EP1255530A2 - Kosmetische oder pharmazeutische zusammensetzung enthaltend eine sesquiterpen-lactone - Google Patents
Kosmetische oder pharmazeutische zusammensetzung enthaltend eine sesquiterpen-lactoneInfo
- Publication number
- EP1255530A2 EP1255530A2 EP01907830A EP01907830A EP1255530A2 EP 1255530 A2 EP1255530 A2 EP 1255530A2 EP 01907830 A EP01907830 A EP 01907830A EP 01907830 A EP01907830 A EP 01907830A EP 1255530 A2 EP1255530 A2 EP 1255530A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- extract
- plant
- composition according
- sesquiterpene
- cosmetic
- 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- Withdrawn
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- 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
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
Definitions
- the present invention relates to a more particularly cosmetic composition, intended for the treatment of alopecia and related conditions, the use of a composition for the manufacture of a medicament for treating these disorders, a process for the preparation of said compositions, as well as a cosmetic treatment process
- Hair loss can be caused by various causes such as age, pathology (pityriasis capitis), external aggression (discoloration or dyeing) It can be local or generalized, and can cause a simple aesthetic inconvenience or constitute a real pathology
- Cyclosporine is active systemically and locally, while FK506 is only active locally.
- the present invention relates to a composition intended for topical application, in particular cosmetic application, characterized in that it comprises, as active principle, at least one sesquiterpene lactone or an analog of sesquiterpene lactones in a suitable physiologically acceptable medium.
- said composition being more particularly intended for treating alopecia, stimulating hair growth, stimulating hair growth and / or treating seborrheic states as well as related states
- physiologically acceptable medium suitable for topical application is meant a medium compatible with the active principle and acceptable in cosmetics or in pharmacy, in particular compatible with the skin and the scalp.
- sesquiterpene lactones which can be used in the compositions according to the present invention are in particular described in “Pharmacognosy, Phytochemistry and Medicinal Plants” of BRUNETON J, Edition Lavoisier, PARIS 2 nd edition 1993, pages 499-510
- sesquiterpene lactone analogues within the meaning of the present invention is meant the derivative or substituted forms of these lactones having an alpha-methylene-gamma-lactone group, as well as their bioequivalent derivatives defined by the compounds having an active structure having properties vis-à-vis the hair growth (that is to say favoring the passage of the hair from the anagen phase to the telogen phase) similar to those highlighted in the present text for the helenalme, the dehydroheursnation, parthenolide and cnicin
- the sesquiterpene lactone is preferably chosen from the group consisting of helena ne, dihydroheursnahne, parthenohde, cnicine and their derivatives, by “derivatives” is meant essentially esters, in particular the fatty acid esters of these lactones
- Sesquiterpene lactones are especially present in plant extracts, in particular in Asteracae and in particular in extracts of Arnica montana, Tanacetum parthenium and Cnicus benedictus
- the invention also relates to a composition intended for topical application, in particular cosmetic, containing as active principle an extract of plant rich in sesquiterpene lactone, in particular of a plant of the plant species of the Asteracae family, for example Arnica montana, Tanacetum parthenium and Cnicus benedictus
- the extract of plant is an extract of the flower for Arnica Montana and the extract of flowering aerial parts for Tanacetum parthenium and Cnicus benedictus
- these substances of plant origin have been found to have a very marked effect on the induction of the anagen phase of the hair in rabbits or in C57 / B16 mice.
- lactones are known to have different pharmacological properties related to the anti-inflammatory or anti-tumor effect, but it has never been reported that these molecules could have any effectiveness on hair cycles or hair growth
- the biological efficacy in general of these substances is to relate to the presence of certain functional groups within the molecule and in particular the alpha-methylene-gamma-lactone group
- the present invention also relates to processes for the preparation of plant extracts rich in sesquiterpene lactones, in particular extracts of Asteracae obtained by a process comprising the following steps a) extraction of at least part of the plant, in particular flowers and aerial parts of plants of the Asteracae family, by means of a hydro-organic solution containing an organic solvent miscible with water, followed by the evaporation of said solvent and b) extraction of the resulting aqueous phase using an organic solvent immiscible with water, then c) recovering the extract contained in said organic phase
- the part of the plant extracted will preferably be the flower or the aerial parts richer in sesquiterpene lactones.
- the organic solvent miscible with water used for the first decoctions is chosen from the alcohols containing from 1 to 5 carbon atoms, acetonitrile, tetrahydrofuran and acetone This solvent is preferably a low molecular weight alcohol such as methanol, ethanol or an alcohol containing 3 to 5 carbon atoms, even more preferably ethanol will be used.
- the solution containing water and an organic solvent miscible with water preferably contains from 40 to 60% of water by weight. Stage a) may comprise several extractions
- the extraction of the aqueous phase obtained is preferably carried out with an organic solvent immiscible with water chosen from ethers such as ether ethyl, other organic solvents can nevertheless be used, such as for example methylene chloride, chloroform and ethyl acetate.
- ethers such as ether ethyl
- other organic solvents can nevertheless be used, such as for example methylene chloride, chloroform and ethyl acetate.
- An organic phase is then obtained containing the extract rich in sesquiterpene lactones which will be optionally purified, in particular by chromatography and for example by re-solution and chromatography of the solution.
- Chromatography can in particular be carried out using a silica gel as support after fixing the active principle in an alkane type medium such as hexane and then elution using a chlorinated solvent such as chloroform for example.
- compositions in particular cosmetic compositions, according to the present invention may of course be in the forms which are usually known for this type of administration, that is to say in particular lotions, foams, gels, dispersions, sprays or creams for example, but also can be administered in shampoos, with excipients allowing in particular skin penetration to improve the properties and accessibility of the active ingredient.
- These compositions essentially intended for topical application contain, in addition to the active principle, plant extract for example, a physiologically acceptable medium, generally based on water or solvent, for example alcohols, ethers or glycols
- compositions according to the present invention preferably contain from 0.001 to 10% by weight of sesquiterpene lactone
- compositions can also contain - surfactants
- compositions for the treatment of hair loss are known in the cosmetic field, in particular for the production of compositions for the treatment of hair loss.
- the present invention further relates to a cosmetic treatment method such as topically applied, in particular to the scalp, a cosmetic composition comprising at least one sesquiterpene lactone according to the invention and preferably containing an extract rich in sesquiterpene lactones obtained from a plant in the Asteracae family in order to improve the aesthetics of the hair and / or treat alopecia
- the present invention also relates to compositions containing sesquiterpene lactones as well as the extracts described above in a pharmaceutical type application, these will in particular be cases where alopecia or seborrheic states have a pathological character.
- the present invention also relates to the use of a composition containing at least one sesquiterpene lactone or an analog of sesquiterpene lactones for the manufacture of a medicament intended for treating alopecia, seborrheic states, stimulating hair growth and capillary growth or related states when these have a pathological character
- compositions containing at least one sesquiterpene lactone mentioned above can of course be obtained as has been described in the case of cosmetic applications
- sesquiterpene lactones chosen from the group consisting of helenahne, dihydrohommenahne, parthenohde, cnicine and their derivatives, among these derivatives should be mentioned more particularly the esters and in particular the fatty acid esters of these lactones
- the drugs containing these active ingredients may be in forms suitable for their administration, that is to say in particular lotions, creams, sprays or possibly if necessary may be presented in forms of injectable form, especially intradermal
- the present invention relates to plant extracts from the Asteraceae family rich in sesquiterpene lactones as they can be obtained by the process described above.
- a chromatography column is then produced with silica gel 60 in hexane 4 cm in diameter and 20 cm in height.
- the mixture produced 1-chloroform gel is placed on the surface of the gel.
- the fraction which is eluted is collected.
- the chloroform is evaporated off A residue of 0.19 g is obtained (product 2)
- the support part is taken between Rf 0.55 and Rf 0.75 where we can observe yellow-greenish spots
- the silica thus obtained is extracted 4 times at reflux with 50 ml of pure methanol The methanol is evaporated at dry
- the three products are analyzed by gas chromatography coupled to a mass spectrometer
- products 1, 2 and 3 respectively contain 17.5%, 42.6% and 43% by weight of helenahne + dihydrohelenahne relative to the mass of the total composition
- the purification provided between products 2 and 3 mainly consists of the elimination of chlorophyll pigments (discoloration)
- the difference between the average time taken by the hair to grow on the treated parts and the control parts is then evaluated.
- a solution containing 1% of pure commercial parthenohde (Ald ⁇ ch ref 38 428-3) and a solution containing 1% of pure commercial cnicin (Extrasynthesis ref 8725), are prepared in the same excipient as the extract of Arnica montana and subjected to rabbit test There is a growth of hair roughly equivalent between the extract of Arnica and the parthenohde and a growth about two times lower for cnicine
- mice Male mice of 5 weeks of age all identical The mice are shorn on the back so as to make the hair invisible
- the product is placed on the back without using gauze once a day for 5 days straight
- a solution containing 1% of pure commercial parthenohde (Ald ⁇ ch ref 38,428-3) and a solution containing 1% of pure commercial cnicin (Extrasynthesis ref 8725), are prepared in the same excipient as the extract of Arnica montana and subjected to the test. on the rabbit There is a growth of hair roughly equivalent between the extract of arnica at 2.5% and the parthenohde at 1% and a growth about twice less for the cnicine at 1%
- compositions studied are effective for the treatment of pathologies linked to hair disorders.
- Tanacetum parthenium by four reflux decoctions for 30 minutes in 5 liters of ethanol at 50% water
- Extractive solutions are combined and the alcohol is evaporated
- the aqueous phase is concentrated to one liter and extracted against the current with ethyl ether until the ether no longer contains any significant residue on evaporation.
- the ethereal phase is taken up in one liter of methanol at 50% water and passed through a column 5 cm in diameter containing 100 g of Sephadex LH20 suspended in 50% methanol.
- One kilogram of aerial flowering parts of Cnicus benedictus is extracted by four reflux decoctions for 30 minutes in 5 liters of methanol at 60% water. The extracting solutions are combined and the methanol is evaporated.
- the aqueous phase is concentrated to 0.5 liters and extracted against the current with ethyl ether until the ether no longer contains any significant residue on evaporation.
- the ethereal phase is taken up in one liter of methanol at 50% water and passed through a column 5 cm in diameter containing 100 g of Sephadex LH20 in suspension in 50% methanol. Eluted with three liters of the same solvent.
- the solvent is evaporated to dryness under reduced pressure.
- Carrier gas helium, constant flow of 1 ml / min - Temperature program: 150 ° C for 5 min, then increase by 5 ° C / min up to 250 ° C.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0002023A FR2805158B1 (fr) | 2000-02-18 | 2000-02-18 | Composition cosmetique ou medicamenteuse contenant une lactone sesquiterpenique ou un analogue pour traiter les desordres lies a la croissance pilaire, et son procede de preparation. |
FR0002023 | 2000-02-18 | ||
PCT/FR2001/000471 WO2001060326A2 (fr) | 2000-02-18 | 2001-02-16 | Composition cosmetique ou pharmaceutique contenant une lactone sesquiterpenique |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1255530A2 true EP1255530A2 (de) | 2002-11-13 |
Family
ID=8847129
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01907830A Withdrawn EP1255530A2 (de) | 2000-02-18 | 2001-02-16 | Kosmetische oder pharmazeutische zusammensetzung enthaltend eine sesquiterpen-lactone |
Country Status (6)
Country | Link |
---|---|
US (1) | US20040115289A1 (de) |
EP (1) | EP1255530A2 (de) |
JP (1) | JP2003522779A (de) |
AU (1) | AU2001235706A1 (de) |
FR (1) | FR2805158B1 (de) |
WO (1) | WO2001060326A2 (de) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2861293B1 (fr) * | 2003-10-22 | 2008-10-17 | Greenpharma Sas | Composition pour prevenir ou traiter des affections resultant d'un processus de mort cellulaire comprenant une lactone sesquiterpenique |
JP2008179540A (ja) * | 2005-01-07 | 2008-08-07 | Noevir Co Ltd | 細胞分化、発生、増殖を制御する物質および該物質を含む細胞分化・発生・増殖調節剤 |
JPWO2008075466A1 (ja) * | 2006-12-20 | 2010-04-08 | 株式会社エム・エム・ティー | 発毛促進用飲食物、医薬部外品、医薬組成物ならびに発毛促進方法 |
WO2008075649A1 (ja) * | 2006-12-20 | 2008-06-26 | Mmt Co., Ltd. | 発毛促進用飲食物、医薬部外品、医薬組成物ならびに発毛促進方法 |
JP5714365B2 (ja) * | 2011-03-11 | 2015-05-07 | 国立大学法人 東京大学 | 育毛及び発毛促進剤 |
KR101816159B1 (ko) * | 2016-05-04 | 2018-01-08 | 주식회사 에이치피앤씨 | 이소알란토락톤을 유효성분으로 함유하는 탈모 방지 또는 발모 촉진용 조성물 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE789002A (fr) * | 1971-09-22 | 1973-01-15 | Sori Soc Rech Ind | Procede d'obtention d'un extrait d'arnica montana |
FR2504009A1 (en) * | 1981-04-17 | 1982-10-22 | Yersin David | Topical compsns. contg. arnica extract - together with camphor, menthol and surfactant for topical treatment of inflammations and infections |
US4916204A (en) * | 1987-07-31 | 1990-04-10 | Massachusetts Institute Of Technology | Pure polyanhydride from dicarboxylic acid and coupling agent |
US5057501A (en) * | 1990-03-13 | 1991-10-15 | Dermatologic Research Corporation | Methods for treatment of papulosquamous and eczematous diseases |
GB9100581D0 (en) * | 1991-01-11 | 1991-02-27 | Rhodes Technology | Method for the extraction of sesquiterpene lactones |
JPH05306231A (ja) * | 1992-04-24 | 1993-11-19 | Pola Chem Ind Inc | 皮膚外用剤 |
JPH1067621A (ja) * | 1996-08-23 | 1998-03-10 | Shiseido Co Ltd | 養毛料 |
US6254899B1 (en) * | 1997-03-03 | 2001-07-03 | Laboratoires Remilea | Plant extract compositions, method of preparation, and pharmaceutical compositions containing them |
US5804206A (en) * | 1997-03-06 | 1998-09-08 | Bio-Botanica, Inc. | Therapeutic composition and method for treating skin using Centipeda cunninghami extract |
US5902809A (en) * | 1997-07-03 | 1999-05-11 | Paracure, Inc. | Arglabin compounds and therapeutic uses thereof |
TWI234467B (en) * | 1997-06-04 | 2005-06-21 | Univ Michigan | Composition for inhibiting photoaging of skin |
JPH1179948A (ja) * | 1997-09-12 | 1999-03-23 | Noevir Co Ltd | 養毛剤及び毛髪用化粧料、並びに皮脂分泌抑制用皮膚外用剤 |
-
2000
- 2000-02-18 FR FR0002023A patent/FR2805158B1/fr not_active Expired - Fee Related
-
2001
- 2001-02-16 WO PCT/FR2001/000471 patent/WO2001060326A2/fr not_active Application Discontinuation
- 2001-02-16 AU AU2001235706A patent/AU2001235706A1/en not_active Abandoned
- 2001-02-16 US US10/204,018 patent/US20040115289A1/en not_active Abandoned
- 2001-02-16 JP JP2001559424A patent/JP2003522779A/ja active Pending
- 2001-02-16 EP EP01907830A patent/EP1255530A2/de not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO0160326A2 * |
Also Published As
Publication number | Publication date |
---|---|
WO2001060326A2 (fr) | 2001-08-23 |
FR2805158B1 (fr) | 2004-12-03 |
WO2001060326A3 (fr) | 2002-06-20 |
FR2805158A1 (fr) | 2001-08-24 |
JP2003522779A (ja) | 2003-07-29 |
AU2001235706A1 (en) | 2001-08-27 |
US20040115289A1 (en) | 2004-06-17 |
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