WO2015006803A1 - Uv absorbing compounds, compositions comprising same and uses thereof - Google Patents

Uv absorbing compounds, compositions comprising same and uses thereof Download PDF

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Publication number
WO2015006803A1
WO2015006803A1 PCT/AU2014/000721 AU2014000721W WO2015006803A1 WO 2015006803 A1 WO2015006803 A1 WO 2015006803A1 AU 2014000721 W AU2014000721 W AU 2014000721W WO 2015006803 A1 WO2015006803 A1 WO 2015006803A1
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WIPO (PCT)
Prior art keywords
substituted
unsubstituted
group
alkyl
hydrogen
Prior art date
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Ceased
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PCT/AU2014/000721
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English (en)
French (fr)
Inventor
Mark York
John Ryan
Gregory Paul SAVAGE
Adam Gerhard Meyer
Karen Jarvis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
CORAL SUNSCREEN Pty Ltd
Original Assignee
CORAL SUNSCREEN Pty Ltd
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
Priority claimed from AU2013902607A external-priority patent/AU2013902607A0/en
Priority to AU2014292799A priority Critical patent/AU2014292799B2/en
Priority to EP14825938.5A priority patent/EP3022180B1/en
Priority to US14/905,217 priority patent/US9920009B2/en
Priority to SG11201600266VA priority patent/SG11201600266VA/en
Priority to HK16109216.1A priority patent/HK1221146B/en
Priority to CA2918065A priority patent/CA2918065C/en
Priority to KR1020167003689A priority patent/KR20160032174A/ko
Priority to CN201480050795.5A priority patent/CN105793239B/zh
Priority to BR112016000844A priority patent/BR112016000844A8/pt
Application filed by CORAL SUNSCREEN Pty Ltd filed Critical CORAL SUNSCREEN Pty Ltd
Priority to JP2016526374A priority patent/JP6879621B2/ja
Priority to DK14825938.5T priority patent/DK3022180T3/da
Publication of WO2015006803A1 publication Critical patent/WO2015006803A1/en
Anticipated expiration legal-status Critical
Priority to US15/888,631 priority patent/US10519111B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—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
    • 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
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/32—Radiation-absorbing paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/48—Stabilisers against degradation by oxygen, light or heat
    • C—CHEMISTRY; METALLURGY
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43—Compounds containing sulfur bound to nitrogen
    • C08K5/435—Sulfonamides

Definitions

  • the compound of formula I is selected from the group consisting of:
  • Scheme 1 1 Process used for the synthesis of bis(enaminone) compounds with monoacylated/hydrolysis product also obtained.
  • Bis(/V-aryl-enaminone) compound 172 was a strongly absorbing high molecular weight compound with an ⁇ in excess of 52000 due to the presence of 2 chromophores. As expected, the presence of an /V-aryl substituent gives compounds with a higher A max than the corresponding /V-alkyl compound. The presence of either a p-methyl (176) or p-f-butyl (177) substituent provides a similar increase in A max . The use of the 1 -naphthyl group gives a compound (178) that is almost identical to unsubstituted phenyl, in terms of A max and ⁇ values. The p-dimethylamino substituent gives a large increase in A max and a Acrit value of 371 nm.
  • Humectants may be used including glycols such as propylene glycol and butylene glycol as well as glycerine.
  • a fourth aspect of the present invention resides in a method of protecting a surface or tissue from UV rays including the step of applying a compound of formula formula I, lla, Mb, III, IV, V or VI to the surface or tissue.
  • the use of the third embodiment or the method of the fourth aspect has the compound as a component of a coating composition.
  • the compound of formula formula I, lla, lib, III, IV, V or VI may be present in the coating composition with a range of standard formulation agents including, one or more the agents described above.
  • the coating composition may be a paint, staining, UV protective, tinting or polymeric matrix formulation wherein the compound of formula formula I, lla, Mb, III, IV, V or VI provides UV protective or additional UV protective properties to the formulation.
  • the present compounds may also be used n the formation of plastic materials whereby their presence within the plastics matrix, either in the sense of being captured therein or being chemically bonded to the plastics backbone, imparts UV protective properties.
  • the material thus obtained was then purified by preparative thin layer chromatography eluting with 50% ethyl acetate : petroleum, ether.
  • the residue was dissolved in DCM (0.5 ml_) and 2M HCI in ether (4 drops) added drop wise. Diethyl ether (5 ml_) was then added and the solvent decanted leaving a yellow residue in the flask.
  • the residue was washed further with diethyl ether, then dissolved in DCM (1 ml_) and treated with triethylamine (3 drops).
  • the solution was then washed with 5% NaC0 3 solution, the organic phase separated, dried with magnesium sulfate and evaporated in-vacuoio afford the title compound as a yellow oil (12 mg, 3%).
  • Ri 4 , Ri 4 ' and R 15 when present, may be independently selected from the group consisting of amino, cyano, Ci to C 6 alkyl substituted or unsubstituted, Ci to C 6 alkenyi substituted or unsubstituted and aryl substituted or unsubstituted.
  • R 3 is seiected from the group consisting of hydrogen, sulfonyl, substituted or unsubstituted Ci to C 6 alkyl, substituted or unsubstituted C s to C 6 a!kenyi, substituted or unsubstituted Ci to C 6 alkoxy, and
  • W is sulphur or oxygen and R 7 is selected from the group consisting of Ci to C 6 alkyl, trihaioalkyl, C 2 to C 6 alkenyl, C 2 to C 6 aikynyi, aryl, aroyi, C 2 to C i2 alkanone, C 2 to C 9 alkanoyl, C 2 to C 9 alkanoyloxy, C 2 to Cg alkoxycarbonyl, C 2 to C 6 carboxyi, Ci to C 6 haioalky!, C 4 to G 7 cycioalkanone, N- C-i to C 6 alkyl, M ⁇ C 5 to C 7 aryi, N- C 5 to C 7 heterocycly, N-SO 2 ⁇ R 20 and C 5 or C 6 heterocyclic ail of which groups may be substituted or unsubstituted and wherein R 20 is selected from the group consisting of d to C 6 alkyl and phenyl each of which may be substituted or unsubstit
  • R 3 is selected from the group consisting of hydrogen, benzenesu!fonyl and

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Paints Or Removers (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/AU2014/000721 2013-07-15 2014-07-15 Uv absorbing compounds, compositions comprising same and uses thereof Ceased WO2015006803A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DK14825938.5T DK3022180T3 (da) 2013-07-15 2014-07-15 Uv-absorberende sammensætninger, der omfatter samme, og anvendelser deraf
KR1020167003689A KR20160032174A (ko) 2013-07-15 2014-07-15 Uv 흡수성 화합물, 이를 포함하는 조성물 및 이의 용도
US14/905,217 US9920009B2 (en) 2013-07-15 2014-07-15 UV absorbing compounds, compositions comprising same and uses thereof
SG11201600266VA SG11201600266VA (en) 2013-07-15 2014-07-15 Uv absorbing compounds, compositions comprising same and uses thereof
HK16109216.1A HK1221146B (en) 2013-07-15 2014-07-15 Uv absorbing compounds, compositions comprising same and uses thereof
CA2918065A CA2918065C (en) 2013-07-15 2014-07-15 Uv absorbing 1,2,3,4-tetrahydropyridine compounds, compositions comprising same and uses thereof
CN201480050795.5A CN105793239B (zh) 2013-07-15 2014-07-15 紫外吸收化合物、其组合物及其用途
AU2014292799A AU2014292799B2 (en) 2013-07-15 2014-07-15 UV absorbing compounds, compositions comprising same and uses thereof
BR112016000844A BR112016000844A8 (pt) 2013-07-15 2014-07-15 compostos absorvedores de uv, composições que compreendem os mesmos, usos destes e método de proteger uma superfície ou tecido dos raios uv
EP14825938.5A EP3022180B1 (en) 2013-07-15 2014-07-15 Uv absorbing compounds, compositions comprising same and uses thereof
JP2016526374A JP6879621B2 (ja) 2013-07-15 2014-07-15 Ｕｖ吸収化合物、同化合物を含む組成物及びそれらの使用
US15/888,631 US10519111B2 (en) 2013-07-15 2018-02-05 UV absorbing compounds, compositions comprising same and uses thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AU2013902607A AU2013902607A0 (en) 2013-07-15 Uv absorbing compounds and compositions comprising same
AU2013902607 2013-07-15
AU2014902000A AU2014902000A0 (en) 2014-05-27 Uv absorbing compounds and compositions comprising same
AU2014902000 2014-05-27

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US14/905,217 A-371-Of-International US9920009B2 (en) 2013-07-15 2014-07-15 UV absorbing compounds, compositions comprising same and uses thereof
US15/888,631 Continuation-In-Part US10519111B2 (en) 2013-07-15 2018-02-05 UV absorbing compounds, compositions comprising same and uses thereof

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WO2015006803A1 true WO2015006803A1 (en) 2015-01-22

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PCT/AU2014/000721 Ceased WO2015006803A1 (en) 2013-07-15 2014-07-15 Uv absorbing compounds, compositions comprising same and uses thereof

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US (1) US9920009B2 (enExample)
EP (1) EP3022180B1 (enExample)
JP (1) JP6879621B2 (enExample)
KR (1) KR20160032174A (enExample)
CN (1) CN105793239B (enExample)
AU (1) AU2014292799B2 (enExample)
BR (1) BR112016000844A8 (enExample)
CA (1) CA2918065C (enExample)
DK (1) DK3022180T3 (enExample)
SG (1) SG11201600266VA (enExample)
WO (1) WO2015006803A1 (enExample)

Cited By (2)

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WO2017088031A1 (en) 2015-11-27 2017-06-01 Commonwealth Scientific And Industrial Research Organisation Photostable compounds, absorbing compounds and uses thereof
WO2017106930A1 (en) 2015-12-23 2017-06-29 Commonwealth Scientific And Industrial Research Organisation Compounds

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10519111B2 (en) 2013-07-15 2019-12-31 Coral Sunscreen Pty Ltd UV absorbing compounds, compositions comprising same and uses thereof
CN115925607B (zh) * 2022-10-24 2025-07-08 中国农业大学 一种吡咯啉-2(3h)-酮类化合物、其制备方法和用途
CN118652497B (zh) * 2024-08-19 2024-11-15 安徽泽泓塑业股份有限公司 一种基于毛竹纤维粉的生物基可降解复合材料及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988002251A1 (en) * 1986-09-26 1988-04-07 Ici Australia Operations Proprietary Limited Sunscreen compositions and compounds for use therein
WO1990009995A1 (en) * 1989-02-23 1990-09-07 Ici Australia Operations Proprietary Limited Uv-absorbing compounds and compositions
GB2286774A (en) 1994-02-23 1995-08-30 Ciba Geigy Ag Sunscreen compositions
US5637718A (en) 1989-02-23 1997-06-10 Ici Australia Operations Proprietary Ltd. UV-absorbing compounds
WO2014082124A1 (en) * 2012-11-27 2014-06-05 Coral Sunscreen Pty Ltd Synthesis of uv absorbing compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR206937A1 (es) * 1974-09-06 1976-08-31 Lilly Co Eli Procedimiento para preparar compuestos de 1-sustituido-4-alquil-4-fenil-piperidina
NZ221849A (en) * 1986-09-26 1990-09-26 Ici Australia Operations Sunscreen compositions containing tetrahydropyridines
CN1229370A (zh) 1996-07-17 1999-09-22 佩雷茨·罗森贝格 滴罐喷射器结构
US7476679B2 (en) * 2005-07-26 2009-01-13 Research Triangle Institute Octahydroisoquinoline compounds as opioid receptor modulators

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988002251A1 (en) * 1986-09-26 1988-04-07 Ici Australia Operations Proprietary Limited Sunscreen compositions and compounds for use therein
WO1990009995A1 (en) * 1989-02-23 1990-09-07 Ici Australia Operations Proprietary Limited Uv-absorbing compounds and compositions
US5637718A (en) 1989-02-23 1997-06-10 Ici Australia Operations Proprietary Ltd. UV-absorbing compounds
GB2286774A (en) 1994-02-23 1995-08-30 Ciba Geigy Ag Sunscreen compositions
WO2014082124A1 (en) * 2012-11-27 2014-06-05 Coral Sunscreen Pty Ltd Synthesis of uv absorbing compounds

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
"The Chemistry and Manufacture of Cosmetics", COSMETICS & TOILETRIES, vol. 116, no. 9, September 2001 (2001-09-01)
DATABASE REGISTRY [online] 13 May 2010 (2010-05-13), "3-PYRIDINECARBOXAMIDE, 1,4-DIHYDRO-1,4,4-TRIMETHYL-N-PROPYL-(CA INDEX NAME)", XP055313563, accession no. STN Database accession no. 1222816-87-6 *
DATABASE REGISTRY [online] 13 May 2010 (2010-05-13), "3-PYRIDINECARBOXAMIDE, 1,4-DIHYDRO-4,4-DIMETHYL-1-(PHENYLMETHYL)-N-PROPYL-(CA INDEX NAME)", XP055313566, accession no. STN Database accession no. 1222802-59-6 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "1H-PYRROLE-1-ETHANOL, 2,3-DIHYDRO-3,3,5-TRIMETHYL- (CA INDEX NAME)", XP055313585, accession no. STN Database accession no. 86177-91-5 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "2H-PYRROL-2-ONE, 1-[2-(2,4-DICHLOROPHENOXY)ETHYL]-1,3-DIHYDRO-3,3,5-TRIMETHYL- (CA INDEX NAME)", XP055313571, accession no. STN Database accession no. 86310-33-0 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "2H-PYRROL-2-ONE, 1-[2-(ETHENYLOXY)ETHYL]-1,3-DIHYDRO-3,3,5-TRIMETHYL- (CA INDEX NAME)", XP055313574, accession no. STN Database accession no. 86240-04-2 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "2H-PYRROL-2-ONE, 1-CYCLOHEXYL-1,3-DIHYDRO-3,3,5-TRIMETHYL- (CA INDEX NAME)", XP055313581, accession no. STN Database accession no. 86219-57-0 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "2-PROPENOIC ACID, 2-METHYL-, 2-(2,3-DIHYDRO-3,3,5-TRIMETHYL-2-OXO-1HPYRROL-1-YL)ETHYL ESTER (CA INDEX NAME)", XP055313577, accession no. STN Database accession no. 86219-66-1 *
DATABASE REGISTRY [online] 25 July 1987 (1987-07-25), "PYRIDINIUM, 1,2,3,4-TETRAHYDRO-1,1,4,4-TETRAMETHYL- (CA INDEX NAME)", XP055313568, accession no. STN Database accession no. 109434-61-9 *
DATABASE REGISTRY [online] 7 December 2011 (2011-12-07), "2H-PYRROL-2-ONE, 1,3-DIHYDRO-3,3-DIMETHYL-1-[2-METHYL-4'-[(2,5,6,7-TETRAHYDRO-1'-METHYLSPIRO[3H-FURO[2,3-F]INDOLE-3,4'-PIPERIDIN]-5-YL)CARBONYL][1,1'-BIPHENYL]-4-YL]-(CA INDEX NAME)", XP055313561, accession no. STN Database accession no. 1349997-46-1 *
HESSE, K. ET AL.: "Über zweistufige Redoxsysteme, XXX: Spektroskopische und elecktrochemische Eigenschaften N-substituierter 1,4-Dihydro-4,4-dimethylpyridine", LIEBIGS ANNALEN DER CHEMIE, 1982, pages 2079 - 2086, XP055313158 *
KOSOWER, E.M. ET AL.: "The Synthesis and Properties of Some Simple 1,4- Dihydropyridines", JOURNAL OF ORGANIC CHEMISTRY, vol. 27, no. 11, 1962, pages 3746 - 3771, XP055313159 *
OHNO, A. ET AL.: "Reduction by a Model of NAD(P)H. 35. Spectroscopic Detection of Charge-transfer Intermediate", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 54, 1981, pages 3489 - 3491, XP055315191 *
See also references of EP3022180A4
TANNER. P.R., DERMATOL. CLIN., vol. 24, no. 1, January 2006 (2006-01-01), pages 53 - 62

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* Cited by examiner, † Cited by third party
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WO2017088031A1 (en) 2015-11-27 2017-06-01 Commonwealth Scientific And Industrial Research Organisation Photostable compounds, absorbing compounds and uses thereof
CN107108503A (zh) * 2015-11-27 2017-08-29 联邦科学与工业研究组织 光稳定化合物、吸收化合物及其用途
KR20180087134A (ko) * 2015-11-27 2018-08-01 커먼웰쓰 사이언티픽 앤 인더스트리알 리서치 오거니제이션 광안정성 화합물, 흡수성 화합물 및 이들의 용도
JP2019504818A (ja) * 2015-11-27 2019-02-21 コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガナイゼーション 光安定化合物、吸収化合物およびそれらの用途
US10315994B2 (en) 2015-11-27 2019-06-11 Commomwealth Scientific And Industrial Research Organization Photostable compounds, absorbing compounds and uses thereof
CN107108503B (zh) * 2015-11-27 2022-10-04 联邦科学与工业研究组织 光稳定化合物、吸收化合物及其用途
KR102779069B1 (ko) * 2015-11-27 2025-03-07 커먼웰쓰 사이언티픽 앤 인더스트리알 리서치 오거니제이션 광안정성 화합물, 흡수성 화합물 및 이들의 용도
WO2017106930A1 (en) 2015-12-23 2017-06-29 Commonwealth Scientific And Industrial Research Organisation Compounds
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US20160244409A1 (en) 2016-08-25
CA2918065A1 (en) 2015-01-22
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BR112016000844A2 (pt) 2017-07-25
CN105793239A (zh) 2016-07-20
DK3022180T3 (da) 2022-05-23
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CA2918065C (en) 2021-09-14
CN105793239B (zh) 2019-11-05
JP2016526575A (ja) 2016-09-05
EP3022180A4 (en) 2017-05-10
AU2014292799A1 (en) 2016-02-04
BR112016000844A8 (pt) 2020-01-07
EP3022180A1 (en) 2016-05-25
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