CH495750A - Treatment of seborrhea - Google Patents
Treatment of seborrheaInfo
- 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
Links
- 206010039792 Seborrhoea Diseases 0.000 title abstract description 5
- 208000008742 seborrheic dermatitis Diseases 0.000 title abstract description 5
- 239000002304 perfume Substances 0.000 claims abstract description 7
- 239000000975 dye Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 230000000149 penetrating effect Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- FBPINGSGHKXIQA-BYPYZUCNSA-N (2r)-2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CSCCC(O)=O FBPINGSGHKXIQA-BYPYZUCNSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- FBPINGSGHKXIQA-UHFFFAOYSA-N S-carboxyethyl-L-cysteine Natural products OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 claims description 5
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-L cysteinate(2-) Chemical compound [S-]CC(N)C([O-])=O XUJNEKJLAYXESH-UHFFFAOYSA-L 0.000 claims description 4
- -1 methoxy carbonyl methyl Chemical group 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 2
- 229960001305 cysteine hydrochloride Drugs 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 claims 1
- DLMYFMLKORXJPO-FQEVSTJZSA-N (2R)-2-amino-3-[(triphenylmethyl)thio]propanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](N)C(O)=O)C1=CC=CC=C1 DLMYFMLKORXJPO-FQEVSTJZSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 210000001732 sebaceous gland Anatomy 0.000 abstract description 2
- 241000700159 Rattus Species 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 5
- 229960002433 cysteine Drugs 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960001913 mecysteine Drugs 0.000 description 2
- WHOHXJZQBJXAKL-UHFFFAOYSA-N methyl 2-amino-3-sulfanylpropanoate;hydrochloride Chemical compound Cl.COC(=O)C(N)CS WHOHXJZQBJXAKL-UHFFFAOYSA-N 0.000 description 2
- MCYHPZGUONZRGO-VKHMYHEASA-N methyl L-cysteinate Chemical compound COC(=O)[C@@H](N)CS MCYHPZGUONZRGO-VKHMYHEASA-N 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 101100382541 Escherichia coli (strain K12) casD gene Proteins 0.000 description 1
- 241000880493 Leptailurus serval Species 0.000 description 1
- 101100387131 Myxococcus xanthus (strain DK1622) devS gene Proteins 0.000 description 1
- ILVGMCVCQBJPSH-WDSKDSINSA-N Ser-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CO ILVGMCVCQBJPSH-WDSKDSINSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 101150049463 cas5 gene Proteins 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic 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
- C07D213/02—Heterocyclic 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
- C07D213/04—Heterocyclic 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
- C07D213/60—Heterocyclic 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
-
- 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
- A61Q5/006—Antidandruff preparations
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (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)
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)
| 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)
| 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 |
-
0
- GB GB1051870D patent/GB1051870A/en active Active
-
1964
- 1964-01-29 FR FR961897A patent/FR1472021A/en not_active Expired
-
1965
- 1965-01-18 BE BE658449D patent/BE658449A/xx unknown
- 1965-01-18 IT IT263265A patent/IT943009B/en active
- 1965-01-22 NL NL6500849A patent/NL142587B/en not_active IP Right Cessation
- 1965-01-25 AT AT59365A patent/AT267754B/en active
- 1965-01-26 DE DE1965O0010624 patent/DE1492071B2/en active Granted
- 1965-01-28 CH CH119365A patent/CH495750A/en not_active IP Right Cessation
Cited By (2)
| 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 |
|---|---|
| DE1492071A1 (en) | 1969-11-13 |
| NL6500849A (en) | 1965-07-30 |
| IT943009B (en) | 1973-04-02 |
| DE1492071B2 (en) | 1973-11-08 |
| AT267754B (en) | 1969-01-10 |
| NL142587B (en) | 1974-07-15 |
| FR1472021A (en) | 1967-03-10 |
| BE658449A (en) | 1965-07-19 |
| GB1051870A (en) |
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