CA2950950A1 - Topical formulations for uv protection - Google Patents
Topical formulations for uv protection Download PDFInfo
- Publication number
- CA2950950A1 CA2950950A1 CA2950950A CA2950950A CA2950950A1 CA 2950950 A1 CA2950950 A1 CA 2950950A1 CA 2950950 A CA2950950 A CA 2950950A CA 2950950 A CA2950950 A CA 2950950A CA 2950950 A1 CA2950950 A1 CA 2950950A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- topical composition
- uva
- uvb
- acid
- 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.)
- Abandoned
Links
- 239000012049 topical pharmaceutical composition Substances 0.000 title description 15
- 230000006750 UV protection Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 232
- 239000000203 mixture Substances 0.000 claims abstract description 208
- 230000000699 topical effect Effects 0.000 claims abstract description 121
- 230000005855 radiation Effects 0.000 claims abstract description 109
- 206010042496 Sunburn Diseases 0.000 claims abstract description 15
- 239000000516 sunscreening agent Substances 0.000 claims description 81
- 230000000475 sunscreen effect Effects 0.000 claims description 77
- -1 menthyl Chemical group 0.000 claims description 71
- 229960005193 avobenzone Drugs 0.000 claims description 60
- 239000000126 substance Substances 0.000 claims description 36
- 238000009472 formulation Methods 0.000 claims description 30
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 28
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 28
- 238000002835 absorbance Methods 0.000 claims description 27
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 23
- 229960001173 oxybenzone Drugs 0.000 claims description 23
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 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 claims description 21
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 239000004615 ingredient Substances 0.000 claims description 21
- 239000006210 lotion Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 15
- 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 claims description 15
- 239000012965 benzophenone Substances 0.000 claims description 15
- 150000008366 benzophenones Chemical class 0.000 claims description 15
- 229960004960 dioxybenzone Drugs 0.000 claims description 15
- 229960004881 homosalate Drugs 0.000 claims description 15
- 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 claims description 15
- 229960000368 sulisobenzone Drugs 0.000 claims description 15
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 14
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 14
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 claims description 14
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 claims description 14
- 239000001263 FEMA 3042 Substances 0.000 claims description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 14
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 14
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 14
- 239000004904 UV filter Substances 0.000 claims description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000003902 salicylic acid esters Chemical class 0.000 claims description 14
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 14
- 229940033123 tannic acid Drugs 0.000 claims description 14
- 235000015523 tannic acid Nutrition 0.000 claims description 14
- 229920002258 tannic acid Polymers 0.000 claims description 14
- 150000007968 uric acids Chemical class 0.000 claims description 14
- 239000000499 gel Substances 0.000 claims description 13
- 239000011787 zinc oxide Substances 0.000 claims description 13
- 230000001965 increasing effect Effects 0.000 claims description 12
- 235000019271 petrolatum Nutrition 0.000 claims description 12
- 239000004264 Petrolatum Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229940066842 petrolatum Drugs 0.000 claims description 11
- 230000004224 protection Effects 0.000 claims description 11
- 239000007921 spray Substances 0.000 claims description 11
- 230000037072 sun protection Effects 0.000 claims description 11
- 229960003921 octisalate Drugs 0.000 claims description 10
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 9
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 9
- 229960000655 ensulizole Drugs 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- SOXAGEOHPCXXIO-DVOMOZLQSA-N menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 claims description 9
- 229960002248 meradimate Drugs 0.000 claims description 9
- 229960001679 octinoxate Drugs 0.000 claims description 9
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 claims description 9
- 239000004408 titanium dioxide Substances 0.000 claims description 9
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- CMDKPGRTAQVGFQ-RMKNXTFCSA-N cinoxate Chemical compound CCOCCOC(=O)\C=C\C1=CC=C(OC)C=C1 CMDKPGRTAQVGFQ-RMKNXTFCSA-N 0.000 claims description 8
- 229960001063 cinoxate Drugs 0.000 claims description 8
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 8
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 7
- VFOKYTYWXOYPOX-PTNGSMBKSA-N (e)-2,3-diphenylprop-2-enenitrile Chemical compound C=1C=CC=CC=1C(/C#N)=C\C1=CC=CC=C1 VFOKYTYWXOYPOX-PTNGSMBKSA-N 0.000 claims description 7
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 7
- MMEXPSCGRYPZKY-UHFFFAOYSA-N 1-(3-bromoindazol-2-yl)ethanone Chemical compound C1=CC=CC2=C(Br)N(C(=O)C)N=C21 MMEXPSCGRYPZKY-UHFFFAOYSA-N 0.000 claims description 7
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 claims description 7
- XPKVYKWWLONHDF-UHFFFAOYSA-N 2,3-dihydroxy-3-(2-hydroxyphenyl)prop-2-enoic acid Chemical class OC(=O)C(O)=C(O)C1=CC=CC=C1O XPKVYKWWLONHDF-UHFFFAOYSA-N 0.000 claims description 7
- DRBARRGCABOUIE-UHFFFAOYSA-N 2,3-dihydroxy-3-phenylprop-2-enoic acid Chemical class OC(=O)C(O)=C(O)C1=CC=CC=C1 DRBARRGCABOUIE-UHFFFAOYSA-N 0.000 claims description 7
- WZPLEIAOQJXZJX-UHFFFAOYSA-N 2,3-dihydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(O)=CC2=C1 WZPLEIAOQJXZJX-UHFFFAOYSA-N 0.000 claims description 7
- VHWSRELATOUTAG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCC(O)CO VHWSRELATOUTAG-UHFFFAOYSA-N 0.000 claims description 7
- ORWUQAQITKSSRZ-UHFFFAOYSA-N 2-hydroxyethyl 4-[bis[2-(2-hydroxyethoxy)ethyl]amino]benzoate Chemical compound OCCOCCN(CCOCCO)C1=CC=C(C(=O)OCCO)C=C1 ORWUQAQITKSSRZ-UHFFFAOYSA-N 0.000 claims description 7
- JCTNVNANPZAULC-UHFFFAOYSA-N 2-methylbenzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=C(O3)C)=C3C=CC2=C1 JCTNVNANPZAULC-UHFFFAOYSA-N 0.000 claims description 7
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 claims description 7
- HMKKFLSUPRUBOO-IUPFWZBJSA-N 3,4-dihydroxy-5-[3,4,5-tris[[(z)-octadec-9-enoyl]oxy]benzoyl]oxybenzoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC1=C(OC(=O)CCCCCCC\C=C/CCCCCCCC)C(OC(=O)CCCCCCC\C=C/CCCCCCCC)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(O)=O)O)=C1 HMKKFLSUPRUBOO-IUPFWZBJSA-N 0.000 claims description 7
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 7
- KKJKXQYVUVWWJP-JLHYYAGUSA-N 4-[(e)-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C\C1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-JLHYYAGUSA-N 0.000 claims description 7
- KVOJTUXGYQVLAJ-UHFFFAOYSA-N 6,7-dihydroxy-4-methylcoumarin Chemical compound C1=C(O)C(O)=CC2=C1OC(=O)C=C2C KVOJTUXGYQVLAJ-UHFFFAOYSA-N 0.000 claims description 7
- ATEFPOUAMCWAQS-UHFFFAOYSA-N 7,8-dihydroxycoumarin Chemical compound C1=CC(=O)OC2=C(O)C(O)=CC=C21 ATEFPOUAMCWAQS-UHFFFAOYSA-N 0.000 claims description 7
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 claims description 7
- 150000004325 8-hydroxyquinolines Chemical class 0.000 claims description 7
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 claims description 7
- UCTWSQYDMPNTRI-UHFFFAOYSA-N C1(CC(C(CC1)C(C)C)C1=CC=C(C=C2C(C3(CCC2C3(C)C)C)=O)C=C1)C Chemical compound C1(CC(C(CC1)C(C)C)C1=CC=C(C=C2C(C3(CCC2C3(C)C)C)=O)C=C1)C UCTWSQYDMPNTRI-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- WNBCMONIPIJTSB-BGNCJLHMSA-N Cichoriin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1)c1c(O)cc2c(OC(=O)C=C2)c1 WNBCMONIPIJTSB-BGNCJLHMSA-N 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- QNHQEUFMIKRNTB-UHFFFAOYSA-N aesculetin Natural products C1CC(=O)OC2=C1C=C(O)C(O)=C2 QNHQEUFMIKRNTB-UHFFFAOYSA-N 0.000 claims description 7
- GUAFOGOEJLSQBT-UHFFFAOYSA-N aesculetin dimethyl ether Natural products C1=CC(=O)OC2=C1C=C(OC)C(OC)=C2 GUAFOGOEJLSQBT-UHFFFAOYSA-N 0.000 claims description 7
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 7
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 7
- 229960001716 benzalkonium Drugs 0.000 claims description 7
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 claims description 7
- 150000001559 benzoic acids Chemical class 0.000 claims description 7
- 229940111759 benzophenone-2 Drugs 0.000 claims description 7
- 229940047187 benzoresorcinol Drugs 0.000 claims description 7
- 150000001565 benzotriazoles Chemical class 0.000 claims description 7
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 claims description 7
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 claims description 7
- YEAYGXLRPMKZBP-KQGICBIGSA-N bis(2-hydroxyethyl)azanium;(e)-3-(4-methoxyphenyl)prop-2-enoate Chemical compound OCCNCCO.COC1=CC=C(\C=C\C(O)=O)C=C1 YEAYGXLRPMKZBP-KQGICBIGSA-N 0.000 claims description 7
- HEIBHROOHCJHCD-MDZDMXLPSA-N butyl (e)-2,4-dioxo-6-phenylhex-5-enoate Chemical compound CCCCOC(=O)C(=O)CC(=O)\C=C\C1=CC=CC=C1 HEIBHROOHCJHCD-MDZDMXLPSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 7
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 7
- 150000004775 coumarins Chemical class 0.000 claims description 7
- YBGKGTOOPNQOKH-UHFFFAOYSA-N daphnetin Natural products OC1=CC=CC2=C1OC(=O)C=C2O YBGKGTOOPNQOKH-UHFFFAOYSA-N 0.000 claims description 7
- HOIXTKAYCMNVMY-PVOAASPHSA-N daphnin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C=CC(=O)O2)C2=C1O HOIXTKAYCMNVMY-PVOAASPHSA-N 0.000 claims description 7
- HOIXTKAYCMNVMY-UHFFFAOYSA-N daphnin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C=CC(=O)O2)C2=C1O HOIXTKAYCMNVMY-UHFFFAOYSA-N 0.000 claims description 7
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims description 7
- 229940113120 dipropylene glycol Drugs 0.000 claims description 7
- 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 claims description 7
- ILEDWLMCKZNDJK-UHFFFAOYSA-N esculetin Chemical compound C1=CC(=O)OC2=C1C=C(O)C(O)=C2 ILEDWLMCKZNDJK-UHFFFAOYSA-N 0.000 claims description 7
- XHCADAYNFIFUHF-TVKJYDDYSA-N esculin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC2=C1OC(=O)C=C2 XHCADAYNFIFUHF-TVKJYDDYSA-N 0.000 claims description 7
- 229940093496 esculin Drugs 0.000 claims description 7
- AWRMZKLXZLNBBK-UHFFFAOYSA-N esculin Natural products OC1OC(COc2cc3C=CC(=O)Oc3cc2O)C(O)C(O)C1O AWRMZKLXZLNBBK-UHFFFAOYSA-N 0.000 claims description 7
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 claims description 7
- 229930182478 glucoside Natural products 0.000 claims description 7
- 150000008131 glucosides Chemical class 0.000 claims description 7
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 7
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- 229940030300 trolamine salicylate Drugs 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462013276P | 2014-06-17 | 2014-06-17 | |
| US62/013,276 | 2014-06-17 | ||
| PCT/US2015/035803 WO2015195546A1 (en) | 2014-06-17 | 2015-06-15 | Topical formulations for uv protection |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2950950A1 true CA2950950A1 (en) | 2015-12-23 |
Family
ID=54936008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2950950A Abandoned CA2950950A1 (en) | 2014-06-17 | 2015-06-15 | Topical formulations for uv protection |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10064797B2 (enExample) |
| EP (1) | EP3164196B1 (enExample) |
| JP (1) | JP2017519823A (enExample) |
| KR (1) | KR20170019427A (enExample) |
| AU (1) | AU2015277474A1 (enExample) |
| CA (1) | CA2950950A1 (enExample) |
| IL (1) | IL249412A0 (enExample) |
| WO (1) | WO2015195546A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102587916B1 (ko) * | 2017-11-16 | 2023-10-11 | (주)아모레퍼시픽 | 유기계 자외선 차단제를 포함하는 실리콘중수 타입의 화장료 조성물 |
| WO2019098637A2 (ko) * | 2017-11-16 | 2019-05-23 | (주)아모레퍼시픽 | 유기계 자외선 차단제를 포함하는 실리콘중수 타입의 화장료 조성물 |
| JP2020180070A (ja) * | 2019-04-25 | 2020-11-05 | サンスター株式会社 | 抗皮膚老化外用組成物 |
| CN115210215B (zh) * | 2020-01-22 | 2024-08-06 | 巴斯夫欧洲公司 | 杀枝曲菌素类氨基酸类似物及其作为防晒剂的用途 |
| JP6818927B2 (ja) * | 2020-07-30 | 2021-01-27 | サンスター株式会社 | 抗皮膚老化外用組成物 |
| US20240148623A1 (en) * | 2021-03-01 | 2024-05-09 | Gadusol Laboratories, Inc. | Gadusol and gadusporine compound formulations for topicals |
| WO2024027926A1 (en) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition comprising a uv-filter stabilizer |
| CN119923247A (zh) * | 2022-08-05 | 2025-05-02 | 西姆莱斯股份公司 | 具有改进的spf和uva光防护的组合物 |
| CN119584951A (zh) * | 2022-08-05 | 2025-03-07 | 西姆莱斯股份公司 | 包含uv滤光剂稳定剂的组合物 |
| WO2024027928A1 (en) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition with improved spf and uva photoprotection |
| WO2024027927A1 (en) * | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition with improved spf and uva photoprotection |
| CN119604267A (zh) * | 2022-08-05 | 2025-03-11 | 西姆莱斯股份公司 | 具有改进的spf和uva光防护的组合物 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259444A (en) | 1972-06-07 | 1981-03-31 | General Electric Company | Microorganisms having multiple compatible degradative energy-generating plasmids and preparation thereof |
| WO1986002350A1 (en) * | 1984-10-10 | 1986-04-24 | Australian Institute Of Marine Science | Ultra violet agents |
| EP0311469A3 (en) | 1987-09-02 | 1990-05-30 | Plant Genetic Systems N.V. | Transformed lactic acid bacteria |
| FR2658075B1 (fr) | 1990-02-14 | 1992-05-07 | Oreal | Composition cosmetique filtrante photostable contenant un filtre uv-a et un beta,beta-diphenylacrylate ou alpha-cyano-beta,beta-diphenylacrylate d'alkyle. |
| US5587150A (en) | 1990-02-14 | 1996-12-24 | L'oreal | Photostable cosmetic screening composition containing a UV-A screening agent and an alkyl β, β-diphenylacrylate or α-cyano-β,β-diphenylacrylate |
| US5207998A (en) | 1991-05-07 | 1993-05-04 | Richardson-Vicks Inc. | Suncare compositions |
| GB2278358B (en) | 1992-02-27 | 1995-07-26 | Lynxvale Ltd | Heterologous gene expression in Lactococcus,and the expression products therefrom |
| JPH0662878A (ja) * | 1992-08-12 | 1994-03-08 | Kaiyo Bio Technol Kenkyusho:Kk | 微生物によるマイコスポリン様アミノ酸の製造法 |
| US5620682A (en) * | 1993-03-25 | 1997-04-15 | Bernel Chemical Co. | Sunscreen compositions |
| IT1270123B (it) | 1994-10-05 | 1997-04-28 | Dompe Spa | Composizioni farmaceutiche contenenti microorganismi ingegnerizzati e loro uso per terapia |
| GB9521568D0 (en) | 1995-10-20 | 1995-12-20 | Lynxvale Ltd | Delivery of biologically active polypeptides |
| EP0975227B1 (en) | 1997-04-18 | 2005-11-09 | Ganeden Biotech, Inc. | Topical use of probiotic bacillus spores to prevent or control microbial infections |
| CA2251457A1 (en) | 1998-10-23 | 2000-04-23 | Norman Huner | Compositions including naturally occurring compounds from plants, algae and cyanobacteria for protection against solar radiation |
| FR2803201B1 (fr) | 1999-12-30 | 2004-11-26 | Gelyma | Extrait d'algue a activite filtrante vis a vis des radiations ultraviolettes |
| US7547527B2 (en) | 2000-10-06 | 2009-06-16 | Markus Baur | Use of probiotic lactic acid bacteria for balancing the skin's immune system |
| GB0028161D0 (en) | 2000-11-17 | 2001-01-03 | Natural Environment Res | Personal care compositions |
| US7081442B2 (en) | 2001-05-21 | 2006-07-25 | Johnson & Johnson Consumer Companies, Inc. | Composition containing a peptide and a pigment and the use thereof in darkening the skin |
| WO2003020236A2 (en) | 2001-09-03 | 2003-03-13 | Hadasit Medical Research Services & Development Limited | The utilization of natural pigments from lichens, cyanobacteria, fungi and plants for sun protection |
| US6899866B2 (en) | 2002-09-06 | 2005-05-31 | Cph Innovations Corporation | Photostabilization of a sunscreen composition with a combination of an α-cyano-β, β-diphenylacrylate compound and a dialkyl naphithalate |
| US6926887B2 (en) | 2002-09-17 | 2005-08-09 | The C.P. Hall Company | Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition |
| CH702571B1 (de) | 2003-04-30 | 2011-07-29 | Mibelle Ag Cosmetics | Kosmetische Hautbehandlungsmittel und kosmetische Wirkstoffkombination zum Schutz gegen frühzeitige Hautalterung. |
| ITMI20041550A1 (it) | 2004-07-29 | 2004-10-29 | Proge Farm Srl | Uso di batteri probiotici per la preparazione di composizioni topiche per la protezione dell'epidermide |
| DK1789529T3 (da) | 2004-08-20 | 2013-11-11 | Actogenix Nv | Fremgangsmåde til forbedring af konserveringen af lactococcus |
| EP1934328A1 (en) | 2005-09-19 | 2008-06-25 | Basf Se | Microorganisms inhibiting the formation of foot malodor |
| JP2009515898A (ja) * | 2005-11-14 | 2009-04-16 | タンニング リサーチ ラボラトリーズ，インコーポレーテッド | 高日焼け止め効率油中水型エマルション |
| US8431112B2 (en) | 2007-08-09 | 2013-04-30 | Hallstar Innocations Corp. | Photostabilization of cholecalciferol with alkoxycrylene compounds |
| EP2501777B1 (en) | 2009-11-20 | 2022-10-26 | Guerry L. Grune | Broad spectrum uva stable, non-toxic, zinc oxide based complex |
| PH12012500740A1 (en) | 2009-11-25 | 2012-11-26 | Nestec Sa | Nutritional compositions including a high protein component and exogenous nucleotides |
| FR2953408B1 (fr) | 2009-12-08 | 2013-02-08 | Oreal | Microorganismes probiotiques a titre d'actif pour l'eclat du teint de la peau |
| PL2364712T3 (pl) | 2010-03-11 | 2013-08-30 | Kloarys Invest Ltd | Miejscowa kompozycja kosmetyczna lub farmaceutyczna zawierająca probiotyczne szczepy pałeczek bakterii kwasu mlekowego i jej stosowanie |
| WO2011150127A2 (en) | 2010-05-25 | 2011-12-01 | The Board Of Trustees Of The University Of Illinois | Novel systems, vectors, and methods for delivery of biomolecules to eukaryotic cells |
| GB201009271D0 (en) | 2010-06-02 | 2010-07-21 | Promar As | Compositions |
| US20140065209A1 (en) | 2011-05-03 | 2014-03-06 | Dupont Nutrition Biosciences Aps | Probiotic bacteria for the topical treatment of skin disorders |
| EP2561853A1 (de) | 2011-08-24 | 2013-02-27 | PM-International AG | Sonnenschutzspray mit Sonnenschutzfaktor SPF 20 bis SPF 30 |
| US9376686B2 (en) | 2011-09-23 | 2016-06-28 | Forsyth Dental Infirmary For Children | Vaccine and therapeutic delivery system |
| CN104470906B (zh) * | 2012-06-04 | 2016-08-24 | 爱尔克米亚 | 作为抵抗紫外线辐射的保护剂的亚氨基化合物 |
| MX2015001751A (es) | 2012-08-07 | 2015-11-13 | Topgenix Inc | Composicion topica comprendiendo bacterias transformadas que expresan un compuesto de interes. |
-
2015
- 2015-06-15 AU AU2015277474A patent/AU2015277474A1/en not_active Abandoned
- 2015-06-15 JP JP2017519212A patent/JP2017519823A/ja active Pending
- 2015-06-15 CA CA2950950A patent/CA2950950A1/en not_active Abandoned
- 2015-06-15 WO PCT/US2015/035803 patent/WO2015195546A1/en not_active Ceased
- 2015-06-15 US US15/317,131 patent/US10064797B2/en active Active
- 2015-06-15 KR KR1020177001023A patent/KR20170019427A/ko not_active Withdrawn
- 2015-06-15 EP EP15809399.7A patent/EP3164196B1/en active Active
-
2016
- 2016-12-06 IL IL249412A patent/IL249412A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3164196B1 (en) | 2021-08-18 |
| AU2015277474A1 (en) | 2016-12-22 |
| EP3164196A4 (en) | 2017-12-06 |
| EP3164196A1 (en) | 2017-05-10 |
| KR20170019427A (ko) | 2017-02-21 |
| IL249412A0 (en) | 2017-02-28 |
| US20170119641A1 (en) | 2017-05-04 |
| JP2017519823A (ja) | 2017-07-20 |
| WO2015195546A1 (en) | 2015-12-23 |
| US10064797B2 (en) | 2018-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20200831 |