EP1853352A2 - Utilisation de derives de 3-sulfanylpropanamide pour stimuler la croissance des cheveux et des cils et/ou pour arreter leur chute et/ou limiter leur depigmentation - Google Patents

Utilisation de derives de 3-sulfanylpropanamide pour stimuler la croissance des cheveux et des cils et/ou pour arreter leur chute et/ou limiter leur depigmentation

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Publication number
EP1853352A2
EP1853352A2 EP06723068A EP06723068A EP1853352A2 EP 1853352 A2 EP1853352 A2 EP 1853352A2 EP 06723068 A EP06723068 A EP 06723068A EP 06723068 A EP06723068 A EP 06723068A EP 1853352 A2 EP1853352 A2 EP 1853352A2
Authority
EP
European Patent Office
Prior art keywords
substituent
optionally substituted
nrr
group
alkyl
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Withdrawn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
EP06723068A
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German (de)
English (en)
Inventor
Philippe Breton
Christophe Boulle
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
Priority claimed from FR0550279A external-priority patent/FR2881427A1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1853352A2 publication Critical patent/EP1853352A2/fr
Withdrawn legal-status Critical Current

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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
    • A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
    • A61K31/10—Sulfides; Sulfoxides; Sulfones
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Definitions

  • 3-sulfanylpropanamide compound in a composition for promoting and/or inducing and/or stimulating the pigmentation of keratin fibres and also for limiting their depigmentation and/or bleaching.
  • the invention also relates to novel
  • the invention also relates to a cosmetic treatment process for stimulating the growth of keratin fibres and/or for stopping their loss and/or for stimulating their pigmentation and/or for limiting their depigmentation and/or bleaching .
  • the human keratin fibres to which the invention applies are especially head hair, the eyebrows, the eyelashes , beard hairs , moustache hairs and pubic hairs . More especially, the invention applies to human head hair and/or eyelashes .
  • the invention also applies to human nails .
  • the hair follicles determined by the activity of the hair follicles and of their matrix environment . Their activity is cyclical and comprises essentially three phases, namely the anagenic phase, the catagenic phase and the telogenic phase .
  • the anagenic phase (active phase or growth phase) , which lasts several years and during which the hair gets longer, is followed by a very short and transient catagenic phase that lasts a few weeks .
  • active phase or growth phase active phase or growth phase
  • transient catagenic phase that lasts a few weeks .
  • the hair undergoes a change, the follicle becomes atrophied and its dermal implantation appears higher and higher .
  • the terminal phase or telogenic phase which lasts a few months, corresponds to a resting phase of the follicle and the hair ends up by falling out . At the end of this rest period, a new follicle is regenerated in situ and another cycle begins .
  • the head of hair is thus under permanent renewal, and, out of the approximately 150 000 hairs that make up a head of hair, about 10% are at rest and will be replaced within a few months .
  • the natural loss or falling-out of the hair may be estimated, on average, as being a few hundred hairs per day for a normal physiological state .
  • This process of permanent physical renewal undergoes a natural change during ageing, the hairs become finer and their cycles shorter .
  • various causes may result in a substantial, temporary or permanent loss of hair .
  • This may be loss and impairment of hair at the terminal stage of pregnancy (post-partum) , during states of dietary malnutrition or imbalance, during physiological stress, or during states of asthenia or of hormonal dysfunction, as may be the case during or at the terminal stage of the menopause . It may also be a case of loss or impairment of the hair related to seasonal phenomena .
  • alopecia which is essentially due to a disturbance in hair renewal, resulting, in a first stage, in acceleration of the frequency of the cycles to the detriment of the quality of the hair, and then of their quantity.
  • the successive growth cycles result in hairs that are finer and finer and shorter and shorter, gradually transforming into an unpigmented down, thus resulting in a progressive impoverishment of the head of hair.
  • Certain areas are preferentially affected, especially the temporal or frontal lobes in men, and a diffuse alopecia of the crown of the head in women .
  • alopecia also covers a whole family of afflictions of hair follicles whose final consequence is the permanent, partial or general loss of the hair . This is more particularly a matter of androgenic alopecia . In a large number of cases , early loss of hair occurs in genetically predisposed individuals ; this is then a matter of androchronogenetic alopecia. This form of alopecia especially affects men . In certain dermatoses of the scalp with an inflammatory component, for instance psoriasis or seborrhoeic dermatitis, hair loss may be greatly accentuated or may result in highly disrupted follicular cycles .
  • compositions for eliminating or reducing alopecia, and especially for inducing or stimulating hair growth or reducing its loss .
  • compositions comprising very diverse active agents have already been proposed, for instance 2, 4-diamino- 6-piperidinopyrimidine 3-oxide, or "minoxidil",, described in patents US 4 139 619 and US 4 596 812 , or the numerous derivatives thereof such as those described in patent applications EP 0 353 123, EP 0 356 271 , EP 0 408 442, EP 0 522 964 , EP 0 420 707 , EP 0 459 890 and EP 0 519 819.
  • PGF2- ⁇ analogues have the property of inducing the growth of body hairs and eyelashes in man and animals (Murray A . and Johnstone M. D . , 1997 , Am . J. Opht . , 124 ( 4 ) , 544- 547) .
  • a prostaglandin E2 analogue (viprostol) has the property of increasing the hair density (Roenigk H . H. , 1988, Clinic Dermatol . , 6 (4) , 119-121) .
  • patent WO 98/33497 describes pharmaceutical compositions containing prostaglandins or prostaglandin derivatives, for combating hair loss in man .
  • Prostaglandins of the type A2, F2 ⁇ and E2 are mentioned as being preferred .
  • prostaglandins are molecules with a very short biological half-life, which act 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) .
  • 145 : 558- 568) are expressed in the hair follicle, in particular in the inner sheath, but not in the epidermis, and that type-1 cyclooxygenase, although 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 compartment that is a decisive factor in the life of the hair .
  • the Applicant has now proven the presence of type-1 15-hydroxyprostaglandin dehydrogenase (abbreviated to 15-PGDH) at this level .
  • the Applicant has also shown that the inhibition of type-1 15-PGDH has a beneficial effect on hair growth (see WO 03/090699) .
  • Type-1 15-PGDH is a key enzyme in the deactivation of prostaglandins, in particular of PGF2- ⁇ and PGE2, which are important mediators of hair growth and survival . It corresponds to the classification EC 1.1.1.141 and is NAD + -dependent . This enzyme catalyses an oxidation reaction on carbon 15 of the hydroxyl into ketone . It has been isolated from pig kidney; its inhibition with a thyroid hormone, triiodothyronine, at doses very much higher than the physiological doses, has especially been observed . Type-2 15-PGDH is itself NADP-dependent .
  • one subj ect of the present invention is the use of at least one particular 15-hydroxyprostaglandin dehydrogenase inhibitor in a composition or for the preparation of a composition for promoting the growth of human keratin fibres such as head hair and/or other bodily hairs .
  • the colour of human hair and skin depends on various factors and especially on the seasons of the year, race, sex and age . It is mainly determined by the concentration of melanin produced by the melanocytes . These melanocytes are specialized cells that synthesize melanin via particular organelles, the melanosomes . Melanin synthesis (or melanogenesis) is complex and schematically involves the following main steps :
  • Tyrosinase (monophenol dihydroxyl phenylalanine : oxygen oxidoreductase EC 1.14.18.1) participates in this sequence of reactions by especially catalysing the reaction for conversion of 45
  • the upper part of the hair follicle appears as a tubular invagination of the epidermis , which is buried just down to the deep layers of the dermis .
  • the lower part, or hair bulb itself comprises an invagination in which is found the dermal papilla .
  • the cells that result from the proliferation of these precursors migrate vertically in the bulb and become gradually keratinized in the upper part of the bulb; this assembly of keratinized cells will form the hair stem.
  • Pigmentation of the hair and of other bodily hairs requires the presence of melanocytes in the bulb of the hair follicle . These melanocytes are in an active state, i . e . they synthesize melanins (or melanin pigments) . These pigments are transferred to the keratinocytes intended to form the hair stem, which will give rise to the growth of a pigmented head hair or other bodily hair. This structure is known as a "follicular pigmentation unit" .
  • compositions containing a phosphodiesterase inhibitor (WO 95/17161) , DNA fragments (WO 95/01773) , diacylglycerol (WO 94/04122) , prostaglandins
  • one subject of the present invention is also the use of at least one particular 15-hydroxyprostaglandin dehydrogenase inhibitor in a composition or for the preparation of a composition for promoting the pigmentation of the skin or the integuments , in particular human keratin fibres such as head hair and/or other bodily hairs .
  • prostaglandins are molecules with a very short biological half-life and as a result of the local and labile nature of their metabolism (Narumiya S . et al . ) , it appears important to be able to prolong the activity of the prostaglandins involved in the pigmentation of human skin, bodily hairs and/or head hair .
  • the Applicant has shown that 15-hydroxyprostaglandin dehydrogenase is also expressed in the melanocyte of head hairs, which had never been demonstrated hitherto (see WO 04/073 594) .
  • the Applicant has demonstrated the presence of 15-PGDH in the dermal papilla and the melanocyte of head hairs, and has proposed using a 15-PGDH inhibitor to promote the pigmentation of human skin, bodily hairs and/or head hair . It is now possible to locally regulate the level of prostaglandins and especially that present in the melanocyte, in particular of head hair, by acting on the degradation catalysed both by the 15-PGDH of the melanocyte and of the fibroblast of the dermal papilla .
  • the Applicant has also shown that the melanocytes of head hairs express prostaglandin H synthase 1 (PGHS-I or COX-I, E . C : 1.14.99.1) . This demonstrates for the first time that the melanocytes of head hair have an autonomous metabolism of prostaglandins .
  • the present invention thus relates to a composition for caring for and/or treating the skin and/or keratin fibres, especially human skin and/or keratin fibres such as the hair, containing at least one particular 15-hydroxyprostaglandin dehydrogenase inhibitor especially of type 1 and a physiologically acceptable medium .
  • the term ⁇ 15-PGDH inhibitor means any substance, simple or complex compound, of natural or synthetic origin, capable of inhibiting or of reducing the activity of the enzyme 15-PGDH, and/or capable of inhibiting, reducing or slowing down the reaction catalysed by this enzyme .
  • the 15-PGDH inhibitors according to the invention are preferably type-1 15-PGDH inhibitors .
  • the inhibitor is a specific NAD-dependent type-1 15-PGDH inhibitor .
  • the present invention relates to the use, especially the cosmetic use, of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof :
  • Ri and Ra independently represent : 1) a hydrogen atom, 2) a Ci-C 2 O alkyl radical optionally substituted with at least one substituent Ai,
  • R 3 represents :
  • Ci-C 2 O alkyl radical optionally substituted with at least one substituent A 3 ,
  • Ai represents :
  • Hy 1 chosen from pyrrole, furan, dihydrofuran, tetrahydrofuran, thiophene, thiazole, oxazole, oxazolidine, isoxazole, isoxazolidine, oxadiazole, pyridine, pyran, dihydropyran, tetrahydropyran, pyrimidine, piperazine, pyridazine, pyrazine, morpholine, quinoline, isoquinoline, 2-thiohydantoin,
  • a 3 represents :
  • a 4 represents :
  • R, R' and R which may be identical or different, represent :
  • heterocycle Hy2 comprising at least one hetero atom chosen from N, S and O or a combination thereof and possibly being substituted with at least one substituent A 4 .
  • a subject of the invention is also the use, especially the cosmetic use, of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof, as defined above, as an agent for promoting and/or inducing and/or stimulating the pigmentation of the skin and/or keratin fibres, especially human skin and/or keratin fibres, and/or as an agent for preventing and/or limiting the depigmentation and/or bleaching of the skin and/or keratin fibres , especially human skin and/or keratin fibres , and, especially as an agent for preventing and/or limiting the canities of human keratin fibres .
  • a subject of the invention is also the cosmetic use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof in a care and/or makeup composition for keratin fibres, especially human keratin fibres, to induce and/or stimulate their growth, to stop their loss and/or to increase their density.
  • a subject of the invention is also the cosmetic use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof in a care and/or makeup composition for the skin and/or keratin fibres, especially human skin and/or keratin fibres, to induce and/or stimulate the pigmentation of the said skin and/or the said fibres and/or to limit their depigmentation and/or bleaching.
  • a subject of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof for the manufacture of a care or treatment composition for keratin fibres, especially human keratin fibres, which is intended to induce and/or stimulate the growth of the said fibres and/or to stop their loss and/or to increase their density.
  • a subject of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof for the manufacture of a care or treatment composition for the skin and/or keratin fibres, especially human skin and/or keratin fibres, which is intended to induce and/or stimulate the pigmentation of the skin and/or the said keratin fibres and/or to limit the depigmentation and/or bleaching of the skin and/or keratin fibres, and which is especially intended to prevent and/or limit the bleaching or canities of human keratin fibres .
  • a subject of the invention is also the cosmetic use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof in a care and/or makeup composition for keratin fibres, especially human keratin fibres, as an agent for reducing their loss and/or for increasing their density and/or for limiting their bleaching .
  • This composition also makes it possible to keep the keratin fibres in good condition and/or to improve their appearance .
  • the invention also applies to the keratin fibres of mammals of the animal species (for example dog, horse or cat) .
  • the human keratin fibres to which the invention applies are especially head hair, the eyebrows, the eyelashes, beard hairs, moustache hairs and pubic hairs, and also the nails . More especially, the invention applies to human head hair and/or eyelashes .
  • the invention also relates to the cosmetic use of at least one 3 ⁇ sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof, in a cosmetic composition for human haircare to reduce the loss of the hair and/or to increase its density and/or to treat androchronogenetic alopecia and/or to reduce its depigmentation and/or bleaching.
  • a subject of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof for the preparation of a human hair composition, which is intended to induce and/or stimulate the growth of the hair and/or to stop its loss and/or to increase its density and/or to treat androgenic alopecia and/or to induce and/or stimulate its pigmentation and/or to limit its depigmentation and/or bleaching .
  • the invention also relates to the cosmetic use of at least one 3-sulfanylpropanamide compound of formula (I ) or a salt and/or solvate thereof, in a cosmetic composition for human haircare to treat alopecia of natural origin and in particular androgenic alopecia, and also to the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof for the preparation of a human haircare composition for treating alopecia of natural origin and in particular androgenic alopecia .
  • this composition makes it possible to keep the hair in good condition and/or to combat the natural loss of the hair and more especially that of men .
  • a subject of the invention is also the cosmetic use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof, in a cosmetic composition for caring for and/or making up human eyelashes, to induce and/or stimulate the growth of the eyelashes and/or to increase their density and/or to limit their bleaching, and also to the use of at least one
  • 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof for the preparation of a composition for caring for and/or treating human eyelashes , which is intended to induce and/or stimulate the growth of the eyelashes and/or to increase their density and/or to induce and/or stimulate their pigmentation and/or to limit their depigmentation and/or bleaching.
  • This composition thus makes it possible to keep the eyelashes in good condition and/or to improve their condition and/or appearance .
  • a subj ect of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof, as an inhibitor of 15-hydroxyprostaglandin dehydrogenase, especially of type 1.
  • a subject of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I) or a salt and/or solvate thereof, for the manufacture of a composition for treating disorders associated with the activity of type-1 15-hydroxyprostaglandin dehydrogenase in particular in man .
  • a subject of the present invention is also a cosmetic process for treating human keratin fibres (especially the hair or the eyelashes) and/or the skin, in particular that from which the said fibres emerge, for instance the scalp and the eyelids, characterized in that it consists in applying to the said keratin fibres and/or the said skin a cosmetic composition comprising at least one compound of formula (I) or a salt and/or solvate thereof, leaving this composition in contact with the said keratin fibres and/or the said skin, and optionally rinsing the said fibres and/or the said skin .
  • This treatment process does indeed have the characteristics of a cosmetic process insofar as it makes it possible to improve the aesthetic appearance of human keratin fibres and especially the hair and the eyelashes and also the aesthetic appearance of the skin by giving them greater vigour and/or an improved appearance . In addition, it may be used daily for several months, without medical prescription.
  • one subject of the present invention is a cosmetic process for caring for human hair and/or the scalp, to improve their condition and/or their appearance, characterized in that it consists in applying to the hair and/or to the scalp a cosmetic composition comprising an effective amount of at least one compound of formula (I) or a salt and/or solvate thereof, leaving the composition in contact with the hair and/or the scalp, and optionally rinsing the hair and/or the scalp .
  • a subject of the invention is also a cosmetic process for caring for human skin, in order to improve its condition and/or its appearance, characterized in that it consists in applying to the said skin a cosmetic composition comprising an effective amount of at least one compound of formula (I) or a salt and/or solvate thereof, leaving the composition in contact with the said skin, and optionally rinsing it off .
  • a subject of the invention is also a cosmetic process for caring for and/or making up human eyelashes, to improve their condition and/or their appearance, characterized in that it consists in applying to the eyelashes and/or the eyelids a mascara composition comprising at least one compound of formula (I) or a salt and/or solvate thereof, and then leaving the composition in contact with the eyelashes and/or the eyelids .
  • This mascara composition may be applied alone or as a base coat for a standard pigmented mascara and may be removed like a standard pigmented mascara .
  • a subject of the invention is also the cosmetic use of a 3-sulfanylpropanamide compound of formula ( I ) or a salt and/or solvate thereof, as an agent for preserving the amount and/or the activity of the prostaglandins, especially in the hair follicles .
  • a subj ect of the invention is also the use of at least one 3-sulfanylpropanamide compound of formula (I ) or a salt and/or solvate thereof, for the manufacture of a composition for preserving the amount and/or the activity of the prostaglandins especially in the hair follicles .
  • Q represents : a) a phenyl radical substituted with at least one radical Z ; or b) an aromatic heterocycle chosen from pyrimidine, quinoline, isoquinoline, pyrrole, furan or thiophene, optionally substituted with at least one radical Z, with Z representing : fluorine , - the groups CF 3 , CN, OR, SR, NRR' , SO 2 NRR' , NRSO 2 R' , SO 2 R, SiRR' R", with R, R' and R" having the same meaning as above, - a group of formula (II) :
  • T represents : a) a saturated alkyl radical chosen from methyl, ethyl , n-butyl, isobutyl and tert-butyl; or b) a saturated C 4 -C 6 hydrocarbon-based ring:
  • a subject of the invention is also a care and/or mascara composition for the hair or the eyelashes, containing a cosmetically acceptable medium for topical application and a 3-sulfanylpropanamide compound that satisfies at least one of the formulae (III) , (IV) , (V) , (VII ) and (VIII) below, or a salt and/or solvate thereof as defined above .
  • a subject of the invention is also a care and/or makeup composition for keratin fibres, comprising, in a physiologically acceptable medium, in particular a cosmetic medium, at least one 3-sulfanylpropanamide compound that satisfies at least one of the formulae (III) , ( IV) , (V) , (VII) and (VIII) below or a salt and/or solvate thereof and at least one additional active agent that promotes the regrowth of human keratin fibres and/or that limits their loss , chosen from aminexil, FP receptor agonists, prostaglandins and derivatives thereof, and vasodilators, and more especially chosen from aminexil, minoxidil, latanoprost, (5E) -7- ⁇ (IR, 2R, 3R, 5S) -3 , 5-di- hydroxy-2- [ (3R) -3-hydroxy-5-phenylpentyl] cyclopentyl ⁇ - hept-5-eno
  • 15-hydroxyprostaglandin dehydrogenase inhibitor means a compound of formula (I) capable of inhibiting or reducing the activity of the enzyme 15-PGDH, especially of type 1 and in particular human 15-PGDH, and/or capable of inhibiting, reducing or slowing down the reaction catalysed by this enzyme .
  • the compound of formula (I) is a specific inhibitor of 15-PGDH, in particular of type 1 ;
  • the term "specific inhibitor” means an active agent that has little or no inhibitory effect on prostaglandin synthesis, in particular on the synthesis of PGF2- ⁇ or PGE2.
  • the inhibitor of 15-PGDH especially of type 1 has little or no inhibitory effect on prostaglandin synthase (abbreviated to PGF synthase or PGFS) .
  • PGF synthase is also expressed in the dermal papilla . Maintenance of an effective amount of prostaglandins at the site of action thus results from a complex biological equilibrium between the synthesis and the degradation of these molecules . The exogenous supply of compounds that inhibit catabolism will thus be less effective if this activity is combined with an inhibition of the synthesis of these prostaglandins .
  • the compounds of formula (I) in salified or non-salified, solvated or non-solvated form, have inhibitory activity on 15-PGDH that is higher than the inhibitory activity on PGF synthase, and are thus selective inhibitors .
  • the ratio between the inhibitory activities on PGF synthase and on 15-PGDH, respectively, for a given concentration, determined especially by the concentrations that inhibit 50% of the enzymatic activity of PGF synthase ( IC 50 fc) relative to the concentration that inhibits 50% of the enzymatic activity of 15-PGDH ( IC 50 dh) is at least greater than 1 and especially at least 3 : 1.
  • the compounds of formula ( I ) are in isolated form, i . e . non-polymeric form .
  • salts of a compound of formula ( I ) means the organic or mineral salts of a compound of formula ( I ) .
  • mineral salts that may be used according to the invention, mention may be made of the sodium or potassium salts and also the ammonium, zinc (Zn 2+ ) , calcium (Ca 2+ ) , copper (Cu 2+ ) , iron (Fe 2+ and Fe 3+ ) , strontium (Sr 2+ ) , magnesium (Mg 2+ ) and manganese (Mn 2+ ) salts; hydroxides, hydrohalides (for example hydrochlorides ) , carbonates , hydrogen carbonates, sulfates, hydrogen phosphates , phosphates .
  • the organic salts that may be used according to the invention are, for example, the triethanolamine, monoethanolamine, diethanolamine, hexadecylamine, N, N,N' ,N' -tetrakis (2-hydroxypropyl) ethylenediamine, tris-hydroxymethylaminomethane, hydroxide, hydrohalide, carbonate, hydrogen carbonate, citrate, lactate, glycolate, gluconate, acetate, propionate, fumarate, oxalate, tartrate, sulfate, phosphate and hydrogen phosphate salts .
  • solvates of the compounds of formula (I) mention may be made of the hydrates, alcoholates and hydroalcoholates .
  • the term "at least one" means one or more (2, 3 or more) .
  • the composition may contain one or more compounds of formula (I) .
  • This or these compound (s ) may be cis or trans or Z or E isomers or a mixture of cis/trans or Z/E isomers . They may also be in tautomeric form.
  • This or these compound (s) may be enantiomers and/or diastereoisomers or a mixture of these isomers , in particular a racemic mixture .
  • hydrocarbon-based means a group of hydrogen and carbon atoms .
  • alkyl radical means a hydrocarbon-based radical that may be linear or branched and saturated or unsaturated.
  • the alkyl radical contains from 1 to 20 and preferably from 1 to 10 carbon atoms .
  • alkyl radicals that may be used in the invention, mention may be made of methyl, ethyl, isopropyl, n-butyl, tert-butyl, n-hexyl, 2-ethylhexyl, ethylene and propylene radicals .
  • the rings C 1 to C 7 and Hy ⁇ of formula (I) contain from 3 to 7 atoms, for example 4, 5 or 6 atoms, and may be saturated or unsaturated, unless otherwise mentioned.
  • the heterocycles may contain from 1 to 4 hetero atoms, which may be identical or different, chosen from N, S and O and a combination thereof . These rings may moreover be fused to another ring of identical or different chemical nature, to form fused rings .
  • these rings may be substituted with one or more identical or different substituents, in particular A ⁇ or A 4 .
  • These rings may be linked via any atom thereof capable of forming a covalent bond with a carbon atom.
  • saturated hydrocarbon-based rings that may be used in the invention, mention may be made of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl radicals .
  • Unsaturated hydrocarbon-based rings that may be mentioned include cyclohexenyl and phenyl rings .
  • fused hydrocarbon-based rings mention may be made of aryl radicals, for instance the naphthyl ring .
  • aryl rings for instance phenyl or naphthyl rings .
  • heterocycles that may be used in the invention, in particular for the heterocycle Hy2, mention may be made of the following monoheterocycles : azetidine, pyrrole, dihydropyrrole, pyrrolidine, furan, dihydrofuran, tetrahydrofuran, thiophene, dihydrothiophene, tetrahydrothiophene, imidazole, dihydroimidazole, imidazolidine, dihydrothiazole, thiazole, dihydrothiazole, thiazolidine, pyrazole, dihydropyrazole, pyrazolidine, oxazole, dihydrooxazole, oxazolidine, isoxazole, dihydroisoxazole, isoxazolidine, isothiazole, dihydroisothiazole, isothiazolidine, triazole, dihydrotriazole, triazolidine, oxadiazole, dihydroo
  • This monoheterocycle Hy 2 may also be fused to a saturated or unsaturated hydrocarbon-based or heterocyclic ring C 7 of 4 to 7 atoms and better still of 5 to 6 atoms, which may be identical to or different from the heterocycle Hy 2 .
  • this fused ring C 7 is a heterocycle, it may contain from 1 to 4 identical or different hetero atoms chosen from O, N and S and a combination thereof .
  • fused heterocycles that may be used in the invention, mention may be made of purine and pteridine rings .
  • heterocycles fused to a hydrocarbon-based ring that may be used in the invention, mention may be made of benzofuran, benzothiophene, benzothiazole, indole, benzimidazole, quinoline, isoquinoline and quinazoline radicals .
  • one from among R 1 and R 2 represents hydrogen .
  • the 3-sulfanylpropanamide derivatives have the formula (Ia) below, or a corresponding salt and/or solvate thereof : in which R 1 and R3 have the same definitions as above .
  • Ri represents a linear or, branched, saturated or unsaturated Ci to Ci 0 alkyl radical or a saturated or unsaturated hydrocarbon-based ring, this radical or this ring being substituted with an unsaturated hydrocarbon-based or heterocyclic ring C 5 , this ring C 5 itself being optionally substituted with one or more substituents Ai, which may be identical or different, chosen in particular from: linear or branched, saturated or unsaturated Ci to Cio alkyl radicals, preferably saturated C x -C 6 alkyl radicals and more preferentially methyl and ethyl radicals; - Ci-C ⁇ alkoxy radicals , preferentially methoxy; aryl rings such as phenyl and naphthyl .
  • the (hetero) ring C 5 represents furan or phenyl .
  • this ring C 5 represents a phenyl radical, optionally substituted with a trifluoromethyl group .
  • R 3 represents a linear or branched, saturated or unsaturated Ci to Ci 0 alkyl radical or a saturated or unsaturated hydrocarbon-based ring. More preferentially, R3 is chosen from methyl, tert-butyl, cyclopentyl and cyclohexyl .
  • 3-sulfanylpropanamide compounds of formula (I) and more particularly of formula (Ia) that may be used in the invention mention may be made of the following compounds : 3- (tert-butylsulfanyl) -N- [ (5-methyl-2-furyl) methyl] - propanamide,
  • the invention relates to novel compounds corresponding to formula (I) and satisfying one of the formulae (III) , (IV) , (V) , (VII) and (VIII) below or a corresponding salt and/or solvate thereof:
  • Q represents : a) a phenyl radical substituted with at least one radical Z ; or b) an aromatic heterocycle chosen from pyrimidine, quinoline, isoquinoline, pyrrole, furan and thiophene, optionally substituted with at least one radical Z, with Z representing: fluorine,
  • T represents : a) a saturated alkyl radical chosen from methyl, ethyl, n-butyl, isobutyl and tert-butyl; or b) a saturated C 4 -C 6 hydrocarbon-based ring; 45
  • the salified or non-salified and/or solvated or non-solvated compounds of formula (I) may be manufactured according to the reaction scheme indicated below:
  • Step 2
  • the 3-sulfanyl- propanamide compounds of formula (I) or salts and/or solvates thereof have the property of inducing and/or stimulating the growth of human keratin fibres and in particular human hair and eyelashes , and/or of stopping their loss and/or of stimulating the pigmentation of the skin and/or keratin fibres and/or of limiting their pigmentation and/or bleaching, or that these compounds may be used topically to increase the density of human keratin fibres and/or to limit their bleaching and more especially to increase the density and/or bleaching of the hair and the eyelashes .
  • the effective amount of a compound of formula (I) or salts and/or solvates thereof have the property of inducing and/or stimulating the growth of human keratin fibres and in particular human hair and eyelashes , and/or of stopping their loss and/or of stimulating the pigmentation of the skin and/or keratin fibres and/or of limiting their pigmentation and/or bleaching, or that these compounds may be used
  • (I) (salified or non-salified, and solvated or non- solvated) corresponds to the amount of compound required to obtain the desired result (i . e . to increase the density of keratin fibres and especially the hair and the eyelashes or to promote their growth or reduce their bleaching) .
  • a person skilled in the art is thus capable of evaluating this effective amount, which depends on the nature of the compound used, the person on whom it is applied and the time of this application .
  • the amounts of the various ingredients in the composition are given as weight percentages relative to the total weight of the composition .
  • the compound of formula (I) (salified or non-salified, and solvated or non-solvated) or a mixture of compounds of formula (I) (salified or non- salified, and solvated or non-solvated) may be used in an amount ranging from 10 ⁇ 3 % to 10% of the total weight of the composition, preferably in an amount representing from 10 "3 % to 5% and better still from ICT 2 to 2% of the total weight of the composition, for example from 0.5% to 2% .
  • composition of the invention may be for cosmetic or pharmaceutical use .
  • the composition of the invention is preferably for cosmetic use .
  • the composition must contain a non-toxic, physiologically acceptable medium that can be applied to human skin, including the scalp and the eyelids and to keratin fibres .
  • cosmetic means a composition of pleasant appearance, odour and feel .
  • the compound of formula (I) (salified or non- salified, and solvated or non-solvated) may be used in a composition that should be ingested, injected or applied to the skin or to keratin fibres (to any area of skin or fibres to be treated) .
  • the compound of formula (I) or a mixture of compounds of formula (I) may be used orally in an amount of from 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 fibres , and more especially to the scalp, the hair and the eyelashes .
  • composition may be in any known presentation form that is suitable for the mode of use .
  • the composition may be in the form of an aqueous , alcoholic or aqueous-alcoholic solution or suspension, or an oily suspension or solution, an emulsion or dispersion of more or less fluid consistency and especially of liquid or semi-liquid consistency, obtained by dispersion of a fatty phase in an aqueous phase (O/W) or conversely (W/O) , a solid (O/W) or (W/O) emulsion or dispersion, a more or less fluid or solid aqueous, aqueous-alcoholic or oily gel, ' a free or compacted powder to be used in unmodified form or to be incorporated into a physiologically acceptable medium, or alternatively microcapsules, microparticles or vesicular dispersions of ionic and/or nonionic type .
  • the composition for application to the scalp or the hair may be in the form of a haircare lotion, for example for daily or twice- weekly application, a shampoo or a hair conditioner, in particular for twice-weekly or weekly application, a liquid or solid scalp cleansing soap for daily application, a hairstyle shaping product (lacquer, hair setting product or styling gel) , a treatment mask, a foaming gel or cream for cleansing the hair . It may also be in the form of a hair dye or mascara to be applied with a brush or a comb .
  • the composition to which the invention applies may be in the form of a pigmented or unpigmented mascara, to be applied with a brush to the eyelashes or alternatively to beard or moustache hair .
  • 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 hair lotion, a shampoo, a conditioner for the hair or a mascara for the hair or for the 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 may 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) and also of that of the optional additional ingredients , to obtain 100% by weight . In practice, the aqueous phase represents from 5% to 99.9% by weight .
  • the fatty phase may contain fatty or oily compounds that are liquid at room temperature (25 "C) and atmospheric pressure (760 mm Hg) , which are generally known as oils . These oils may be mutually compatible or incompatible and may form a macroscopically homogeneous liquid fatty phase or a two-phase or three-phase system. In addition to the oils, the fatty phase may contain waxes , gums, lipophilic polymers or "pasty" or viscous products containing solid parts and liquid parts .
  • the aqueous phase contains water and optionally an ingredient that is miscible in all proportions with water, for instance Ci to C 8 lower alcohols such as ethanol or isopropanol, polyols, for 6 001545
  • propylene glycol glycerol or sorbitol, or alternatively acetone or ether .
  • the composition may contain one or more emulsifiers optionally combined with one or more co-emulsifiers used to obtain a composition in emulsion form, these emulsifiers and co-emulsifiers being those generally used in cosmetics and pharmaceuticals . Their nature also depends on the sense of the emulsion. In practice, the emulsifier and, where appropriate, 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% by weight .
  • the emulsion may also contain microcapsules or microparticles, and vesicular dispersions and especially lipid vesicles and especially liposomes .
  • the fatty phase may represent more than 90% of the total weight of the composition .
  • the composition of the invention is an aqueous, alcoholic or aqueous-alcoholic solution or suspension and better still a water/ethanol solution or suspension .
  • the alcoholic fraction may represent from 5% to 99.9% and better still from 8% to 80% .
  • the composition of the invention is especially in the form of a wax-in- water or wax-in-oil dispersion, a gelled oil or an aqueous gel, which may be pigmented or unpigmented.
  • the composition of the invention may also comprise other additional ingredients usually used in the fields under consideration, chosen from solvents , aqueous-phase or oily-phase solvents, thickeners or gelling agents, dyes that are soluble in the medium of the composition, solid particles such as fillers or pigments, antioxidants, sequestrants , preserving agents , fragrances, electrolytes, neutralizers , film- forming polymers, UV blockers, for instance sunscreens, cosmetic and pharmaceutical active agents with a beneficial effect on the skin or keratin fibres, other than the compounds of formula (I ) , and mixtures thereof .
  • additives may be present in the composition in the amounts generally used in cosmetics and dermatology, and especially in a proportion of from 0.01% to 50% and better still from 0.1% to 20%, for example from 0.1% to 10% , relative to the total weight of the composition .
  • these additives may be introduced into the fatty phase, into the aqueous phase and/or into the lipid vesicles and especially liposomes .
  • a person skilled in the art will take care to select the optional additional ingredients and/or the amount thereof such that the advantageous properties of the composition according to the invention, i . e . the inhibition of 15-PGDH and in particular the increase in the density of keratin fibres and/or the reduction in their bleaching, are not, or are not substantially, adversely affected by the envisaged addition .
  • oils that may be used in the invention mention may be made of oils of mineral origin (liquid petroleum jelly or hydrogenated isoparaffin) , oils of plant origin (liquid fraction of shea butter, sunflower oil, apricot oil, fatty alcohol or fatty acid) , oils of animal origin (perhydrosqualene) , synthetic oils (fatty acid ester, purcellin oil) , silicone oils (linear or cyclic polydimethylsiloxane, phenyl trimethicone) and fluoro oils (perfluoropolyethers) .
  • Waxes that may be mentioned include silicone waxes , beeswax, rice wax, candelilla wax, carnauba wax, paraffin wax and polyethylene wax .
  • Polyethylene glycol monostearate or monolaurate, polyoxyethylenated sorbitol stearate or oleate, and dimethicone copolyols , and mixtures thereof may also be used for an 0/W emulsion .
  • hydrophilic gelling agents that may be used in the invention, mention may be made of carboxyvinyl polymers (carbomer) , acrylic copolymers such as acrylate/alkylacrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays , and, as lipophilic gelling agents that may be used, mention may be made of modified clays , for instance Bentones, metal salts of fatty acids , for instance aluminium stearates , hydrophobic-treated silica and ethylcellulose, and mixtures thereof .
  • hydrophilic active agents chosen from proteins or protein hydrolysates, amino acids , polyols, urea, allantoin, sugars and sugar derivatives, water-soluble vitamins , plant extracts (those from Iridacea plants or from soybean) and hydroxy acids such as fruit acids or salicylic acid; and lipophilic active agents such as retinol (vitamin A) and its derivatives, especially an ester (retinyl palmitate) , tocopherol (vitamin E) and 006/001545
  • esters especially an ester (tocopheryl acetate) , essential fatty acids , ceramides , essential oils , salicylic acid derivatives , for instance 5-n-octanoylsalicylic acid, hydroxy acid esters , and phospholipids, for instance lecithin, and mixtures thereof .
  • the compound of formula (I) may be combined with at least one additional active compound that promotes the regrowth and/or limits the loss of keratin fibres (hair or eyelashes) .
  • additional compounds are chosen especially from the lipoxygenase inhibitors as described in EP 0 648 488, the bradykinin inhibitors described especially in EP 0 845 700, prostaglandins and derivatives thereof, especially those described in WO 98/33497, WO 95/11003, JP 97-100 091 and JP 96-134 242, prostaglandin receptor agonists or antagonists, the non-prostanoic prostaglandin analogues as described in EP 1 175 891, EP 1 175 890 , WO 01/74307 , WO 01/74313, WO 01/74314, WO 01/74315 or WO 01/72268, and mixtures thereof.
  • vasodilators As other additional active compounds that promote the growth of keratin fibres and/or limit their loss, which may be present in the composition according to the invention, mention may be made of vasodilators , antiandrogens, cyclosporins and analogues thereof, antimicrobial and antifungal agents, anti-inflammatory 6 001545
  • vasodilators that may be used are especially potassium-channel agonists, including minoxidil, and also the compounds described in patents US 3 382 247, 5 756 092, 5 772 990, 5 760 043, 5 466 694, 5 438 058 and 4 973 474, cromakalim, nicorandil and diaxozide, alone or in combination .
  • the antiandrogens that may be used especially include steroidal and non-steroidal 5 ⁇ -reductase inhibitors, for instance finasteride and the compounds described in US 5 516 779, cyprosterone acetate, azelaic acid and the salts and derivatives thereof, and the compounds described in US 5 480 913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in patents US 5 411 981 , 5 565 467 and 4 910 226.
  • steroidal and non-steroidal 5 ⁇ -reductase inhibitors for instance finasteride and the compounds described in US 5 516 779, cyprosterone acetate, azelaic acid and the salts and derivatives thereof, and the compounds described in US 5 480 913, flutamide, oxendolone, spironolactone, diethylstilbestrol and the compounds described in patents US 5 411 9
  • the antimicrobial or antifungal compounds may be chosen from selenium derivatives , octopirox, triclocarban, triclosan, zinc pyrithione, itraconazole, asiatic acid, hinokitiol, mipirocine, tetracyclines, especially erythromycin and the compounds described in EP 0 680 745 , clinycin hydrochloride, benzoyl peroxide or benzyl peroxide, minocycline and compounds belonging to the imidazole class, such as econazole, ketoconazole or miconazole or salts thereof, nicotinic acid esters, especially including tocopheryl nicotinate, benzyl nicotinate and C 1 -C 6 alkyl nicotinates , for instance methyl nicotinate or hexyl nicotinate ..
  • the anti-inflammatory agents may be chosen from steroidal anti-inflammatory agents, for instance glucocorticoids , corticosteroids (for example : hydrocortisone) and non-steroidal anti-inflammatory agents, for instance glycyrrhetinic acid and ⁇ -bisabolol, benzydamine, salicylic acid and the compounds described in EP 0 770 399, WO 94/06434 and FR 2 268 523.
  • the retinoids may be chosen from isotretinoin, acitretin, tazarotene, retinal and adapalene .
  • active compounds for promoting the growth and/or limiting the loss of hair that may be used in combination with the compound of formula (I) , which may or may not be salified and may or may not be solvated, mention may be made of aminexil, diethyl 2, 4- pyridinedicarboxylate, 6-0- [ ( 9Z, 12Z) octadeca- 9, 12-dienoyl] hexapyranose, benzalkonium chloride, benzethonium chloride, phenol, oestradiol, chlorpheniramine maleate, chlorophylline derivatives , cholesterol, cysteine, methionine, menthol, peppermint oil , calcium pantothenate, panthenol, resorcinol, protein kinase C activators , glycosidase inhibitors , glycosaminoglycanase inhibitors, pyroglutamic acid esters, hexosaccharide or acylhex
  • the composition according to the invention comprises at least one 15-PGDH inhibitor as defined above and at least one prostaglandin or prostaglandin derivative, for instance the prostaglandins of series 2 especially including PGF2- ⁇ and PGE2 in salt or ester form (for example the isopropyl esters) , derivatives thereof, for instance 16, 16-dimethyl PGE2, 17-phenyl PGE2 , 16, 16-dimethyl PGF2- ⁇ , 17-phenyl PGF2 ⁇ , prostaglandins of series 1, for instance 11-deoxyprostaglandin El, 1-deoxy- prostaglandin El in salt or ester form, analogues thereof, especially latanoprost, fluprostenol, bimatoprost, cloprostenol , viprostol, butaprost, misoprostol, unoprostone, and the salts or esters thereof .
  • PGF2- ⁇ and PGE2 in salt or ester form for example the isopropyl esters
  • composition advantageously contains at least one non-prostanoic EP2 and/or EP4 receptor agonist as described especially in EP 1 175 892.
  • composition comprising at least the compound of formula (I) , salified or non-salified, solvated or non-solvated, to be encapsulated in particular in liposomal form, as described especially in document WO 94/22468.
  • the compound encapsulated may be delivered selectively to the hair follicle .
  • composition according to the invention may be applied to the areas of the skin to be treated and in particular to the alopecic areas of the scalp and the hair of an individual, or only to the white hairs , and optionally left in contact for several hours and optionally rinsed off .
  • composition containing an effective amount of a compound of formula (I) , salified or non- salified, solvated or non-solvated may, for example, be applied in the evening, kept in contact throughout the night and optionally shampooed out in the morning . These applications may be repeated daily for one or more months according to the individual .
  • a solution or composition as defined above comprising from 0.001% to 5% of 15-PGDH inhibitor, are applied to the areas of the scalp and/or the hair to be cared for or treated.
  • Examples 14 and 15 The synthesis of compounds 14 and 15 is that described in patent application EP 652 210.
  • Compound 16 may be synthesized via a synthetic method similar to that for compound 14.
  • EXAMPLE 17 Demonstration of the 15-PGDH-specific inhibitory properties of the compounds of formula (I) .
  • the enzyme 15-PGDH is obtained as described in patent application FR 02/05067 filed in the name of L' Oreal , as a suspension in a medium adjusted to a concentration of 0.3 mg/mL and then blocked at -80 0 C .
  • this suspension is thawed and stored in ice .
  • test values (containing the compounds (I) ) are compared with the control value (without compound (I) ) ; the results indicated represent the concentration at which the compound of formula (I ) reduces the enzymatic activity of 15-PGDH by 50%, namely IC 50 dh - 2) Test on PGF synthase
  • the enzyme PGFS is obtained as described in document FR-A-02/05067, at a concentration of 0.5 mg/mL, as a suspension in a suitable medium, and blocked at -80 0 C .
  • this suspension is thawed and stored in ice .
  • test values (containing compound (I) ) are compared with the control value (without compound (I) ) ; the results indicated represent the concentration at which the compound of formula ( I) reduces the enzymatic activity of PGFS by 50%, namely IC 50fS .
  • compound 5 inhibits 15-PGDH to a proportion of 21% at 100 ⁇ M.
  • compounds 1 to 8 are indeed 15-PGDH inhibitors . Furthermore, they inhibit 15-PGDH more efficiently and more selectively than PGFS : the IC 50d h is lower than the IC 5Of3 .
  • compositions below are obtained via the usual techniques commonly used in the cosmetic or pharmaceutical field.
  • a fluid is obtained that may be used as an application once or twice a day to the scalp, to reduce hair loss and/or to promote hair growth .
  • EXAMPLE 18 Hair lotion
  • This lotion is applied to the scalp, once or twice a day, at a rate of 1 mL per application .
  • This lotion makes it possible to reduce hair loss and to promote hair regrowth; it also makes it possible to repigment the hair and thus to hide the white and/or grey hairs .
  • EXAMPLE 19 Hair lotion
  • This lotion is applied to the scalp, once or twice a day, at a rate of 1 mL per application, by gently massaging the scalp to make the active agent penetrate in . The head of hair is then dried in the open air .
  • This lotion makes it possible to reduce hair loss and to promote regrowth of the hair, and also to repigment grey and/or white hairs .
  • ESg&MBL ⁇ 20 Was/water mascara
  • This mascara is applied to the eyelashes like a standard mascara with a mascara brush . It promotes the regrowth and the repigmentation of the eyelashes .
  • EXAMPLE 21 Hair lotion
  • This lotion is applied to the scalp, once or twice a day, at. a rate of 1 mL per application, by gently massaging the scalp to make the active agents penetrate in . The head of hair is then dried in the open air .
  • This lotion makes it possible to reduce hair loss and to promote regrowth of the hair while at the same time repigmenting it .

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Abstract

L'invention concerne l'utilisation d'une quantité efficace d'au moins un composé 3-sulfanylpropanamide de la formule (1) ou d'un sel et/ou un solvate de ce dernier: (1) dans laquelle: a) R1 et R2 représentent indépendamment: un atome d'hydrogène; un radical alkyle C1-C2O facultativement substitué; un noyau à base d'hydrocarbures facultativement substitué, saturé ou non saturé; b) R3 représente: un atome d'hydrogène; un radical alkyle C1-C20 facultativement substitué; un noyau à base d'hydrocarbures facultativement substitué saturé; dans une composition cosmétique destinée au soin et/ou au maquillage des fibres kératiniques, en particulier des fibres kératiniques humaines, permettant d'induire et/ou de stimuler la croissance, d'arrêter la chute et/ou d'augmenter la densité de ces dernières. L'invention porte également sur l'utilisation de nouveaux composés 3-sulfanylpropanamide et sur des compositions les contenant, qui sont destinés à augmenter la densité des fibres kératiniques et/ou à améliorer leur apparence et/ou réduire la canitie. L'invention concerne aussi un procédé de traitement cosmétique qui est destiné à stimuler la croissance des fibres kératiniques et/ou à arrêter leur chute et/ou à stimuler leur pigmentation et/ou à limiter leur dépigmentation et/ou leur blanchiment.
EP06723068A 2005-01-31 2006-01-23 Utilisation de derives de 3-sulfanylpropanamide pour stimuler la croissance des cheveux et des cils et/ou pour arreter leur chute et/ou limiter leur depigmentation Withdrawn EP1853352A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0550279A FR2881427A1 (fr) 2005-01-31 2005-01-31 Derives de 3-sulfanylpropanamide, composition les contenant et leur utilisation pour stimuler la pousse des cheveux et des cils et/ou freiner leur chute et/ou limiter leur depigmentation
US67002005P 2005-04-11 2005-04-11
PCT/EP2006/001545 WO2006079568A2 (fr) 2005-01-31 2006-01-23 Utilisation de derives de 3-sulfanylpropanamide pour stimuler la croissance des cheveux et des cils et/ou pour arreter leur chute et/ou limiter leur depigmentation

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EP1853352A2 true EP1853352A2 (fr) 2007-11-14

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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
FR2991873B1 (fr) * 2012-06-15 2014-08-29 Oreal Composition comprenant un ester d'acide pyridine dicarboxylique et un ester de glucose et d'acide gras, procede et utilisation
FR2991875B1 (fr) * 2012-06-15 2015-10-02 Oreal Composition comprenant un ester d'acide pyridine dicarboxylique et un polymere fixant, procede et utilisation

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WO2004073594A2 (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

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