EP1545708A2 - Heterocyclische verbindung zur stimulierung oder induzierung des haar- oder wimpernwachstums und/oder zur verlangsamung des haarausfalls, diese enthaltende zusammensetzung und ihre verwendungen - Google Patents

Heterocyclische verbindung zur stimulierung oder induzierung des haar- oder wimpernwachstums und/oder zur verlangsamung des haarausfalls, diese enthaltende zusammensetzung und ihre verwendungen

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Publication number
EP1545708A2
EP1545708A2 EP03798227A EP03798227A EP1545708A2 EP 1545708 A2 EP1545708 A2 EP 1545708A2 EP 03798227 A EP03798227 A EP 03798227A EP 03798227 A EP03798227 A EP 03798227A EP 1545708 A2 EP1545708 A2 EP 1545708A2
Authority
EP
European Patent Office
Prior art keywords
saturated
linear
branched
unsaturated
rings
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Withdrawn
Application number
EP03798227A
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English (en)
French (fr)
Inventor
Christophe Boulle
Roger Rozot
Maria Dalko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1545708A2 publication Critical patent/EP1545708A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • A61K35/36—Skin; Hair; Nails; Sebaceous glands; Cerumen; Epidermis; Epithelial cells; Keratinocytes; Langerhans cells; Ectodermal cells
    • 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
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • 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
    • A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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

  • Hair growth and renewal is mainly determined by the activity of the hair follicles and their matrix environment. Their activity is cyclical and essentially comprises three phases, namely the anagen phase, the catagen phase and the telogen phase.
  • Natural hair loss or loss can be estimated, on average, a few hundred hairs per day for a normal physiological state. This permanent physical renewal process undergoes a natural evolution during aging, the hair becomes thinner and their cycles shorter.
  • alopecia also covers a whole family of damage to the hair follicle, the final consequence of which is the permanent, partial or general loss of hair. It is more particularly about androgenic alopecia. In a significant number of cases, early hair loss occurs in genetically predisposed subjects, it is then andro-chrono-genetic alopecia; this form of alopecia especially concerns men.
  • prostaglandins are molecules with a very short biological half-life time and acting in an autocrine or paracrine manner, this reflecting the local and labile nature of the metabolism of prostaglandins (Narumiya S. et al., 1999, Physiol. Rev., 79 (4), 1193-1226).
  • keratin K6irs are expressed in the hair follicle as particularly in the internal sheath but not in the epidermis, and that type 1 cyclooxygenase, if it is expressed in the epidermis, is not expressed in the keratinocytes of the hair follicle but in the dermal papilla (Michelet. et al., 1997, J. Invest. Dermatol. 108: 205-209).
  • the applicant has now demonstrated that an enzyme specifically involved in the degradation of these prostaglandins is present in the dermal papilla of the hair, which is a determining compartment for the life of the hair. Indeed, the applicant has now proven the presence of 15-hydroxy prostaglandin dehydrogenase (15-PGDH for short) at this level. He also showed that inhibition of 15-PGDH has a beneficial effect on hair growth.
  • 15-hydroxy prostaglandin dehydrogenase 15-hydroxy prostaglandin dehydrogenase
  • the present invention relates to a composition for caring for or treating human keratin fibers and in particular capillary fibers containing at least one particular inhibitor of 15-hydroxy prostaglandin dehydrogenase and a physiologically acceptable medium.
  • heterocyclic compounds and in particular certain phenyl-furans, phenyl-thiophenes, phenyl-pyrroles, salified or not, are surprisingly endowed with an activity favorable to the improvement of the density of human keratin fibers, especially capillary. He also found that these compounds are inhibitors of 15-hydroxy prostaglandin dehydrogenase.
  • the invention also applies to keratin fibers of mammals of the animal species (dog, horse or cat for example).
  • the invention also relates to the cosmetic use of at least one heterocycle of formula (I) or of a salt thereof in a cosmetic composition for caring for and / or making up human keratin fibers to induce and / or stimulate their growth, curb their fall and / or increase their density and / or treat androgenic alopecia as well as the use of at least one compound of formula (I) or one of its salts for the preparation of a composition for caring for or treating human keratin fibers, intended to induce and / or stimulate the growth of fibers and / or slow down their fall and / or increase their density and / or treat androgenic alopecia.
  • the invention also relates to the cosmetic use of at least one heterocyclic compound of formula (I) or of one of its salts in a cosmetic composition of human hair care to reduce hair loss and / or increase their density.
  • Another subject of the invention is the use of at least one heterocyclic compound of formula (I) or one of its salts for the preparation of a human hair composition intended to induce and / or stimulate hair growth and / or curb their fall and / or increase their density.
  • the invention relates to the cosmetic use of at least one heterocyclic compound of formula (I) or of one of its salts in a cosmetic composition for human hair care for treating alopecia of natural origin and in particular andro-chrono-genetic or the use of at least one heterocyclic compound of formula (I) or one of its salts for the preparation of a hair composition of human being intended to treat alopecia of natural origin and in particular androgenic.
  • this composition makes it possible to maintain the hair in good condition and / or fight against natural hair loss and more particularly that of men.
  • the subject of the invention is also the cosmetic use of at least one heterocyclic compound of formula (I) or one of its salts, in a cosmetic composition for caring for and / or making up the eyelashes of human beings, for induce and / or stimulate the growth of eyelashes and / or increase their density as well as the use of at least one heterocyclic compound of formula (I) or one of its salts, for the preparation of a composition of care and / or treatment of human eyelashes, intended to induce and / or stimulate the growth of eyelashes and / or increase their density.
  • This composition thus makes it possible to maintain the eyelashes in good condition and / or to improve their condition and / or their appearance.
  • the subject of the invention is also a composition for caring for and / or making up keratin fibers, in particular human fibers, containing a physiologically acceptable medium and at least one heterocyclic compound of formula (I) or one of its salts.
  • Another subject of the invention is the use of at least one heterocyclic compound of formula (I) or of one of its salts as an inhibitor of 15-hydroxy prostaglandin dehydrogenase in human skin. It also relates to the use of at least one heterocyclic compound of formula (I) or one of its salts for the manufacture of a composition intended to treat disorders linked to 15-hydroxy prostaglandin dehydrogenase in particularly in humans.
  • the subject of the invention is also a process for the cosmetic treatment of keratin fibers (hair or eyelashes in particular) and / or of the skin from which the said emerge fibers, including the scalp and the eyelids, in particular intended to stimulate the growth of human keratin fibers and / or to slow their fall, characterized in that it consists in applying to keratin fibers and / or the skin from which said fibers emerge, a cosmetic composition comprising an effective amount of at least one compound of formula (I) or one of its salts, to leave the latter in contact with the keratin fibers and / or the skin from which said fibers emerge, and optionally to rinse the fibers and / or said skin.
  • This treatment process has the characteristics of a cosmetic process insofar as it makes it possible to improve the aesthetics of keratin fibers by giving them greater vigor and an improved appearance. In addition, it can be used daily for several months, without medical prescription.
  • Another subject of the invention is the use of at least one heterocyclic compound of formula (I) or one of its salts for the manufacture of a composition intended to preserve the quantity and / or the activity of prostaglandins in the level of the hair follicle.
  • the ratio between the inhibitory activities of PGF synthase and 15-PGDH respectively for a given concentration, determined in particular by the inhibitory concentrations of 50% of the enzymatic activity of PGF synthase IC 50 sf respectively, and of 15-PGDH IC 50 dh, is at least greater than 1, and in particular at least 3: 1, advantageously greater than or equal to 5: 1.
  • the preferred compounds of the invention have an IC 50 sf / IC 5 odh ratio greater than or equal to 10: 1.
  • alkyl radical is meant within the meaning of the invention a hydrocarbon radical which can be linear or branched and saturated or unsaturated.
  • the alkyl radical contains from 1 to 10 carbon atoms.
  • alkyl radical which can be used in the invention, mention may be made of methyl, ethyl, isopropyl, n-butyl, ter-butyl, n-hexyl, ethyl-2-hexyl, ethylene, propylene radicals.
  • This radical can optionally be substituted in particular by OR 0 , with R 0 being H or an alkyl radical, linear or branched, saturated in CC 20 and better in CC 10 and for example in C ⁇ Cs.
  • the heteroatom (s) of Hy can be O, N, S, P, Si, Se and in particular O, N, S.
  • the heterocycle Hy can be saturated or unsaturated. In addition, it can have 4, 5, 6 or 7 atoms and one or more carbonyl or thio-carbonyl functions or both, the carbon of these functions being part of the heterocycle.
  • Hy represents a 5-atom aromatic ring comprising as heteroatom sulfur, nitrogen and their associations.
  • this heterocycle Hy comprises one or two carbonyl groups, groups in which the carbon is part of the heterocycle.
  • this heterocycle has the following formula (II):
  • the rings used as substituent (S-i) contain from 4 to 7 atoms and better still from 5 to 6 atoms. They can be saturated or unsaturated and optionally contain one or more heteroatoms such as S, N, O or their associations.
  • these cycles can be alone or joined to another cycle with the same chemical structure or not. When they are joined, they form condensed cycles.
  • saturated hydrocarbon rings which can be used, mention may be made of the cyclopentyl or cyclohexyl radical and as unsaturated hydrocarbon rings, mention may be made of the cyclohexenyl or phenyl ring.
  • unsaturated hydrocarbon rings mention may be made of the cyclohexenyl or phenyl ring.
  • combined hydrocarbon rings mention may be made of the naphthyl radical.
  • heterocycle mention may be made of pyridine, piperidine, morpholine, pyrrole, furan, thiazole rings. In addition, these rings can be substituted by one or more substituents having the definition indicated above for R or R 0 .
  • the compounds of formula (I) are in isolated form, that is to say non-polymeric. These are phenyl-furans, phenyl-thiophenes or phenyl-pyrroles.
  • Ri can be located in position 3 or 4, considering G in position 1 of the 5-atom heterocycle.
  • R 2 and R 3 can be located in any position of the phenyl ring carrying them and in particular in the para or meta position of the following part (A):
  • Ri represents a hydrogen atom.
  • at least one of R 2 and R 3 represents CF 3 , OR 0 or COOR 0 with Ro equal to H or an alkyl radical, linear or branched, saturated or not with CC 20 and better with CC 1o .
  • an alkyl radical which can be used, mention may be made of methyl, ethyl, tert-butyl, isopropyl, n-butyl and n-hexyl.
  • COOR 0 represents COOH or COOCH 2 -CH 3 .
  • OR 0 represents in particular OH or OCH 3.
  • R 2 represents COOH or OH and R 3 represents H;
  • R 2 represents COOCH 2 -CH 3 and R 3 represents H; or
  • R 2 and R 3 represent CF 3 or OCH 3 .
  • salts of compound of formula (I) is meant according to the invention the organic or inorganic salts, single or double, of a compound of formula (I).
  • inorganic salts which can be used according to the invention, mention may be made of: single or double sodium or potassium salts as well as zinc (Zn 2+ ), calcium (Ca 2+ ), copper (Cu 2+ ) salts, iron (Fe 2+ ), strontium (Sr 2 * ), magnesium (Mg 2+ ), ammonium and manganese (Mn 2+ ); hydroxides, carbonates, halides (such as chlorides), sulfates, nitrates, phosphates.
  • the salt is a sodium salt.
  • organic salts which can be used according to the invention are, for example, the salts of tri-ethanolamine, mono-ethanolamine, di-ethanolamine, hexadecylamine, N, N, N ', N'-tetrakis- (hydroxy-propyl-2) ethylene diamine, tris-hydroxymethyl aminomethane.
  • heterocyclic compounds to which the invention applies have the formula (III) and better still the following formula (IIIa) or the corresponding salt form (mono or disel):
  • Z, Z 'and G independently represent O or S; at least one of R 2 and R 3 represents CF 3 , OR 0 or COOR 0 with R 0 being H or an alkyl radical, linear or branched, saturated or not with CC 20 and better with C ⁇ -C 10 .
  • the subject of the invention is also a new heterocyclic compound of formula (IV) below or in the form of one of its salts, having in particular the property of inhibiting 15-PGDH and / or of preserving the quantity and / or the activity of prostaglandins in particular in the hair follicle of human beings:
  • Z, Z 'and G independently represent O or S;
  • X represents O, NH or S;
  • the heterocyclic compound has the following formula (V) or a corresponding salt:
  • Z, Z 'and G independently represent O or S; at least one of R 2 and R 3 represents phenyl, NO 2 , CF 3 , OR 0 , OR 0 , COOR 0 or a linear or branched alkyl radical, saturated with C r C 20 and better still with C r C 10 , optionally substituted by OR 0 , with
  • At least one of R 2 and R 3 represents CF 3 , ORo or COORo with R 0 being an alkyl radical, linear or branched, saturated with CC 10 and better with CC 5 .
  • at least one of R 2 and R 3 represents CF 3 or COOR 0 , with Ro being H.
  • the heterocyclic compound has the following formula (VI) or a corresponding salt form:
  • Z, Z 'and G independently represent O or S; at least one of R 2 and R 3 represents a hydrogen, CN, CF 3 , NO 2 , OR 0 , COOR 0 or a linear or branched alkyl radical, saturated with CrC 20 and better with CC 10 , optionally substituted by ORo , with R 0 equal to H or an alkyl radical, linear or branched, saturated in CC 20 and better in C ⁇ -C 10 .
  • Z, Z 'and G independently represent O or S;
  • R represents a linear or branched alkyl radical, saturated with CC 10 ;
  • at least one of R 2 and R 3 represents a linear or branched alkyl radical, saturated with C 1 -C 20 and better with CC 10 , NO 2 , ORo with R 0 equal to H or an alkyl radical, linear or branched, saturated in CC 20 and better in CC 10 .
  • the heterocyclic compound of the invention is in Z form.
  • heterocyclic compounds of formula (I) or one of their salts have the property of inducing and / or stimulating the growth of human keratin fibers and in particular hair and eyelashes and / or to curb their loss, or that these compounds can be used topically to increase the density of human keratin fibers and more especially that of hair and eyelashes.
  • the compounds of formula (I) or their salts can be produced in a known manner as described in document WO01 / 066541.
  • the compounds of formula (I) are solid at room temperature.
  • the compound of formula (I) or one of its salts or a mixture of compounds of formula (I) and / or their salts can be used in an amount representing 10 "3 % to 10% of the total weight of the composition and preferably in an amount representing from 10 " 3 % to 5% and better still from 10 "2 % to 2% of the total weight of the composition, for example 0.5 at 2%.
  • composition of the invention can be for cosmetic or pharmaceutical use.
  • the composition of the invention is for cosmetic use.
  • the composition must contain a physiologically acceptable medium which is non-toxic and capable of being applied to the skin, including the scalp and the eyelids, and on human keratin fibers.
  • cosmetic is meant within the meaning of the invention a composition of pleasant appearance, odor and feel.
  • the compound of formula (I) or one of its salts can be used orally in an amount of 0.1 to 300 mg per day, for example from 5 to 10 mg / day.
  • a preferred composition of the invention is a composition for cosmetic use and in particular for topical application to the skin and keratin fibers, and more especially to the scalp, hair and eyelashes.
  • the subject of the invention is also a composition for caring for or making up keratin fibers, in particular a composition for caring for hair or mascara, for topical application containing a physiologically acceptable medium and an effective amount of at least one compound of formula (I) or one of these salts, as described above.
  • composition can be in any known dosage form and adapted to the mode of use.
  • the composition may take the form of an aqueous, alcoholic or hydroalcoholic solution or suspension or of an oily suspension, of an emulsion of more or less fluid consistency and in particular liquid or semi- liquid, obtained by dispersing a fatty phase in an aqueous phase (O / W) or vice versa (W / O), a solid emulsion (O / W) or (W / O), an aqueous gel, hydroalcoholic or oily more or less fluid or solid, of a free or compacted powder to be used as it is or to be incorporated in a physiologically acceptable medium, or alternatively of microcapsules or microparticles, of vesicular dispersions of ionic and / or nonionic type .
  • compositions in the form of a foam or else in the form of a spray or aerosol then comprising a propellant under pressure can thus be in the form of a lotion, serum, milk, O / W or W / O cream, gel, ointment, ointment, powder, balm, patch, soaked tampon, bread, mousse.
  • the composition for application to the scalp or the hair may be in the form of a hair care lotion, for example of daily or bi-weekly application, of a shampoo or of a hair conditioner in particular. bi-weekly or weekly application, a liquid or solid soap for cleaning the scalp daily application, a product for shaping the hairstyle (hairspray, product for styling, styling gel), a treating mask, a cream or a foaming gel for cleaning the hair. It can also be in the form of a hair dye or mascara to be applied by brush or comb.
  • composition to which the invention applies can be in the form of a mascara, pigmented or not, to be applied by brush to the eyelashes or even to the hairs. beard or mustache.
  • the composition may be in the form of an aqueous lotion or an oily suspension.
  • the composition may be in the form of capsules, granules, drinkable syrups or tablets.
  • the composition according to the invention is in the form of a hair cream or lotion, hair shampoo or conditioner, hair mascara or for eyelashes.
  • compositions according to the invention are those generally used in the fields under consideration.
  • these compositions are prepared according to the usual methods.
  • the proportion of the fatty phase can range from 2% to 80% by weight, and preferably from 5% to 50% by weight relative to the total weight of the composition.
  • the aqueous phase is adjusted as a function of the content of fatty phase and of compound (s) (I) as well as that of any additional ingredients, to obtain 100% by weight. In practice, the aqueous phase represents from 5 to 99.9%.
  • the fatty phase can contain fatty or oily compounds, liquid at room temperature (25 ° C) and atmospheric pressure (760 mm Hg), generally called oils. These oils may or may not be compatible with each other and form a macroscopically homogeneous liquid fatty phase or a two- or three-phase system.
  • the fatty phase can, in addition to oils, contain waxes, gums, lipophilic polymers, "pasty” or viscous products containing solid parts and liquid parts.
  • the aqueous phase contains water and optionally an ingredient miscible in any proportion with water such as lower alcohols in d to C 8 such as ethanol, isopropanol, polyols such as propylene glycol, glycerol, sorbitol or acetone or ether.
  • water such as lower alcohols in d to C 8 such as ethanol, isopropanol, polyols such as propylene glycol, glycerol, sorbitol or acetone or ether.
  • the emulsifiers and co-emulsifiers used to obtain a composition in the form of an emulsion are those generally used in the cosmetic and pharmaceutical fields. Their nature is, moreover, a function of the direction of the emulsion.
  • the emulsifier and optionally the co-emulsifier are present in the composition in a proportion ranging from 0.1% to 30% by weight, preferably from 0.5 to 20% by weight and better still from 1 to 8%.
  • the emulsion can, in addition, contain lipid vesicles and in particular liposomes.
  • the fatty phase can represent more than 90% of the total weight of the composition.
  • the composition is an aqueous, alcoholic or hydro-alcoholic solution or suspension and better still a water / ethanol solution or suspension.
  • the alcohol fraction can represent from 5 to 99.9% and better still from 8 to 80%.
  • the composition of the invention is a wax-in-water or wax-in-oil dispersion, a gelled oil, an aqueous gel, pigmented or not.
  • composition of the invention may also comprise other ingredients usually used in the fields concerned, chosen from solvents, thickeners or gelling agents of aqueous phase or of oily phase, coloring matters soluble in the medium of the composition , solid particles of the type fillers or pigments, antioxidants, preservatives, perfumes, electrolytes, neutralizers, film-forming polymers, UN blocking agents.
  • sunscreens cosmetic and pharmaceutical active agents with beneficial action for the skin or keratin fibers, other than the compounds of formula (I), their mixtures.
  • These additives can be present in the composition according to the quantities generally used in the cosmetic and dermatological field and in particular at a rate of 0.01 to 50% of the total weight of the composition and better still from 0.1 to 20% and for example of 0 , 1 to 10%.
  • additives depending on their nature, can be introduced into the fatty phase, into the aqueous phase and / or into the lipid vesicles and in particular liposomes.
  • solvents used in the invention include lower alcohols, C 2 -C 8, such as ethanol, isopropanol, propylene glycol and certain light cosmetic oils, alkanes C 6 C ⁇ 6.
  • oils which can be used in the invention mention may be made of oils of mineral origin (petrolatum oil, hydrogenated isoparaffin), oils of vegetable origin (liquid fraction of shea butter, sunflower oil, apricot oil, alcohol or fatty acid), oils of animal origin (perhydrosqualene), synthetic oils (fatty acid ester, Purcellin oil), silicone oils (linear or cyclic polydimethylsiloxane, phenyltrimethicone) and fluorinated oils (perfluoropolyethers).
  • oils of mineral origin petrolatum oil, hydrogenated isoparaffin
  • oils of vegetable origin liquid fraction of shea butter, sunflower oil, apricot oil, alcohol or fatty acid
  • oils of animal origin perhydrosqualene
  • synthetic oils fatty acid ester, Purcellin oil
  • silicone oils linear or cyclic polydimethylsiloxane, phenyltrimethicone
  • fluorinated oils perfluoropolyethers.
  • waxes mention may be made
  • emulsifiers which can be used in the invention, mention may, for example, be made of glycerol stearate or laurate, sorbitol stearates or oleates, alkyl dimethiconecopolyol (with alkyl> 8) and their mixtures for a W / O emulsion.
  • Polyethylene glycol monostearate or monolaurate, polyoxyethylenated sorbitol stearate or oleate, dimethiconecopolyols and their mixtures can also be used for an O / W emulsion.
  • hydrophilic gelling agents which can be used in the invention, mention may be made of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays, and, as lipophilic gelling agents, mention may be made of modified clays such as Bentones, metal salts of fatty acids such as aluminum stearates, hydrophobic treated silica, ethylcellulose, their mixtures.
  • the composition can contain, in addition, a cosmetic or pharmaceutical active other than the compounds of formula (I) which can be hydrophilic, and chosen from proteins, protein hydrolysates, amino acids, polyols, urea, l 'allantoin, sugars and sugar derivatives, water-soluble vitamins, plant extracts (those of Iridaceae or soya) and hydroxy acids such as fruit acids or salicylic acid; or lipophilic and chosen from retinol (vitamin A) and its derivatives, in particular ester (retinol palmitate), tocopherol (vitamin E) and its derivatives, in particular ester (tocopherol acetate), essential fatty acids, ceramides, essential oils , salicylic acid derivatives such as n-octanoyl-5 salicylic, hydroxy acid esters, phospholipids such as lecithin, mixtures thereof.
  • a cosmetic or pharmaceutical active other than the compounds of formula (I) which can be hydrophilic, and chosen from proteins, protein
  • the compound of formula (I) or one of its salts with at least one additional active compound promoting regrowth and / or limiting the fall of keratin fibers (hair, eyelashes).
  • additional compounds are in particular chosen from lipoxygenase inhibitors as described in EP 0648488, bradykinin inhibitors described in particular in EP 0845700, prostaglandins and their derivatives in particular those described in WO 98/33497, WO 95/11003, JP 97- 100091, JP 96-134242, prostaglandin receptor agonists or antagonists, non-prostanoic prostaglandin analogs as described in EP 1175891 and EP 1175890, WO 01/74307, WO 01/74313, WO 01/74314, WO 01 / 74315 or WO 01/72268, mixtures thereof.
  • vasodilators As other additional active agents promoting the growth of keratin fibers (in particular of the hair) and / or limiting their fall which may be present in the composition according to the invention, mention may be made of vasodilators, antiandrogens, cyclosporins and their analogs, antimicrobials and antifungals, anti-inflammatories, retinoids, alone or as a mixture.
  • the vasodilators which can be used are in particular potassium channel agonists including minoxidil and the compounds described in US Pat. , alone or in combination.
  • the antiandrogens which can be used in particular include steroidal or nonsteroidal inhibitors of 5 ⁇ -reductase such as finasteride as well as the compounds described in US 5 516779, cyprosterone acetate, azelaic acid, its salts and its derivatives and the compounds described in US 5,480,913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in US Patents 5,411,981, 5,565,467 and 4,910,226.
  • steroidal or nonsteroidal inhibitors of 5 ⁇ -reductase such as finasteride as well as the compounds described in US 5 516779, cyprosterone acetate, azelaic acid, its salts and its derivatives and the compounds described in US 5,480,913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in US Patents 5,411,981, 5,56
  • the antimicrobial or antifungal compounds can be chosen from selenium derivatives, octopirox, ketoconazole, triclocarban, triclosan, pyrithione zinc, itraconazole, asian acid, hinokitiol, mipirocin, tetracyclines, in particular Perythromycin and the compounds described in EP 0680745, clinycin hydrochloride, benzoyl or benzyl peroxide, minocycline and the compounds belonging to the class of imidazoles such as econazole, ketoconazole or miconazole or their salts, nicotinic acid esters, especially including tocopheryl nicotinate, benzyl nicotinate and alkyl nicotinates C ⁇ C g such as methyl or hexyl nicotinate.
  • the anti-inflammatory drugs can be chosen from steroidal anti-inflammatory drugs such as glucocorticoids, corticosteroids (for example: hydrocortisone) and non-steroidal anti-inflammatory drugs such as glycyrrhetinic acid and ⁇ -bisabolol, benzydamine, salicylic acid and the compounds described in EP 0770399, WO 94/06434 and FR 2268523.
  • steroidal anti-inflammatory drugs such as glucocorticoids, corticosteroids (for example: hydrocortisone) and non-steroidal anti-inflammatory drugs such as glycyrrhetinic acid and ⁇ -bisabolol, benzydamine, salicylic acid and the compounds described in EP 0770399, WO 94/06434 and FR 2268523.
  • the retinoids can be chosen from isotretinoin, acitretin and tazarotene.
  • the composition according to the invention will comprise at least one 15PGDH inhibitor as defined above and at least one prostaglandin or a prostaglandin derivative such as, for example, prostaglandins of series 2, in particular PGF2- ⁇ and PGE2 in saline form or esters (example isopropyl esters), their derivatives such as 16.16 dimethyl PGE2, 17 phenyl PGE2, 16.16 dimethyl PGF2- ⁇ , 17 phenyl PGF2- ⁇ prostaglandins of series 1 such as 11 deoxy prostaglandin E1 , 1 deoxy prostaglandin E1 in saline or ester form, their analogs in particular latanoprost, travoprost, bimatoprost, fluprostenol, cloprostenol, viprostol, butaprost, misoprostol, unoprostone, their salts or their esters.
  • prostaglandin or a prostaglandin derivative such as, for example, prostaglandins
  • Step 1 K j CO g , Pd (OAc) 2 Bu 4 N + Br, H 2 0
  • the aqueous phase is acidified to pH-1-2 with an aqueous solution of hydrochloric acid: 35%.
  • the beige-pink solid formed (compound A) is filtered and then rinsed with water (3 times with 20 ml) and dried under vacuum in the presence of 1.1 g of phosphorus pentoxide.
  • the reaction yield obtained is 82%.
  • the solid is then dispersed in 100 ml of water.
  • a 2N aqueous sodium hydroxide solution is then added until the product is completely dissolved and then acidified to a pH of 1-2 with an aqueous 1N hydrochloric acid solution.
  • the brown solid formed is filtered then washed with water (2 times with 50 ml) and dried under vacuum in the presence of 0.86 g of phosphorus pentoxide. The yield is 63%.
  • test values (containing the compounds (I)) are compared to the control value (without compound (I)); the results indicated represent the concentration at which the compound (I) inhibits 50% of the enzymatic activity of 15-PGDH, noted IC 50 dh.
  • the PGF synthase enzyme is obtained as described in document FR-A-02/05067, at a concentration of 0.5 mg / ml, in suspension in an appropriate medium, and blocked at - 80 ° C. For the purposes of the test, this suspension is thawed and stored in ice.
  • a stock solution titrating 1 mM is prepared in absolute ethanol, brought to 40 ° C; the bottle is placed in an ultrasonic tank to facilitate the solubilization of the product.
  • test values (containing the compound (I)) are compared to the control value (without compound (I)), the results indicated represent the concentration at which the compound (I) inhibits the activity, enzymatic of PGFS by 50%, noted IC 50 fs.
  • This lotion is applied to the scalp, once or twice a day, at the rate of 1 ml per application, massaging the scalp lightly to make the active ingredient penetrate. The hair is then dried in the open air. This lotion reduces hair loss and promotes regrowth.
  • This lotion is applied to the scalp, once or twice a day, at the rate of 1 ml per application, massaging the scalp lightly to make the active ingredient penetrate. The hair is then dried in the open air.
  • the present study aims to evaluate the compounds of formula (I) in a cellular model. This study makes it possible to know the penetration of the active ingredient into the cytosol as well as its effectiveness as a selective inhibitor of 15-PGDH, under more complex experimental conditions than a simple reaction medium.
  • the stock solutions of molecules to be tested are at 25 mM in DiMethylSulfOxide.
  • This mascara is applied to the eyelashes like a classic mascara with a mascara brush.
  • This lotion is applied to the scalp, once or twice a day, at the rate of 1 ml per application, massaging the scalp lightly to make the active ingredient penetrate. The hair is then dried in the open air. This lotion reduces hair loss and promotes regrowth. It also improves the appearance of hair.

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EP03798227A 2002-09-27 2003-09-25 Heterocyclische verbindung zur stimulierung oder induzierung des haar- oder wimpernwachstums und/oder zur verlangsamung des haarausfalls, diese enthaltende zusammensetzung und ihre verwendungen Withdrawn EP1545708A2 (de)

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FR0212018 2002-09-27
FR0212018A FR2845000B1 (fr) 2002-09-27 2002-09-27 Utilisation d'un compose heterocyclique ou de l'un de ses sels pour stimuler ou induire la pousse des cheveux et/ou freiner leur chute
PCT/FR2003/002823 WO2004028441A2 (fr) 2002-09-27 2003-09-25 Compose heterocyclique pour stimuler ou induire la pousse des cheveux ou des cils et/ou freiner leur chute, composition le contenant, ses utilisations

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CA2515440A1 (fr) * 2003-02-12 2004-09-02 L'oreal Utilisation d'un inhibiteur de 15-hydroxy prostaglandine deshydrogenase pour favoriser la pigmentation de la peau ou des phaneres
FR2887444A1 (fr) * 2005-06-28 2006-12-29 Oreal Composes benzylidene-1,3-thiazolidine-2,4-diones, leurs utilisations et compositions pour stimuler ou induire la pousse des fibres keratiniques et/ou freiner leur chute et/ou augmenter leur densite.
FR2891543A1 (fr) * 2005-10-05 2007-04-06 Oreal Composes phenyl-furyl-methyl-thiazolidine-2,4-diones ou phenyl-thienyl-methyl-thiazolidine-2,4-diones ; utilisations pour stimuler ou induire la pousse des fibres keratiniques et/ou freiner leur chute ; compositions le contenant
US20070078175A1 (en) * 2005-10-05 2007-04-05 L'oreal Administration of novel phenylfurylmethylthiazolidine-2,4-dione and phenylthienylmethylthiazolidine-2,4-dione compounds for stimulating or inducing the growth of keratinous fibers and/or slowing loss thereof
US20080059313A1 (en) * 2006-08-30 2008-03-06 Oblong John E Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair
ES2646787T3 (es) * 2008-02-29 2017-12-18 The Procter & Gamble Company Composiciones para el cuidado del cabello y métodos para aumentar el diámetro del cabello
US20080275118A1 (en) * 2008-06-12 2008-11-06 Shaw Mari M Health and cosmetic composition and regime for stimulating hair growth and thickening on the head, including the scalp, eyelashes, and eyebrows, and which discourages hair loss
DE102009044974A1 (de) * 2009-07-23 2011-01-27 Henkel Ag & Co. Kgaa Verwendung von Dihydroquercetin und mindestens einer Aminosäure zur positiven Beeinflussung des natürlichen Pigmentierungsprozesses
AU2010336027A1 (en) * 2009-12-23 2012-07-19 Auckland Uniservices Limited Compounds, preparations and uses thereof
EP2519653A4 (de) * 2009-12-31 2013-07-10 Univ Columbia Verfahren zur detektion und regulierung von kreisrundem haarausfall und genkohorten davon
US9139575B2 (en) 2010-04-13 2015-09-22 The Regents Of The University Of California Broad spectrum antiviral and antiparasitic agents
CN105188850A (zh) 2013-05-16 2015-12-23 宝洁公司 毛发增稠组合物及使用方法
EP3057973B1 (de) 2013-10-15 2019-09-04 Case Western Reserve University Zusammensetzungen mit einem 15-pgdh-hemmer zur wundheilung
CN104306168B (zh) * 2014-10-15 2017-05-24 华东师范大学 氮‑(4‑氯‑2,5‑二甲氧基苯基)‑5‑异丙基‑2‑甲氧基苯磺酰胺在促进毛发生长的应用
CN118059093A (zh) 2015-03-08 2024-05-24 卡斯西部储备大学 用于治疗纤维症的短链脱氢酶活性的抑制剂
WO2018102552A1 (en) 2016-11-30 2018-06-07 Case Western Reserve University Combinations of 15-pgdh inhibitors with corcosteroids and/or tnf inhibitors and uses thereof
AU2018215678A1 (en) 2017-02-06 2019-08-22 Board Of Regents Of The University Of Texas System Compositions and methods of modulating short-chain dehydrogenase activity
JOP20210115A1 (ar) 2018-11-21 2023-01-30 Univ Texas تركيبات وطرق لتعديل نشاط ديهيدروجيناز بسلسلة قصيرة

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AU2003299068B2 (en) 2008-06-05
WO2004028441A2 (fr) 2004-04-08
CN1703259A (zh) 2005-11-30
FR2845000B1 (fr) 2005-05-27
JP2006518338A (ja) 2006-08-10
BR0314490A (pt) 2005-08-02
WO2004028441A3 (fr) 2004-05-06
CA2499689A1 (fr) 2004-04-08
US20080076809A1 (en) 2008-03-27
RU2005112734A (ru) 2006-02-27
US20060008436A1 (en) 2006-01-12
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US7294641B2 (en) 2007-11-13
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