WO2006064366A1 - 6- (1h-pyrazol-5-yl)-1, 3, 5-triazine derivatives and their use as protective agents against uv radiation - Google Patents

6- (1h-pyrazol-5-yl)-1, 3, 5-triazine derivatives and their use as protective agents against uv radiation Download PDF

Info

Publication number
WO2006064366A1
WO2006064366A1 PCT/IB2005/003931 IB2005003931W WO2006064366A1 WO 2006064366 A1 WO2006064366 A1 WO 2006064366A1 IB 2005003931 W IB2005003931 W IB 2005003931W WO 2006064366 A1 WO2006064366 A1 WO 2006064366A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
carbon atoms
general formula
optionally substituted
phenyl
Prior art date
Application number
PCT/IB2005/003931
Other languages
English (en)
French (fr)
Inventor
Carles Trullas
Carles Pelejero
David Panyella
Jordi Corbera
Jorg Holenz
Original Assignee
Isdin, S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Isdin, S.A. filed Critical Isdin, S.A.
Priority to EP05823239A priority Critical patent/EP1833818A1/en
Publication of WO2006064366A1 publication Critical patent/WO2006064366A1/en

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • This invention is related with the cosmetic, dermatological and pharmaceutical fields.
  • the present invention relates to new triazine derivatives whose physiochemical properties make them useful as protective agents against UV radiation, as well as to 0 their use for the manufacture of cosmetic, dermatological and pharmaceutical formulations which protect the skin, lips, nails and hair from UV radiation.
  • UV radiation in particular can under certain circumstances give rise to harmful effects on the skin, occasioning pathological manifestations such as burns, photodermatosis and photo- ageing, among others.
  • the main agent responsible for such pathological manifestations is ultraviolet radiation, whose energy is inversely proportional to its wavelength. Thus, the shorter the wavelength the more powerful will be the radiation.
  • UVC radiation can accordingly be 5 classified into UVC (200-290 nm) , UVB (290-320 nm) and UVA (320-400 nm) , with UVC waves being the most harmful, although they are absorbed by the ozone layer.
  • UV-A and UV-B radiation can cause, people have various natural protective systems 0 in their skins that either absorb or deflect the radiation, such as melanin, hair, the fatty layer of the skin, etc.
  • solar filters are currently used in order to reduce the effects of solar radiation.
  • Such 5 solar filters are compounds that are applied on the skin, lips, nails or hair and can be found in cosmetic, dermatological and pharmaceutical formulations as well as in other cosmetic products for protecting against solar radiation, preventing the decomposition of active ingredients or radiation-sensitive components.
  • Ri, R 2 and R 3 are, each independently of the others, Ci_i 8 alkyl, C2- 10 alkenyl or Ci_ 4 phenylalkyl; and R 4 is hydrogen or C 1 -C 5 alkyl.
  • a first aspect of the present invention is a triazine derivative of general formula (I) :
  • Ri represents a hydrogen atom; an optionally substituted cycloalkyl radical from 3 to 7 carbon atoms; an aryl radical optionally substituted with a group selected from aryl, halogen, alkoxy group containing from 1 to 6 carbon atoms and an alkyl group containing from 1 to 6 carbon atoms; an arylalkyl radical in which the alkyl group is an optionally substituted chain from 1 to 6 carbon atoms; a straight-chain or branched alkyl radical that has from 1 to 18 carbon atoms optionally substituted with a group selected from -SO 3 M, -N(R 4 J 3 + and a group of general formula (II)
  • R 5 , Re, R 7 , Re and Rg are the same as or different from each other and are selected from an optionally substituted alkyl radical from 1 to 6 carbon atoms, an alkoxy radical from 1 to 6 carbon atoms, an optionally substituted aryl radical and a -OSi (R 10 ) 3 radical; Rio represents an alkyl radical from 1 to 6 carbon atoms, an alkoxy radical from 1 to 6 carbon atoms or an optionally substituted aryl radical; M is H, Na or K;
  • R 4 is an optionally substituted alkyl group
  • R 2 and R 3 are the same as or different from each other and are selected from hydrogen; an optionally substituted, straight-chain or branched alkyl radical that has from 1 to 4 carbon atoms; and an optionally substituted aryl radical; or
  • R 2 and R 3 are condensate with an optionally heterosubstituted mono- or polycyclic annular system;
  • Ai is a radical of general formula (III) or (IV)
  • a 2 is a radical of general formula (III), (V) or (VI]
  • Ru represents a hydrogen atom; an optionally- substituted, straight-chain or branched, saturated or unsaturated alkyl radical that contains from 1 to 6 carbon atoms; a -OH radical;
  • R 12 represents a hydrogen atom; a hydroxyl radical; a
  • Ri 5 , Ri 6 and Ri 7 are the same as or different from each other and are selected from hydrogen, an optionally substituted, straight-chain or branched, alkyl radical from 1 to 18 atoms of carbon;
  • Ri 4 is H or -SO 3 M, being M as defined above; Ri 3 and R' 13 can be the same as or different from each other and are selected from hydrogen; an optionally substituted acyl radical from 1 to 18 carbon atoms; a straight-chain or branched, saturated or unsaturated, alkyl radical which contains from 1 to 18 carbon atoms, optionally substituted with at least one -OH radical, a - SO 3 M group or -N(R 4 ) 3 + group, where M and R 4 are as defined above, or a group of general formula (H)/ as defined above.
  • this invention relates to a triazine derivative of general formula (I) in accordance with the first aspect of the invention, in which:
  • Ri represents a hydrogen atom; an optionally substituted cycloalkyl radical of 3 to 7 carbon atoms; an aryl radical optionally substituted with a group selected from aryl, halogen, an alkoxy group containing from 1 to 6 carbon atoms and an alkyl group that contains from 1 to 6 carbon atoms; an arylalkyl radical in which the alkyl group is a chain from 1 to 6 carbon atoms optionally substituted; a straight-chain or branched alkyl radical, which has from 1 to 18 atoms of carbon, optionally substituted with a group of general formula (II)
  • n 0, 1, 2, 3 or 4
  • R 5 , Re, R 7 , Rs and R 9 are the same as or different from each other and are selected from an optionally substituted alkyl radical having from 1 to 6 carbon atoms, an alkoxy radical from 1 to 6 carbon atoms, an optionally substituted aryl radical and a -OSi (Rio) 3 radical;
  • Rio represents an alkyl radical from 1 to 6 carbon atoms, an alkoxy radical from 1 to 6 carbon atoms or an optionally substituted aryl radical;
  • R 2 and R 3 are the same as or different from each other and are selected from hydrogen; an optionally substituted, straight-chain or branched, alkyl radical which has from 1 to 4 carbon atoms; and an optionally substituted aryl radical; or
  • R 2 and R 3 are condensate with an optionally heterosubstituted mono- or polycyclic annular system;
  • Ai is a radical of general formula (III) or (IV)
  • a 2 is a radical of general formula (III), (V) or (VI]
  • Rn represents a hydrogen atom; an optionally substituted, straight-chain or branched, saturated or unsaturated alkyl radical that contains from 1 to 6 atoms of carbon; an -OH radical;
  • Ri 2 represents a hydrogen atom; a hydroxyl radical; a -COORi 5 radical; a -CONRi 6 Ri 7 radical; an optionally substituted alkoxy radical from 1 to 18 carbon atoms; a phenoxy radical; a cycloalkyl radical having from 3 to 7 carbon atoms; a phenyl o naphtyl radical; a phenyl or naphtyl radical having 1 or 2 identical o different substituents, such as phenyl, chlorine, alkoxy having from 1 to 6 carbon atoms, alkyl having from 1 to 6 carbon atoms; a straight-chain or branched, saturated or unsaturated alkyl radical that contains from 1 to 18 carbon atoms, optionally substituted with at least one -OH radical, a phenyl or a group of general formula (II) as defined above; Ri 5 , Ri 6 and Ri 7 are the same as or different from each other and are selected from hydrogen; an optionally substituted, straight-chain
  • Ri 4 is H or -SO 3 M, being M as defined above; Ri 3 and R 13 ' can be the same as or different from each other and are selected from hydrogen; an optionally substituted acyl radical from 1 to 18 carbon atoms; a straight-chain or branched, saturated or unsaturated alkyl radical that contains from 1 to 18 carbon atoms, optionally substituted by at least one -OH radical, a - SO 3 M group, a -N(R 4 )3 + group, being M and R 4 as defined above, or a group of general formula (II) as defined above.
  • the present invention relates to a triazine derivative of general formula (I), in accordance with the first aspect of the invention, in which
  • Ri represents a hydrogen atom; a straight-chain or branched alkyl radical having from 1 to 18 carbon atoms; a cycloalkyl radical from 3 to 7 carbon atoms; a phenyl or naphthyl radical; a phenyl or naphthyl radical that has 1 or 2 identical or different substituents, such as phenyl, chlorine, alkoxy from 1 to 6 carbon atoms, alkyl containing from 1 to 6 carbon atoms; a phenylalkyl radical in which the alkyl group is a chain from 1 to 6 carbon atoms;
  • R 2 represents a hydrogen atom; a straight-chain or branched alkyl radical, having from 1 to 4 carbon atoms; a phenyl or naphthyl radical;
  • R 3 represents a hydrogen atom; a straight-chain or branched alkyl radical, having from 1 to 4 carbon atoms; a phenyl or naphthyl radical;
  • Ai is a radical of general formula (III) or (IV)
  • a 2 is a radical of general formula (III), (V) or (Vi;
  • Rn represents a hydrogen atom; a straight-chain or branched, saturated or unsaturated, alkyl radical, containing from 1 to 6 carbon atoms; a -OH radical;
  • Ri 2 represents a hydrogen atom; a hydroxyl radical; a -COOR 15 radical; a -CONRi 6 Ri 7 radical; an optionally substituted alkoxy radical from 1 to 18 carbon atoms; a phenoxy radical; a cycloalkyl radical having from 3 to 7 carbon atoms; a phenyl o naphtyl radical; a phenyl or naphtyl radical having 1 or 2 identical o different substituents, such as phenyl, chlorine, alkoxy having from 1 to 6 carbon atoms, alkyl having from 1 to 6 carbon atoms; a straight-chain or branched, saturated or unsaturated alkyl radical that contains from 1 to 18 carbon atoms, optionally substituted with at least one -OH radical, a phenyl or a group of general formula (II) as defined above; R ⁇ 3 and R' 13 are the same and represent a hydrogen atom; an acyl radical from 1 to 18 carbon atoms; a
  • R 14 is H.
  • alkyl, cycloalkyl, acyl, aryl or alkoxy radical as defined above, which can be substituted in at least one position, said substituent being an alkyl, alkenyl, alkinyl, aryl, heteroaryl, alkoxide radical such as methoxide, ethoxide or butoxide, halogen such as chlorine or fluorine, nitro, amine, amide or silyl.
  • a 2 is selected from a compound of general formula (III) and one of general formula (V)
  • Rn, R12, R13, R'13 and R14 are as defined above.
  • Ri is a straight-chain or branched alkyl radical that has from 7 to 18 carbon atoms.
  • Ri is selected from hydrogen, methyl, phenyl and naphthyl optionally substituted in at least one position by a phenyl, chlorine, alkoxy or alkyl and phenylalkyl group;
  • R 2 is selected from hydrogen, phenyl, naphthyl and methyl;
  • R 3 is selected from hydrogen, phenyl, naphthyl, methyl and ethyl;
  • Rn is selected from hydrogen, hydroxyl, methyl and ethyl;
  • R 12 is selected from hydrogen, hydroxyl, methyl, ethyl, tert-butyl, benzyl, cyclohexyl, methoxyphenyl, biphenyl, -COOR15 and -CONR1 6 R17;
  • R1 3 and R' 13 are indistinctly selected from hydrogen, methyl, ethyl, propyl, butyl and 2-ethylhexyl;
  • Ri 5 is selected from hydrogen, methyl,
  • said derivative of general formula (I) according to the first aspect of the invention is selected from the group consisting of:
  • the inventors of the present invention have found that the triazine derivatives of general formula (I) absorb in the ultraviolet radiation range of both type A and type B, thus making said derivatives useful as UV radiation absorbent agents while simultaneously provides effective protection against UV-A and UV-B radiation.
  • Another aspect of this invention are the procedures of preparation of a triazine derivative in accordance with the first aspect of the invention.
  • 2, 4-dichloro-6- (RiR 2 R 3 -pyrazol-5-yl) -1, 3, 5- triazine compounds of general formula (VIII) are prepared by lithiation of the pyrazol of general formula (VII) with n-BuLi in an inert solvent such as tetrahydrofuran and subsequent reaction with cyanuric chloride at a temperature ranging between -78°C and room temperature in accordance with the process described in the literature (J.K. Chakrabarti and D.E. Tupper, Tetrahedron, 31, 1879- 1882 (1975)) .
  • the 2, 4-bis-2, 4-dihydroxyphenyl-6- (RiR 2 R 3 -pyrazol-5- yl) -1, 3, 5-triazine of general formula (IX) is prepared by Friedel-Crafts acylation of resorcinol with 2, 4-dichloro- 6- (RiR 2 R 3 -pyrazol-5-yl) -1, 3, 5-triazine (VIII) in the presence of a Lewis acid, in particular aluminium chloride, in an inert solvent such as xylene (mixture of 5 isomers) and at a temperature between 60°C and 100 0 C, in accordance with the process disclosed in US patent 5.955.060.
  • the trialkylated compounds of general formula (Ia) are obtained by alkylation of the compound of general formula (IX) or (XI), in the presence of a base, such as
  • N(R 4 ) S + group has been inserted into an alkylic chain, with
  • R 4 being as defined above, can be obtained, for example, following the procedures described in Sharma, M.L. et al., J. Indian Chem. Soc, 74(1997)4, 343-344.
  • the 2, 4-dichloro-6- (RiR 2 R 3 -pyrazol-5-yl) - 1, 3, 5-triazine of general formula (VIII) reacts with at least 2 equivalents of an aniline of formula (XIII) , in the presence of a base such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide or potassium hydroxide in a solvent such as dioxane or acetone, at a temperature ranging between 0 0 C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 50°C and the boiling temperature of the solvent.
  • a base such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide or potassium hydroxide in a solvent such as dioxane or acetone
  • R 14 H and R 1 , R 2 , R 3 , Rn, Ri2, R13 and R' 13 have the meaning stated above, can be prepared according to the process disclosed in the US patent 3278534.
  • the triazine derivatives of general formula (I) according to the first aspect of this invention have physiochemical properties such as ultraviolet light absorption that allow them to be used as protective agents against UV radiation.
  • object of the present invention are, therefore, cosmetic, dermatological or pharmaceutical formulations that include one or more derivatives of general formula
  • said cosmetic, dermatological or pharmaceutical formulation further includes at least one organic, inorganic or organomineral filter against solar radiation.
  • said formulation also includes at least one active ingredient.
  • Said cosmetic, dermatological or pharmaceutical formulation can be adapted for application thereof onto the skin and lips in the form of: non-ionic vesicular dispersion, emulsion, cream, lotion, gel, aerosol, cream- gel, gel-cream, suspension, dispersion, ointment, powder, solid stick, foam, spray, oil and fluid, among others.
  • said formulation can be adapted for application thereof onto the hair in the form of a shampoo, lotion, gel, fluid, lacquer, foam, dye, emulsion, cream, spray, among others, and onto the nails in the form of a nail varnish, oil and gel, among others.
  • the organic, inorganic and organomineral filters are chosen from ones acceptable under the country's legislation.
  • the organic filters can be selected from those approved by the Council of the European Communities (Revised Text of European Directive 76/768/EEC Annexe-7, pages 76-81, published on 15.10.2003) and by the U.S. Food and Drug Administration (see, for example, "Food and Drugs, Sunscreen drug products for over the counter human use", title 21, volume 5 of the Code of Federal Regulations, as revised on 1 April 2004), such as: antranilates; derivatives of camphor; derivatives of dibenzoylmethane; derivatives of benzotriazoles; derivatives of diphenylacrylates; cinnamic derivatives; salycylic derivatives; triazine derivatives such as those described in patents EP-863145, EP-517104, EP-570838, EP- 796851, EP-775698 and EP-878469, derivatives of benzophenone; derivatives of benzalmalonate; derivatives of benzimidazole, imidizolines; derivatives of p- amino acids
  • the inorganic filters can be selected from a group that includes: metallic oxides as pigments, nanopigments, treated and untreated, such as dioxide of titanium (amorphous or crystalline) , iron, zinc, zirconium or cerium. Moreover, alumina and/or aluminium stearate are conventional coating agents. Examples of untreated metallic oxides as inorganic filters (uncoated) are described in patent applications EP518772 and EP518773.
  • the cosmetic, dermatological and pharmaceutical formulations of the present invention can additionally contain additives and adjuvants that can be selected from fatty acids, organic solvents, thickening agents, softening agents, antioxidants, opacifiers, stabilisers, emollients, hydroxyacids, anti-foaming agents, wetting agents, vitamins, fragrances, preservatives, surfactants, sequestering agents, polymers, propellants, acidifying or basifying agents, colorants, dyes, dihydroxyacetone, insect repellents or any other ingredient commonly used in cosmetic formulations, and particularly in the production of photoprotective compositions.
  • additives and adjuvants can be selected from fatty acids, organic solvents, thickening agents, softening agents, antioxidants, opacifiers, stabilisers, emollients, hydroxyacids, anti-foaming agents, wetting agents, vitamins, fragrances, preservatives, surfactants, sequestering agents, polymers, propellants, acidifying
  • substances/fatty acids include among others oils or waxes or mixtures thereof and can include fatty acids, fatty alcohols and esters of fatty acids.
  • the oils are selected, advantageously, from animal, vegetable, mineral or synthetic oils and in particular from liquid petrolatum, liquid paraffin, volatile and non-volatile silicone oils, isoparaffins, polyalphaolefins or fluorated or perfluorated oils.
  • the waxes are selected, advantageously, from animal, vegetable, mineral or synthetic waxes known to the skilled in the art.
  • organic solvents examples include short-chain alcohols and polyoles.
  • the thickeners are selected, advantageously, from crosslinked polymers of acrylic acid, modified and unmodified carob gum rubbers, celluloses and xantan rubber, such as hydroxypropylated carob gum rubbers, methylhydroxyethylcellulose, hydroxypropylmethylcellulose or hydroxyethylcellulose.
  • the present invention relates to the use of a triazine derivative according to the first aspect of the invention in a cosmetic, dermatological or pharmaceutical formulation as a UV radiation filtering agent.
  • the present invention relates to the use of a triazine derivative according to the first aspect of the invention for the manufacture of a formulation for protecting the skin, lips and/or related tissues of a mammal against solar radiation.
  • the present invention relates to the use of at least one triazine derivative according to the first aspect of the invention for the manufacture of a formulation for the prevention, coadjuvant in the treatment or for the treatment of pathologies caused by ultraviolet radiation on the skin, lips and/or related tissues of a mammal, such as light- induced polymorphic eruptions, photoageing, actinic keratosis, vitiligo, solar urticaria, chronic actinic dermatitis, xeroderma pigmentosum.
  • said formulation is applied topically and, more preferably still, said mammal is a human.
  • the properties of the triazine derivatives of general formula (I) make them also useful as photostabilisers of synthetic polymers and solar filters for textile fibres.
  • AICI 3 (0.64 g, 4.80 mmol) is slowly to a mixture of 2, 4-dichloro-6- (l-methyl-lH-pyrazol-5-yl) -1, 3, 5-triazine (0.5 g, 2.17 mmol) and resorcinol (0.58 g, 4.77 mmol) in 25 20 mL of xylene heated to 40-50°C, added and the mixture is maintained at 8O 0 C for 2 hours. The solvent is decanted, the residue is washed with ethylic ether and decanted.
  • Resorcinol (1.4 g, 5.82 mmol) is dissolved in 70 mL of xylene at 40-50 0 C, 2, 4-dichloro-6- (1-phenyl-lH-pyrazol- 5-yl) -1,3, 5-triazine (1.7 g, 12.72 mmol) is added at this temperature and portions of AICI 3 (1.7 g, 12, 75 mmol) are then added quickly.
  • the mixture is heated to 80-83 0 C and is kept at this temperature for 3 hours.
  • the solution is cooled, the solvent is decanted and is added to a solution of HCl 2N (60 mL) and left under stirring, forming a yellowish solid which is filtered, washed with a solution of HCl 2N and dried.
  • a mixture o phenyl-lH-pyrazol-5-yl) -1, 3, 5-triazine (0.35 g, 0.80 mmol) and a 30% NaOH solution (0.24 g, 1.8 mmol) in 2- methoxyethanol (Methyl Cellosolve, 4 mL) is heated to 80°C for 30 minutes.
  • a solution of 3- (bromomethyl) heptane (0.40 g, 2.07 mmol) in 2-methoxyethanol (Methyl Cellosolve, 1 mL) is then added slowly for 20 minutes maintaining the reaction temperature at 80 0 C. Once the addition is finished, the mixture is heated to 110-114°C for 16 hours following the alkylation by TLC.
  • Example 11 Formulation in form of oil/water cream
  • Dicaprilate/dicaprate (Estol 1526 PDCC) 7.50 Triglyceride (Myritol 318 (Henkel) Caprillic/capric 3.00
  • PNC 30 (Sodium Acrylates/Crosslinked Polymer Vinyl Isodecanoate) 0 .15
  • ABIOL Imidazolidinyl Urea
  • Methylparaben 0 20
  • Propylparaben 0 • 10
  • F. 0 30
  • PARSOL® MCX (CTFA: octyl methoxycinnamate) 7.50
  • Cutina HR Hydrogenated Castor Oil
  • SATOL Oleilic Alcohol
  • Betacarotene (1% sol'n) 0.30
  • CTFA Panthenol
  • CTFA Propylenglycol
  • Example 14 Formulation in fluid form
  • Crodamol DA (CTFA: Diisopropyl adipate ) 15.50
  • Example 15 Formulation in form of Water/Oil emulsion % in weight
  • Tioveil 50 FCM Tianium Dioxide, Alkyl Ci 2 -Ci 5 benzoate Cyclomethicone, polyhydroxystearic acid, aluminium stearate, alumina 12.00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Birds (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/IB2005/003931 2004-12-16 2005-12-14 6- (1h-pyrazol-5-yl)-1, 3, 5-triazine derivatives and their use as protective agents against uv radiation WO2006064366A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05823239A EP1833818A1 (en) 2004-12-16 2005-12-14 6-(1h-pyrazol-5-yl)-1,3,5-triazine derivatives and their use as protective agents against uv radiation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200402986A ES2264624B1 (es) 2004-12-16 2004-12-16 Nuevos derivados de triazina, asi como procedimientos para su obtencion y su utilizacion como agentes protectores contra la radiacion uv.
ESP-200402986 2004-12-16

Publications (1)

Publication Number Publication Date
WO2006064366A1 true WO2006064366A1 (en) 2006-06-22

Family

ID=36077586

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2005/003931 WO2006064366A1 (en) 2004-12-16 2005-12-14 6- (1h-pyrazol-5-yl)-1, 3, 5-triazine derivatives and their use as protective agents against uv radiation

Country Status (7)

Country Link
EP (1) EP1833818A1 (es)
AR (1) AR052818A1 (es)
ES (1) ES2264624B1 (es)
PE (1) PE20060744A1 (es)
TW (1) TW200637848A (es)
UY (1) UY29280A1 (es)
WO (1) WO2006064366A1 (es)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008067928A1 (en) * 2006-12-04 2008-06-12 Isdin S.A. Uv absorbing compositions containing a pyrrolyltriazine
CN101081847B (zh) * 2007-06-15 2010-06-09 北京大学 N,n-二烷基胺基苯基-二吡唑三嗪结构光敏分子的合成方法
WO2010081835A2 (en) 2009-01-14 2010-07-22 Isdin, S. A. Bis-resorcinyl-triazine derivatives as protecting agents against uv radiation
CN115109466A (zh) * 2022-07-28 2022-09-27 佛山市帆思科材料技术有限公司 抗老化型水性色彩喷墨打印墨水产品及制造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165608A2 (de) * 1984-06-22 1985-12-27 Ilford Ag Hydroxyphenyltriazine, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber
WO2003075875A1 (en) * 2002-03-12 2003-09-18 Ciba Specialty Chemicals Holding Inc. Uv absorber compositions comprising a hydroxyphenyltriazine compound
EP1380583A2 (de) * 1995-11-23 2004-01-14 Ciba Specialty Chemicals Holding Inc. Bis-Resorcinyl-Triazine und deren Verwendung als Sonnenschutzmittel
WO2004064797A1 (en) * 2003-01-20 2004-08-05 Ciba Specialty Chemicals Holding, Inc. Triazine derivatives as uv absorbers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0165608A2 (de) * 1984-06-22 1985-12-27 Ilford Ag Hydroxyphenyltriazine, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber
EP1380583A2 (de) * 1995-11-23 2004-01-14 Ciba Specialty Chemicals Holding Inc. Bis-Resorcinyl-Triazine und deren Verwendung als Sonnenschutzmittel
WO2003075875A1 (en) * 2002-03-12 2003-09-18 Ciba Specialty Chemicals Holding Inc. Uv absorber compositions comprising a hydroxyphenyltriazine compound
WO2004064797A1 (en) * 2003-01-20 2004-08-05 Ciba Specialty Chemicals Holding, Inc. Triazine derivatives as uv absorbers

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008067928A1 (en) * 2006-12-04 2008-06-12 Isdin S.A. Uv absorbing compositions containing a pyrrolyltriazine
CN101081847B (zh) * 2007-06-15 2010-06-09 北京大学 N,n-二烷基胺基苯基-二吡唑三嗪结构光敏分子的合成方法
WO2010081835A2 (en) 2009-01-14 2010-07-22 Isdin, S. A. Bis-resorcinyl-triazine derivatives as protecting agents against uv radiation
EP2210887A1 (en) 2009-01-14 2010-07-28 Isdin, S.A. Bis resorcinyl triazine derivatives as protecting agents against UV radiation
WO2010081835A3 (en) * 2009-01-14 2010-09-16 Isdin, S. A. Bis-resorcinyl-triazine derivatives as protecting agents against uv radiation
ES2367390A1 (es) * 2009-01-14 2011-11-03 Isdin, S. A. Derivados de bis-resorcinil triazina como agentes protectores frente a la radiación uv.
CN115109466A (zh) * 2022-07-28 2022-09-27 佛山市帆思科材料技术有限公司 抗老化型水性色彩喷墨打印墨水产品及制造方法

Also Published As

Publication number Publication date
EP1833818A1 (en) 2007-09-19
ES2264624A1 (es) 2007-01-01
TW200637848A (en) 2006-11-01
ES2264624B1 (es) 2007-11-01
PE20060744A1 (es) 2006-09-10
UY29280A1 (es) 2006-04-28
AR052818A1 (es) 2007-04-04

Similar Documents

Publication Publication Date Title
KR101737662B1 (ko) Ｕｖ 선 흡수용 2-페닐-1,2,3-벤조트라이아졸
US7772242B2 (en) Merocyanine derivatives
EP1701695B1 (en) Merocyanine derivatives for cosmetic use
EP1606270B1 (en) Symmetrical triazine derivatives
KR101390075B1 (ko) 벤질리덴 말로네이트를 포함하는 ｕｖ 필터 조합물
EP2016059B1 (en) Triazine derivatives
EP1904500A1 (en) New derivatives of heptaazaphenalene, methods for obtaining them, and their use as protecting agents against uv radiation
US20080253978A1 (en) Derivatives of Pyrrolyltriazine Together with Methods for Obtaining Them and Their Use as Protecting Agents Uv Radiation
EP2210887A1 (en) Bis resorcinyl triazine derivatives as protecting agents against UV radiation
WO2006064366A1 (en) 6- (1h-pyrazol-5-yl)-1, 3, 5-triazine derivatives and their use as protective agents against uv radiation
KR20140112561A (ko) 벤질리덴 말로네이트
US7217821B2 (en) Photoprotective cosmetic compositions comprising para-aminobenzalmalonate-substituted s-triazine compounds
JPH092930A (ja) 光安定性の化粧品用光遮断組成物
US8323624B2 (en) S-triazine sunscreens bearing hindered para-aminobenzalmalonate/para-aminobenzalmalonamide and aminobenzoate/aminobenzamide substituents
JP2006070035A (ja) ヒンダードパラ−アミノベンザルマロネートおよびパラ−アミノベンザルマロンアミド基から選択された２つの置換基とアミノベンゾエート置換基を有するｓ−トリアジン化合物、組成物、ならびに使用
US20110263846A1 (en) NOVEL SILANIC PARA-AMINOBENZALMALONATE-SUBSTITUTED s-TRIAZINE COMPOUNDS AND PHOTOPROTECTIVE COMPOSITIONS COMPRISED THEREOF
DE10037846A1 (de) Neue Flavonoide und ihre Verwendung in kosmetischen und dermatologischen Zubereitungen

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KN KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2005823239

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 2005823239

Country of ref document: EP