AU2003229665B2 - Aminophenylbenzothiazole compounds - Google Patents
Aminophenylbenzothiazole compounds Download PDFInfo
- Publication number
- AU2003229665B2 AU2003229665B2 AU2003229665A AU2003229665A AU2003229665B2 AU 2003229665 B2 AU2003229665 B2 AU 2003229665B2 AU 2003229665 A AU2003229665 A AU 2003229665A AU 2003229665 A AU2003229665 A AU 2003229665A AU 2003229665 B2 AU2003229665 B2 AU 2003229665B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- alkyl
- formula
- preparations
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- FVWQTWZWXKBAQO-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazol-4-amine Chemical class N=1C=2C(N)=CC=CC=2SC=1C1=CC=CC=C1 FVWQTWZWXKBAQO-UHFFFAOYSA-N 0.000 title description 5
- -1 amino- Chemical class 0.000 claims abstract description 111
- 238000002360 preparation method Methods 0.000 claims abstract description 79
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000002537 cosmetic Substances 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 230000005855 radiation Effects 0.000 claims description 7
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 239000004904 UV filter Substances 0.000 abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 62
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- 239000006096 absorbing agent Substances 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 33
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- 150000002148 esters Chemical class 0.000 description 26
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- 229920001577 copolymer Polymers 0.000 description 22
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 22
- 239000006071 cream Substances 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
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- 239000000839 emulsion Substances 0.000 description 12
- 150000002191 fatty alcohols Chemical class 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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- 239000000243 solution Substances 0.000 description 9
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- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
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- 239000004215 Carbon black (E152) Substances 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 6
- 229940008099 dimethicone Drugs 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229940075529 glyceryl stearate Drugs 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 239000002453 shampoo Substances 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
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- 238000004061 bleaching Methods 0.000 description 5
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- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
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- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
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- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
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- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
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- 239000003039 volatile agent Substances 0.000 description 1
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- 238000001238 wet grinding Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02405311 | 2002-04-17 | ||
| EP02405311.8 | 2002-04-17 | ||
| CH21352002 | 2002-12-16 | ||
| CH2135/02 | 2002-12-16 | ||
| PCT/EP2003/003870 WO2003086341A2 (en) | 2002-04-17 | 2003-04-14 | Aminophenylbenzothiazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003229665A1 AU2003229665A1 (en) | 2003-10-27 |
| AU2003229665B2 true AU2003229665B2 (en) | 2008-09-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003229665A Ceased AU2003229665B2 (en) | 2002-04-17 | 2003-04-14 | Aminophenylbenzothiazole compounds |
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| Country | Link |
|---|---|
| US (3) | US20050175554A1 (enExample) |
| EP (1) | EP1494641B1 (enExample) |
| JP (1) | JP4068066B2 (enExample) |
| KR (1) | KR20040108742A (enExample) |
| CN (1) | CN100352809C (enExample) |
| AT (1) | ATE449592T1 (enExample) |
| AU (1) | AU2003229665B2 (enExample) |
| BR (1) | BR0309308A (enExample) |
| DE (1) | DE60330229D1 (enExample) |
| MX (1) | MX266917B (enExample) |
| WO (1) | WO2003086341A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8158136B2 (en) | 2004-08-18 | 2012-04-17 | L'oréal | Emulsification system for use in cosmetics |
| JP2007254323A (ja) * | 2006-03-22 | 2007-10-04 | Shiseido Co Ltd | 毛髪はり・こし改善剤および毛髪用化粧料 |
| JP4914664B2 (ja) * | 2006-07-13 | 2012-04-11 | 花王株式会社 | 乳化型毛髪化粧料 |
| CN102245725B (zh) * | 2008-10-21 | 2014-12-03 | 汉高爱尔兰有限公司 | 用于双组分氰基丙烯酸酯粘合剂的活化剂 |
| ES2503731T3 (es) * | 2008-10-24 | 2014-10-07 | Cognis Ip Management Gmbh | Mezclas de alquilsulfosuccinatos y su empleo |
| US20120134937A1 (en) * | 2009-01-30 | 2012-05-31 | Laurence Halimi | Personal care compositions having reduced eye irritation |
| US20110086075A1 (en) * | 2009-01-30 | 2011-04-14 | Laurence Halimi | Personal care sunscreen compositions having reduced eye irritation |
| US20100196291A1 (en) * | 2009-01-30 | 2010-08-05 | Laurence Halimi | Personal care sunscreen compositions having reduced eye irritation |
| CA2760554A1 (en) * | 2009-05-01 | 2010-11-04 | Signal Investment And Management Co. | Moisturizing antimicrobial composition |
| CN102250134B (zh) * | 2010-05-21 | 2013-12-04 | 中国科学院化学研究所 | 一种识别氟离子的荧光探针及其制备方法和用途 |
| CN103209677B (zh) * | 2010-10-01 | 2015-08-19 | 玫琳凯有限公司 | 皮肤增湿剂和老化抑制配制剂 |
| CN103429299A (zh) | 2011-01-28 | 2013-12-04 | 迈图高新材料有限责任公司 | 防uv光化妆品组合物 |
| CN106349184B (zh) * | 2016-08-08 | 2021-10-26 | 江西师范大学 | 2-(邻烷基芳基)苯并噻唑的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2334348A (en) * | 1941-06-23 | 1943-11-16 | Nat Marking Mach Co | Sunburn preventive |
| US2715629A (en) * | 1952-07-16 | 1955-08-16 | Du Pont | Sulfonic acid derivatives of 2-(4'-dialkylaminophenyl)-benzothiazole |
| NL126227C (enExample) * | 1958-08-22 | |||
| DE2333378A1 (de) * | 1973-06-30 | 1975-01-23 | Basf Ag | Neue verbindungen der benzoxazol- und der benzthiazolreihe und farbbildner fuer kopierverfahren |
| US4002733A (en) * | 1974-07-26 | 1977-01-11 | Minnesota Mining And Manufacturing Company | Sunscreening compositions |
| DE3307364A1 (de) * | 1983-03-02 | 1984-09-06 | Hoechst Ag, 6230 Frankfurt | Zweikomponenten-diazontypiematerial |
| JPH01247453A (ja) * | 1988-03-29 | 1989-10-03 | Mitsubishi Kasei Corp | 熱可塑性ポリエステル樹脂組成物 |
| US4992204A (en) * | 1989-08-22 | 1991-02-12 | Miliken Research Corporation | Irradiation detection and identification method and compositions useful therein |
| US5223250A (en) * | 1991-02-05 | 1993-06-29 | Sun Smart, Inc. | Visibly transparent UV sunblock cosmetic compositions |
| FR2720639B1 (fr) * | 1994-06-03 | 1996-07-05 | Oreal | Compositions cosmétiques photoprotectrices et utilisations. |
| FR2803194A1 (fr) * | 2000-01-03 | 2001-07-06 | Oreal | Nouveaux derives de s-triazine, leur procede de preparation, compositions les contenant et leurs utilisations |
| DE10206562A1 (de) * | 2002-02-18 | 2003-08-28 | Haarmann & Reimer Gmbh | Neue UV-Absorber und Lichtschutzzubereitungen |
-
2003
- 2003-04-14 AU AU2003229665A patent/AU2003229665B2/en not_active Ceased
- 2003-04-14 MX MXPA04009176 patent/MX266917B/es active IP Right Grant
- 2003-04-14 CN CNB038086387A patent/CN100352809C/zh not_active Expired - Fee Related
- 2003-04-14 EP EP03722472A patent/EP1494641B1/en not_active Expired - Lifetime
- 2003-04-14 US US10/511,852 patent/US20050175554A1/en not_active Abandoned
- 2003-04-14 DE DE60330229T patent/DE60330229D1/de not_active Expired - Lifetime
- 2003-04-14 BR BR0309308-5A patent/BR0309308A/pt not_active IP Right Cessation
- 2003-04-14 WO PCT/EP2003/003870 patent/WO2003086341A2/en not_active Ceased
- 2003-04-14 JP JP2003583365A patent/JP4068066B2/ja not_active Expired - Fee Related
- 2003-04-14 KR KR10-2004-7016616A patent/KR20040108742A/ko not_active Abandoned
- 2003-04-14 AT AT03722472T patent/ATE449592T1/de not_active IP Right Cessation
-
2008
- 2008-09-18 US US12/284,043 patent/US20090068129A1/en not_active Abandoned
- 2008-09-18 US US12/284,044 patent/US20090060853A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04009176A (es) | 2004-12-07 |
| ATE449592T1 (de) | 2009-12-15 |
| EP1494641A2 (en) | 2005-01-12 |
| US20050175554A1 (en) | 2005-08-11 |
| US20090060853A1 (en) | 2009-03-05 |
| DE60330229D1 (en) | 2010-01-07 |
| AU2003229665A1 (en) | 2003-10-27 |
| JP4068066B2 (ja) | 2008-03-26 |
| EP1494641B1 (en) | 2009-11-25 |
| US20090068129A1 (en) | 2009-03-12 |
| BR0309308A (pt) | 2005-02-15 |
| WO2003086341A2 (en) | 2003-10-23 |
| KR20040108742A (ko) | 2004-12-24 |
| WO2003086341A3 (en) | 2004-04-01 |
| JP2005529869A (ja) | 2005-10-06 |
| MX266917B (es) | 2009-05-22 |
| CN1646507A (zh) | 2005-07-27 |
| CN100352809C (zh) | 2007-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |