ES2527341T3 - Bioprecursor a base de polifenol - Google Patents
Bioprecursor a base de polifenol Download PDFInfo
- Publication number
- ES2527341T3 ES2527341T3 ES06778610.3T ES06778610T ES2527341T3 ES 2527341 T3 ES2527341 T3 ES 2527341T3 ES 06778610 T ES06778610 T ES 06778610T ES 2527341 T3 ES2527341 T3 ES 2527341T3
- Authority
- ES
- Spain
- Prior art keywords
- polyphenol
- acid
- phenyl
- bioprecursor
- diacetoxystyryl
- 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.)
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- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 86
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
- 150000001733 carboxylic acid esters Chemical group 0.000 claims abstract description 25
- 239000002537 cosmetic Substances 0.000 claims abstract description 24
- 239000002243 precursor Substances 0.000 claims abstract description 24
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 13
- 125000006850 spacer group Chemical group 0.000 claims abstract description 12
- 235000019136 lipoic acid Nutrition 0.000 claims abstract description 11
- 229960002663 thioctic acid Drugs 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 239000012049 topical pharmaceutical composition Substances 0.000 claims abstract description 6
- 235000019155 vitamin A Nutrition 0.000 claims abstract description 6
- 239000011719 vitamin A Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000004508 retinoic acid derivatives Chemical class 0.000 claims abstract description 5
- 229940016667 resveratrol Drugs 0.000 claims description 50
- -1 cyclic carboxylic acid Chemical class 0.000 claims description 48
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 39
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 38
- 235000021283 resveratrol Nutrition 0.000 claims description 38
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 10
- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 claims description 10
- LBTVHXHERHESKG-UHFFFAOYSA-N tetrahydrocurcumin Chemical compound C1=C(O)C(OC)=CC(CCC(=O)CC(=O)CCC=2C=C(OC)C(O)=CC=2)=C1 LBTVHXHERHESKG-UHFFFAOYSA-N 0.000 claims description 10
- 235000009498 luteolin Nutrition 0.000 claims description 9
- LRDGATPGVJTWLJ-UHFFFAOYSA-N luteolin Natural products OC1=CC(O)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 LRDGATPGVJTWLJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 7
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 5
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 5
- 235000005875 quercetin Nutrition 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 5
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 4
- 229920002079 Ellagic acid Polymers 0.000 claims description 4
- 235000004132 ellagic acid Nutrition 0.000 claims description 4
- 229940114124 ferulic acid Drugs 0.000 claims description 4
- 235000001785 ferulic acid Nutrition 0.000 claims description 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 4
- 235000004515 gallic acid Nutrition 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 4
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical compound CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims description 3
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims description 3
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 229960002852 ellagic acid Drugs 0.000 claims description 3
- 229940074391 gallic acid Drugs 0.000 claims description 3
- 229940095066 hydroxytyrosol Drugs 0.000 claims description 3
- 235000003248 hydroxytyrosol Nutrition 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 claims description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 claims description 3
- 229960004245 silymarin Drugs 0.000 claims description 3
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- 239000013067 intermediate product Substances 0.000 claims description 2
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- FHUDZSGRYLAEKR-UHFFFAOYSA-N 3-hydroxybutanoic acid;4-hydroxybutanoic acid Chemical compound CC(O)CC(O)=O.OCCCC(O)=O FHUDZSGRYLAEKR-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 235000002906 tartaric acid Nutrition 0.000 claims 2
- 239000011975 tartaric acid Substances 0.000 claims 2
- VBMNHJSZHSTCAK-UHFFFAOYSA-N 4-(2H-chromen-6-yloxy)-4-oxobutanoic acid Chemical compound C1C=CC2=C(O1)C=CC(=C2)OC(=O)CCC(=O)O VBMNHJSZHSTCAK-UHFFFAOYSA-N 0.000 claims 1
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- PSBAIJVSCTZDDB-UHFFFAOYSA-N phenyl acetylsalicylate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 PSBAIJVSCTZDDB-UHFFFAOYSA-N 0.000 claims 1
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- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 abstract 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- TVHVQJFBWRLYOD-UHFFFAOYSA-N rosmarinic acid Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=Cc2ccc(O)c(O)c2)C=O TVHVQJFBWRLYOD-UHFFFAOYSA-N 0.000 description 1
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
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- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 1
- IELOKBJPULMYRW-UHFFFAOYSA-N α-tocopherol succinate Chemical compound OC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C IELOKBJPULMYRW-UHFFFAOYSA-N 0.000 description 1
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- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A61P17/18—Antioxidants, e.g. antiradicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/40—Succinic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
-
- 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
- A61K2800/522—Antioxidants; Radical scavengers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0506169 | 2005-06-17 | ||
| FR0506169A FR2887251B1 (fr) | 2005-06-17 | 2005-06-17 | Bioprecurseur a base de polyphenol |
| PCT/FR2006/001375 WO2006134282A1 (fr) | 2005-06-17 | 2006-06-16 | Bioprecurseur a base de polyphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2527341T3 true ES2527341T3 (es) | 2015-01-22 |
Family
ID=35788537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06778610.3T Active ES2527341T3 (es) | 2005-06-17 | 2006-06-16 | Bioprecursor a base de polifenol |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9067908B2 (https=) |
| EP (1) | EP1893555B1 (https=) |
| JP (1) | JP5469339B2 (https=) |
| ES (1) | ES2527341T3 (https=) |
| FR (1) | FR2887251B1 (https=) |
| WO (1) | WO2006134282A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005069998A2 (en) | 2004-01-20 | 2005-08-04 | Brigham Young University Technology Transfer Office | Novel sirtuin activating compounds and methods for making the same |
| US8344024B2 (en) | 2007-07-31 | 2013-01-01 | Elc Management Llc | Anhydrous cosmetic compositions containing resveratrol derivatives |
| US20090035240A1 (en) * | 2007-07-31 | 2009-02-05 | Maes Daniel H | Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent |
| US9295621B2 (en) | 2007-07-31 | 2016-03-29 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and silicone surfactant |
| US20090035236A1 (en) | 2007-07-31 | 2009-02-05 | Maes Daniel H | Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent |
| US8080583B2 (en) | 2007-07-31 | 2011-12-20 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone |
| WO2009017866A1 (en) * | 2007-07-31 | 2009-02-05 | Elc Management Llc | Cosmetic compositions containing resveratrol derivatives |
| CN102617348B (zh) * | 2007-09-08 | 2016-05-18 | Elc管理有限责任公司 | 阿魏酸白藜芦醇酯化合物、包含该化合物的组合物及其使用方法 |
| FI125590B (en) | 2008-04-10 | 2015-12-15 | Neste Oyj | A process for the preparation of a composition for the preparation of pinosylvine and its compounds, a composition for the preparation of stilbene compounds, a process for the recovery of stilbene compounds, and fatty acid and resin acid esters of pinosylvine and its monomethyl ether |
| EP2429481A4 (en) * | 2008-06-25 | 2014-08-13 | Elc Man Llc | METHOD AND COMPOSITIONS FOR IMPROVING THE APPEARANCE OF SKIN AND BODY |
| KR101063876B1 (ko) | 2009-03-03 | 2011-09-08 | 한밭대학교 산학협력단 | 신규 리포익산/폴리페놀 컨쥬게이트 화합물 및 그의 용도 |
| KR101515692B1 (ko) * | 2009-10-05 | 2015-04-27 | 닛본 덴끼 가부시끼가이샤 | 셀룰로오스 수지 및 그 제조 방법 |
| US20120237941A1 (en) | 2009-12-07 | 2012-09-20 | Chanel Parfums Beaute | Method for screening active agents that stimulate the expression of arnt2 to improve the skin's barrier function |
| US8030432B2 (en) * | 2009-12-10 | 2011-10-04 | The United States Of America As Represented By The Secretary Of The Army | Copolymerization of hydroxytyrosol with flavonoids mediated by horseradish peroxidases |
| US8134020B2 (en) * | 2009-12-10 | 2012-03-13 | The United States Of America As Represented By The Secretary Of The Army | Polymerization of hydroxytyrosol mediated by horseradish peroxidases |
| US8715651B2 (en) | 2010-01-08 | 2014-05-06 | Chanel Parfums Beaute | Use of at least one extract of flowers of Camellia japonica alba plena for moisturizing the skin |
| JP2013528574A (ja) * | 2010-04-12 | 2013-07-11 | ベルケム エス.ア. | 安定化ポリフェノール誘導体、その生産方法、及びその使用 |
| FR2959230B1 (fr) | 2010-04-27 | 2016-03-25 | Chanel Parfums Beaute | Polypeptide exprime dans la couche cornee et son utilisation |
| WO2012070656A1 (ja) * | 2010-11-26 | 2012-05-31 | ユーハ味覚糖株式会社 | 生理活性を有するヒドロキシスチルベン誘導体の製造方法 |
| CN103619311B (zh) | 2011-06-16 | 2016-01-20 | 香奈儿香水美妆品公司 | 半透明糖浆状化妆品组合物 |
| FR2989271B1 (fr) * | 2012-04-12 | 2014-08-22 | Chanel Parfums Beaute | Composition stable comprenant un compose anti-age et un solvant |
| US9187402B2 (en) | 2012-06-14 | 2015-11-17 | North Carolina Agricultural And Technical State University | Aspirin derivatives and uses thereof |
| KR101480600B1 (ko) * | 2013-01-22 | 2015-01-08 | 경북대학교 산학협력단 | 레스베라트롤 유도체의 피부미백 용도 |
| ES2786306T3 (es) * | 2014-02-06 | 2020-10-09 | Biocogent Llc | Composiciones y métodos mejorados que comprenden resveratrol |
| WO2015162265A1 (en) * | 2014-04-24 | 2015-10-29 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | New lipophenol compounds and uses thereof |
| GB201416273D0 (en) * | 2014-09-15 | 2014-10-29 | Isis Innovation | Therapeutic compounds |
| KR101601685B1 (ko) * | 2015-08-24 | 2016-03-09 | 여명바이오켐 주식회사 | 항산화 효과가 우수한 택시폴린 유도체 및 이를 함유하는 화장료 조성물 |
| US9844526B2 (en) * | 2015-10-28 | 2017-12-19 | Gateway Health Alliances, Inc. | Methods and compositions for improving microvascular function, suppressing cyclooxygenase activity, reducing platelet aggregation and increasing levels of resveratrol in plasma |
| US9782375B2 (en) * | 2015-10-28 | 2017-10-10 | Shil Kothari | Methods and compositions for improving microvascular function, suppressing cyclooxygenase activity, reducing platelet aggregation and increasing levels of resveratrol in plasma |
| US11241396B2 (en) * | 2015-10-28 | 2022-02-08 | Gateway Health Alliances, Inc. | Methods and compositions for improving microvascular function, suppressing cyclooxygenase activity, reducing platelet aggregation and increasing levels of resveratrol in plasma |
| US10851042B2 (en) | 2016-03-07 | 2020-12-01 | Elc Management Llc | Solubization of resveratrol glycolate and tartrate derivatives |
| AU2017229094B2 (en) * | 2016-03-07 | 2019-10-10 | Elc Management Llc | Resveratrol glycolate and tartrate derivatives and synthetic methods therefor |
| GR20180100094A (el) | 2018-03-07 | 2019-10-16 | Εθνικο Ιδρυμα Ερευνων | Βιο-εμπνευσμενοι ενεργοποιητες του πρωτεασωματος με αντιγηραντικη δραση |
| CA3116556A1 (en) | 2018-10-16 | 2020-04-23 | President And Fellows Of Harvard College | Sirt1 activating compounds |
| FR3094224B1 (fr) | 2019-03-29 | 2021-05-28 | Chanel Parfums Beaute | Composition permettant le transfert d’un motif coloré sur la peau et utilisations |
| FR3094222B1 (fr) | 2019-03-29 | 2021-09-10 | Chanel Parfums Beaute | Composition cosmétique longue tenue |
| FR3094228B1 (fr) | 2019-03-29 | 2022-04-01 | Chanel Parfums Beaute | Base de teint conférant un maquillage longue tenue |
| FR3094226B1 (fr) | 2019-03-29 | 2021-11-26 | Chanel Parfums Beaute | Composition cosmétique longue tenue |
| FR3094220B1 (fr) | 2019-03-29 | 2022-02-25 | Chanel Parfums Beaute | Composition cosmétique filmogène pelable |
| FR3096581B1 (fr) | 2019-05-31 | 2021-10-22 | Chanel Parfums Beaute | Gel aqueux solide comprenant un mélange de gomme de xanthane et de gomme de carroube |
| FR3098108B1 (fr) | 2019-07-03 | 2022-04-01 | Chanel Parfums Beaute | Composition cosmétique solide longue tenue |
| FR3098110B1 (fr) | 2019-07-03 | 2022-02-04 | Chanel Parfums Beaute | Composition cosmétique solide |
| FR3098107B1 (fr) | 2019-07-03 | 2022-07-29 | Chanel Parfums Beaute | Composition cosmétique solide |
| FR3098109B1 (fr) | 2019-07-03 | 2022-02-04 | Chanel Parfums Beaute | Composition cosmétique solide hydratante |
| EP3895683A1 (fr) | 2020-04-14 | 2021-10-20 | Chanel Parfums Beauté | Composition cosmétique multi-phases comprenant au moins deux phases huileuses non miscibles |
| CN119751414A (zh) * | 2024-12-23 | 2025-04-04 | 江苏同禾药业有限公司 | 一种具有抗氧化和抗炎功能的硫辛酸衍生物及其制备方法与应用 |
| CN120866433B (zh) * | 2025-09-26 | 2025-12-30 | 杭州媄丽媄生物技术有限公司 | 改性羟基酪醇、化妆品、制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5935884B2 (ja) * | 1980-10-27 | 1984-08-31 | 株式会社 薬理学中央研究所 | ピラノンを含有するメラニン生成抑制剤 |
| JPS5879951A (ja) * | 1981-11-06 | 1983-05-13 | Yasuaki Fukuda | トロポロンの脂肪酸エステルおよび該エステルを有効成分とする美白化粧料 |
| TW197375B (https=) * | 1990-11-19 | 1993-01-01 | Hayashibara Biochem Lab | |
| FR2725897B1 (fr) * | 1994-10-24 | 1996-12-06 | Oreal | Produit pour application topique contenant une lipase et un precurseur d'actif |
| FR2750328B1 (fr) * | 1996-06-28 | 1998-08-14 | Oreal | Composition cosmetique et/ou dermatologique contenant au moins un precurseur d'actif et un poly(acide 2 -acrylamido 2 -methylpropane sulfonique) reticule |
| FR2766176B1 (fr) * | 1997-07-15 | 1999-10-29 | Caudalie | Compositions a base de derives de resveratrol |
| FR2778663B1 (fr) * | 1998-05-15 | 2001-05-18 | Coletica | Nouveaux esters de flavonoides,leur utilisation en cosmetique, dermopharmacie, en pharmacie et en agro-alimentaire |
| FR2789577B1 (fr) * | 1999-02-17 | 2002-04-05 | Oreal | Utilisation de derives substitues en 3 du stilbene comme actifs deodorants dans les compositions cosmetiques |
| DE10056400A1 (de) * | 2000-11-14 | 2002-05-23 | Merck Patent Gmbh | Galenische Formulierung |
| JP2003055314A (ja) * | 2001-08-20 | 2003-02-26 | Fujita Masao | ヒドロキシけい皮酸誘導体及びこれを用いた抗酸化剤 |
-
2005
- 2005-06-17 FR FR0506169A patent/FR2887251B1/fr not_active Expired - Fee Related
-
2006
- 2006-06-16 JP JP2008516380A patent/JP5469339B2/ja not_active Expired - Fee Related
- 2006-06-16 WO PCT/FR2006/001375 patent/WO2006134282A1/fr not_active Ceased
- 2006-06-16 EP EP06778610.3A patent/EP1893555B1/fr not_active Not-in-force
- 2006-06-16 ES ES06778610.3T patent/ES2527341T3/es active Active
- 2006-06-16 US US11/922,331 patent/US9067908B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2887251A1 (fr) | 2006-12-22 |
| JP5469339B2 (ja) | 2014-04-16 |
| JP2008546675A (ja) | 2008-12-25 |
| WO2006134282A1 (fr) | 2006-12-21 |
| EP1893555B1 (fr) | 2014-10-29 |
| US20090215881A1 (en) | 2009-08-27 |
| FR2887251B1 (fr) | 2008-02-01 |
| EP1893555A1 (fr) | 2008-03-05 |
| US9067908B2 (en) | 2015-06-30 |
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