JP5528651B2 - ジベンゾイルメタン誘導体の光安定化 - Google Patents
ジベンゾイルメタン誘導体の光安定化 Download PDFInfo
- Publication number
- JP5528651B2 JP5528651B2 JP2001581778A JP2001581778A JP5528651B2 JP 5528651 B2 JP5528651 B2 JP 5528651B2 JP 2001581778 A JP2001581778 A JP 2001581778A JP 2001581778 A JP2001581778 A JP 2001581778A JP 5528651 B2 JP5528651 B2 JP 5528651B2
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- JP
- Japan
- Prior art keywords
- uva
- acid
- avb
- dibenzoylmethane
- bis
- 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.)
- Expired - Lifetime
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- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 230000000176 photostabilization Effects 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- -1 2-ethylhexyl Chemical group 0.000 claims description 36
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical group C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 53
- 239000002537 cosmetic Substances 0.000 abstract description 20
- 230000037072 sun protection Effects 0.000 abstract description 9
- 238000002835 absorbance Methods 0.000 abstract description 7
- 230000005855 radiation Effects 0.000 abstract description 6
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 abstract 1
- 241001402987 Arracacha virus B Species 0.000 description 30
- 206010003671 Atrioventricular Block Diseases 0.000 description 30
- 238000009472 formulation Methods 0.000 description 21
- 239000000839 emulsion Substances 0.000 description 19
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 18
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 18
- 230000000475 sunscreen effect Effects 0.000 description 18
- 239000000516 sunscreening agent Substances 0.000 description 18
- 150000003904 phospholipids Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004904 UV filter Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 9
- 238000006731 degradation reaction Methods 0.000 description 9
- 229960002216 methylparaben Drugs 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 239000000600 sorbitol Substances 0.000 description 9
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 9
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 8
- 229940008099 dimethicone Drugs 0.000 description 8
- 239000004205 dimethyl polysiloxane Substances 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 8
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 8
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 8
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 8
- 229960003415 propylparaben Drugs 0.000 description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 229960000281 trometamol Drugs 0.000 description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- 229920001213 Polysorbate 20 Polymers 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229940114081 cinnamate Drugs 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000787 lecithin Substances 0.000 description 5
- 235000010445 lecithin Nutrition 0.000 description 5
- 229940067606 lecithin Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007764 o/w emulsion Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 4
- 229960001631 carbomer Drugs 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- TVWTZAGVNBPXHU-NXVVXOECSA-N dioctyl (z)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCC TVWTZAGVNBPXHU-NXVVXOECSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 3
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960004101 bemotrizinol Drugs 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000001687 destabilization Effects 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229940068977 polysorbate 20 Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229950006451 sorbitan laurate Drugs 0.000 description 3
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical group CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 2
- 239000004808 2-ethylhexylester Substances 0.000 description 2
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 2
- 244000144927 Aloe barbadensis Species 0.000 description 2
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- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OQILCOQZDHPEAZ-UHFFFAOYSA-N Palmitinsaeure-octylester Natural products CCCCCCCCCCCCCCCC(=O)OCCCCCCCC OQILCOQZDHPEAZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000008156 Ringer's lactate solution Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- 230000000254 damaging effect Effects 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
- DHNGCHLFKUPGPX-UHFFFAOYSA-N ethyl 3-(4-methoxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(OC)C=C1 DHNGCHLFKUPGPX-UHFFFAOYSA-N 0.000 description 2
- GJQLBGWSDGMZKM-UHFFFAOYSA-N ethylhexyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(CC)CCCCC GJQLBGWSDGMZKM-UHFFFAOYSA-N 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
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- 239000001540 sodium lactate Substances 0.000 description 2
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- 230000003595 spectral effect Effects 0.000 description 2
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- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
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- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- YKNCPXOFSKBINA-UHFFFAOYSA-N (2-hydroxy-4-methoxyphenyl)-phenylmethanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1.OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 YKNCPXOFSKBINA-UHFFFAOYSA-N 0.000 description 1
- AALXZHPCKJILAZ-UHFFFAOYSA-N (4-propan-2-ylphenyl)methyl 2-hydroxybenzoate Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)C1=CC=CC=C1O AALXZHPCKJILAZ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- ORHYCSCVVQBDLZ-UHFFFAOYSA-N 1-(2-methylphenyl)-2,2-diphenylethanone Chemical compound CC1=CC=CC=C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 ORHYCSCVVQBDLZ-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CJQZCWGJQXVSIO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1C1=NC=NC=N1 CJQZCWGJQXVSIO-UHFFFAOYSA-N 0.000 description 1
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- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 1
- LUKNZSDCSDDKNC-UHFFFAOYSA-N 3-benzylidene-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one methyl hydrogen sulfate Chemical compound COS(O)(=O)=O.CC1(C)C2CCC1(C)C(=O)C2=CC1=CC=CC=C1 LUKNZSDCSDDKNC-UHFFFAOYSA-N 0.000 description 1
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- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
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- VZRKEAFHFMSHCD-UHFFFAOYSA-N Ethyl 3-(N-butylacetamido)propionate Chemical compound CCCCN(C(C)=O)CCC(=O)OCC VZRKEAFHFMSHCD-UHFFFAOYSA-N 0.000 description 1
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- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound 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 1
- 206010042496 Sunburn Diseases 0.000 description 1
- HEAHZSUCFKFERC-LRVMPXQBSA-N [(2e)-2-[[4-[(z)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)\C2=C/C(C=C1)=CC=C1\C=C/1C(=O)C2(CS(O)(=O)=O)CCC\1C2(C)C HEAHZSUCFKFERC-LRVMPXQBSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
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- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003581 cosmetic carrier Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229960003949 dexpanthenol Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HEAHZSUCFKFERC-UHFFFAOYSA-N ecamsule Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2=CC(C=C1)=CC=C1C=C1C(=O)C2(CS(O)(=O)=O)CCC1C2(C)C HEAHZSUCFKFERC-UHFFFAOYSA-N 0.000 description 1
- 229960003747 ecamsule Drugs 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- HEOCBCNFKCOKBX-SDNWHVSQSA-N enzacamene Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)C2(C)CCC\1C2(C)C HEOCBCNFKCOKBX-SDNWHVSQSA-N 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- ZZZDJGNJUUJEAS-UHFFFAOYSA-N ethyl 2-amino-3-(2-hydroxypropyl)benzoate Chemical compound C(C)OC(C1=C(C(=CC=C1)CC(C)O)N)=O ZZZDJGNJUUJEAS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- ZUVCYFMOHFTGDM-UHFFFAOYSA-N hexadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(O)=O ZUVCYFMOHFTGDM-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KUYQDJOFVBGZID-UHFFFAOYSA-N n,n-diethyl-2-methylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1C KUYQDJOFVBGZID-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000007908 nanoemulsion Substances 0.000 description 1
- 239000006070 nanosuspension Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960003921 octisalate Drugs 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 description 1
- 229940056211 paraffin Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/4966—Triazines or their condensed derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH933/00 | 2000-05-12 | ||
| CH9332000 | 2000-05-12 | ||
| PCT/CH2001/000275 WO2001085123A1 (de) | 2000-05-12 | 2001-05-03 | Photostabilisierung von dibenzoylmethan-derivaten |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012129059A Division JP5554373B2 (ja) | 2000-05-12 | 2012-06-06 | ジベンゾイルメタン誘導体の光安定化 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003532665A JP2003532665A (ja) | 2003-11-05 |
| JP2003532665A5 JP2003532665A5 (enExample) | 2008-06-19 |
| JP5528651B2 true JP5528651B2 (ja) | 2014-06-25 |
Family
ID=4548916
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001581778A Expired - Lifetime JP5528651B2 (ja) | 2000-05-12 | 2001-05-03 | ジベンゾイルメタン誘導体の光安定化 |
| JP2012129059A Expired - Lifetime JP5554373B2 (ja) | 2000-05-12 | 2012-06-06 | ジベンゾイルメタン誘導体の光安定化 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012129059A Expired - Lifetime JP5554373B2 (ja) | 2000-05-12 | 2012-06-06 | ジベンゾイルメタン誘導体の光安定化 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6803063B2 (enExample) |
| EP (1) | EP1280505B1 (enExample) |
| JP (2) | JP5528651B2 (enExample) |
| AT (1) | ATE361123T1 (enExample) |
| AU (1) | AU2001250237A1 (enExample) |
| DE (1) | DE50112444D1 (enExample) |
| ES (1) | ES2284634T3 (enExample) |
| WO (1) | WO2001085123A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2833169B1 (fr) * | 2001-12-07 | 2004-07-16 | Oreal | Composition filtrante contenant un derive de 1,3,5-triazine, un derive du dibenzoylmethane, et un derive de 2-hydroxybenzophenone aminosubstitue |
| FR2833168B1 (fr) | 2001-12-07 | 2004-08-27 | Oreal | Composition filtrante contenant un filtre du type derive du dibenzoylmethane et un derive de 2-hydroxybenzophenone aminosubstitue |
| DE10210337A1 (de) * | 2002-03-08 | 2003-09-25 | Beiersdorf Ag | Lippenpflegeprodukte mit UV-Schutz |
| DE10229997A1 (de) * | 2002-07-03 | 2004-01-15 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitung zum Schutz fotolabiler Wirkstoffe |
| FR2847811B1 (fr) * | 2002-11-29 | 2005-01-07 | Oreal | Composition filtrante contenant au moins un derive du dibenzoylmethane et au moins un derive de 3-(2-azacycloalkylidene)-1,3-dihydro-indol-2-one;procede de photostabilisation |
| GB0318160D0 (en) * | 2003-08-02 | 2003-09-03 | Ssl Int Plc | Parasiticidal composition |
| DE102004020060B3 (de) * | 2004-04-20 | 2005-06-02 | Coty B.V. | Kosmetisches Verfahren zur Behandlung der Haut mit Sonnenprodukten und Sonnenprodukt-Kombination |
| US7368105B2 (en) | 2004-07-02 | 2008-05-06 | L'oreal | Photostabilization of dibenzoylmethane UV-screening agents with arylalkyl benzoate/bis-resorcinyl triazine compounds and photoprotective compositions comprised thereof |
| FR2872414B1 (fr) | 2004-07-02 | 2006-09-22 | Oreal | Procede de photostabilisation d'un derive de dibenzoylmethane par un derive arylalkyl benzoate et un compose bis-resorcinyl triazine et compositions cosmetiques photoprotectrices |
| US7357919B2 (en) | 2004-10-19 | 2008-04-15 | L'oreal | Photostable photoprotective compositions comprising dibenzoylmethane and arylalkyl benzoate compounds and a compound that accepts the excited triplet level energy of said dibenzoylmethane(s) |
| US7431917B2 (en) * | 2004-10-19 | 2008-10-07 | L'oreal | Photostable photoprotective compositions comprising dibenzoylmethane and bis-resorcinyl triazine compounds and a compound that accepts the excited triplet level energy of said dibenzoylmethane(s) |
| FR2876579B1 (fr) * | 2004-10-19 | 2007-04-13 | Oreal | Composition antisolaire a base d'un derive de dibenzoylmetha ne et d'un agent photostabilisant particulier;procede de pho tostabilisation |
| FR2886144B1 (fr) * | 2005-05-27 | 2007-06-29 | Oreal | Procede de photostabilisation d'un derive de dibenzoylmethane par un derive sulfone de merocyanine ; compositions cosmetiques photoprotectrices contenant cette associaton. |
| FR2908988B1 (fr) * | 2006-11-28 | 2009-01-23 | Oreal | Photostabilisation d'un dibenzoylmethane par une s-triazine siliciee et substituee par deux groupes aminobenzaotes ou aminobenzamides et une bis-resorcinyltriazine; compositions photoprotectrices contenant cette association ternaire |
| KR102127963B1 (ko) * | 2007-08-30 | 2020-06-29 | 바스프 에스이 | 미용 조성물의 안정화 |
| FR2949326B1 (fr) * | 2009-08-28 | 2012-02-17 | Oreal | Composition contenant un derive de dibenzoylmethane, une 2-hydroxybenzophenone lipophile et une s-triazine siliciee ; procede de photostabilisation |
| ES2608456T3 (es) | 2009-08-28 | 2017-04-11 | L'oréal | Composición que contiene al menos un filtro de tipo 2-hidroxibenzofenona lipófila y una s-triazina siliciada sustituida por al menos dos grupos alquilaminobenzoatos |
| DE102010044682A1 (de) | 2010-09-08 | 2012-03-08 | Beiersdorf Ag | Emulsion mit UV-Schutz |
| DE102010044681A1 (de) | 2010-09-08 | 2012-03-08 | Beiersdorf Ag | Stabilisierte Emulsion |
| FR2978041B1 (fr) * | 2011-07-21 | 2014-01-10 | Lvmh Rech | Solution parfumante stabilisee vis-a-vis des rayons ultraviolets |
| WO2013114004A1 (fr) | 2012-01-31 | 2013-08-08 | Pierre Fabre Dermo-Cosmetique | Composition et association de filtres solaires photostabilisatrices de bmdbm |
| CA2880772C (en) | 2012-08-06 | 2020-11-17 | Unilever Plc | A photostable sunscreen composition |
| DE102013204097A1 (de) * | 2013-03-11 | 2014-10-30 | Beiersdorf Ag | Wirkstoffkombinationen aus Alkylamidothiazolen und einer oder mehreren kosmetisch oder dermatologisch unbedenklichen UV-Filtersubstanzen |
| EP3817731B1 (en) * | 2018-07-05 | 2025-09-03 | Celista Pharmaceuticals Llc | Testosterone and estradiol transdermal spray |
| WO2020217499A1 (ja) | 2019-04-26 | 2020-10-29 | 大塚製薬株式会社 | アデノシンリン酸を含有するｏ／ｗ型低粘度乳化組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1286504B1 (it) * | 1996-11-26 | 1998-07-15 | 3V Sigma Spa | Composizioni cosmetiche antisolari comprendenti derivati del dibenzoilmetano del benzofenone e della triazina |
| FR2763851B1 (fr) * | 1997-05-28 | 1999-07-09 | Oreal | Compositions comprenant un derive de dibenzoylmethane et un polymere polyamine |
| DE19756921A1 (de) * | 1997-12-19 | 1999-06-24 | Beiersdorf Ag | Verwendung von synthetischem Bienenwachs zur Verstärkung der UV-A-Schutzleistung kosmetischer oder dermatologischer Formulierungen |
| DE19833634A1 (de) * | 1998-07-25 | 2000-02-03 | Beiersdorf Ag | Kosmetische oder dermatologische W/O-Emulsionen, welche nichtionische Tenside enthalten und sich durch einen Gehalt an Siliconemulatoren auszeichnen |
| DE19846772A1 (de) | 1998-10-10 | 2000-04-13 | Beiersdorf Ag | Kosmetische und dermatoligische Hydrodispersionen mit einem Gehalt an Triglyceridwachsen |
| DE19910477A1 (de) * | 1999-03-10 | 2000-09-14 | Beiersdorf Ag | Verwendung von Octocrylen zur Solubilisierung von 2,4-Bis-{[4-(2-Ethyl-hexyloxy-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazin in kosmetischen oder dermatologischen Lichtschutzmitteln |
| NO20002309L (no) * | 1999-05-12 | 2000-11-13 | Hoffmann La Roche | Fotostabile kosmetiske lysavskjermende sammensetninger |
-
2001
- 2001-05-03 US US10/275,870 patent/US6803063B2/en not_active Expired - Lifetime
- 2001-05-03 AU AU2001250237A patent/AU2001250237A1/en not_active Abandoned
- 2001-05-03 AT AT01923464T patent/ATE361123T1/de not_active IP Right Cessation
- 2001-05-03 EP EP01923464A patent/EP1280505B1/de not_active Expired - Lifetime
- 2001-05-03 DE DE50112444T patent/DE50112444D1/de not_active Expired - Lifetime
- 2001-05-03 ES ES01923464T patent/ES2284634T3/es not_active Expired - Lifetime
- 2001-05-03 JP JP2001581778A patent/JP5528651B2/ja not_active Expired - Lifetime
- 2001-05-03 WO PCT/CH2001/000275 patent/WO2001085123A1/de not_active Ceased
-
2012
- 2012-06-06 JP JP2012129059A patent/JP5554373B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1280505A1 (de) | 2003-02-05 |
| JP5554373B2 (ja) | 2014-07-23 |
| DE50112444D1 (de) | 2007-06-14 |
| US20030185770A1 (en) | 2003-10-02 |
| WO2001085123A1 (de) | 2001-11-15 |
| JP2012188445A (ja) | 2012-10-04 |
| ATE361123T1 (de) | 2007-05-15 |
| JP2003532665A (ja) | 2003-11-05 |
| AU2001250237A1 (en) | 2001-11-20 |
| US6803063B2 (en) | 2004-10-12 |
| EP1280505B1 (de) | 2007-05-02 |
| ES2284634T3 (es) | 2007-11-16 |
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