WO2011069898A1 - Nouvelles aminopyridines cationiques, composition de colorant comprenant une aminopyridine cationique, leurs procédés de fabrication et leurs applications - Google Patents

Nouvelles aminopyridines cationiques, composition de colorant comprenant une aminopyridine cationique, leurs procédés de fabrication et leurs applications Download PDF

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WO2011069898A1
WO2011069898A1 PCT/EP2010/068801 EP2010068801W WO2011069898A1 WO 2011069898 A1 WO2011069898 A1 WO 2011069898A1 EP 2010068801 W EP2010068801 W EP 2010068801W WO 2011069898 A1 WO2011069898 A1 WO 2011069898A1
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amino
diaminopyridin
cationic
radical
chosen
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PCT/EP2010/068801
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Aziz Fadli
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L'oreal
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Priority to US13/514,560 priority Critical patent/US8491669B2/en
Priority to JP2012542464A priority patent/JP5866293B2/ja
Priority to BR112012013759-0A priority patent/BR112012013759B1/pt
Priority to EP10790532.5A priority patent/EP2509951B1/fr
Priority to ES10790532.5T priority patent/ES2575105T3/es
Priority to CN201080055377.7A priority patent/CN102712592B/zh
Publication of WO2011069898A1 publication Critical patent/WO2011069898A1/fr

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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    • 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
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings
    • C—CHEMISTRY; METALLURGY
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/432—Direct dyes
    • A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass

Definitions

  • the present invention relates to novel cationic aminopyridines, to their use for dyeing keratin fibres, in particular human keratin fibres such as the hair, to dye compositions comprising such cationic aminopyridines, and to processes and devices using these cationic aminopyridines.
  • oxidation bases such as ortho- or para-phenylenediamines, ortho- or para-aminopheno ls and heterocyclic compounds .
  • oxidation bases are colourless or weakly co loured compounds, which, when combined with oxidizing products, may give rise to coloured compounds via a process o f oxidative condensation.
  • couplers or coloration modifiers the latter being chosen especially from aromatic meta- diaminobenzenes, meta-aminophenols, meta-diphenols and certain heterocyclic compounds such as indole compounds.
  • the "permanent" co loration obtained by means of these oxidation dyes must moreover satisfy a certain number o f requirements . Thus, it must have no toxicological drawbacks, it must allow shades to be obtained in the desired intensity and it must show good remanence with respect to external agents such as light, bad weather, washing, permanent-waving, perspiration and rubbing.
  • the dyes must also allow grey hair to be covered, and they must be as unselective as possible, i.e . they must produce the smallest possible co loration differences along the same length of a keratin fibre, which is generally differently sensitized (i. e. damaged) between its end and its root.
  • the Applicant has discovered, surprisingly and advantageously, a novel family o f heterocyclic couplers formed from cationic aminopyridines. These couplers can produce novel compositions for dyeing keratin fibres, which are capable of giving colorations in varied, powerful, chromatic shades.
  • compositions are also sparingly selective and are fast : they show good resistance to the various attacking factors to which the fibres may be subjected, and especially to repeated washing and to light.
  • heterocyclic couplers show good solubility, allowing satisfactory uptake of the co lour.
  • Patent application FR 2 874 821 describes the use of an aminopyridine : 4- [(3 ,5 -diaminopyridin-2-yl)] - 1 , 1 -dimethylpiperazin- 1 - ium methyl sulfate of formula
  • O-S-0 as an intermediate in the synthesis of a heteroaromatic dinuclear direct dye.
  • a first subj ect of the invention concerns a family o f cationic aminopyridines and processes for synthesizing them.
  • a subj ect of the invention is also a composition containing at least one cationic aminopyridine, dyeing processes using this composition, the uses of the said composition according to the present invention for dyeing keratin fibres, in particular human keratin fibres such as the hair, and multi-compartment devices or dyeing "kits".
  • the present invention relates to a cationic aminopyridine chosen from:
  • Zi is an oxygen atom or a group NR 2 ;
  • R 2 is a hydrogen atom or a linear or branched C 1 -C 4 alkyl radical, a benzyl radical or an acetyl radical;
  • Ri is a linear or branched saturated C 1 -C 10 alkyl radical, substituted or interrupted with a cationic radical, optionally interrupted with one or more oxygen atoms and/or with one or more groups NR 2 , optionally substituted with one or more radicals chosen from hydroxyl and C 1 -C 4 alkoxy or hydroxyalkyl radicals, the said cationic radical being a linear, branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium; or Ri is a saturated, unsaturated or aromatic, 5- to 8-membered cationic heterocycle optionally substituted with one or more radicals chosen from C 1 -C 4 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci- C 4 )alkyl
  • ⁇ Ri and R 2 may form, together with the nitrogen atom to which they are attached, an unsaturated 5- to 8-membered non-cationic heterocycle, substituted with a cationic radical and optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci- C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci-C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals; the said cationic radical being a linear, branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium;
  • R is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine and bromine, and linear or branched C 1 -C 4 alkyl, carboxyl (-COOH) and (Ci-C 4 )alkoxycarbonyl radicals,
  • An- represents an anion or a mixture of anions
  • cationic radical present in the compound of formula (I) or ( ⁇ ) as defined later means any linear, branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium, this quaternary ammonium preferably being o f the type -N RaRbRc, with Ra, Rb and Rc, which may be identical or different, representing a C i -C 6 alkyl radical that may be substituted with a hydroxyl.
  • Ra and Rb may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5 - to 8-membered cationic heterocycle, the radical Rc, when it is present, then being a C i -C 6 alkyl radical that may be substituted with a hydroxyl.
  • the cationic radical may also be N,N- dimethylpiperazinium.
  • the cationic radical present in the compound of formula (I) or ( ⁇ ) comprises a quaternary ammonium of the type -N RaRbRc, and when Ra and Rb form, together with the nitrogen atom to which they are attached, an unsaturated cationic heterocycle such as a pyridinium, then the quaternary ammonium does not bear a group Rc.
  • Examples o f quaternary ammoniums of the type -N RaRbRc that may be mentioned include trimethylammonium, triethyl- ammonium, dimethylethylammonium, diethylmethylammonium, diisopropylmethylammonium, diethylpropylammonium, hydroxyethyl- diethylammonium, di- -hydroxyethylmethylammonium, tri- -hydroxy- ethylammonium, N-methylpiperidinium, N-methylpyrro lidinium, N-methylmorpho linium, imidazo lium, hydroxyethylimidazolium, methylimidazolium and N-methylpiperazinium radicals .
  • the term "cationic heterocycle” means a 5 - to 8-membered heterocycle in which at least one of the ring members is a quaternary ammonium.
  • Examples o f cationic heterocyclic radicals that may be mentioned include imidazo lium, pyridinium, piperidinium, piperazinium, pyrrolidinium, morpholinium, pyrimidinium, thiazo lium, benzimidazo lium, benzothiazo lium, oxazolium, benzotriazolium, pyrazolium, triazolium and benzoxazolium radicals .
  • Z ⁇ represents a group NR 2 with R 2 chosen from a hydrogen atom and a C i -C 2 alkyl radical, and more preferentially NR 2 is chosen from NH and NMe.
  • Ri is a C i -Cs alkyl radical substituted or interrupted with a cationic radical as defined previously, optionally interrupted with one or more oxygen atoms and/or with one or more groups NR 2 , optionally substituted with a hydroxyl radical.
  • the cationic radicals are chosen from trimethylammonium, triethylammonium, dimethylethylammonium, diethylmethylammonium, diisopropylmethylammonium, hydroxyethyl- diethylammonium, imidazolium, pyridinium, pyrimidinium, thiazolium and benzimidazo lium radicals.
  • the cationic radicals are chosen from trimethylammonium and imidazo lium radicals.
  • Z ⁇ is an oxygen atom or NR 2 with R 2 chosen from hydrogen and a linear or branched C 1 - C4 alkyl radical, preferably R 2 represents H or Me; and Ri represents a saturated linear C 2 -Cs alkyl radical, optionally interrupted with an oxygen atom or with a group NH, optionally substituted with a hydroxyl radical, and substituted or interrupted with a cationic radical chosen from trimethylammonium and imidazo lium radicals.
  • Z ⁇ is a group NR 2 and Ri and R 2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5 - to 8-membered cationic heterocycle, optionally substituted with one or more radicals chosen from C i - C i o alkyl and C i - C i o hydroxyalkyl radicals .
  • This heterocycle may contain one or more heteroatoms chosen from N and O, preferably N .
  • Z i is a group NR 2 and Ri and R 2 form, together with the nitrogen atom to which they are attached, a piperidinium, imidazolium, pyrrolidinium, morpholinium or piperazinium radical substituted with one or more radicals chosen from C 1 - C4 hydroxyalkyl and C 1 - C4 alkyl radicals.
  • Z i is a group NR 2 and Ri and R 2 form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5 - to 8-membered non-cationic heterocycle, substituted with a cationic radical as defined previously, preferably chosen from trimethylammonium, diethylmethylammonium and imidazo lium radicals.
  • the saturated or unsaturated 5 - to 8-membered non-cationic heterocycle is preferably chosen from pyrrolidinine, piperidine and morpho line, this ring being substituted with a cationic radical chosen from trimethylammonium, diethylmethylammonium and imidazo lium radicals.
  • R is chosen from a hydrogen atom and C 1 - C4 alkyl radicals. Even more preferably, R is a hydrogen atom.
  • the cationic aminopyridines of the invention may be present in free form or in the form o f salts, such as addition salts with a mineral acid preferably chosen from hydrochlorides, hydrobromides, sulfates, or phosphates, or with an organic acid, for instance citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, acetates, para-toluenesulfonates, formates or methanesulfonates.
  • a mineral acid preferably chosen from hydrochlorides, hydrobromides, sulfates, or phosphates
  • organic acid for instance citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, acetates, para-toluenesulfonates, formates or methanesulfonates.
  • the cationic aminopyridines of the invention may also be in the form o f so lvates, for example a hydrate or a solvate of a linear or branched alcohol such as ethanol or isopropanol.
  • cationic aminopyridines of the invention means any mesomeric or isomeric form.
  • the electrical neutrality o f the cationic aminopyridines of the invention is ensured by one or a mixture of cosmetically acceptable organic or mineral anions, noted An- .
  • An- represents an anion or a mixture of anions chosen, for example, from a halide, such as chloride, bromide, fluoride or iodide; a hydroxide; a sulfate; a hydrogen sulfate; an alkyl sulfate for which the linear or branched alkyl part is C i -C 6 , for instance the methyl sulfate or ethyl sulfate ion; carbonates and hydrogen carbonates; carboxylic acid salts such as formate, acetate, citrate, tartrate or oxalate; alkylsulfonates for which the linear or branched alkyl part is C i -C 6 , for instance the methylsulfonate ion; arylsulfonates for which the aryl part, preferably phenyl, is optionally substituted with one or more C 1 - C4 alkyl radicals, for instance 4-tolylsulf
  • the cationic aminopyridines of the invention are chosen from the fo llowing compounds :
  • the cationic aminopyridines of the invention may be prepared according to various synthetic routes.
  • R is chosen from a hydrogen atom, halo genes chosen from fluorine, chlorine and bromine, and linear or branched C 1 -C 4 alkyl, carboxyl (- C OOH) and (C i -C 4 )alkoxycarbonyl radicals, and x represents 1 or 2.
  • the present patent application also relates to a process for synthesizing a cationic aminopyridine according to the invention, starting with a compound o f formula (III) :
  • X represents a halogen or a group S O 2 R 3 with R 3 chosen from C 1 -C 4 alkyls, preferably methyl, a phenyl radical and a methylphenyl radical,
  • R is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine and bromine, and linear or branched C 1 -C 4 alkyl, carboxyl (-CO OH) and (C i - C4)alkoxycarbonyl radicals, the said process comprising at least the following steps, in this order:
  • Ri represents a C i -C i o alkyl radical substituted with a cationic radical, the said alkyl radical being interrupted with one or more oxygen atoms and/or with one or more groups NR 2 , then the synthetic process used may be fo llowing :
  • the substitution reaction is performed in a dipolar so lvent such as acetonitrile or THF or in DMF or NMP, or in an alcohol such as ethano l, in the presence of a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, and one or more HOAZ 1 H for 1 to 24 hours at a temperature from 20°C to the reflux temperature of the solvent.
  • a dipolar so lvent such as acetonitrile or THF or in DMF or NMP
  • an alcohol such as ethano l
  • a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, and one or more HOAZ 1 H for 1 to 24 hours at a temperature from 20°C to the reflux temperature of the solvent.
  • hydroxyl function thus introduced is then substituted with a halide (for example mesyl or tosyl halide) in a solvent such as acetonitrile, THF or in an alcoho l such as ethano l, for example, in the presence of a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, for 1 to 24 hours at a temperature from 20° C to the reflux temperature of the so lvent.
  • a halide for example mesyl or tosyl halide
  • a solvent such as acetonitrile, THF or in an alcoho l such as ethano l
  • a base such as triethylamine, ethyldiisopropylamine, sodium hydroxide or potassium hydroxide, for example, for 1 to 24 hours at a temperature from 20° C to the reflux temperature of the so lvent.
  • substitution o f the leaving group introduced in the preceding step is performed either by reaction with an aromatic tertiary amine such as methylimidazole to give the cationic compounds directly, or by reaction with a particular primary or secondary amine, for instance ⁇ , ⁇ -dimethylethylenediamine or 2-piperidin- 1 - ylethanamine to give compounds that are alkylated with at least one equivalent of an alkyl halide or methyl sulfate in a solvent such as THF, acetonitrile, dioxane or ethyl acetate, for 15 minutes to 24 hours at a temperature ranging from 15 ° C to the reflux temperature of the so lvent, to give the cationic nitro compounds.
  • an aromatic tertiary amine such as methylimidazole
  • 2-piperidin- 1 - ylethanamine to give compounds that are alkylated with at least one equivalent of an alkyl halide or methyl sulfate in a solvent
  • the reduction o f the nitro group of these compounds is performed under standard conditions, for example by performing a hydrogenation reaction under heterogeneous catalysis in the presence of Pd/C , Pd(II)/C , Ni/Ra, etc . , or alternatively by performing a reduction reaction with a metal, for example with zinc, iron, tin, etc. (see Advanced Organic Chemistry, 3rd edition, J. March, 1985 , Wiley Interscience, and Reduction in Organic Chemistry, M . Hudlicky, 1 983 , Ellis Horwood Series Chemical Science) .
  • the present patent application also relates to the uses of a cationic aminopyridine of general formula (I), the acid-addition salts thereof and the solvates thereof:
  • Zi is an oxygen atom or a group NR 2 ;
  • R 2 is a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical, a benzyl radical or an acetyl radical;
  • Ri is a linear or branched saturated C 1 -C 10 alkyl radical, substituted or interrupted with a cationic radical, optionally interrupted with one or more oxygen atoms and/or with one or more groups NR 2 , optionally substituted with one or more radicals chosen from hydroxyl and C 1 -C 4 alkoxy or hydroxyalkyl radicals, the said cationic radical being a linear or branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium; or Ri is a saturated, unsaturated or aromatic, 5- to 8-membered cationic heterocycle optionally substituted with one or more radicals chosen from C 1 -C 4 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci- C 4 )alkyl
  • ⁇ Ri and R 2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 8-membered cationic heterocycle, at least one of the ring members of which is a quaternary ammonium, optionally substituted with one or more radicals chosen from Ci-Cio alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci-C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals, this heterocycle possibly containing one or more heteroatoms chosen from N and O, preferably N, or
  • ⁇ Ri and R 2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 8-membered non-cationic heterocycle, substituted with a cationic radical and optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci- C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci-C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals; the said cationic radical being a linear or branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium;
  • R is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine and bromine, and linear or branched C 1 -C 4 alkyl, carboxyl (-COOH) and (Ci-C 4 )alkoxycarbonyl radicals,
  • An- represents an anion or a mixture of anions
  • keratin fibres especially human keratin fibres such as the hair.
  • the present patent application also relates to a cosmetic composition for dyeing, especially keratin fibres such as the hair, comprising, in a suitable dyeing medium, at least one cationic aminopyridine of general formula (I), an acid-addition salt thereof and/or a solvate thereof:
  • Zi is an oxygen atom or a group NR 2 ;
  • R 2 is a hydrogen atom, a linear or branched C 1 -C 4 alkyl radical, a benzyl radical or an acetyl radical;
  • Ri is a linear or branched saturated C 1 -C 10 alkyl radical, substituted or interrupted with a cationic radical, optionally interrupted with one or more oxygen atoms and/or with one or more groups NR 2 , optionally substituted with one or more radicals chosen from hydroxyl and C 1 -C 4 alkoxy or hydroxyalkyl radicals or Ri is a saturated, unsaturated or aromatic, 5- to 8-membered cationic heterocycle optionally substituted with one or more radicals chosen from C 1 -C 4 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci- C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals; the said cationic radical being a linear
  • ⁇ Ri and R 2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 8-membered cationic heterocycle, at least one of the ring members of which is a quaternary ammonium, optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci-C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci-C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals, this heterocycle possibly containing one or more heteroatoms chosen from N and O, preferably N, or
  • ⁇ Ri and R 2 may form, together with the nitrogen atom to which they are attached, a saturated or unsaturated 5- to 8-membered non-cationic heterocycle, substituted with a cationic radical and optionally substituted with one or more radicals chosen from C 1 -C 10 alkyl, hydroxyl, C 1 -C 4 alkoxy, amino, (Ci-C 4 )alkylamino, di(Ci- C 4 )alkylamino, thio, (Ci-C 4 )alkylthio, carboxyl, (Ci-C 4 )alkylcarbonyl, sulfonyl, amido and C 1 -C 4 hydroxyalkyl radicals; the said cationic radical being a linear or branched or cyclic, saturated or unsaturated radical, comprising a quaternary ammonium;
  • R is chosen from a hydrogen atom, halogens chosen from fluorine, chlorine and bromine, and linear or branched C 1 -C 4 alkyl, carboxyl (-CO OH) and (C i -C 4 )alkoxycarbonyl radicals,
  • An- represents an anion or a mixture of anions.
  • the concentration of the cationic aminopyridine o f general formula (I) is between 0.0001 % and 20% and preferably between 0.005 % and 6% by weight relative to the total weight of the composition.
  • the suitable dyeing medium generally comprises water or a mixture of water and of at least one organic solvent, for instance linear or branched C 1 -C 4 lower alcohols, such as ethanol and isopropanol; polyo ls and po lyo l ethers, for instance 2-butoxyethano l, propylene glyco l, propylene glycol monomethyl ether, diethylene glyco l monomethyl ether and monoethyl ether, glycerol and also aromatic alcoho ls, for instance benzyl alcohol or phenoxyethano l, and mixtures thereof.
  • organic solvent for instance linear or branched C 1 -C 4 lower alcohols, such as ethanol and isopropanol
  • polyo ls and po lyo l ethers for instance 2-butoxyethano l, propylene glyco l, propylene glycol monomethyl ether, diethylene glyco l monomethyl ether and monoethyl ether, glycerol and also aromatic
  • the cosmetic composition comprises at least one cosmetic adjuvant chosen from the group formed by antioxidants, penetrants, sequestrants, fragrances, buffers, dispersants, surfactants, conditioning agents, film-forming agents, polymers, ceramides, preserving agents, nacreous agents or opacifiers, and vitamins or provitamins .
  • the above adjuvants are generally present in an amount for each o f them o f between 0.01 % and 20% by weight relative to the weight of the composition.
  • the composition also comprises at least one oxidation base.
  • bases may be chosen especially from para-phenylenediamines, bis (phenyl) alky lene diamines, para-aminophenols, ortho-aminopheno ls and heterocyclic bases, and the addition salts thereof.
  • para-phenylenediamines examples that may be mentioned more particularly include para-phenylenediamine, para- toluenediamine, 2 -chloro -para-phenylenediamine, 2, 3 -dimethyl-par a- phenylene diamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl- para-phenylenediamine, 2,5 -dimethyl-para-phenylenediamine, N,N- dimethyl-para-phenylenediamine, ⁇ , ⁇ -diethyl-para-phenylene diamine, N,N-dipropyl-para-phenylenediamine, 4 -amino -N,N- diethyl- 3 -methyl- aniline, N,N-bis( -hydroxyethyl)-para-phenylenediamine, 4-N,N- bis( -hydroxy ethyl) amino -2 -met hylaniline
  • para-phenylenediamine para-toluenediamine, 2-isopropyl-para- phenylenediamine, 2- -hydroxyethyl-para-phenylenediamine, 2- -hydroxyethyloxy-para-phenylenediamine, 2, 6 -dimethyl-par a- phenylene diamine, 2, 6 -diethyl-par a-phenylene diamine, 2, 3 -dimethyl- par a-phenylene diamine, N,N-bis( -hydroxy ethyl) -para-phenylenediamine, 2-chloro-para-phenylenediamine and 2- -acetyl- aminoethyloxy-para-phenylenediamine, and the addition salts thereo f with an acid, are particularly preferred.
  • bis(phenyl)alkylenediamines examples that may be mentioned include N,N'-bis( -hydroxyethyl)-N,N'-bis(4'-amino- phenyl)-l ,3-diaminopropanol, N,N'-bis( -hydroxyethyl)-N,N'-bis(4'- aminophenyl) ethylene diamine, N,N'-bis(4-aminophenyl)tetra- methylenediamine, N, N'-bis( -hydroxy ethyl) -N,N '-bis -(4 -amino - phenyl)tetramethylene diamine, N,N'-bis(4-methylaminophenyl)tetra- methylenediamine, N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methyl- phenyl)ethylenediamine and 1
  • para-aminophenols examples that may be mentioned include para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-2-chlorophenol, 4-amino-3-chloro- phenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-( -hydroxyethylamino- methyl)phenol, 4-amino-2-fluorophenol, 4-amino-2,6-dichlorophenol, 4-amino-6[((5 '-amino-2 '-hydroxy- 3 '-methyl)phenyl)methyl] -2 -methyl- phenol and bis[(5 '-amino-2 '-hydroxy)phenylmethane, and the addition salts thereof with an acid.
  • ortho-aminophenols examples that may be mentioned include 2-aminophenol, 2-amino-5-methylphenol, 2-amino- 6-methylphenol and 5-acetamido-2-aminophenol, and the addition salts thereof with an acid.
  • heterocyclic bases examples that may be mentioned include pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
  • pyridine derivatives mention may be made of the compounds described, for example, in patents GB 1 026978 and GB 1 153 196, for instance 2,5-diaminopyridine, 2-(4-methoxy- phenyl)amino-3-aminopyridine and 3,4-diaminopyridine, and the addition salts thereof with an acid.
  • pyridine oxidation bases that are useful in the present invention are the 3-aminopyrazolo[ 1 ,5-a]pyridine oxidation bases or the addition salts thereof described, for example, in patent application FR 2801 308.
  • Examples that may be mentioned include pyrazolo[ 1 ,5-a]pyridin-3-ylamine; 2-acetylaminopyrazolo-[ 1 ,5-a]- pyridin-3-ylamine; 2-morpholin-4-ylpyrazolo[ 1 ,5-a]pyridin-3-ylamine; 3-aminopyrazolo[ 1 ,5-a]pyridine-2-carboxylic acid; 2-methoxy- pyrazolo[ 1 ,5-a]pyridin-3-ylamine; (3-aminopyrazolo[l ,5-a]pyridin-7- yl)methanol; 2-(3-aminopyrazolo[ 1 ,5-a]pyridin-5-y
  • pyrazole derivatives that may be mentioned are the compounds described in patents DE 3843892, DE 4 133957 and patent applications WO 94/08969, WO 94/08970, FR-A-2733749 and DE 19543988, for instance 4,5-diamino-l-methylpyrazole,
  • the concentration of the oxidation base(s) is between 0.0001% and 20% and preferably between 0.005% and 6% by weight relative to the total weight of the composition.
  • composition according to the invention preferably contains at least one additional oxidation coupler, other than the cationic aminopyridines of general formula (I).
  • oxidation couplers mention may be made especially of meta-phenylenediamines, meta-aminophenols, meta- diphenols, naphthalene-based couplers and heterocyclic couplers, and also the addition salts thereof.
  • Examples that may be mentioned include 2-methyl-5- aminophenol, 5-N-(B-hydroxyethyl)amino-2-methylphenol, 6-chloro-2- methyl-5-aminophenol, 3-aminophenol, 1 ,3-dihydroxybenzene (or resorcinol), 1 ,3-dihydroxy-2-methylbenzene, 4-chloro - 1 ,3-dihydroxybenzene, 2, 4 -diamino - 1 -(B -hydroxy ethy loxy)benzene, 2 -amino -4 -(B- hydro xy ethy lamino)- 1 -methoxybenzene, 1 ,3-diaminobenzene, 1 ,3-bis- (2,4-diaminophenoxy)propane, 3-ureidoaniline, 3-ureido-l- dimethylaminobenzene, sesamol, l-B-hydroxyethylamino-3,
  • the concentration o f the oxidation coupler(s) is between 0.0001 % and 20% and preferably between 0.005 % and 6% by weight relative to the total weight of the composition.
  • the addition salts with an acid that may be used for the oxidation bases and couplers are chosen especially from the hydrochlorides, hydrobromides, sulfates, citrates, succinates, tartrates, lactates, tosylates, benzenesulfonates, phosphates and acetates.
  • the dye composition in accordance with the invention may also contain one or more direct dyes, which may be chosen especially from neutral, acidic or cationic nitrobenzene dyes, neutral, acidic or cationic azo direct dyes, neutral, acidic or cationic quinone and in particular anthraquinone direct dyes, azine direct dyes, methine, azomethine, triarylmethane or indoamine direct dyes and natural direct dyes .
  • the composition according to the invention comprises at least one dye chosen from cationic direct dyes and natural direct dyes.
  • the direct dye(s) preferably represent from 0.001 % to 20%> by weight approximately and even more preferentially from 0.005 % to 10% by weight approximately relative to the total weight of the composition.
  • the pH of the dye composition in accordance with the invention is generally between 3 and 12 approximately and preferably between 5 and 1 1 approximately. It may be adjusted to the desired value by means o f acidifying or basifying agents usually used in the dyeing o f keratin fibres, or alternatively using standard buffer systems.
  • acidifying agents examples that may be mentioned include mineral or organic acids other than carboxylic acids, for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • mineral or organic acids other than carboxylic acids for instance hydrochloric acid, orthophosphoric acid, sulfuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkali metal carbonates, alkanolamines such as monoethanolamine, diethanolamine and triethanolamine, and also derivatives thereo f, sodium hydroxide, potassium hydroxide and the compounds o f formula : in which W is a propylene residue optionally substituted with a hydro xyl group or a C 1 -C 4 alkyl radical; R a , R b , R c and R d , which may be identical or different, represent a hydrogen atom or a C 1 -C 4 alkyl or C 1 -C 4 hydro xyalkyl radical.
  • the cosmetic composition according to the invention may be in various forms, such as in the form o f liquids , creams or gels , or in any other form that is suitable for dyeing keratin fibres, and esp ecially human hair.
  • the present patent application relates to a process in which the composition according to the present invention as defined previous ly is applied to keratin fibres for a time sufficient to develop the desired co louring in the presence o f an o xidizing agent, the oxidizing agent being applied before, simultaneously with or after the composition.
  • the co lour may be revealed at acidic , neutral or alkaline pH and the oxidizing agent may b e added to the composition o f the invention just before the time of use , or it may be used starting with an oxidizing composition containing it, which is app lied simultaneously with or sequentially to the composition o f the invention.
  • the compositio n according to the present invention is mixed, preferably at the time o f use, with a composition containing, in a suitable dyeing medium, at least one oxidizing agent, this o xidizing agent being present in an amount sufficient to develop a co loration.
  • a ready-to -use composition which is a mixture o f a compositio n according to the invention with an oxidizing composition comprising at least one oxidizing agent preferab ly chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulfates, peracids and oxidase enzymes, among which mention may be made o f peroxidases, 2-electron oxidoreductases such as uricases, and 4-electron oxygenases, for instance laccases . Hydrogen peroxide is particularly preferred.
  • the mixture obtained is then applied to the keratin fibres for a time sufficient to develop the desired coloration. After a leave-on time of 3 to 50 minutes approximately and preferably 5 to 30 minutes approximately, the keratin fibres are rinsed, washed with shampoo, rinsed again and then dried.
  • the oxidizing composition may also contain various adjuvants conventionally used in hair dye compositions and as defined previously.
  • the pH o f the oxidizing composition containing the oxidizing agent is such that after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres preferably ranges between 3 and 12 approximately and even more preferentially between 5 and 1 1 . It may be adjusted to the desired value by means o f acidifying or basifying agents usually used in the dyeing o f keratin fibres and as defined previously.
  • the ready-to-use composition that is finally applied to the keratin fibres may be in various forms, such as in the form o f liquids, creams or gels, or in any other form that is suitable for dyeing keratin fibres, and especially human hair.
  • a subj ect of the present patent application is also a process for dyeing keratin fibres, in which the ready-to-use composition is applied to the said fibres for a time sufficient to develop the desired co loration.
  • the time sufficient to develop the desired coloration generally corresponds to a leave-on time o f 3 to 50 minutes approximately and preferably 5 to 30 minutes approximately.
  • a subj ect of the invention is also a multi-compartment dyeing device or "kit" in which a first compartment contains the dye composition defined above and a second compartment contains an oxidizing agent.
  • This device may be equipped with a means for dispensing the desired mixture on the hair, such as the devices described in patent FR-2 586 913 in the name of the Applicant.
  • this device it is possible to dye keratin fibres by means of a process that includes the mixing of a dye composition in accordance with the invention with an oxidizing agent as defined previously, and the application of the mixture obtained onto the keratin fibres for a time sufficient to develop the desired coloration.
  • Example 1 synthesis of 2-[(3 ,5-diaminopyridin-2-yl)amino]- ⁇ , ⁇ , ⁇ -trimethylethaneammonium chloride dihydrochloride (compound 1 ).
  • the yellow solid formed is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of a drying agent, to constant weight. 10.5 g (yield of 82.5%) of expected compound are thus obtained in the form of a yellow solid.
  • the yellow solid formed is filtered off, dried by suction, washed with ethyl acetate and then dried under vacuum at 50°C in the presence of a drying agent, to constant mass. 7 g (73% yield) of expected compound are thus obtained in the form of a yellow solid.
  • reaction medium is filtered under a stream o f argon on a sinter funnel packed with Celite and over a vacuum flask containing 200 ml o f 6.0 N hydrochloric 2-propanol at
  • the expected compound crystallizes in the vacuum flask with stirring.
  • the so lid is filtered off, dried quickly by suction on a sinter funnel under argon, and rinsed with a minimum amount of co ld iPrOH and then with 3x 100 ml o f iPr 2 0.
  • the compound is dried under vacuum at 50°C in the presence of a drying agent, to constant weight. 17.5 g (87.4% yield) o f expected compound are thus obtained in the form of a beige-co loured so lid.
  • Example 2 synthesis o f 2- [(3 ,5 -diaminopyridin-2-yl)(methyl)- amino] -N,N,N-trimethylethaneammonium chloride dihydrochloride.
  • reaction medium After cooling the reaction medium, it is poured into a mixture of 200 g of ice and water, with stirring.
  • the yellow solid formed is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of a drying agent, to constant weight. 10.7 g (yield of 62%) of yellow solid corresponding to the expected compound are thus isolated. Analysis by mass spectrometry confirms the expected
  • the medium is brought to 50°C, 5 g of palladium-on-charcoal are added portionwise, and the mixture is refluxed for 2 hours.
  • reaction medium After cooling under argon, the reaction medium is filtered under a stream of argon on a sinter funnel packed with Celite and over a vacuum flask containing 250 ml of 6.0 N hydrochloric 2-propanol at 0°C.
  • the expected compound which crystallizes in the flask with stirring, is filtered off, dried rapidly by suction on a sinter funnel under argon, and rinsed with a minimum amount of cold iPrOH and then with 3x100 ml of iPr 2 0.
  • the compound is dried under vacuum at 50°C in the presence of a drying agent, to constant weight. 12.1 g (81% yield) of expected compound are thus isolated in the form of a beige-coloured solid.
  • Example 3 synthesis of 4-(3,5-diaminopyridin-2-yl)-l,l- dimethylpiperazin- 1 -ium chloride dihydrochloride.
  • a yellow solid crystallizes from the medium. It is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of a drying agent, to constant weight. 5.7 g (yield of 88%) of expected compound are thus isolated in the form of a yellow solid.
  • the yellow solid formed is filtered off on a sinter funnel, dried by suction, washed with THF and then dried under vacuum at 50°C in the presence of a drying agent, to constant mass. 7.4 g (yield 94%) of expected compound are thus isolated in the form of a yellow solid.
  • the medium is brought to 50°C, 3.5 g of palladium-on-charcoal are added portionwise, and the mixture is then refluxed for 24 hours.
  • reaction medium is filtered under argon on a sinter funnel packed with Celite and over a vacuum flask containing 250ml of 6.0 N hydrochloric 2-propanol at 0°C.
  • the expected compound crystallizes in the flask with stirring; it is filtered off on a sinter funnel, dried rapidly by suction under argon, and rinsed with a minimum amount of cold iPrOH and then with 3x100 ml of iPr 2 0. The solid is then dried under vacuum at 50°C in the presence of a drying agent, to constant weight. 4.6 g (88% yield) of expected compound are thus isolated in the form of a beige- coloured solid.
  • Example 4 synthesis of l- ⁇ 2-[(3,5-diaminopyridin-2-yl)- amino]ethyl ⁇ -l-methylpiperidinium chloride dihydrochloride.
  • the medium which has become heterogeneous, is then poured onto 500 g of ice.
  • a yellow solid precipitates more abundantly; it is isolated by filtration on a sinter funnel, washed with water and dried under vacuum at 30°C in the presence of a drying agent, to constant weight. 11.5 g (78% yield) of expected compound are thus isolated in the form of a yellow solid.
  • the yellow solid formed is filtered off on a sinter funnel, dried by suction, washed with ethyl acetate and then dried under vacuum at 50°C in the presence of a drying agent, to constant mass. 7.6 g (90% yield) of expected compound are thus isolated in the form of a yellow solid.
  • the beige-coloured solid that crystallizes slowly under cold conditions is dried rapidly by suction on a sinter funnel under argon, and rinsed with a minimum amount of cold iPrOH and then with 3x100 ml of iPr 2 0.
  • the solid obtained is dried under vacuum at 50°C in the presence of a drying agent, to constant weight. 4.8 g (94% yield) of expected compound are thus isolated in the form of a beige-coloured solid.
  • Example 5 synthesis of l-(3,5-diaminopyridin-2-yl)-N,N,N- trimethylpyrrolidine-3-ammonium chloride hydrochloride.
  • Example 6 synthesis of l- ⁇ 3-[(3,5-diaminopyridin-2-yl)- amino] propyl ⁇ - 3-(2-hydroxyethyl) - lH-imidazol-3-ium chloride dihydrochloride.
  • Example 4 The process is performed in an identical manner to that of Example 4, with substitution using 3-aminopropylimidazole and cationization using chloroethanol, followed by a catalytic reduction in an autoclave.
  • the expected cation [Ci 3 H 2 iN 5 0] + is mainly detected.
  • each composition is mixed with an equal weight of 20-volumes aqueous hydrogen peroxide solution (6%> by weight). A final pH of 9.5 is obtained.

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Abstract

La présente invention concerne une aminopyridine cationique de formule générale (I), ses sels d'addition acide et ses solvates : où : R1 représente un radical alkyle en C1-C20 saturé, linéaire ou ramifié, substitué et/ou interrompu par un radical cationique. La présente invention concerne également un procédé de synthèse de ladite aminopyridine cationique, ainsi que les compositions, les utilisations, les procédés de coloration capillaire et les dispositifs employant ladite aminopyridine cationique.
PCT/EP2010/068801 2009-12-07 2010-12-03 Nouvelles aminopyridines cationiques, composition de colorant comprenant une aminopyridine cationique, leurs procédés de fabrication et leurs applications WO2011069898A1 (fr)

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US13/514,560 US8491669B2 (en) 2009-12-07 2010-12-03 Cationic 4-aminopyridine, dye composition comprising a cationic 4-aminopyridine, processes therefor and uses thereof
JP2012542464A JP5866293B2 (ja) 2009-12-07 2010-12-03 新規カチオン性アミノピリジン、カチオン性アミノピリジンを含む染料組成物、そのための方法およびその使用
BR112012013759-0A BR112012013759B1 (pt) 2009-12-07 2010-12-03 New cationic aminopyridins, composition of dyeing composition of a cationic aminopyridine, processes for those and their uses.
EP10790532.5A EP2509951B1 (fr) 2009-12-07 2010-12-03 Nouvelles aminopyridines cationiques, composition de colorant comprenant une aminopyridine cationique, leurs procédés de fabrication et leurs applications
ES10790532.5T ES2575105T3 (es) 2009-12-07 2010-12-03 Nuevas aminopiridinas catiónicas, composición de tinte que comprende una aminopiridina catiónica, procesos de obtención de las misma y usos de las mismas
CN201080055377.7A CN102712592B (zh) 2009-12-07 2010-12-03 阳离子型氨基吡啶、含阳离子型氨基吡啶的染料组合物及其方法和用途

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102344411A (zh) * 2011-08-01 2012-02-08 宜兴市新宇化工有限公司 一种制备2，6-二甲氧基-3，5-二氨基吡啶盐酸盐的方法
FR2968967A1 (fr) * 2010-12-17 2012-06-22 Oreal Composition tinctoriale comprenant une base d'oxydation pyrazolopyridine secondaire et un coupleur 3,5-diamino pyridine cationique
WO2012080286A3 (fr) * 2010-12-17 2012-12-13 L'oreal Composition colorante comprenant une base d'oxydation hétérocyclique et un agent de couplage 3,5-diaminopyridine cationique
CN113402454A (zh) * 2021-05-26 2021-09-17 华东理工大学 氨基吡啶型季铵盐阳离子表面活性剂、制备方法及应用

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FR2979343B1 (fr) * 2011-08-25 2013-10-04 Oreal Coupleurs pyridiniques cationiques, composition tinctoriale comprenant une 6-hydroxy-pyridine cationique, procedes et utilisations
JP6571930B2 (ja) * 2014-12-08 2019-09-04 ホーユー株式会社 カプラー含有組成物
FR3030244B1 (fr) * 2014-12-17 2018-07-06 L'oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine et un coupleur particulier
FR3030233B1 (fr) 2014-12-17 2016-12-09 Oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine, et un polymere amphotere ou cationique dans un milieu riche en corps gras
FR3030243B1 (fr) 2014-12-17 2018-11-09 L'oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine et une base d'oxydation heterocyclique
FR3030234B1 (fr) 2014-12-17 2018-05-18 Oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un tensio actif non ionique dans un milieu riche en corps gras
FR3030255B1 (fr) 2014-12-17 2016-12-23 Oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un epaississant polysaccharide dans un milieu riche en corps gras
FR3030237B1 (fr) 2014-12-17 2017-07-14 Oreal Composition de coloration comprenant une base d'oxydation para-phenylenediamine, un tensio actif amphotere dans un milieu riche en corps gras
FR3071835B1 (fr) * 2017-09-29 2019-09-27 L'oreal Bases para-phenylenediamines a heterocycles cationiques et leur utilisation pour la teinture d’oxydation des fibres keratiniques

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2968967A1 (fr) * 2010-12-17 2012-06-22 Oreal Composition tinctoriale comprenant une base d'oxydation pyrazolopyridine secondaire et un coupleur 3,5-diamino pyridine cationique
WO2012080286A3 (fr) * 2010-12-17 2012-12-13 L'oreal Composition colorante comprenant une base d'oxydation hétérocyclique et un agent de couplage 3,5-diaminopyridine cationique
CN102344411A (zh) * 2011-08-01 2012-02-08 宜兴市新宇化工有限公司 一种制备2，6-二甲氧基-3，5-二氨基吡啶盐酸盐的方法
CN113402454A (zh) * 2021-05-26 2021-09-17 华东理工大学 氨基吡啶型季铵盐阳离子表面活性剂、制备方法及应用

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EP2509951A1 (fr) 2012-10-17
BR112012013759A2 (pt) 2017-03-28
FR2953517A1 (fr) 2011-06-10
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CN102712592B (zh) 2015-10-14
FR2953517B1 (fr) 2012-04-27

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