WO2024250112A1 - Composés pouvant être fixés sur les tissus kératiniques - Google Patents

Composés pouvant être fixés sur les tissus kératiniques Download PDF

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Publication number
WO2024250112A1
WO2024250112A1 PCT/CA2024/050764 CA2024050764W WO2024250112A1 WO 2024250112 A1 WO2024250112 A1 WO 2024250112A1 CA 2024050764 W CA2024050764 W CA 2024050764W WO 2024250112 A1 WO2024250112 A1 WO 2024250112A1
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Prior art keywords
moiety
hair
group
ceo
compound
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PCT/CA2024/050764
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English (en)
Inventor
Christopher Caputo
Sanjay MANHAS
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BIC Inc
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BIC Inc
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Application filed by BIC Inc filed Critical BIC Inc
Priority to AU2024283922A priority Critical patent/AU2024283922A1/en
Priority to CN202480036949.9A priority patent/CN121712483A/zh
Priority to IL324870A priority patent/IL324870A/en
Priority to KR1020257043001A priority patent/KR20260020958A/ko
Priority to EP24818188.5A priority patent/EP4724035A1/fr
Publication of WO2024250112A1 publication Critical patent/WO2024250112A1/fr
Priority to MX2025014470A priority patent/MX2025014470A/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/02—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings containing insect repellants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • 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
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/94—Involves covalent bonding to the substrate

Definitions

  • This disclosure relates to compounds which can be reliably and efficiently coupled onto keratinous tissues such as hair. More specifically, the present disclosure relates to conjugated molecules comprising an active component and specifically selected anchoring moieties which cannot form extensive conjugated 7t-systems once attached to the keratinous tissue. Therefore, the coupled anchoring moiety does not impart color and allows the compounds of the present disclosure to remain visually unobtrusive after being coupled onto the tissue. The disclosure also relates to topical compositions comprising these compounds and various methods and applications for these compounds.
  • Genipin is the naturally occurring compound methyl (lR,4aS,7aS)-l-hydroxy-7- (hydroxymethyl)-l,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate (CAS RN. 6902- 77-8) and has the following structure:
  • the colorless (or nearly colorless and, thus, not visually perceivable on the hair) state of coupled hydrogenated genipin derivative can be explained by the fact that the 1,4- dihydropyridine moiety formed with lysine is not endowed with a conjugated 7t-electron system with the double bond that is present in the cyclopentene-moiety of genipin (and absent in hydrogenated genipin).
  • the Ci-Ceo moiety or polymeric moiety according to group bl) is configured to act as moisturizer, a cosmetic hair coating, or a primer for attaching dyes to the hair.
  • the Ci-Ceo moiety or polymeric moiety according to group b2) is configured to act as a moisturizer, a cosmetic hair coating or a fragrance after being cleaved off of the 3,4- dihydro-2H-pyran moiety.
  • the 3,4-dihydro-2H-pyran derivatives of the present disclosure are selected such that the formation of a conjugated 7t-electron system to the bound 1,4- dihydropyridine moiety is essentially avoided. Accordingly, the compounds of the present disclosure are restricted such that Li-Ai and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively.
  • the compound of the above formula may also be present as its tautomer and/or as a pharmaceutically acceptable salt.
  • the above compound according to the present disclosure can be expected to provide a long-lasting moisturizing effect to the hair.
  • the moisturizing effect will be given even if the pentaerythritol moiety is still attached to the hair via the 3,4-dihydro-2H-pyran moiety.
  • the moiety is an example of group bl).
  • the ester group linking the pentaerythritol moiety to the remainder of the compound is cleavable by (microbial) esterases which are abundantly found on the hair. Therefore, it is also an example of a moiety which at the same time belongs to group b2). If it is desirable that the pentaerythritol moiety belongs to only group bl) another functional group may be selected. For instance, replacing the ester linkage by an ether linkage may be contemplated.
  • the Ci-Ceo moiety or the polymeric moiety of group b) may comprise a functional group which couples the Ci-Ceo moiety or the polymeric moiety to the corresponding Li, L2 or L3 moiety or, if the corresponding Li, L2 or L3 moiety is absent, to the 3,4-dihydro-2H-pyran moiety.
  • the functional group may comprise one or more of, two or more of, three or more of, four or more of, or all of: 1 and 12 carbon atoms, more specifically between 1 and 6 carbon atoms, and in particular between 1 and 3 carbon atoms; 1 and 12 oxygen atoms, more specifically between 1 and 6 oxygen atoms, and in particular between 1 and 3 oxygen atoms; 1 and 4 nitrogen atoms, more specifically between 1 and 3 nitrogen atoms, and in particular between 1 and 2 nitrogen atoms; 1 and 3 sulfur atoms, more specifically between 1 and 2 sulfur atoms, and in particular 1 sulfur atom; 1 and 3 phosphorus atoms, more specifically between 1 and 2 phosphorus atoms, and in particular 1 phosphorus atom.
  • a suitable in-vitro test is placing 0.1 mol/L of the compound of formula (I) in aqueous solution having a pH of about 5 at 37°C for 24 hours, wherein the group in question qualifies as hydrolysable if a notable amount of the group is hydrolysed (e.g. more than 5 mol%, or more than 10 mol%).
  • the functional group may be enzymatically cleavable under physiological conditions after application of the topical composition onto hair, in particular enzymatically cleavable by enzymes present on the human hair.
  • physiological conditions it should be understood that this in particular refers to the conditions encountered at the locus where the compound of formula (I) is supposed to bind to keratinous tissues in hair of the (mammalian, in particular human) subject to be treated.
  • a suitable in-vitro test is placing 0.1 mol/L of the compound of formula (I) in aqueous solution having a pH of about 5 at 37°C for 24 hours and further containing 50 U of esterase activity, wherein the group in question qualifies as enzymatically cleavable if a notable amount of the group is cleaved (e.g. more than 5 mol-%, or more than 10 mol-%).
  • the functional group may be configured to be cleaved to a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefin or an oxime; or salts thereof.
  • the functional group may be configured to provide a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefin, or an oxime; or salts thereof; on the corresponding Li, L2 or L3 moiety which is attached to the Ci-Ceo moiety or the polymeric moiety of group b) or, if the corresponding Li, L2 or L3 moiety is absent, on the 3,4-dihydro-2H-pyran moiety after cleaving.
  • the functional group may be configured to provide a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefin, or an oxime; or salts thereof; on the Ci-Ceo moiety or the polymeric moiety of group b) after cleaving.
  • Li may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms.
  • L2 may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms.
  • L3 may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms.
  • Li may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and the functional group may be attached to Li.
  • L2 may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and the functional group may be attached to L2.
  • L3 may be present and represent an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and the functional group may be attached to L3.
  • Li and L2 may be present and form an optionally substituted 5-or 6-membered ring, in particular cyclopentyl or cyclohexyl, to which Ai and A2 may be attached, optionally via a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, -NH- C(O)-, -C(O)-NH-, -(CH2)i-4-, -(CH2)I-4-O- and -O-(CH2)i-4-, or combinations thereof.
  • the aforementioned specific groups may be part of a larger functional group, hence the reference to “combinations thereof’.
  • a carbamate may be considered as both -O- and -C(O)-NH- or a combination thereof.
  • Li and L2 may be present and form a cyclopentyl, a cyclopentenyl, a cyclohexyl, or a cyclohexenyl ring to which Ai and A2 may be attached, optionally via a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, -NH-C(O)-, -C(O)-NH-, -(CH 2 )I- 4-, -(CH2)I-4-O- and -O-(CH2)I-4-, or combinations thereof.
  • Ai may be a Ci-Ceo moiety or a polymeric moiety of group b).
  • A3 may be a Ci-Ceo moiety or a polymeric moiety of group b).
  • A2 may represent the substituent of group a), more specifically a C1-C30 moiety, H, hydroxyl, amino, or a halogen, in particular hydrogen.
  • Ai may be a Ci-Ceo moiety of group b) and A2 and A3 may represent substituents of group a), more specifically independently from each other a C1-C30 moiety, H, hydroxyl, amino, or a halogen, and in particular hydrogen.
  • the C1-C30 moiety may be selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 30, more specifically 1 to 16, and in particular 1 to 12, carbon atoms; 0 to 12, more specifically 0 to 8, and in particular 0 to 6 oxygen atoms; 0 to 8, more specifically 0 to 6, and in particular 0 to 4 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 10, more specifically 0 to 8, and in particular 0 to 6 halogen atoms; and/or the C1-C30 moiety may be bound to Li, L2 and L3, respectively, via a carbon atom, an oxygen atom, a nitrogen atom or a sulfur atom.
  • a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 30, more specifically 1 to 16, and in particular 1 to 12, carbon atoms; 0 to 12, more specifically 0 to 8, and in particular
  • A3 may represent a C1-C30 moiety of group a), more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 6, more specifically 0 to 4, and in particular 0 to 3 halogen atoms.
  • group a more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6,
  • A3 may represent a C1-C16 moiety selected from a carboxylic acid or a salt thereof; a (Ci-C4-alkyl)carboxylic ester; or a Ci-C4-alkylcarbonyl.
  • Li and OR 1 together with the carbon atoms to which they are attached, may form a 5- or 6-membered lactone.
  • Ri may represent hydrogen, C1-6 acyl, or C1-6 alkyl. In some embodiments, it may be particularly advantageous that Ri represents H. In some embodiments, it may be particularly advantageous that Ri does not represent a glucoside.
  • At least one of Ai, A2 and A3 may represent a Ci-Ceo moiety or a polymeric moiety of group b2). In some embodiments, at least one of Ai and A2 may represent a Ci-Ceo moiety of group b2).
  • the compound capable of covalently binding to hair is a compound of formula (II), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 , L3, Ai and A3 are as defined as in any preceding embodiment
  • L4 is either absent or a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, -NR 4 -, - NR 4 -C(O)-, -C(O)-NR 4 -, -(CH2)I-4-, -(CH2)I-4-O-, -O-(CH2)I-4-, or combinations thereof;
  • R 4 is selected from H or Ci-C4-alkyl.
  • A3 may represent a C1-C30 moiety of group a), more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 6, more specifically 0 to 4, and in particular 0 to 3 halogen atoms.
  • the compound capable of covalently binding to hair is a compound of formula (III), or a tautomer and/or a pharmaceutically acceptable salt thereof, wherein
  • A3 may represent a C1-C30 moiety of group a), more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 6, more specifically 0 to 4, and in particular 0 to 3 halogen atoms.
  • group a more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6,
  • R 3 represents C1-14 alkyl, C2-14 alkenylene, C2-14 alkynylene, Ce-i4 aryl, C4-14 heteroaryl comprising 1 to 4 nitrogen atoms, 1 to 3 oxygen atoms and/or 1 to 2 sulfur atoms, wherein any of the aforementioned groups is optionally further substituted with the proviso that the aforementioned total sum of the elements recited for R 3 is not exceeded. It may also be advantageous that R 3 represents an optionally substituted phenyl.
  • R 3 is substituted with one or more moieties selected from the group consisting of: -C1-4 alkyl, -O-C1-4 alkyl, -S-C1-4 alkyl, - NH-C1-4 alkyl, -N(CI- 4 alkyl) 2 , -C(O)Ci- 4 alkyl, -CO2C1-4 alkyl, -O2C-C1-4 alkyl, -C(O)NH- C1-4 alkyl, -C(O)N(CI- 4 alkyl) 2 , -NH-C(O)CI- 4 alkyl, -N(CI- 4 alkyl)-C(O)Ci- 4 alkyl, -SO3H, -NO2, -NH2, -OH, -SH, -COOH, -C(O)H, halogen, in particular Cl, Br or F; and -CF3.
  • moieties selected from the group consisting of: -C1-4 alkyl,
  • R 4 may be selected from H or Ci-C4-alkyl.
  • Ai may represent a Ci-Ceo moiety or a polymeric moiety of group b). In some embodiments of formula (IV), Ai may represent a Ci-Ceo moiety of group b).
  • R 3 is substituted with one or more moieties selected from the group consisting of: -Ci-4 alkyl, -O-Ci-4 alkyl, -S-Ci-4 alkyl, -NH-CI-4 alkyl, -N(CI-4 alkyl)2, - C(O)Ci- 4 alkyl, -CO2C1-4 alkyl, -O2C-C1-4 alkyl, -C(O)NH-CI- 4 alkyl, -C(O)N(CI- 4 alkyl) 2 , -NH-C(O)CI- 4 alkyl, -N(CI- 4 alkyl)-C(O)Ci- 4 alkyl, -SO3H, -NO 2 , -NH 2 , -OH, -SH, - COOH, -C(O)H, halogen, in particular Cl, Br or F; and -CF3.
  • moieties selected from the group consisting of: -Ci-4
  • R 3 may represent a C1-C4 alkyl moiety or phenyl.
  • R 3 represents a C1-C4 alkyl moiety or phenyl, or R 3 represents hydrogen or an optionally substituted hydrocarbon moiety comprising, in combination with their optional substituents, 1 to 14 carbon atoms;
  • R 4 is selected from H or Ci-C4-alkyl.
  • R 3 represents C1-14 alkyl, C2-14 alkenylene, C2-14 alkynylene, Ce-i4 aryl, C4-14 heteroaryl comprising 1-4 nitrogen atoms, 1-3 oxygen atoms and/or 1-2 sulfur atoms, wherein any of the aforementioned groups is optionally further substituted with the proviso that the aforementioned total sum of the elements recited for R 3 is not exceeded. It may also be advantageous that R 3 represents an optionally substituted phenyl.
  • the active components linked to the remainder of the compounds according to the invention will be discussed.
  • reference to the active ingredient will be made as if the active ingredient is an individual compound instead of a moiety attached to the remainder of the compound. It should be understood that this is to be interpretated as a reference to a moiety that is attached to the remainder of the compound, typically be elimination of a hydrogen atom from the active ingredient.
  • moisturizer is freely combinable with the above disclosure relating to the compounds according to formulae (I) to (V). Indeed, these combinations represent preferred embodiments of the present disclosure, although it should be understood that the present disclosure is not limited thereto.
  • the plurality of hydrogen bonding groups may comprise three or more, more specifically 4 or more, and in particular 6 or more hydrogen bonding groups.
  • the ratio of C-atoms to the sum of hydrogen bonding groups comprised in the Ci-Ceo moiety or the polymeric moiety may be between about 4: 1 to 1 : 1, more specifically between about 3: 1 to about 1 : 1 and in particular between about 2: 1 to about 1 : 1.
  • the moiety is a Ci-Ceo moiety, more specifically a Ci-Ceo moiety having a molecular weight of at least 60 g/mol, more specifically at least 90 g/mol, and in particular at least 120 g/mol.
  • the polymeric moiety may have a molecular weight ranging from 200 to 50000 g/mol.
  • the moiety is a polymeric moiety.
  • the ratio of C-atoms to the sum of heteroatoms comprised in the Ci- Ceo moiety or the polymeric moiety may be between about 4: 1 to 1 :2, more specifically between about 3 : 1 to about 1 : 1.5, and in particular between about 2: 1 to about 1 : 1, wherein the heteroatoms are selected from nitrogen and oxygen.
  • the Ci-Ceo moiety or the polymeric moiety may comprise: a polyol, more specifically a polyol having n hydroxyl groups with n being 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 8 or more, 10 or more, 12 or more, or 16 or more; a mono- or polyvalent carboxylic acid comprising one or more hydroxyl groups, more specifically glycolic acid, lactic acid, malic acid, tartaric acid or citric acid; a sugar, more specifically a triose, a tetrose, a pentose a hexose, a monosaccharide, a disaccharide, a tri saccharide, an oligosaccharide, or a polysaccharide, in particular glucose, mannose, galactose, glucosamine, N-acetyl-D-glucosamine, myo-Inositol, rhamnose, lyxose
  • the Ci-Ceo moiety or the polymeric moiety may comprise an amino acid or amino acid derivative, more specifically serine, glycine, alanine, histidine, ornithine, arginine, cysteine, or pyroglutamic acid.
  • the amino acid may be present in its L-enantiomer.
  • the Ci-Ceo moiety or polymeric moiety may comprise a plurality of amino acids or amino acid derivatives.
  • the Ci-Ceo moiety may have a molecular weight of 60 g/mol to 2000 g/mol, more specifically 90 g/mol to 1600 g/mol, and in particular 120 g/mol to 1200 g/mol.
  • the Ci-Ceo moiety of group b) may comprise an aliphatic Cio-Ceo moiety, more specifically a Cis-Ceo aliphatic moiety and in particular C20-C60 aliphatic moiety; or an oligo- or polysiloxane, in particular a poly(di-Ci-C4-alkyl)siloxane.
  • the polymeric moiety is a polyamine or a polymer comprising a polyamine such as PEG- 15 tallow amine.
  • the Ci-Ceo moiety or the polymeric moiety may have a molecular weight of 140 g/mol to 2000 g/mol, more specifically 160 g/mol to 1600 g/mol, and in particular 180 g/mol to 1200 g/mol.
  • the Ci-Ceo moiety or the polymeric moiety may have more than 30 carbon atoms.
  • the Ci-Ceo moiety may comprise a saturated or unsaturated Cio-Ceo aliphatic moiety, more specifically a Cis-Ceo aliphatic moiety and in particular a C20-C60 aliphatic moiety.
  • the ratio of C-atoms to the sum of heteroatoms comprised in the Ci- Ceo moiety or the polymeric moiety may be between about 60: 1 to 5: 1, more specifically between about 50: 1 to about 10: 1 and in particular between about 40: 1 to about 20: 1, wherein the heteroatoms are selected from nitrogen and oxygen.
  • the Ci-Ceo moiety may be a fatty acid, fatty alcohol or derivatives thereof, more specifically saturated or unsaturated fatty acids, fatty alcohols or derivatives thereof, and in particular caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, linoleic acid, decyl alcohol, dodecyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol or a fatty acid mono-, di- or triglyceride, in particular caprylic glyceride, capric glyceride or glyceryl stearate.
  • the Ci-Ceo moiety may be a sphingosine or a derivative thereof, in particular a ceramide or a sphingomyelin.
  • the Ci-Ceo moiety or the polymeric moiety of group b) may be configured to act as a moisturizer.
  • the Ci-Ceo moiety or the polymeric moiety of group b) may be configured to act as a moisturizer after being cleaved off of the 3,4-dihydro-2H-pyran moiety.
  • the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a moisturizer, and/or is configured to act as a moisturizer, after being cleaved off of the 3,4-dihydro-2H-pyran moiety, it may be particularly advantageous that the compound of formula (I) is a compound of any one of formulae (II), (III), (IV) or (V) as defined above. It may also be particularly advantageous that R 1 represents H.
  • the moiety of group b) which is configured to act as a moisturizer, and/or which is configured to act as a moisturizer after being cleaved off of the 3,4-dihydro-2H-pyran moiety is a Ci-Ceo moiety.
  • At least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b) which is configured to act as a cosmetic hair coating, and/or which is configured to act as a cosmetic hair coating after being cleaved off of the 3,4-dihydro-2H- pyran moiety.
  • the cosmetic hair coating is providing a conditioning effect to the hair.
  • Compounds providing a hair-conditioning effect are well-known in the art. Suitable examples include compounds/polymers having long hydrocarbon or siloxane backbones which help to lubricate the surface of the hair, thereby reducing the sensation of roughness and assisting combing.
  • Conventional conditioners often also contain quaternary cationic groups. These groups have a dual purpose: First, they help in attaching conventional conditioners to the hair. The outermost layer of a hair is rich in cysteine groups which are mildly acidic. When the hair is washed these groups can deprotonate, giving the hair a negative charge.
  • Positively charged quaternary ammonium species can then become attached to the hair via electrostatic interactions.
  • This functionality is of lesser importance for the present disclosure since the compounds attach to hair in a different manner.
  • the surface coating of cationic groups also results in the hair being repelled from each other electrostatically which reduces clumping. Accordingly, while not essential, the Ci-Ceo moiety or the polymeric moiety of group b) may also benefit from the presence of the quaternary cationic groups.
  • the cosmetic hair coating is providing a gloss effect (or shine) to the hair.
  • a gloss effect or shine
  • Compounds providing a gloss-effect or shine effect are well-known in the art. Typical examples include polymer having a high refractive index and examples (copolymers comprising polyether blocks and polysiloxane blocks) are, for instance, disclosed in European Patent Application EP 3 162408 Al which is incorporated herein in its entirety by reference thereto.
  • the cosmetic hair coating is providing a reinforcing effect to the hair.
  • a reinforcing effect it is meant that the hair is physically coated with e.g. polymer to make it thicker and that the hair is provided with a coating that improves the styling performance of the hair (much like e.g. a styling gel would).
  • Compounds providing such reinforcing effects are well-known in the art and include vinyl (co-)polymers such as polyvinyl pyrrolidone or a copolymer of dimethylaminoethylmethacrylate and polyvinyl pyrrolidone. Such (co-)polymers are capable of forming hydrogen bonds along the entire polymer chain which provides the styling effect.
  • Suitable polymers include derivatives of polyethylene glycol.
  • a reinforcing (styling) effect such as curling can also be provided by enriching the surface with moi eties provided with one or more thiols.
  • moieties include cysteine and cysteine derivatives.
  • These thiols can be oxidized to dithiols (just as in a conventional perm) with an oxidizing agent (such as an peroxide) to provide the hair with a desired shape.
  • the cosmetic hair coating is providing an anti-frizz effect to the hair.
  • a reinforcing effect it is meant that the frizziness of the hair is reduced.
  • Compounds providing an anti-frizz effect are also well-known in the art and include compounds that can act as antistatic agents. Suitable compounds are well-known in the art and in particular encompass compounds/polymers which contain quaternary cationic groups and polycarboxylic acids or polycarboxylates, in particular a polyitaconate.
  • the Ci-Ceo moiety or the polymeric moiety of group b) which is configured to act as a cosmetic hair coating, and/or which is configured to act as a cosmetic hair coating after being cleaved off of the 3,4-dihydro-2H-pyran moiety may in particular be further characterized as follows:
  • the cosmetic hair coating is providing a conditioning effect to the hair. Additionally or alternatively, the cosmetic hair coating is providing a gloss effect to the hair. Additionally or alternatively, the cosmetic hair coating is providing an anti-frizz effect to the hair. Additionally or alternatively, the cosmetic hair coating is providing a reinforcing effect to the hair.
  • the moiety of group b) is a Ci-Ceo moiety.
  • the Ci-Ceo moiety has a molecular weight of 60 g/mol to 2000 g/mol, more specifically 90 g/mol to 1600 g/mol, and in particular 120 g/mol to 1200 g/mol.
  • the Ci-Ceo moiety comprises an aliphatic Cio-Ceo moiety, more specifically a Cis-Ceo aliphatic moiety and in particular C20-C60 aliphatic moiety. In some embodiments, the Ci-Ceo moiety comprises a saturated or unsaturated Cio-Ceo aliphatic moiety, more specifically a Cis-Ceo aliphatic moiety and in particular a C20-C60 aliphatic moiety.
  • the Ci-Ceo moiety has more than 30 carbon atoms.
  • the ratio of C-atoms to the sum of heteroatoms comprised in the Ci- Ceo moiety is between about 60: 1 to 1: 1, more specifically between about 50: 1 to about 5: 1 and in particular between about 40: 1 to about 10:1, wherein the heteroatoms are selected from nitrogen and oxygen.
  • the Ci-Ceo moiety is a sphingosine or a derivative thereof, in particular a ceramide or a sphingomyelin.
  • the Ci-Ceo moiety comprises a cation, in particular a quaternary cation. In some embodiments, the Ci-Ceo moiety is positively charged. This refers to the overall charge of the moiety, i.e. the net sum of positive and negative charges.
  • the Ci-Ceo moiety comprises an anion, in particular a sulfate ion or a carboxylate ion. In some embodiments, the Ci-Ceo moiety is negatively charged. This refers to the overall charge of the moiety, i.e. the net sum of positive and negative charges.
  • the moiety of group b) is a polymeric moiety.
  • the polymeric moiety comprises a cation, in particular a quaternary cation.
  • the polymeric moiety is positively charged. This refers to the overall charge of the moiety, i.e. the net sum of positive and negative charges.
  • the polymeric moiety is a polyquaternium, in particular polyquaternium-16, polyquaternium-46, polyquaternium-11, polyquaternium-28, polyquaternium-6, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-2, polyquaternium-17, or polyquaternium-18.
  • the polymeric moiety comprises an anion, in particular a sulfate ion. In some embodiments, the polymeric moiety is negatively charged. This refers to the overall charge of the moiety, i.e. the net sum of positive and negative charges.
  • the polymeric moiety is a polycarboxylic acid or a polycarboxylate, in particular a polyitaconate.
  • the polymeric moiety comprises a polyether, more specifically a poly-(Ci-C6)ether, and in particular polymers of ethylene oxide and/or propylene oxide.
  • the polymeric moiety comprises a polymer comprising vinylpyrrolidone repeat units.
  • the polymeric moiety comprises a polysiloxane, more specifically a poly(di-Ci-C4-alkyl)siloxane and derivatives thereof.
  • the poly(di- Ci-C4-alkyl)siloxane may have between 20 and 200 repeat units.
  • the polymeric moiety is a copolymer comprising polyether blocks and polysiloxane blocks.
  • the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a cosmetic hair coating, in particular to provide a reinforcing (styling) effect, and is comprising one or more thiols, in particular one or more cysteine moieties or thiol- carrying derivatives thereof.
  • the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a cosmetic hair coating, and/or is configured to act as a cosmetic hair coating after being cleaved off of the 3,4-dihydro-2H-pyran moiety
  • the compound of formula (I) is a compound of any one of formulae (II), (III), (IV) or (V) as defined above. It may also be particularly advantageous that R 1 represents H. dyes to the hair
  • At least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b) which is configured to act as a primer for attaching dyes to the hair.
  • Hair dyes and also reactive hair dyes are well-known in the art.
  • the compounds of the present disclosure can be designed to provide chemical functionalities to the hair surface which subsequently allow the attachment of dyes and pigments or the attachment of precursors which develop to dyes and pigments after application of a developer (such as an oxidizing agent, e.g. a peroxide).
  • a developer such as an oxidizing agent, e.g. a peroxide
  • the compounds of the present disclosure are priming the hair surface for the subsequent attachment/development of color on the hair.
  • Two priming approaches are of particular relevance, namely enriching the hair with chemical groups which are naturally occurring in hair (hydroxyl, amines, sulfides, etc.) but not in sufficient number to adequately color the hair; and (additionally or alternatively) providing functional groups not naturally occurring in hair (e.g. aromatic diamines, aminophenols and resorcinol derivatives) to use their functionality to color the hair.
  • the above concept of hair dyeing may be particularly gentle to the hair, in particular since the core of the hair does not need to be made accessible to entrap the dye in the core of the hair.
  • the Ci-Ceo moiety or the polymeric moiety of group b) which is configured to act as a primer for attaching dyes to the hair may in particular be further characterized as follows:
  • At least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b) which is configured to act as a primer for attaching dyes to the hair.
  • the moiety of group b) is a Ci-Ceo moiety.
  • the Ci-Ceo moiety has a molecular weight of 60 g/mol to 2000 g/mol, more specifically 90 g/mol to 1600 g/mol, and in particular 120 g/mol to 1200 g/mol.
  • the moiety which is configured to act as a primer for attaching dyes to the hair comprises hydroxyl groups and/or amino groups, in particular aromatic hydroxyl groups and/or aromatic amino groups.
  • the moiety which is configured to act as a primer for attaching dyes to the hair is configured to react in the presence of an oxidizing agent (a developer) with a dye precursor under formation of a dye.
  • an oxidizing agent a developer
  • the dye precursor is selected from para-phenylenediamine and para-aminophenol.
  • the oxidizing agent is a peroxide, in particular hydrogen peroxide.
  • the moiety which is configured to act as a primer for attaching dyes to the hair is an aromatic moiety comprising two or more functional groups selected from hydroxyls, primary, secondary or tertiary amines, and ethers.
  • the moiety which is configured to act as a primer for attaching dyes to the hair is selected from resorcinol, m-aminophenol, 2-methyl-5-aminophenol, p- phenylenediamine, 2,4-diaminoanisole, 1,5-dihydroxynaphthalene, 4-methoxy-3- aminophenol, 2,4-diaminophenoxyethanol, m-diethylaminophenol and p-amino-o-cresol; and derivatives thereof.
  • the Ci-Ceo moiety or a polymeric moiety of group b) is configured to act as a primer for attaching dyes to the hair
  • the compound of formula (I) is a compound of any one of formulae (II), (III), (IV) or (V) as defined above. It may also be particularly advantageous that R 1 represents H.
  • At least one of Ai, A2 and A3 may be a Ci-Ceo moiety of group b) which is configured to act as a fragrance after being cleaved off of the 3,4-dihydro-2H- pyran moiety.
  • the Ci-Ceo moiety may comprise a functional group which couples the Ci-Ceo moiety to the corresponding Li, L2 or L3 moiety or, if the corresponding Li, L2 or L3 moiety is absent, to the 3,4-dihydro-2H-pyran moiety.
  • said functional group is configured to be cleaved to an aldehyde, a ketone, a thiol, a hydroxyl or an amine.
  • the functional group may be an imine, an acetal, a 1,1-diester, an enol ether, an ester, an amide, a thioester, or a thioacetal.
  • the Ci-Ceo moiety may have a molecular mass after being cleaved off of less than 400 g/mol, more specifically less than 300 g/mol, and in particular less than 200 g/mol.
  • the fragrance is not benzyl alcohol or hexanol.
  • the Ci-Ceo moiety of group b) is configured to act as a fragrance after being cleaved off of the 3,4-dihydro-2H-pyran moiety
  • the compound of formula (I) is a compound of any one of formulae (II), (III), (IV) or (V) as defined above. It may also be particularly advantageous that R 1 represents H.
  • the Ci-Ceo moiety of group b) may not comprise or be derived from salicylic acid and its derivatives.
  • the compound and/or topical composition according to formula (I) does not comprise an ester of salicylic acid. This includes both esters formed with the hydroxyl group of salicylic acid and esters formed by the carboxylic acid of salicylic acid.
  • the Ci-Ceo moiety and/or the polymeric moiety of group b) is not a color-imparting moiety, in particular not a color-imparting moiety having at least one absorption peak within the wavelength range of 380 to 790 nm.
  • the Ci-Ceo moiety and/or the polymeric moiety of group b) is not a UV-absorbing moiety, in particular not a UVA- and/or UVB- absorbing moiety, in particular not a UVA- and/or UVB-absorbing moiety having at least one absorption peak within the wavelength range of 280 to 379 nm.
  • the compound of formulae (I) to (V) is not a compound disclosed in the international application WO 2023/102652 Al, the contents of which are incorporated herein for this purpose by the reference thereto. Specifically, in some embodiments, the compound of any of formulae (I) to (V) is not a compound comprising a moiety Ai, A2 and/or A3 which is R 3 in formula (IX) of WO 2023/102652 Al.
  • the compound of any of formulae (I) to (V) is not a compound disclosed in the international application WO 2023/102652 Al, the contents of which are incorporated herein for this purpose by the reference thereto.
  • the compound of any of formulae (I) to (V) is not a compound disclosed in the international application WO 2014/155016 Al, and in particular not a compound disclosed in formulae (II) with R”i, R”2 and R”4 being as defined in the table beneath said formula and R”s representing C12H25S-.
  • the contents of WO 2014/155016 Al are incorporated herein for this purpose by the reference thereto.
  • A3 in case of A3 representing a Ci-Ceo moiety or polymeric moiety according to group b2) which is configured to act as a fragrance after being cleaved off of the 3,4-dihydro-2H-pyran moiety, A3 does not represent a benzyloxy moiety or an alkoxy moiety, in particular hexyloxy.
  • the compound of formulae (I) and (II) is not a compound in which L1-A1 represents a moiety comprising a hydroxyl group attached to a carbon atom in alphaposition to the carbon atom marked “a” in formula (I).
  • the compound of any of formulae (I) to (V) is not a compound disclosed in the US patent US 6,022,888, the contents of which are incorporated herein for this purpose by the reference thereto.
  • the compounds of the present disclosure do not comprise an epoxy group.
  • the compound of formula (I) capable of covalently binding to skin is a compound of formula (VI), or a tautomer and/or a pharmaceutically acceptable salt thereof, wherein
  • R 1 , Li, L3, Ai , A2 and A3 are as defined in any preceding embodiment, and wherein Li is in particular selected from the group consisting of -CH2-, -C(O)-, C(O)-O-, -C(O)-NH-, - C(O)-N(Ci-C4-alkyl)-, and combinations thereof.
  • the hair care composition is not particularly limited and includes any such composition for administration to hair.
  • An administration to hair in in the sense of the present disclosure refers to any local (i.e. not systemic) administration, whether through solutions, emulsions, ointments, gels, creams, lotions, or other similar formulations, of the compounds or compositions of the present disclosure, but excludes rectal, intrapulmonary and intranasal administration.
  • a cosmetic or a cosmetic use means that the composition is suitable for external use (i.e. extracorporal use, e.g. not ingested) and is in particular suitable for application to hair.
  • compositions of this disclosure may contain any one of the compounds of the present disclosure described herein in the range of 0.005wt.-% to 99wt.-% with the balance made up from the suitable excipients.
  • the contemplated compositions may contain 0.01 wt.-%- 99 wt.-% of any one of the compounds provided herein, in one embodiment 0.1-95 wt.-%, in another embodiment 75-85 wt.-%, in a further embodiment 20-80 wt.-%, wherein the balance may be made up of any excipient described herein, or any combination of these excipients.
  • the topical composition according to the present disclosure further comprises an excipient suitable for topical administration.
  • the excipient is not particularly limited.
  • the excipient suitable for topical administration comprises one or more excipients selected from water, ethanol, isopropanol, n-propanol, ethylene glycol, diethylene glycol, a propylene glycol, diethylene glycol monoethyl ether, DMSO, and glycerol.
  • the topical composition can also be a pre-dispersed composition comprising the compound of this disclosure and a liquid carrier.
  • a pre-dispersed composition comprising the compound of this disclosure and a liquid carrier.
  • These compositions can be a solution (e.g., free of any undissolved solid particles), a dispersion (e.g., containing a liquid phase and a solid precipitant phase), or an emulsion.
  • the topical composition may contain water and/or organic solvents as suitable carriers and excipients.
  • the liquid composition can be sterile and/or prepared from a sterile aqueous solution for infusion.
  • the composition may also include a surface-active agents, such as an alkylbenzene sulfonate, an alkyl sulfate, an alkyl ether sulfate, a soap, an ethoxylate, an alkyl alcohol, a lignosulfonate, or a triglyceride.
  • a surface-active agents such as an alkylbenzene sulfonate, an alkyl sulfate, an alkyl ether sulfate, a soap, an ethoxylate, an alkyl alcohol, a lignosulfonate, or a triglyceride.
  • the composition may also include a solid matrix.
  • a matrix component include a sugar, a sugar alcohol (e.g., sorbitol, mannitol, xylitol, isomalt, hydrogenated starch hydrolysates), a polymer, or a combination of two or more thereof.
  • the composition may also include a preservative, a thickening agent, a film-forming agent and/or a humectant.
  • thickening agents include starches, gums (e.g., natural and synthetic gums), cellulosics, and arabinogalactan.
  • humectants include polyhydric alcohols, for example, polyalkylene glycols (e.g., alkylene polyols and their derivatives), alpha hydroxy acids, sugars, Aloe vera gel, vegetable oil, lithium chloride, allantoin, urea, and dicyanamide.
  • film-forming agents include volatile silicone resins, polyvinylpyrrolidone, acrylates, acrylamides, copolymers, and isododecane resins.
  • the hair care formulation comprising the compound of formula (I) is storage stable (i.e., the compound of formula (I) retains its original chemical structure at greater than 95 mol.-%) for a period of time from greater than 1 month, more specifically greater than 3 months, and in particular greater than 6 months, when stored at 21 °C and 25% RH.
  • aqueous solubility of the compound of formula (I) is from about 1 g/L to about 100 g/L, from about 5 g/L to about 50 g/L, or from about 10 g/L to about 100 g/L.
  • the topical composition is not too “runny” in order to facilitate that the topical formulation is retained locally on the skin at the site of administration. Accordingly, it may be particularly advantageous that the topical composition is having a dynamic viscosity, measured at 37°C, of more than 2 mPa s, more specifically more than 10 mPa s, and in particular more than 50 mPa s, for instance, in the range of 2 mPa s to 50,000 mPa s, more specifically in the range of 10 mPa- s to 20,000 mPa- s, and in particular in the range of 50 mPa- s to 10,000 mPa- s.
  • a dynamic viscosity measured at 37°C
  • Suitable measuring methods are well-known in the art and include ASTM D-2196-20, using test method A at 30 rpm, or DINEN ISO 2555:2018-09, at 30 rpm, on a rotational viscosimeter, for instance ViscoQC 100, optionally equipped with a PTD 100 Cone-Plate for smaller sample sizes, obtainable from Anton Paar GmbH, Germany.
  • the hair care formulation is enclosed in a container.
  • the container is sealed and/or releasable after opening.
  • the container comprises a label and/or is provided with a packaging.
  • the present disclosure relates to the use of a compound of formula (I), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the compound onto hair;
  • Li, L2 and L3 independently from each other represent a linker group or is absent
  • Ai, A2 and A3 independently from each other represent a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety; at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); the Ci-Ceo moiety or the polymeric moiety of group b) is bl) configured to act as a moisturizer or a cosmetic hair coating; and/or b2) configured to act as a moisturizer, a cosmetic hair coating or a fragrance after being cleaved off of the 3,4-dihydro-2H-pyran moiety; and
  • L1-A1 and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively; for providing a cosmetic effect to hair, more specifically to provide a moisturizing effect, a conditioning effect, a gloss effect, an anti-frizz effect, and/or an olfactory effect to hair.
  • Any of the specific compounds which are disclosed for the first aspect of the present disclosure also represent specific embodiments according to this aspect of the present disclosure.
  • the present disclosure relates to a method of coloring hair, the method comprising applying a compound of formula (I), or a tautomer and/or a pharmaceutically acceptable salt thereof, to hair;
  • R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the compound onto hair;
  • Li, L2 and L3 independently from each other represent a linker group or is absent
  • Ai, A2 and A3 independently from each other represent a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety; at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a primer for attaching dyes to the hair; and
  • L1-A1 and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively; and followed by contacting the primed hair with a dye, a pigment, a precursor of a dye, or a precursor of a pigment to effect a covalent attachment of a dye or a pigment to hair.
  • kit-of-parts comprising: a first container comprising a compound of formula (I), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the compound onto hair;
  • Li, L2 and L3 independently from each other represent a linker group or is absent
  • Ai, A2 and A3 independently from each other represent a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety; at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a primer for attaching dyes to the hair; and
  • L1-A1 and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively; and a second container comprising a dye, a pigment capable of reacting with the primer such that the dye or the pigment is attached to the hair via the primer, or comprising a precursor of a dye or pigment capable of reacting with the primer such that a dye or a pigment is generated when the precursor is attached to the hair via the primer.
  • the attachment is preferably covalent.
  • the present disclosure specifically relates to the compounds of the present disclosure per se, i.e. independent from the topical composition.
  • hair refers to hair and other fibrous keratinous materials such as eyebrows and eye lashes.
  • the term “about” means “approximately” (e.g., plus or minus approximately 10% of the indicated value).
  • “about 20” means or includes amounts from 18 to and including 22.
  • substituents of compounds of the invention are disclosed in groups or in ranges. It is specifically intended that the invention include each and every individual subcombination of the members of such groups and ranges.
  • the term “Ci-6 alkyl” is specifically intended to individually disclose methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and Ce alkyl.
  • carboxy refers to a -C(O)OH group.
  • C n -m indicates a range which includes the endpoints, wherein n and m are integers and indicate the number of carbons. Examples include C1-4, C1-6, and the like.
  • C n -m alkyl employed alone or in combination with other terms, refers to a saturated hydrocarbon group that may be straight-chained or branched, having n to m carbons.
  • alkyl moieties include, but are not limited to, chemical groups such as methyl, ethyl, w-propyl, isopropyl, //-butyl, Zc/7-butyl, isobutyl, ec-butyl; higher homologs such as 2-methyl-l -butyl, //-pentyl, 3-pentyl, //-hexyl, 1,2,2-trimethylpropyl, and the like.
  • the alkyl group contains from 1 to 6 carbon atoms, more specifically from 1 to 4 carbon atoms, even more specifically from 1 to 3 carbon atoms, and in particular 1 to 2 carbon atoms.
  • C n -m acyl employed alone or in combination with other terms, refers to a saturated hydrocarbon group that may be straight-chained or branched, having n to m carbons.
  • C n -m haloalkyl refers to an alkyl group having from one halogen atom to 2s+l halogen atoms which may be the same or different, where “s” is the number of carbon atoms in the alkyl group, wherein the alkyl group has n to m carbon atoms.
  • the haloalkyl group is fluorinated only.
  • the alkyl group has 1 to 6, 1 to 4, or 1 to 3 carbon atoms.
  • C n -m alkenyl refers to an alkyl group having one or more double carboncarbon bonds and having n to m carbons.
  • Example alkenyl groups include, but are not limited to, ethenyl, w-propenyl, isopropenyl, //-butenyl, .scc-butenyl, and the like.
  • the alkenyl moiety contains 2 to 6, 2 to 4, or 2 to 3 carbon atoms.
  • C n -m alkynyl refers to an alkyl group having one or more triple carboncarbon bonds and having n to m carbons.
  • Example alkynyl groups include, but are not limited to, ethynyl, propyn-l-yl, propyn-2-yl, and the like.
  • the alkynyl moiety contains 2 to 6, 2 to 4, or 2 to 3 carbon atoms.
  • C n -m alkylene employed alone or in combination with other terms, refers to a divalent alkyl linking group having n to m carbons.
  • alkylene groups include, but are not limited to, ethan- 1,1 -diyl, ethan-l,2-diyl, propan-1,1, -diyl, propan-1, 3-diyl, propan- 1,2-diyl, butan-l,4-diyl, butan- 1,3 -diyl, butan-l,2-diyl, 2-methyl- propan-l,3-diyl, and the like.
  • the alkylene moiety contains 2 to 6, 2 to 4, 2 to 3, 1 to 6, 1 to 4, or 1 to 2 carbon atoms.
  • amino refers to a group of formula -NEh.
  • fatty in e.g. fatty acids or fatty alcohols, refers to linear-chain or branched-chain saturated, monounsaturated or polyunsaturated hydrocarbon moieties having between 8 and 34 carbon atoms.
  • fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid; linolenic acid, arachidonic acid, oleic acid and mead acid.
  • fatty alcohols include decanol, undecanol, cetylalcohol, stearyl alcohol, oleyl alcohol, myricyl alcohol, and geddyl alcohol.
  • halogen refers in particular to F, Cl, Br and I.
  • the compounds described herein can be asymmetric (e.g., having one or more stereocenters). All stereoisomers, such as enantiomers and diastereomers, are intended unless otherwise indicated.
  • Cis and trans geometric isomers of the compounds of the present invention are described and may be isolated as a mixture of isomers or as separated isomeric forms.
  • the compound has the ⁇ -configuration. In some embodiments, the compound has the ( ⁇ -configuration.
  • Tautomeric forms result from the swapping of a single bond with an adjacent double bond together with the concomitant migration of a proton.
  • Tautomeric forms include prototropic tautomers which are isomeric protonation states having the same empirical formula and total charge.
  • Example prototropic tautomers include ketone - enol pairs, amide - imidic acid pairs, lactam - lactim pairs, enamine - imine pairs, and annular forms where a proton can occupy two or more positions of a heterocyclic system, for example, 1H- and 3H-imidazole, 1H-, 2H- and 4H- 1,2,4- triazole, 1H- and 2H- isoindole, and 1H- and 2H-pyrazole.
  • Tautomeric forms can be in equilibrium or sterically locked into one form by appropriate substitution.
  • a “salt” or “pharmaceutically acceptable salt” of a compound of any one of the formulae disclosed herein is formed between an acid and a basic group of the compound, such as an amino functional group, or a base and an acidic group of the compound, such as a carboxyl functional group.
  • the compound is a pharmaceutically acceptable acid addition salt.
  • acids commonly employed to form pharmaceutically acceptable salts of the compounds of any one of the formulae include inorganic acids such as hydrogen bisulfide, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid and phosphoric acid, as well as organic acids such as para-toluenesulfonic acid, salicylic acid, tartaric acid, bitartaric acid, ascorbic acid, maleic acid, besylic acid, fumaric acid, gluconic acid, glucuronic acid, formic acid, glutamic acid, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, lactic acid, oxalic acid, para-bromophenylsulfonic acid, carbonic acid, succinic acid, citric acid, benzoic acid and acetic acid, as well as related inorganic and organic acids.
  • inorganic acids such as hydrogen bisulfide, hydrochloric acid, hydrobromic acid, hydroiodic acid
  • Such pharmaceutically acceptable salts thus include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, phosphate, monohydrogenphosphate, dihydrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, propionate, decanoate, caprylate, acrylate, formate, isobutyrate, caprate, heptanoate, propiolate, oxalate, malonate, succinate, suberate, sebacate, fumarate, maleate, butyne- 1,4-dioate, hexyne-l,6-dioate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, methoxybenzoate, phthalate, terephthalate, sulfonate, xylene sulfonate, phenyl acetate, phenyl
  • pharmaceutically acceptable acid addition salts include those formed with mineral acids such as hydrochloric acid and hydrobromic acid, and especially those formed with organic acids such as maleic acid.
  • bases commonly employed to form pharmaceutically acceptable salts of the compounds of any one of the formulae disclosed herein include hydroxides of alkali metals, including sodium, potassium, and lithium; hydroxides of alkaline earth metals such as calcium and magnesium; hydroxides of other metals, such as aluminum and zinc; ammonia, organic amines such as unsubstituted or hydroxyl-substituted mono-, di-, or trialkylamines, dicyclohexylamine; tributyl amine; pyridine; N-methyl, N-ethylamine; diethylamine; triethylamine; mono-, bis-, or tris-(2-OH-(Ci-C6)-alkylamine), such as N,N- dimethyl-N-(2-hydroxyethyl)amine or tri-(
  • the terms “individual” or “subject” are used interchangeably, and refer to any animal, including mammals, preferably mice, rats, other rodents, rabbits, dogs, cats, swine, cattle, sheep, horses, or primates, and most preferably humans.
  • protecting group and “protective group” refer to a moiety that reversibly chemically modifies a functional group in order to obtain chemoselectivity or in order to reduce degradation in one or more subsequent chemical reactions. Suitable protecting groups are well known in the art (see, e.g., Greene and Wuts, Protective Groups in Organic John Wiley & Sons, New York, N.Y 1999, which is incorporated herein by reference in its entirety).
  • color refers to wavelengths of electromagnetic radiation visible to the human eye and “colorless” refers to the absence of wavelengths of electromagnetic radiation visible to the human eye.
  • the following examples describe the synthesis of hydrogenated genipin derivatives and show the versatility and robustness of the 3,4-dihydro-2H-pyran moiety in coupling to keratinous tissues in in-vitro tests utilizing lysine.
  • the examples also demonstrate that the lysine conjugates are colorless. Some of the examples are not according to the present disclosure since they do not carry a moiety of group b). These examples serve to demonstrate that the 3,4-dihydro-2H-pyran moiety can be broadly substituted while retaining the described effects (capability to bind to hair and colorless in the bound state).
  • Genipin (methyl l-hydroxy-7-(hydroxymethyl)-l,4a,5,7a-tetrahydrocyclopenta[c]pyran- 4-carboxylate) (1 equivalent) was added to a Schlenk flask along with 10% Pd/C (10 wt. %). The flask was cycled between vacuum and nitrogen gas three times. In a separate flask, nitrogen was bubbled into methanol for 15 minutes. Once complete, methanol was added slowly (0.05 M) to the Schlenk flask under flow of nitrogen. The Schlenk flask was put under vacuum and backfilled with H2 via a balloon. The reaction was warmed to 50 °C and monitored by TLC until complete conversion of starting material. The crude reaction mixture was filtered through a pad of celite and flushed with dichloromethane. The filtered solution was concentrated and isolated by flash column chromatography as a mixture of diastereomers.
  • Step 1 synthesis of methyl l-((tert-butyldimethylsilyl)oxy)-7-(((tert-)
  • Genipin (1 equivalent) was added to an oven-dried round bottom flask along with tertbutyldimethylsilyl chloride (2.4 equivalents) and imidazole (5 equivalents). The reagents were then dissolved in dimethylformamide (0.3 M) and stirred at room temperature for 4 days. After completion, the crude reaction mixture was added to a separatory funnel with ethyl acetate and brine. Organic phase was washed with brine three times. The combined aqueous layer was extracted with ethyl acetate two times. The combined organic phase was dried with magnesium sulfate and concentrated using a rotary evaporator. The title compound was isolated via flash column chromatography using a gradient of ethyl acetate and hexane.
  • Step 2 synthesis of methyl l-((tert-butyldimethylsilyl)oxy)-7-(((tert- butyldimethylsilyl)oxy)methyl)-l, 4a, 5, 6, 7, 7a-hexahydrocyclopenta[c]pyran-4- carboxylate
  • step 1 The product of step 1 (1 equivalent) was added to a Schlenk flask along with 10% Pd/C (10 wt. %). The flask was cycled between vacuum and nitrogen gas three times. In a separate flask, nitrogen was bubbled into methanol for 15 minutes. Once complete, methanol was added slowly (0.05 M) to the Schlenk flask under flow of nitrogen. The Schlenk flask was put under vacuum and backfilled with H2 via balloon. The reaction was warmed to 50 °C and monitored by TLC until complete conversion of starting material. The crude reaction mixture was filtered through a pad of celite and flushed with dichloromethane. The filtered solution was concentrated and isolated by flash column chromatography as a mixture of diastereomers.
  • step 2 The product of step 2 (1 equivalent) was added to an oven-dried flask and dissolved in THF (0.04 M). To this was added TBAF (1 equivalent from a 1 M solution in THF), and the reaction was stirred for 1 hour. The crude reaction mixture was concentrated, and the desired compound (3) was isolated via flash column chromatography.
  • Example 3 preparation of genipin derivative compound methyl 7-formyl-l- hydroxy-l,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate (compound 6) and genipin derivative compound methyl 3-hydroxy-l,2a,2al,3,4a,7a-hexahydro-2H- 4,5-dioxacyclopenta[cd]indene-7-carboxylate (compound 7)
  • Step 1 methyl 7 -(hydroxymethyl) -1 -methoxy- 1, 4a, 5, 7a-tetrahydrocyclo- penta [ c ]pyran-4-carboxylate
  • Genipin (1 equivalent) was added to a round bottom flask and dissolved with methanol (0.05 M). Para-toluenesulfonic acid (0.3 equivalent) was added to the stirring solution of genipin and allowed to react at room temperature until complete conversion of starting material. Once complete, the crude material was concentrated using rotary evaporation and filtered through a plug of silica. The crude material was flushed with dichloromethane and concentrated. The title compound was isolated via flash column chromatography. Step 2 - methyl 7 -formyl- 1 -methoxy- 1,4a, 5, 7 a-tetr ahydrocyclopenta [c]pyran-4- carboxylate
  • Step 3 methyl 7 -formyl- 1 -methoxy- 1, 4a, 5,6, 7, 7a-hexahydrocyclopenta[c]pyran- 4-carboxylate
  • step 2 Product of step 2 (1 equivalent) was added to a Schlenk flask along with 10% Pd/C (10 wt. %). The flask was cycled between vacuum and nitrogen gas three times. In a separate flask, nitrogen was bubbled into methanol for 15 minutes. Once complete, methanol was added slowly (0.05 M) to the Schlenk flask under flow of nitrogen. The Schlenk flask was put under vacuum and backfilled with H2 via balloon. The reaction was warmed to 50 °C and monitored by TLC until complete conversion of starting material. The crude reaction mixture was filtered through a pad of celite and flushed with dichloromethane. The filtered solution was concentrated and isolated by flash column chromatography as a mixture of diastereomers (the title compound).
  • step 3 Product of step 3 was dissolved in acetic acid/1 M HC1/THF in a 3:2:5 ratio at an overall concentration of 0.07 M. The solution was stirred overnight at 60 °C. Once complete, the solution was poured into a separatory funnel with water and ethyl acetate. The combined ethyl acetate extract was dried with sodium sulfate and concentrated under reduced pressure. The desired compound (as a 15:85 mixture of aldehyde compound 6/acetal compound 7) was isolated via flash column chromatography (hexane:ethyl acetate).
  • Example 4 synthesis of l-hydroxy-4-(methoxycarbonyl)-l, 4a, 5,6,7,7a- hexahydrocyclopenta[c]pyran-7-carboxylic acid (compound 8) and methyl 3-oxo- l,2a,2al,3,4a,7a-hexahydro-2H-4,5-dioxacyclopenta[cd]indene-7-carboxylate (compound 9)
  • Step 1 - synthesis of 1 -methoxy-4-(methoxycarbonyl) ⁇ 1,4a, 5,6, 7, 7a-
  • step 3 of example 3 was dissolved in dimethylformamide (0.2 M) and stirred with 4 equivalents of potassium peroxymonosulfate for 48 hours.
  • the crude material was added to a separatory funnel with ethyl acetate and brine.
  • the combined ethyl acetate was dried with sodium sulfate and concentrated before isolation via flash column chromatography to give the title compound.
  • step 1 The product of step 1 was dissolved in acetic acid/1 M HC1/THF in a 3:2:5 ratio at an overall concentration of 0.07 M. The solution was stirred overnight at 60 °C. Once complete, the solution was poured into a separatory funnel with water and ethyl acetate. The combined ethyl acetate extract was dried with sodium sulfate and concentrated. The title compound was isolated via flash column chromatography (hexane : ethyl acetate) to give the desired compound below.
  • Step 1 synthesis of methyl 7-(hydroxymethyl)-l-methoxy-l,4a,5,6, 7, 7a-
  • step 3 of example 3 The compound obtained in step 3 of example 3 (1 equivalent) was dissolved in methanol (0.27 M) and stirred at 0 °C. To this, was added sodium borohydride (1.5 equivalents). The reaction was stirred for 30 minutes as it warmed to room temperature. Once complete, the crude reaction mixture was diluted with saturated NH4CI and extracted with ethyl acetate (3X) in a separatory funnel. The combined organic phase was dried with sodium sulfate and concentrated under reduced pressure. Title compound was isolated via flash column chromatography.
  • step 1 The compound obtained in step 1 (1 equivalent) was dissolved in dichloromethane/pyridine (1 : 1 v/v) (0.2 M) and cooled to 0 °C. 4-(phenylazo)benzoyl chloride (1.2 equivalents) was added dropwise at 0 °C and allowed to react overnight while warming to room temperature. The crude reaction mixture was quenched with saturated sodium bicarbonate and extracted in a separatory funnel with dichloromethane and water. The combined DCM layer was dried with sodium sulfate, concentrated under reduced pressure and isolated via flash column chromatography to give the title compound.
  • step 2 The product of step 2 was dissolved in acetic acid/lM HC1/THF in a 3 :2:5 ratio at an overall concentration of 0.07 M. The solution was stirred overnight at 60 °C. Once complete, the solution was poured into a separatory funnel with water and ethyl acetate. The combined ethyl acetate extract was dried with sodium sulfate and concentrated under reduced pressure. The title compound was isolated via flash column chromatography (hexane:ethyl acetate) to give the desired compound (10).
  • a hydrogenated genipin derivative (compound 1) was conjugated with lysine to obtain compound 1 -lysine conjugate:
  • Figure 3 A shows that reacting the anchor compound (2) with lysine to mimic hair binding results in strong UV-light absorption and no visible color.
  • Figure 3B shows that reacting the anchor compound (6)/(7) with lysine to mimic hair binding results in UV-light absorption and no visible color.
  • Figure 3C shows that reacting the anchor compound (8)/(9) with lysine to mimic hair binding results in UV-light absorption and no visible color.
  • Step 1 synthesis of methyl 7-(hydroxymethyl)-l-methoxy-l,4a,5,6, 7, 7a-
  • step 3 of example 3 The compound obtained in step 3 of example 3 (1 equivalent) was dissolved in methanol (0.27 M) and stirred at 0 °C. To this, was added sodium borohydride (1.5 equivalents). The reaction was stirred for 30 minutes as it warmed to room temperature. Once complete, the crude reaction mixture was diluted with saturated NH4CI and extracted with ethyl acetate (3X) in a separatory funnel. The combined organic phase was dried with sodium sulfate and concentrated under reduced pressure. Title compound was isolated via flash column chromatography.
  • step 1 The product of step 1 (1 equivalent) was dissolved in dichloromethane/pyridine (1 : 1 v/v) (0.2 M) and cooled to 0 °C. O-acetylsalicyloyl chloride (1.2 equivalents) was added dropwise at 0 °C and allowed to react overnight while warming to room temperature. The crude reaction mixture was quenched with saturated sodium bicarbonate and extracted in a separatory funnel with dichloromethane and water. The combined DCM layer was dried with sodium sulfate, concentrated under reduced pressure and isolated via flash column chromatography to give the title compound.
  • step 2 The product of step 2 was dissolved in acetic acid/1 M HC1/THF in a 3:2:5 ratio at an overall concentration of 0.07 M. The solution was stirred overnight at 60 °C. Once complete, the solution was poured into a separatory funnel with water and ethyl acetate. The combined ethyl acetate extract was dried with sodium sulfate and concentrated under reduced pressure. The title compound was isolated via flash column chromatography (hexane:ethyl acetate) to give the desired compound.
  • Example 7 The compound of Example 7 was conjugated with lysine to obtain the lysine conjugate:
  • the aldehyde obtainable as described in WO 2022/036113 Al, was weighed and transferred to a round bottom flask. To this, was added MeOH (0.2 M) and stirred until fully solubilized. DOWEX 50WX8 was first washed with methanol and dried under vacuum. Once dry, the DOWEX 50WX8 (H+ form) was added to the stirred solution of aldehyde. The reaction mixture was heated at 40 °C for 65 hours. Once complete, the methanol was removed via rotary evaporation and the product was precipitated using ether/hexane to obtain a white powder.
  • the obtained aldehyde was added to a suspension of Oxone® (potassium peroxymonosulfate; 4 equivalents) in DMF (0.2 M), and the reaction mixture was stirred at room temperature for four days.
  • the crude mixture was added to a separatory funnel with ethyl acetate and brine.
  • the aqueous layer was washed thoroughly with ethyl acetate.
  • the combined ethyl acetate layers were subsequently extracted (3x) with saturated NHCO3.
  • the combined aqueous basic layer was re-acidified with concentrated HC1 until the pH was below 7.
  • the acidified solution was then extracted with ethyl acetate (3x).
  • the combined ethyl acetate layer was dried with Na2SO4 and concentrated.
  • a rubber septum was placed on the Schlenk flask and evacuated under vacuum, then left under static vacuum.
  • a balloon was filled with H2 and equipped with an 18 G needle. The balloon was added to the reaction flask, warmed to 50 °C, and allowed to react for 24 hours. The crude reaction was carried forward to the next step without further purification.
  • the reduced ester starting material was deprotected using a mixture of HCl/acetic acid in tetrahydrofuran while heating for prolonged periods.
  • the crude reaction mixture was added to a separatory funnel and carefully quenched with a saturated solution of sodium bicarbonate and extracted with ethyl acetate.
  • the combined organic phases were dried with sodium sulfate and concentrated in vacuo.
  • the crude material was isolated via flash column chromatography using a gradient of ethyl acetate and hexanes.
  • glycerol boronic esters are a mixture of isomers and carried to the next step.
  • Step J O -benzyl protection of genipin'. benzyl 7 -(hydroxymethyl) -1-methoxy- 1, 4a, 5, 7a-tetrahydrocyclo-penta[ c ]pyran-4-carboxylate
  • Genipin (1 equivalent) was added to a round bottom flask and dissolved with benzyl alcohol/dichloromethane (1/1 v/v) (0.5 M).
  • Dowex® 50WX8 (20 wt %) was added to the stirring solution of genipin and allowed to react at 40 °C until complete conversion of starting material. Once complete, the crude material was filtered to remove the Dowex® resin and then concentrated via rotary evaporation. The title compound was isolated via flash column chromatography.
  • Step 2 Oxidation of o-benzyl protected genipin: benzyl 7 -formyl- 1-methoxy- 1, 4a, 5, 7a-tetrahydrocyclopenta[ c ]pyran-4-carboxylate
  • step 2 The product of step 2 was dissolved in dimethylformamide (0.2 M) and stirred with 4 equivalents of potassium peroxymonosulfate for 48 hours.
  • the crude material was added to a separatory funnel with ethyl acetate and washed with brine (3x). The aqueous phase was then back-extracted with ethyl acetate (3x). The combined ethyl acetate was dried with sodium sulfate and concentrated before isolation via flash column chromatography to give the title compound.
  • Step 1 Acylation of genipin carboxylate derivative
  • a balloon was filled with H2 and equipped with an 18 G needle. The balloon was added to the reaction flask, warmed to 50 °C, and allowed to react for 24 hours. The crude reaction was purified via flash column chromatography using a gradient of di chloromethane and methanol.
  • the obtained lysine conjugate was nearly colorless (very pale yellow).
  • Example 11 Conjugation of the Compound of Example 10 to skin
  • the pig skin was visually unchanged in normal daylight, but exposure to UV light revealed that the hydrogenated genipin derivatives had coupled to the skin.
  • Example 12 Preparation of a hydrogenated genipin derivative linked to D-glucose with an ethylene glycol linker and its conjugation to lysine Steps 1 and 2: Acylation of genipin carboxylate derivative:
  • Step 3 Selective deprotection of acetyl protecting groups
  • the acetyl -protected product from Step 2 was selectively deprotected by dissolving in methanol (0.2 M), and then adding 4.1 equivalents of n-hexylamine stirring for 2 h at 50 °C.
  • the resulting deprotected product was isolated via flash column chromatography using a gradient of methanol and dichloromethane.
  • Step 4 Reduction and deprotection of acylated genipin derivative
  • a balloon was filled with H2 and equipped with an 18 G needle. The balloon was added to the reaction flask, warmed to 50 °C, and allowed to react for 24 hours. The crude reaction was purified via flash column chromatography using a gradient of methanol and di chi or om ethane .
  • the obtained lysine conjugate was nearly colorless (very pale yellow).
  • a hair care composition comprising a compound capable of covalently binding to hair and an excipient suitable for administration to hair, wherein the compound capable of covalently binding to hair is a compound of formula (I), or a tautomer and/or a pharmaceutically acceptable salt thereof, wherein R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the hair care composition onto hair; wherein Li, L2 and L3 independently from each other represent a linker group or are absent, wherein Ai, A2 and A3 independently from each other represent: a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety; wherein at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); wherein the Ci-Ceo moiety or the polymeric moiety of group b) is: bl) configured to act as a moisturizer
  • Ci-Ceo moiety or the polymeric moiety of group b) comprises a functional group which couples the moiety to the corresponding Li, L2 or L3 moiety or, if the corresponding Li, L2 or L3 moiety is absent, to the 3,4-dihydro-2H-pyran moiety.
  • the hair care composition according to embodiment 2, wherein the functional group comprises a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, or a combination thereof; more specifically a carbon atom, an oxygen atom, a nitrogen atom, or a combination thereof; and in particular a carbon atom and/or an oxygen atom.
  • the hair care composition according to embodiment 3, wherein the functional group comprises one or more of, two or more of, three or more of, four or more of, or all of: 1 and 12 carbon atoms, more specifically between 1 and 6 carbon atoms, and in particular between 1 and 3 carbon atoms;
  • oxygen atoms more specifically between 1 and 6 oxygen atoms, and in particular between 1 and 3 oxygen atoms;
  • 1 and 4 nitrogen atoms more specifically between 1 and 3 nitrogen atoms, and in particular between 1 and 2 nitrogen atoms;
  • 1 and 3 sulfur atoms more specifically between 1 and 2 sulfur atoms, and in particular 1 sulfur atom;
  • 1 and 3 phosphorus atoms more specifically between 1 and 2 phosphorus atoms, and in particular 1 phosphorus atom.
  • composition according to any one of embodiments 2 to 5, wherein the functional group is hydrolysable at the physiological pH of mammal hair, more specifically of human hair, and in particular at a pH of between about 4 to about 6.
  • the functional group is configured to be cleaved to a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefin, an olefine, or an oxime; or salts thereof.
  • the hair care composition according to any one of embodiments 2 to 8, wherein the functional group is configured to provide a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefin, an olefine, or an oxime; or salts thereof; on the corresponding Li, L2 or L3 moiety which is attached to the Ci-Ceo moiety of group b) or, if the corresponding Li, L2 or L3 moiety is absent, on the 3,4-dihydro- 2H-pyran moiety after cleaving.
  • the functional group is configured to provide a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone
  • the functional group is configured to provide a hydroxyl group, a primary or secondary amine group, a carboxylic acid, a thiol, an aldehyde, a ketone, a thiocarbonic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, an olefine, or an oxime;
  • the functional group comprises a carbon ester, in particular a monoester, 1,1 -diester, a carbonate, or a carbamate; an ether or thioether, in particular an acetal, a hemi-acetal, a glycosidic group or a thioacetal; a carbon amide, in particular a peptide or a N-
  • Mannich base an enol; an enamine; an imine; an oxime; a sulfate ester; a sulfonic acid ester; a sulfonic acid amid; a phosphoric acid ester; a phosphonic acid ester; a phosphoric acid amide; or a phosphonic acid amide.
  • A3 represents a Ci-Ceo moiety or a polymeric moiety of group b).
  • the remainder of Ai, A2 and A3 represents a C1-C30 moiety, H, hydroxyl, amino, or a halogen of group a).
  • Li is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms;
  • L2 is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms;
  • L3 is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms.
  • Li is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and wherein the functional group is attached to Li;
  • L2 is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and wherein the functional group is attached to L2;
  • L3 is present and represents an optionally substituted hydrocarbon moiety comprising, in combination with its optional substituents, 1 to 8 carbon atoms and wherein the functional group is attached to L3.
  • Li and L2 are present and form an optionally substituted 5-or 6-membered ring, in particular cyclopentyl or cyclohexyl, to which Ai and A2 are attached, optionally via a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, -NH-C(O)-, -C(O)-NH-, -(CH 2 )i- 4 -, -(CH 2 )I- 4 -O- and -O- (CH 2 )I- 4 -, or combinations thereof.
  • a 2 represents a C1-C30 moiety, H, hydroxyl, amino, or a halogen of group a), in particular hydrogen.
  • a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 30, more specifically 1 to 16, and in particular 1 to 12, carbon atoms; 0 to 12,
  • A3 represents a C1-C30 moiety of group a), more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 oxygen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 6, more specifically 0 to 4, and in particular 0 to 3 halogen atoms.
  • A3 represents a C1-C30 moiety of group a), more specifically a C1-C16 moiety selected from a saturated or unsaturated, cyclic or acylic (hetero)alkyl comprising 1 to 16, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 6, more specifically 0 to 4, and in particular
  • A3 represents a C1-C16 moiety selected from a carboxylic acid or a salt thereof; a carboxylic ester; or a ketone.
  • A3 represents a C1-C16 moiety selected from a carboxylic acid or a salt thereof; a (Ci-C4-alkyl)carboxylic ester; or a Ci-C4-alkylcarbonyl.
  • R 1 represents hydrogen, C1-6 acyl, or C1-6 alkyl; and in particular hydrogen.
  • composition according to any one of embodiments 1 to 32, wherein the compound capable for covalently binding to hair is a compound of formula (II), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 , L3, Ai and A3 are as defined in any of embodiments 1 to 32; wherein (R 2 ) n represents, independently from each other, n moieties selected from H, Ci- C4 alkyl, C1-C4 alkoxyl, hydroxyl, amino, or halogen; wherein n is an integer selected from 1 and 2; and wherein L4 is either absent or a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, - NR 4 -, -NR 4 -C(O)-, -C(O)-NR 4 -, -(CH 2 )I- 4 -, -(CH 2 )I- 4 -O- and -O-(CH 2 )I- 4 -; and wherein R 4 is selected from H or Ci-C4-alkyl.
  • composition according to any one of embodiments 1 to 33, wherein the compound capable for covalently binding to hair is a compound of formula (III), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 , L3, Ai and A3 are as defined in any of embodiments 1 to 32; and wherein L4 is either absent or a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, - NR 4 -, -NR 4 -C(O)-, -C(O)-NR 4 -, -(CH 2 )I- 4 -, -(CH 2 )I- 4 -O-, -O-(CH 2 )I- 4 -, or combinations thereof; and wherein R 4 is selected from H or Ci-C4-alkyl.
  • composition according to any one of embodiments 1 to 33, wherein the compound capable for covalently binding to hair is a compound of formula (IV), or a tautomer and/or a pharmaceutically acceptable salt thereof,
  • R 1 and Ai are as defined in any of embodiments 1 to 32; wherein (R 2 ) n represents, independently from each other, n moi eties selected from H, Ci- C4 alkyl, C1-C4 alkoxyl, hydroxyl, amino, or halogen; wherein n is an integer selected from 1 and 2; wherein L4 is either absent or a group selected from: -O-, -S-, -C(O)-, -CO2-, -O-C(O)-, - NR 4 -, -NR 4 -C(O)-, -C(O)-NR 4 -, -(CH 2 )I- 4 -, -(CH 2 )I- 4 -O-, -O-(CH 2 )I- 4 -, or combinations thereof; wherein R 3 represents hydrogen or an optionally substituted hydrocarbon moiety comprising, in combination with their optional substituents, 1 to 14 carbon atoms; and wherein
  • Ai, A2 and A3 are Ci-Ceo moiety or a polymeric moiety which is configured to act as a moisturizer, and/or which is configured to act as a moisturizer after being cleaved off of the 3,4-dihydro-2H-pyran moiety.
  • Ci-Ceo moiety or the polymeric moiety comprises a plurality of hydrogen bonding groups selected from the group consisting of hydroxyl groups, ether groups, carboxylic acids, amines and amides; and their salts.
  • the hair care composition according to embodiment 38 or embodiment 39, wherein the plurality of hydrogen bonding groups comprises three or more, more specifically 4 or more, and in particular 6 or more hydrogen bonding groups.
  • the hair care composition according to embodiment 39 or embodiment 40, wherein the ratio of C-atoms to the sum of hydrogen bonding groups comprised in the Ci-Ceo moiety or the polymeric moiety is between about 4: 1 to 1:1, more specifically between about 3: 1 to about 1 : 1 and in particular between about 2: 1 to about 1 : 1.
  • Ci-Ceo moiety has a molecular weight of at least 60 g/mol, more specifically at least 90 g/mol, and in particular at least 120 g/mol.
  • the hair care composition according to any one of embodiments 38 to 43, wherein the Ci-Ceo moiety or the polymeric moiety comprises: a polyol, more specifically a polyol having n hydroxyl groups with n being 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 8 or more, 10 or more, 12 or more, or 16 or more; a mono- or polyvalent carboxylic acid comprising one or more hydroxyl groups, more specifically glycolic acid, lactic acid, malic acid, tartaric acid or citric acid; a sugar, more specifically a triose, a tetrose, a pentose a hexose, a monosaccharide, a di saccharide, a tri saccharide, or an oligosaccharide; a sugar alcohol, more specifically a sugar alcohol comprising between 2 and 24 carbon atoms, in particular ethylene glycol, glycerol, erythritol, threitol
  • Ci-Ceo moiety has a molecular weight of 60 g/mol to 2000 g/mol, more specifically 90 g/mol to 1600 g/mol, and in particular 120 g/mol to 1200 g/mol.
  • composition according to any one of embodiments 38 to 45, wherein the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a moisturizer.
  • Ai, A2 and A3 are Ci-Ceo moiety or a polymeric moiety of group b) which is configured to act as a cosmetic hair coating, and/or which is configured to act as a cosmetic hair coating after being cleaved off of the 3,4-dihydro-2H-pyran moiety.
  • the cosmetic hair coating is providing a conditioning effect to the hair.
  • Ci-Ceo moiety has a molecular weight of 60 g/mol to 2000 g/mol, more specifically 90 g/mol to 1600 g/mol, and in particular 120 g/mol to 1200 g/mol.
  • Ci-Ceo moiety comprises an aliphatic Cio-Ceo moiety, more specifically a Cis-Ceo aliphatic moiety and in particular C20-C60 aliphatic moiety.
  • Ci-Ceo moiety comprises a saturated or unsaturated Cio-Ceo aliphatic moiety, more specifically a Cis-Ceo aliphatic moiety and in particular a C20-C60 aliphatic moiety.
  • Ci-Ceo moiety has more than 30 carbon atoms.
  • the hair care composition according to any one of embodiments 48 to 57, wherein the ratio of C-atoms to the sum of heteroatoms comprised in the Ci-Ceo moiety is between about 60: 1 to 1 : 1, more specifically between about 50: 1 to about 5: 1 and in particular between about 40: 1 to about 10: 1, wherein the heteroatoms are selected from nitrogen and oxygen.
  • Ci-Ceo moiety is a sphingosine or a derivative thereof, in particular a ceramide or a sphingomyelin.
  • Ci-Ceo moiety comprises a cation, in particular a quaternary cation.
  • Ci-Ceo moiety comprises an anion, in particular a sulfate ion or a carboxylate ion.
  • the hair care composition according to embodiment 65 or embodiment 66, wherein the polymeric moiety is a polyquaternium, in particular polyquaternium-16, polyquaternium-46, polyquaternium-11, polyquaternium-28, polyquaternium-6, polyquaternium-7, polyquaternium-22, polyquaternium-39, polyquaternium-2, polyquaternium- 17, or polyquaternium- 18.
  • composition according to embodiment 69 wherein the polymeric moiety is a polycarboxylic acid or a polycarboxylate, in particular a polyitaconate.
  • the hair care composition according to embodiment 64, wherein the polymeric moiety comprises a polyether, more specifically a poly-(Ci-C6)ether, and in particular polymers of ethylene oxide and/or propylene oxide.
  • composition according to embodiment 64 wherein the polymeric moiety comprises a polysiloxane, more specifically a poly(di-Ci-C4-alkyl)siloxane and derivatives thereof.
  • the hair care composition according to embodiment 79 wherein the moiety which is configured to act as a primer for attaching dyes to the hair is selected from resorcinol, m-aminophenol, 2-methyl-5-aminophenol, p-phenylenediamine, 2,4-diaminoanisole, 1,5- dihydroxynaphthalene, 4-methoxy-3-aminophenol, 2,4-diaminophenoxyethanol, m- diethylaminophenol and p-amino-o-cresol; and derivatives thereof.
  • the dye precursor is selected from para-phenylenediamine and para-aminophenol.
  • the hair care composition according to embodiment 84 wherein the functional group is an imine, an acetal, a 1,1-diester, an enolether, an ester, an amide, a thioester, or a thioacetal.
  • R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the compound onto hair;
  • Li, L2 and L3 independently from each other represent a linker group or is absent
  • Ai, A2 and A3 independently from each other represent a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety ; at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); the Ci-Ceo moiety or the polymeric moiety of group b) is bl) configured to act as a moisturizer or a cosmetic hair coating; and/or b2) configured to act as a moisturizer, a cosmetic hair coating or a fragrance after being cleaved off of the 3,4-dihydro-2H-pyran moiety; and
  • L1-A1 and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively; for providing a cosmetic effect to hair, more specifically to provide a moisturizing effect, a conditioning effect, a gloss effect, an anti-frizz effect, and/or an olfactory effect to hair.
  • Method of coloring hair comprising applying a compound of formula (I), or a tautomer and/or a pharmaceutically acceptable salt thereof, to hair; wherein
  • R 1 represents hydrogen or a protective group hydrolysable under physiological conditions after application of the compound onto hair;
  • Li, L2 and L3 independently from each other represent a linker group or is absent
  • Ai, A2 and A3 independently from each other represent a) a C1-C30 moiety, H, hydroxyl, amino, or a halogen, or b) a Ci-Ceo moiety or a polymeric moiety; at least one of Ai, A2 and A3 is a Ci-Ceo moiety or a polymeric moiety of group b); the Ci-Ceo moiety or the polymeric moiety of group b) is configured to act as a primer for attaching dyes to the hair; and
  • L1-A1 and L2-A2 do not represent a moiety comprising an unsaturated C-C or C-N bond in alpha-position to the carbon atom marked “a” and “b”, respectively; and followed by contacting the primed hair with a dye, a pigment, a precursor of a dye, or a precursor of a pigment to effect a covalent attachment of a dye or a pigment to hair.
  • R 3 represents a C1-C14 moiety comprising 1 to 14, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 12, more specifically 0 to 8, and in particular 0 to 6 oxygen atoms; 0 to 8, more specifically 0 to 6, and in particular 0 to 4 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 10, more specifically 0 to 8, and in particular 0 to 6 halogen atoms.
  • R 3 represents a C1-C14 moiety comprising 1 to 14, more specifically 1 to 12, and in particular 1 to 8, carbon atoms; 0 to 12, more specifically 0 to 8, and in particular 0 to 6 oxygen atoms; 0 to 8, more specifically 0 to 6, and in particular 0 to 4 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 10, more specifically 0 to 8, and in particular 0 to 6 halogen atoms.
  • R 3 represents C1-14 alkyl, C2-14 alkenylene, C2-14 alkynylene, Ce-i4 aryl, C4-14 heteroaryl comprising 1-4 nitrogen atoms, 1-3 oxygen atoms and/or 1-2 sulfur atoms, wherein any of the aforementioned groups is optionally further substituted with the proviso that the aforementioned total sum of the elements recited for R 3 is not exceeded.
  • R 3 represents an optionally substituted phenyl, in particular an optionally substituted phenyl, in particular an optionally substituted phenyl comprising 6 to 14, more specifically 6 to 12, and in particular 6 to 10, carbon atoms; 0 to 12, more specifically 0 to 8, and in particular 0 to 6 oxygen atoms; 0 to 8, more specifically 0 to 6, and in particular 0 to 4 nitrogen atoms; 0 to 6, more specifically 0 to 4, and in particular 0 to 3 sulfur atoms; and 0 to 10, more specifically 0 to 8, and in particular 0 to 6 halogen atoms.

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Abstract

La présente divulgation concerne une composition de soin capillaire comprenant un composé pouvant se lier de manière covalente aux cheveux et un excipient approprié en vue d'une administration aux cheveux, le composé pouvant se lier de manière covalente à la peau étant un composé de formule (I) ou un tautomère et/ou un sel pharmaceutiquement acceptable de celui-ci, R1 représentant l'hydrogène ou un groupe protecteur hydrolysable dans des conditions physiologiques après application de la composition capillaire sur les cheveux ; L1, L2 et L3 représentant indépendamment l'un de l'autre un groupe lieur ou étant absents, A1, A2 et A3 représentant indépendamment l'un de l'autre : a) une fraction en C1-C30, H, un hydroxyle, un amino ou un halogène ou b) une fraction en C1-C60 ou une fraction polymère ; au moins l'un de A1, A2 et A3 étant une fraction en C1-C60 ou une fraction polymère du groupe b) ; la fraction en C1-C60 ou la fraction polymère du groupe b) étant : b1) conçue pour agir en tant qu'agent hydratant, revêtement cosmétique pour les cheveux ou amorce pour la fixation de colorants sur les cheveux ; et/ou b2) conçue pour agir en tant qu'agent hydratant, revêtement cosmétique pour les cheveux ou parfum après clivage de la fraction 3,4-dihydro-2H-pyrane ; et L1-A1 et L2-A2 ne représentant pas une fraction comprenant une liaison C-C ou C-N insaturée en position alpha par rapport à l'atome de carbone marqué "a" et "b", respectivement.
PCT/CA2024/050764 2023-06-07 2024-06-07 Composés pouvant être fixés sur les tissus kératiniques Ceased WO2024250112A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2024283922A AU2024283922A1 (en) 2023-06-07 2024-06-07 Compounds attachable to keratinous tissues
CN202480036949.9A CN121712483A (zh) 2023-06-07 2024-06-07 可附着到角质组织的化合物
IL324870A IL324870A (en) 2023-06-07 2024-06-07 Compounds that can be attached to keratinous tissues
KR1020257043001A KR20260020958A (ko) 2023-06-07 2024-06-07 케라틴성 조직에 부착가능한 화합물
EP24818188.5A EP4724035A1 (fr) 2023-06-07 2024-06-07 Composés pouvant être fixés sur les tissus kératiniques
MX2025014470A MX2025014470A (es) 2023-06-07 2025-12-02 Compuestos que pueden fijarse a los tejidos queratinosos

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EP23178138 2023-06-07
EP23178138.6 2023-06-07
EP23178139.4 2023-06-07
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2932703A1 (fr) * 2015-06-19 2016-12-19 inkbox ink Inc. Compositions d'encre corporelle et applicateurs
WO2022045385A1 (fr) * 2020-08-25 2022-03-03 주식회사 엘지생활건강 Composition pour prévenir la chute des cheveux ou stimuler la repousse des cheveux

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2581022B2 (ja) * 1994-10-31 1997-02-12 日本電気株式会社 表示部付き電子機器の防塵構造
FR3003860B1 (fr) * 2013-03-29 2015-11-27 Oreal Composes derives d'iridoides proteges ou non, composition les comprenant, utilisation comme colorant des fibres keratiniques et dispositifs
US20190161465A1 (en) * 2016-06-17 2019-05-30 Keiko Izumida Red colorant composition derived from iridoid compounds and method for producing same
AU2022403630A1 (en) * 2021-12-07 2024-06-20 Inkbox Ink Incorporated Compounds attachable to skin

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2932703A1 (fr) * 2015-06-19 2016-12-19 inkbox ink Inc. Compositions d'encre corporelle et applicateurs
WO2022045385A1 (fr) * 2020-08-25 2022-03-03 주식회사 엘지생활건강 Composition pour prévenir la chute des cheveux ou stimuler la repousse des cheveux

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CN121646583A (zh) 2026-03-10
IL324870A (en) 2026-01-01
KR20260020125A (ko) 2026-02-10
EP4724035A1 (fr) 2026-04-15
KR20260020958A (ko) 2026-02-12
IL324869A (en) 2026-01-01
CN121712483A (zh) 2026-03-20
AU2024283922A1 (en) 2025-12-18
AU2024285582A1 (en) 2025-12-18

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