula:
EMI1.6
  or S- (carboxymethyl) -l cysteine, hydrochloride of formula:
EMI2.1
 or methyl S- (methoxy carbonyl methyl) -l cysteinate of formula:
EMI2.2
 or alternatively the hydrochloride of S- (methoxy carbonyl methyl) -1 methyl cysteinate of formula:

  :
EMI2.3

 The antiseborrheic products according to the invention preferably have a concentration of active products as defined above, which is between 0.5 and 5 oxo and more particularly of the order of 1.5 to 2 O / o.



   In the product according to the invention, the active compounds defined above by their general formula can be either alone or in mixtures with one another, or also in mixtures with other compounds already known for their antiseborrheic activity.



   Moreover, it goes without saying that it is possible to incorporate into the hair products according to the invention, ingredients such as penetrating agents, dyes or perfumes, which are generally used in cosmetics.



   The invention is illustrated by the following examples.



   Example I
 An antiseborrheic product according to the invention is obtained by creating a very fine suspension of 1.50 / o of
S-trityl-1 cysteine in olive oil to which is added 0.1% of perfume. This suspension can easily be obtained using a homogenizer of the Serval or Virtis type.



   Example 2
 A hair product according to the invention is prepared by mixing:
 S-trityl-1 cysteine, hydrochloride. 1.5 g
 Ethyl alcohol at 500 q.s.p. 100 cc
 Perfume 0, lg
 Colorant 0, lg
 Example 3
 A hair product according to the invention is prepared by mixing:
 S- (2-carboxyethyl) -l cysteine, hydrochloride 2g
 Ethyl alcohol at 700 q.s.p. . 100 cc
 Example 4
 An antiseborrheic product according to the invention is obtained by dissolving 2 g of methyl S-diphenyl methyl-1 cysteinate hydrochloride in 100 cc of 600 ml of ethyl alcohol and by adding 0.1% of dye thereto.



   Example 5
 A solution of magnesium stearate at the concentration of 5 oxo in isopropyl myristate at the temperature of 120-1300 is prepared. Subsequently and at this same temperature, 2/0 of S-trityl-1 cysteine is added and the mixture is suddenly cooled to room temperature. An opaque gel is thus obtained which can be applied as an antiseborrheic product according to the invention.



   Example 6
 An antiseborrheic lotion according to the invention is obtained by dissolving 0.75 g of S- (carboxymethyl) -l cysteine hydrochloride in 100 cc of ethyl alcohol at 500, also containing 0.1 o / o of dye and 0.1 0 / o perfume.

 

   Example 7
 An antiseborrheic solution according to the invention is prepared, which has the following composition:
 S- (methoxy carbonyl hydrochloride
 methyl) -1 methyl cysteinate 0.75 g
 Ethyl alcohol at 500 q.s.p. . 100 cc
 Perfume 0.1 / o
 The hair products described in these examples were applied to the scalp of a large number of people each presenting a more or less marked seborrheic state and in almost all cases a notable and persistent regression of seborrhea was noted as well. that for many people to stop hair loss which, as everyone knows, is usually linked to the presence of a seborrheic state.

 

Claims (1)

REVENDICATION CLAIM Produit capillaire, caractérisé par le fait qu'il consiste en un mélange qui contient au moins un composé actif correspondant à la formule suivante: R - S - CH2 - CH- COOH NH2 formule dans laquelle: R représente soit le radical (C6H5)3 - C -, soit le radical (C6H5)2 - CII-, soit le radical C6H5 - CH2 -, soit enfin le radical HOOC-(CH2)n-, n étant un nombre entier inférieur ou égal à 4, ou qui contient un sel ou un ester d'un tel composé. Hair product, characterized in that it consists of a mixture which contains at least one active compound corresponding to the following formula: R - S - CH2 - CH- COOH NH2 formula in which: R represents either the radical (C6H5) 3 - C -, or the radical (C6H5) 2 - CII-, or the radical C6H5 - CH2 -, or finally the radical HOOC- (CH2) n-, n being a lower whole number or equal to 4, or which contains a salt or an ester of such a compound. SOUS-REVENDICATIONS 1. Produit selon la revendication, caractérisé par le fait que le composé actif est présent sous la forme de son sel avec un acide minéral ou un acide organique. SUB-CLAIMS 1. Product according to claim, characterized in that the active compound is present in the form of its salt with a mineral acid or an organic acid. 2. Produit selon la revendication, caractérisé par le fait que le composé actif est présent sous forme de chlorhydrate. 2. Product according to claim, characterized in that the active compound is present in the form of hydrochloride. 3. Produit selon la revendication, caractérisé par le fait que le composé actif est présent sous forme d'ester. 3. Product according to claim, characterized in that the active compound is present in ester form. 4. Produit selon la revendication, caractérisé par le fait qu'il se présente sous forme d'une suspension ou dissolution du composé actif dans une huile cosmétique ou dans une crème, ou dans un gel, ou encore dans de l'eau. 4. Product according to claim, characterized in that it is in the form of a suspension or dissolution of the active compound in a cosmetic oil or in a cream, or in a gel, or else in water. 5. Produit selon la revendication, caractérisé par le fait que le composé actif est le S-trityl-l cystéine. 5. Product according to claim, characterized in that the active compound is S-trityl-l cysteine. 6. Produit selon la sous-revendication 2, caractérisé par le fait que le composé actif est le S-trityl-l cystéine chlorhydrate. 6. Product according to sub-claim 2, characterized in that the active compound is S-trityl-1 cysteine hydrochloride. 7. Produit selon la revendication, caractérisé par le fait que le composé actif est la S-(2-carboxyéthyl)-l cys téine. 7. Product according to claim, characterized in that the active compound is S- (2-carboxyethyl) -l cysteine. 8. Produit selon la sous-revendication 2, caractérisé par le fait que le composé actif est le S-diphényl-méthyl-l cystéinate de méthyle, chlorhydrate. 8. Product according to sub-claim 2, characterized in that the active compound is methyl S-diphenyl-methyl-l cysteinate, hydrochloride. 9. Produit selon la sous-revendication 2, caractérisé par le fait que le composé actif est le S-(2-carboxyéthyl)-l cystéine, chlorhydrate. 9. Product according to sub-claim 2, characterized in that the active compound is S- (2-carboxyethyl) -l cysteine, hydrochloride. 10. Produit selon la revendication, caractérisé par le fait que le composé actif est la S-(carboxyméthyl)-l cystéine. 10. Product according to claim, characterized in that the active compound is S- (carboxymethyl) -l cysteine. 11. Produit selon la sous-revendication 2, caractérisé par le fait que le composé actif est le S-(carboxyméthyl)-l cystéine, chlorhydrate. 11. Product according to sub-claim 2, characterized in that the active compound is S- (carboxymethyl) -l cysteine, hydrochloride. 12. Produit selon la revendication, caractérisé par le fait que le composé actif est le S-(méthoxy carbonyl méthyl)-l cystéinate de méthyle. 12. Product according to claim, characterized in that the active compound is methyl S- (methoxy carbonyl methyl) -l cysteinate. 13. Produit selon la sous-revendication 2, caractérisé par le fait que le composé actif est le chlorhydrate de S-(méthoxy carbonyl mcthyl)-l cystéinate de méthyle. 13. Product according to sub-claim 2, characterized in that the active compound is hydrochloride. Methyl S- (methoxy carbonyl mcthyl) -l cysteinate. 14. Produit selon la revendication, caractérisé par le fait qu'il contient en outre des adjuvants cosmétiques, tels que des agents de pénétration, des alcools, des parfums ou des colorants. 14. Product according to claim, characterized in that it also contains cosmetic adjuvants, such as penetrating agents, alcohols, perfumes or dyes. 15. Produit selon la revendication, caractérisé par le fait qu'il contient une concentration en composés actifs, qui est comprise entre 0,5 et 5 o/o et de préférence entre 1,5 et 20/o. 15. Product according to claim, characterized in that it contains a concentration of active compounds which is between 0.5 and 5 o / o and preferably between 1.5 and 20 / o. 16. Produit selon la revendication, caractérisé par le fait qu'il contient d'autres composés antiséborrhéiques. 16. Product according to claim, characterized in that it contains other antiseborrheic compounds.
CH119365A 1964-01-29 1965-01-28 Treatment of seborrhea CH495750A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR961897A FR1472021A (en) 1964-01-29 1964-01-29 New hair product

Publications (1)

Publication Number Publication Date
CH495750A true CH495750A (en) 1970-09-15

Family

ID=8821950

Family Applications (1)

Application Number Title Priority Date Filing Date
CH119365A CH495750A (en) 1964-01-29 1965-01-28 Treatment of seborrhea

Country Status (8)

Country Link
AT (1) AT267754B (en)
BE (1) BE658449A (en)
CH (1) CH495750A (en)
DE (1) DE1492071B2 (en)
FR (1) FR1472021A (en)
GB (1) GB1051870A (en)
IT (1) IT943009B (en)
NL (1) NL142587B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015136A1 (en) * 1997-09-22 1999-04-01 The Gillette Company Reduction of hair growth

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU55371A1 (en) * 1968-01-29 1969-08-21 Oreal
LU55935A1 (en) * 1968-04-19 1969-11-14 Oreal
US3624143A (en) * 1968-05-10 1971-11-30 Merck & Co Inc Compounds of the class {62 -aralkylthio-substituted-{60 -amino acids
BE733993A (en) * 1968-06-14 1969-12-03
LU58634A1 (en) * 1969-05-12 1971-03-09 Oreal
BE755674A (en) * 1969-09-04 1971-03-03 Oreal NEW COMPOUNDS DERIVED FROM PYRIDINE AND COSMETIC COMPOSITIONS CONTAINING THEM

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999015136A1 (en) * 1997-09-22 1999-04-01 The Gillette Company Reduction of hair growth
US5939458A (en) * 1997-09-22 1999-08-17 Henry; James P. Reduction of hair growth

Also Published As

Publication number Publication date
AT267754B (en) 1969-01-10
FR1472021A (en) 1967-03-10
NL6500849A (en) 1965-07-30
IT943009B (en) 1973-04-02
DE1492071B2 (en) 1973-11-08
GB1051870A (en)
DE1492071A1 (en) 1969-11-13
NL142587B (en) 1974-07-15
BE658449A (en) 1965-07-19

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