WO1999000079A1 - Traitement du vieillissement et des lesions de la peau a l'aide d'agents de migration cellulaire - Google Patents
Traitement du vieillissement et des lesions de la peau a l'aide d'agents de migration cellulaireInfo
- Publication number
- WO1999000079A1 WO1999000079A1 PCT/US1998/013675 US9813675W WO9900079A1 WO 1999000079 A1 WO1999000079 A1 WO 1999000079A1 US 9813675 W US9813675 W US 9813675W WO 9900079 A1 WO9900079 A1 WO 9900079A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cell migration
- indole
- agent
- dosage
- migration agent
- Prior art date
Links
- 230000012292 cell migration Effects 0.000 title claims abstract description 29
- 206010052428 Wound Diseases 0.000 title abstract description 13
- 208000027418 Wounds and injury Diseases 0.000 title abstract description 13
- 230000009759 skin aging Effects 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 52
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000035876 healing Effects 0.000 claims abstract description 13
- 239000003617 indole-3-acetic acid Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000001737 promoting effect Effects 0.000 claims abstract description 6
- BUGQHORRADGONS-KRWDZBQOSA-N Indole-3-acetyl-L-phenylalanine Chemical compound C([C@@H](C(=O)O)NC(=O)CC=1C2=CC=CC=C2NC=1)C1=CC=CC=C1 BUGQHORRADGONS-KRWDZBQOSA-N 0.000 claims abstract description 5
- 230000000699 topical effect Effects 0.000 claims abstract description 4
- 230000032683 aging Effects 0.000 claims description 3
- VAFNMNRKDDAKRM-LLVKDONJSA-N Indole-3-acetyl-L-aspartic acid Natural products C1=CC=C2C(CC(=O)N[C@H](CC(=O)O)C(O)=O)=CNC2=C1 VAFNMNRKDDAKRM-LLVKDONJSA-N 0.000 claims description 2
- YDXXLJMIHMIOIF-UHFFFAOYSA-N N-(indol-3-ylacetyl)glycine Chemical compound C1=CC=C2C(CC(=O)NCC(=O)O)=CNC2=C1 YDXXLJMIHMIOIF-UHFFFAOYSA-N 0.000 claims description 2
- FBDCJLXTUCMFLF-QMMMGPOBSA-N N-(indole-3-acetyl)-L-alanine Chemical compound C1=CC=C2C(CC(=O)N[C@@H](C)C(O)=O)=CNC2=C1 FBDCJLXTUCMFLF-QMMMGPOBSA-N 0.000 claims description 2
- VAFNMNRKDDAKRM-NSHDSACASA-N N-(indole-3-acetyl)-L-aspartic acid Chemical compound C1=CC=C2C(CC(=O)N[C@@H](CC(=O)O)C(O)=O)=CNC2=C1 VAFNMNRKDDAKRM-NSHDSACASA-N 0.000 claims description 2
- 230000037406 food intake Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- KTHADMDGDNYQRX-UHFFFAOYSA-N 3-indoleacetic acid methyl ester Natural products C1=CC=C2C(CC(=O)OC)=CNC2=C1 KTHADMDGDNYQRX-UHFFFAOYSA-N 0.000 claims 2
- 210000004027 cell Anatomy 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 210000002950 fibroblast Anatomy 0.000 abstract description 10
- 230000005012 migration Effects 0.000 abstract description 9
- 238000013508 migration Methods 0.000 abstract description 9
- 230000000977 initiatory effect Effects 0.000 abstract description 3
- 239000011800 void material Substances 0.000 abstract description 2
- 230000033001 locomotion Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 6
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 6
- 229940126864 fibroblast growth factor Drugs 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 230000029663 wound healing Effects 0.000 description 6
- 230000010261 cell growth Effects 0.000 description 5
- 230000019305 fibroblast migration Effects 0.000 description 5
- 230000002297 mitogenic effect Effects 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 229940061720 alpha hydroxy acid Drugs 0.000 description 4
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 229930192334 Auxin Natural products 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229930191978 Gibberellin Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002363 auxin Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003448 gibberellin Substances 0.000 description 2
- 239000003102 growth factor Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 210000005260 human cell Anatomy 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000037380 skin damage Effects 0.000 description 2
- QOPBEBWGSGFROG-UHFFFAOYSA-N 2-(1h-indol-2-yl)acetic acid Chemical compound C1=CC=C2NC(CC(=O)O)=CC2=C1 QOPBEBWGSGFROG-UHFFFAOYSA-N 0.000 description 1
- 239000005980 Gibberellic acid Substances 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- 206010051246 Photodermatosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000008845 photoaging Effects 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 210000001626 skin fibroblast Anatomy 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 230000007995 vascular wound healing Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61Q19/08—Anti-ageing preparations
Definitions
- the present invention relates to a plant derived cell migration agent, such as Indole-3- Acetic acid, that facilitates the healing of tissue such as skin.
- the cell migration agent is useful in treating wrinkled skin and can minimize the effects of photo aging on the skin by itself, or in conjunction with alpha-hydroxy acid (AHA), retinoic acid, or other chemical peel agents.
- AHA alpha-hydroxy acid
- retinoic acid or other chemical peel agents.
- Human tissue can be damaged in numerous ways.
- the skin can be burned by the sun or the application of acids such as alpha-hydroxy acid (AHA).
- AHA alpha-hydroxy acid
- Muscle tissue can suffer damage from a lack of oxygen or from traumatic injury. In either case, the body produces a certain healing response.
- Cell migration agents generally promote the migration of fibroblast cells from the periphery of the wounded tissue to a location inside the wounded area.
- Fibroblast cells are mesenchyme cells which give rise to connective tissue.
- a wound includes any damage to tissue from any source.
- the tissue such as skin, heals inward from the peripheral edge of the wound. Improved healing speed has been observed when fibroblast cells migrate to the middle of the wound and heal outward to meet the inward progression from the periphery.
- Patent No. 5,188,655 to Jones et al. discloses a plant growth enhancing composition comprising as an active ingredient a synergistic mixture of (a) gibberellins, (b) the heteroauxin indole-3-
- acetic acid and the cytokinin 6-(4-hydroxy-3-methyl-2trans-betenylamino) purine have very low molecular weights typically between 175 and 346. There has been no correlation between the use of plant growth hormones and wound healing in human cell studies. A need exists for a plant derived cell migration agent that can be used to improve the
- Such a cell migration agent should be useful for human application with particular benefits in healing skin. Skin damage can include aging from sun or chemical exposure. Therefore, a suitable cell migration agent should be useful in minimizing or healing skin damage associated with aging and sun or chemical exposure.
- Indole- 3-Acetic acid also known as "Auxin”
- its derivatives significantly increases the migration of fibroblast cells at five days after treatment initiation.
- Derivatives such as Indole-3-Acetyl-L- Phenylalanine have shown improved cell migration results.
- derivatives such as Indole-
- Auxin and its derivative Indole-3-Acetyl-L-Phenylalanine maintained increased migration rates throughout the study. When administered in a dosage of at least 0.1 ppm, these compounds appear to have the ability to move healthy human fibroblast cells into areas void of cells more rapidly than if the agent were not present. Dosage levels of between 2 and 250 ppm showed better results. Once migrated, the healthy cells can then divide at their normal rate thus effectively filling the voided area quicker. This results in the plumping of the skin or healing of
- the compounds can be delivered by topical or internal methods of application.
- Figure 1 is a bar chart showing the observed relative cell migration distances under the effect of three compounds under test for three days;
- Figure 2 is a bar chart showing the observed relative cell migration distances under the effect of three compounds under test for five days;
- Figure 3 is a bar chart showing the observed relative cell migration distances under the effect of three compounds under test for ten days;
- Figure 4 is a bar chart showing the observed relative cell migration distances under the effect of three compounds under test for fourteen days.
- Figure 5 is a bar chart showing the migration response of Agent B versus fibroblast growth factor.
- Agent C was a compound containing gibberellic acid. Agent A was significantly inhibitory and agent B was mildly inhibitory of fibroblast cell growth. Fibroblasts are the chief cell of interest for these studies due to their central role in wound healing. Agent C had no significant influence on cell growth.
- the agents could be administered by injection, topical application, ingestion or inhalation.
- Treatment groups were statistically compared using Student's unpaired / - analysis.
- the results as represented in Figures 1 to 4 indicate that agent B consistently and significantly increased fibroblast cell migration relative to cells treated with control media alone starting at day 5 after treatment initiation.
- Cells treated with agent A also showed a small but significant increase in cell migration relative to control cells at days 5 and 14.
- FGF fibroblast growth factor
- agents A and B had significant effects to stimulate fibroblast cell migration.
- the fact that these agents are not mitogenic may be a positive characteristic in terms of an agent that might be therapeutically applied.
- a mitogenic agent might provoke concerns relative to its potential effects as a carcinogen.
- the stimulation of migration by agents A and B raise the possibility that it may be an effective agent in promoting wound healing.
- Agents A and B should reduce the signs of skin aging.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
Abstract
Un agent de migration cellulaire favorise la cicatrisation de lésions en stimulant le mouvement de cellules fibroblastiques à l'opposé de la périphérie de la lésion. Les agents peuvent comprendre de l'acide indole-3-acétique et ses dérivés tels que indole-3-acétyle-L-phénylalanine. On a observé des augmentations significatives de la migration des cellules fibroblastiques à 5 jours après le début du traitement. Lorsqu'on les administre en un dosage compris entre 0,1 et 250 ppm, ces composés s'avèrent présenter la capacité de mouvoir les cellules fibroblastiques humaines dans des zones dépourvues de cellules plus rapidement que si l'agent était absent. Le résultat se traduit par l'arrondissement de la peau ou la cicatrisation de lésions. Les composés peuvent être administrés par des méthodes d'application locale ou interne.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50590299A JP2002504933A (ja) | 1997-06-30 | 1998-06-30 | 皮膚の老化及び傷の治療に用いられる細胞移動剤 |
| EP98934222A EP1009345A4 (fr) | 1997-06-30 | 1998-06-30 | Traitement du vieillissement et des lesions de la peau a l'aide d'agents de migration cellulaire |
| AU83797/98A AU8379798A (en) | 1997-06-30 | 1998-06-30 | Skin aging and wound treatment using cell migration agents |
| US09/273,681 US6174541B1 (en) | 1998-06-30 | 1999-03-22 | Skin aging and wound treatment using cell migration agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88477997A | 1997-06-30 | 1997-06-30 | |
| US08/884,779 | 1997-06-30 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/273,681 Continuation US6174541B1 (en) | 1998-06-30 | 1999-03-22 | Skin aging and wound treatment using cell migration agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999000079A1 true WO1999000079A1 (fr) | 1999-01-07 |
Family
ID=25385375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1998/013675 WO1999000079A1 (fr) | 1997-06-30 | 1998-06-30 | Traitement du vieillissement et des lesions de la peau a l'aide d'agents de migration cellulaire |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1009345A4 (fr) |
| JP (1) | JP2002504933A (fr) |
| AU (1) | AU8379798A (fr) |
| WO (1) | WO1999000079A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008050198A3 (fr) * | 2006-10-23 | 2008-06-19 | Clelia Barini | Méthode cosmétique pour tonifier le derme |
| FR2929115A1 (fr) * | 2008-03-31 | 2009-10-02 | Exsymol Sa | Utilisation cosmetique de composes conjugues d'auxines indoliques. |
| WO2013087834A3 (fr) * | 2011-12-16 | 2013-10-24 | Syntivia | Composition cosmétique pour stimuler les fonctions cellulaires anti-vieillissement de la peau |
| WO2021254754A1 (fr) * | 2020-06-19 | 2021-12-23 | Unilever Ip Holdings B.V. | Utilisation de composés indoliques pour traiter les signes du vieillissement de la peau |
| WO2021254753A1 (fr) * | 2020-06-19 | 2021-12-23 | Unilever Ip Holdings B.V. | Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4847283A (en) * | 1983-01-10 | 1989-07-11 | Harendza Harinxma Alfred J | Ointment and method for treating skin lesions due to herpes virus |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1269573A (fr) * | 1959-06-09 | 1961-08-18 | Produits de beauté à base d'auxines | |
| US3271394A (en) * | 1964-12-31 | 1966-09-06 | Merck & Co Inc | Alpha-indolyl-3-acetic acid esters |
| FR2597339A1 (fr) * | 1986-04-16 | 1987-10-23 | Bounan Michel | Trois substances a activite antitumorale preparees par dilutions successives d'hormones vegetales de croissance. |
-
1998
- 1998-06-30 EP EP98934222A patent/EP1009345A4/fr not_active Withdrawn
- 1998-06-30 WO PCT/US1998/013675 patent/WO1999000079A1/fr not_active Application Discontinuation
- 1998-06-30 AU AU83797/98A patent/AU8379798A/en not_active Abandoned
- 1998-06-30 JP JP50590299A patent/JP2002504933A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4847283A (en) * | 1983-01-10 | 1989-07-11 | Harendza Harinxma Alfred J | Ointment and method for treating skin lesions due to herpes virus |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP1009345A4 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008050198A3 (fr) * | 2006-10-23 | 2008-06-19 | Clelia Barini | Méthode cosmétique pour tonifier le derme |
| FR2929115A1 (fr) * | 2008-03-31 | 2009-10-02 | Exsymol Sa | Utilisation cosmetique de composes conjugues d'auxines indoliques. |
| EP2116222A1 (fr) * | 2008-03-31 | 2009-11-11 | Exsymol S.A.M. | Utilisation cosmétique de composés conjugués d'auxines indoliques |
| WO2013087834A3 (fr) * | 2011-12-16 | 2013-10-24 | Syntivia | Composition cosmétique pour stimuler les fonctions cellulaires anti-vieillissement de la peau |
| WO2021254754A1 (fr) * | 2020-06-19 | 2021-12-23 | Unilever Ip Holdings B.V. | Utilisation de composés indoliques pour traiter les signes du vieillissement de la peau |
| WO2021254753A1 (fr) * | 2020-06-19 | 2021-12-23 | Unilever Ip Holdings B.V. | Utilisation de composés d'indole pour traiter les signes du vieillissement de la peau |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002504933A (ja) | 2002-02-12 |
| EP1009345A4 (fr) | 2002-03-13 |
| EP1009345A1 (fr) | 2000-06-21 |
| AU8379798A (en) | 1999-01-19 |
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