WO2002058664A1 - Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant - Google Patents
Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant Download PDFInfo
- Publication number
- WO2002058664A1 WO2002058664A1 PCT/FR2002/000288 FR0200288W WO02058664A1 WO 2002058664 A1 WO2002058664 A1 WO 2002058664A1 FR 0200288 W FR0200288 W FR 0200288W WO 02058664 A1 WO02058664 A1 WO 02058664A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- isothiocyanate
- general formula
- carboxylic acid
- advantageously
- Prior art date
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/31—Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
-
- 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
-
- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Definitions
- the present invention relates to depigmentants and in particular the use of isothiocyanates or thiocyanates as depigmentants.
- melanocytes Skin pigmentation in humans comes from a complex series of cellular processes that take place in a single population of cells called melanocytes.
- Melanocytes are located in the lower part of the epidermis, and their function is to synthesize a brown pigment, melanin, which protects the body from the damaging effects of ultraviolet radiation.
- Melanin is deposited in the melanosomes, vesicles present inside the melanocytes. Melanosomes are expelled from melanocytes and transported to the surface of the skin by keratinocytes, which assimilate the melanin contained in the melanosomes.
- the dark shade of the skin is proportional to the amount of melanin synthesized by the melanocytes and transferred to the keratinocytes. In some cases, it is better to reduce or inhibit melanogenesis, for example, to lighten the skin, to remove age spots or to reduce the hyperactivity of melanocytes.
- kojic acid has been used effectively as a substance that inhibits the formation of melanin in human skin. Consequently, various cosmetic preparations intended for depigmenting the skin and containing kojic acid (Japanese patent publication No. 56-18569) or an ester of kojic acid with an aromatic carboxylic acid such as cinnamic acid or l benzoic acid (Japanese Patent Publication No.
- kojic acid diesters Japanese patent publications Nos. 61-60801 and 60-17961 have been described. These kojic acids and esters of kojic acid are therefore known to be substances capable of inhibiting melanogenesis. However, kojic acid has variable efficacy depending on the individual and on average insufficient.
- Isothiocyanates can be extracted from various cruciferous plants, including broccoli, Lepidium dabra and radishes, such as sulforaphane and sulforaphene.
- Sulforaphane and some of its synthetic analogues are known to protect against the mutagenic effect of chemicals such as those found in tobacco smoke, for example. This effect goes through the induction of enzyme systems involved in the evacuation of mutagenic molecules out of the body. It would also seem that these molecules also act directly on the mechanism of mutagenesis (WO 94/19948, Carcinogenesis, 8, 12, 1987, pages 1971-1973; Cancer Research, 51, 13, 1991, pages 2063-2068).
- the present invention therefore relates to the use of an isothiocyanate of general formula I below:
- R 2 represents an alkyl, alkenyl, alkynyl, aryl, acety
- alkyl group in the sense of the present invention any alkyl group of 1 to 10 carbon atoms, linear or branched substituted or not, in particular the group CH.
- alkenyl group is meant in the sense of the present invention any alkenyl group of 2 to 10 carbon atoms, linear or branched, substituted or not, in particular the vinyl group.
- alkynyl group is meant within the meaning of the present invention any alkynyl group of 2 to 10 carbon atoms, linear or branched, substituted or not, in particular the ethynyl group.
- alkylcarbonyl group is meant in the sense of the present invention any alkyl group as defined above linked via a carbonyl group.
- An example of an alkylcarbonyl group is the acetyl group.
- alkoxy group is meant within the meaning of the present invention any alkoxy group of 1 to 10 carbon atoms, linear or branched substituted or not, in particular the OCH group.
- cycloalkyl group in the sense of the present invention any cycle composed of alkyl group of 1 to 10 carbon atoms, substituted or not, in particular, the cyclohexyl group.
- aryl group is meant within the meaning of the present invention one or more aromatic rings having 5 to 8 carbon atoms, which can be joined or fused, substituted or not.
- the aryl groups can be phenyl or naphthyl groups and the substituents of the halogen atoms, alkoxy groups as defined above, alkyl groups as defined above or the nitro group.
- aryloxy group in the sense of the present invention any aryl group as defined above, linked via an alkoxy group as defined above.
- aralkyl group is meant in the sense of the present invention any aryl group as defined above, linked via an alkyl group as defined above.
- an aralkyl group is a benzyl group.
- arylcarbonyl group in the sense of the present invention any aryl group as defined above, linked via a carbonyl group.
- An example of an arylcarbonyl group is the benzoyl group.
- carboxylic acid in the sense of the present invention any alkyl group as defined above to which is linked a carboxy group (-COOH).
- sulfonyl group is meant in the sense of the present invention any alkyl, cycloalkyl or aryl group as defined above, linked via an SO 2 group.
- sulfinyl group is meant within the meaning of the present invention any alkyl, cycloalkyl or aryl group as defined above, linked via an SO group.
- alkylthio group in the sense of the present invention any alkyl group as defined above linked via a sulfur atom.
- the present invention also relates to the use of an isothiocyanate of general formula I, of a thiocyanate of general formula II or of their mixtures for the manufacture of a medicament or of a cosmetic composition intended to lighten or depigment the epidermis. or to remove age spots.
- the thiocyanate is a thiocyanate of general formula II in which R 2 represents the aralkyl group, even more advantageously, it is benzylthiocyanate.
- the thiocyanate of general formula II is in the form of a salt, even more advantageously of sodium or potassium.
- Thiocyanates can be obtained in parallel with isothiocyanates during the breakdown of cruciferous glucosinolates by myrosinase
- the isothiocyanate of general formula I is a synthetic isothiocyanate, in particular wherein R i represents a group, aryl, acetyl, alkylcarbonyl, cycloalkyl, arylalkyl or arylcarbonyl.
- R i represents a group, aryl, acetyl, alkylcarbonyl, cycloalkyl, arylalkyl or arylcarbonyl.
- the isothiocyanate is chosen from the group consisting of cyclohexylisothiocyanate, benzylisothiocyanate, acetylisothiocyanate and benzoylisothiocyanate.
- Synthetic isothiocyanates are commercially available.
- cyclohexylisothiocyanate, benzylisothiocyanate and benzoylisothiocyanate are available from the company Aldrich (ref. Cl 0-540-6; 25,249-2 and 26,165-
- the isothiocyanate of general formula I is obtained by extraction of a cruciferous plant, advantageously chosen from the group consisting of broccoli, Lepidium dabra and radish. Even more advantageously, it is chosen from the group consisting of sulforaphane or sulforaphene.
- the cruciferous extraction process comprises the following stages: treatment of the cruciferous plant, advantageously lyophilized, with a water-miscible solvent or a water-solvent mixture, advantageously acetone,
- the suspension obtained is then extracted into a separatory funnel with six times 50 ml of an ethyl ether-chloroform mixture (8/2 v / v).
- the organic phase is dried over sodium sulfate and then evaporated under reduced pressure. 32 mg of crude sulforaphane are obtained.
- the residue is deposited on a preparative chromatography plate of silica gel and eluted with a mixture of isopropanol and methanol (7/3 v / v).
- the plaque is revealed by ammoniacal silver nitrate on a small part in order to determine the migration zone of the sulforaphane. This area is scratched and the sulforaphane is extracted from the silica with chloroform. The chloroform is evaporated and 9 mg of sulforaphane are obtained. Sulforaphane is identified by gas chromatography coupled to a mass spectrometer.
- Example 2 preparation of sulforaphene: The procedure is the same as on broccoli but using radish seeds (raphanus sativus).
- a suspension of 25 g of lithium aluminum hydride in 400 ml of ethyl ether is prepared.
- the solution of 4-methylthiobutyronitrile is gradually added to the suspension of lithium aluminum hydride, then the mixture is brought to reflux for 2 h 30 min.
- the suspension is then neutralized by slowly adding 80 ml of distilled water under reflux. When boiling ceases, 120 ml of distilled water are then added to complete the neutralization of the remaining hydride. Filter on sintered glass. The insoluble material is washed on the filter with 200 ml of ethyl ether. The ethereal fractions are combined and evaporated to dryness. 26.9 g of methylthiobutylamine are obtained. The product obtained is taken up in 80 ml of acetone to which 23 ml of 35% hydrogen peroxide is added little by little. One night is placed in a water bath at 50 ° C.
- Inhibitor solutions The inhibitor molecules are dissolved directly in the pH 6.5 buffer, in 50% methanol (methanol-distilled water) or in pure methanol depending on their solubility.
- the weight-by-volume concentrations of the various inhibitor solutions are: 0.2%, 0.1%, 0.05%, 0.025%, 0.0125%, 0.00625% and 0.00312%.
- tyrosinase The action of tyrosinase is evaluated by the initial speed of the reaction measured on the D.O.
- the inhibitory power of a molecule is defined as the concentration which reduces the action of tyrosinase by 50%.
- Sulforaphane inhibits tyrosinase about 1.5 times more than hydroquinone. It is therefore found that all the isothiocyanates used in the table are superior to hydroquinone and that the most active of them, the benzoylisothiocyanate is approximately 24 times more active than hydroquinone. Thiocyanates have an activity similar to that of hydroquinone.
- the results are expressed in mg / ml of melanin insofar as the cells are seeded at the same concentration.
- Type 6 pigmented epidemics (corresponding to black skin), three samples per test were treated daily for 5 days with a control cream with the following composition (in% by weight):
- kojic acid inhibits the synthesis of melatonin by 8% and sulforaphane by 30% although its concentration is ten times lower than that of kojic acid.
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- 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)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Emergency Medicine (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002435942A CA2435942A1 (fr) | 2001-01-26 | 2002-01-24 | Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant |
JP2002558998A JP2004520371A (ja) | 2001-01-26 | 2002-01-24 | イソチオシアネート、チオシアネート、又はそれらの混合物の脱色剤としての使用 |
KR10-2003-7009921A KR20030086256A (ko) | 2001-01-26 | 2002-01-24 | 이소티오시아네이트, 티오시아네이트 또는 이들의혼합물의 탈색소제로서의 용도 |
EP02700395A EP1353644A1 (fr) | 2001-01-26 | 2002-01-24 | Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant |
PL02364826A PL364826A1 (en) | 2001-01-26 | 2002-01-24 | Use of an isothiocyanate, a thiocyanate or a mixture thereof as depigmenting agent |
HU0303018A HUP0303018A2 (hu) | 2001-01-26 | 2002-01-24 | Izocianátok, tiocianátok vagy ezek keverékének alkalmazása depigmentálószerként |
MXPA03006731A MXPA03006731A (es) | 2001-01-26 | 2002-01-24 | Uso de un isotiocianato, de un tiocianato, o una mezcla de los mismos, como agente de despigmentacion. |
US10/470,079 US20040077715A1 (en) | 2001-01-26 | 2002-01-24 | Use of an isothiocyanate, a thiocyanate or a mixture thereof as depigmenting agent |
SK961-2003A SK9612003A3 (en) | 2001-01-26 | 2002-01-24 | Use of an isothiocyanate, a thiocyanate or a mixture thereof as depigmenting agent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0101078A FR2820036B1 (fr) | 2001-01-26 | 2001-01-26 | Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant |
FR01/01078 | 2001-01-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002058664A1 true WO2002058664A1 (fr) | 2002-08-01 |
Family
ID=8859278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2002/000288 WO2002058664A1 (fr) | 2001-01-26 | 2002-01-24 | Utilisation d'un isothiocyanate, d'un thiocyanate ou de leur melange en tant que depigmentant |
Country Status (12)
Country | Link |
---|---|
US (1) | US20040077715A1 (fr) |
EP (1) | EP1353644A1 (fr) |
JP (1) | JP2004520371A (fr) |
KR (1) | KR20030086256A (fr) |
CA (1) | CA2435942A1 (fr) |
CZ (1) | CZ20032012A3 (fr) |
FR (1) | FR2820036B1 (fr) |
HU (1) | HUP0303018A2 (fr) |
MX (1) | MXPA03006731A (fr) |
PL (1) | PL364826A1 (fr) |
SK (1) | SK9612003A3 (fr) |
WO (1) | WO2002058664A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2845599A1 (fr) * | 2002-10-11 | 2004-04-16 | Lmd | Medicament comprenant une thiouree pour son utilisation en tant que depigmentant |
FR2880022A1 (fr) * | 2004-12-24 | 2006-06-30 | Mayoly Spindler Soc Par Action | Nouveaux derives de la n-hydroxy-n'-phenyluree et de la n-hydroxy-n'-phenylthiouree et leur utilisation comme inhibiteurs de la synthese de la melanine |
WO2012010644A1 (fr) | 2010-07-23 | 2012-01-26 | Auriga International | Procede de synthese d'isothiocyanates et leurs derives et utilisations de ceux-ci |
CN103327957A (zh) * | 2010-12-21 | 2013-09-25 | 荷兰联合利华有限公司 | 亮肤组合物 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2879444B1 (fr) * | 2004-12-22 | 2007-05-18 | Oreal | Utilisation d'un compose capable d'augmenter le taux de glutathion dans les melanocytes pour le traitement de la canitie |
DE102008047362A1 (de) * | 2008-09-15 | 2010-04-15 | Henkel Ag & Co. Kgaa | Zusammensetzung zur Hautaufhellung |
BE1019434A3 (fr) * | 2010-07-23 | 2012-07-03 | Auriga Internat | Stabilisation du sulforaphane. |
DE102012222970A1 (de) * | 2012-12-12 | 2014-06-12 | Henkel Ag & Co. Kgaa | Wirkstoffkombination zur Hautaufhellung I |
WO2015002279A1 (fr) * | 2013-07-03 | 2015-01-08 | 味の素株式会社 | Composition favorisant la production de glutathion |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8903954A (pt) * | 1989-08-01 | 1991-02-05 | Chiaki Ohama | Cosmetico inibidor da formacao de melanina |
JPH05163135A (ja) * | 1991-12-16 | 1993-06-29 | Suntory Ltd | 美白用化粧料組成物 |
JPH05213857A (ja) * | 1992-01-31 | 1993-08-24 | Kao Corp | メラニン抑制剤 |
JPH08325130A (ja) * | 1995-05-29 | 1996-12-10 | Kyoei Kagaku Kogyo Kk | 化粧料 |
FR2769837A1 (fr) * | 1997-10-17 | 1999-04-23 | Bio Sphere 99 Lab | Composition pour dietetique ou cosmetique a base d'extraits vegetaux |
-
2001
- 2001-01-26 FR FR0101078A patent/FR2820036B1/fr not_active Expired - Fee Related
-
2002
- 2002-01-24 CZ CZ20032012A patent/CZ20032012A3/cs unknown
- 2002-01-24 WO PCT/FR2002/000288 patent/WO2002058664A1/fr not_active Application Discontinuation
- 2002-01-24 PL PL02364826A patent/PL364826A1/xx not_active Application Discontinuation
- 2002-01-24 US US10/470,079 patent/US20040077715A1/en not_active Abandoned
- 2002-01-24 KR KR10-2003-7009921A patent/KR20030086256A/ko not_active Application Discontinuation
- 2002-01-24 EP EP02700395A patent/EP1353644A1/fr not_active Withdrawn
- 2002-01-24 JP JP2002558998A patent/JP2004520371A/ja active Pending
- 2002-01-24 SK SK961-2003A patent/SK9612003A3/sk unknown
- 2002-01-24 HU HU0303018A patent/HUP0303018A2/hu unknown
- 2002-01-24 CA CA002435942A patent/CA2435942A1/fr not_active Abandoned
- 2002-01-24 MX MXPA03006731A patent/MXPA03006731A/es unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8903954A (pt) * | 1989-08-01 | 1991-02-05 | Chiaki Ohama | Cosmetico inibidor da formacao de melanina |
JPH05163135A (ja) * | 1991-12-16 | 1993-06-29 | Suntory Ltd | 美白用化粧料組成物 |
JPH05213857A (ja) * | 1992-01-31 | 1993-08-24 | Kao Corp | メラニン抑制剤 |
JPH08325130A (ja) * | 1995-05-29 | 1996-12-10 | Kyoei Kagaku Kogyo Kk | 化粧料 |
FR2769837A1 (fr) * | 1997-10-17 | 1999-04-23 | Bio Sphere 99 Lab | Composition pour dietetique ou cosmetique a base d'extraits vegetaux |
Non-Patent Citations (4)
Title |
---|
DATABASE WPI Section Ch Week 199110, Derwent World Patents Index; Class D21, AN 1991-065787, XP002185635 * |
DATABASE WPI Section Ch Week 199330, Derwent World Patents Index; Class B04, AN 1993-239913, XP002185636 * |
DATABASE WPI Section Ch Week 199338, Derwent World Patents Index; Class B05, AN 1993-299599, XP002185637 * |
PATENT ABSTRACTS OF JAPAN vol. 1997, no. 04 30 April 1997 (1997-04-30) * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2845599A1 (fr) * | 2002-10-11 | 2004-04-16 | Lmd | Medicament comprenant une thiouree pour son utilisation en tant que depigmentant |
WO2004032912A1 (fr) * | 2002-10-11 | 2004-04-22 | Lmd | Medicament comprenant une thiouree pour son utilisation en tant que depigmentant ou agent antimutagene et anticarcinogene |
FR2880022A1 (fr) * | 2004-12-24 | 2006-06-30 | Mayoly Spindler Soc Par Action | Nouveaux derives de la n-hydroxy-n'-phenyluree et de la n-hydroxy-n'-phenylthiouree et leur utilisation comme inhibiteurs de la synthese de la melanine |
WO2012010644A1 (fr) | 2010-07-23 | 2012-01-26 | Auriga International | Procede de synthese d'isothiocyanates et leurs derives et utilisations de ceux-ci |
BE1019431A3 (fr) * | 2010-07-23 | 2012-07-03 | Auriga Internat | Procede de synthese d'isothiocyanates et leurs derives et utilisations de ceux-ci. |
AU2011281617B2 (en) * | 2010-07-23 | 2015-05-14 | Auriga International | Process for the synthesis of isothiocyanates and derivatives thereof and uses of same |
CN103327957A (zh) * | 2010-12-21 | 2013-09-25 | 荷兰联合利华有限公司 | 亮肤组合物 |
CN103327957B (zh) * | 2010-12-21 | 2015-05-13 | 荷兰联合利华有限公司 | 亮肤组合物 |
Also Published As
Publication number | Publication date |
---|---|
US20040077715A1 (en) | 2004-04-22 |
FR2820036B1 (fr) | 2005-12-09 |
SK9612003A3 (en) | 2004-03-02 |
HUP0303018A2 (hu) | 2003-12-29 |
KR20030086256A (ko) | 2003-11-07 |
PL364826A1 (en) | 2004-12-27 |
CA2435942A1 (fr) | 2002-08-01 |
FR2820036A1 (fr) | 2002-08-02 |
MXPA03006731A (es) | 2004-10-15 |
CZ20032012A3 (cs) | 2004-01-14 |
EP1353644A1 (fr) | 2003-10-22 |
JP2004520371A (ja) | 2004-07-08 |
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