BR112012002268A2 - fotoestabailização de retinóides com compostos de alcóxicrileno - Google Patents
fotoestabailização de retinóides com compostos de alcóxicrilenoInfo
- Publication number
- BR112012002268A2 BR112012002268A2 BR112012002268A BR112012002268A BR112012002268A2 BR 112012002268 A2 BR112012002268 A2 BR 112012002268A2 BR 112012002268 A BR112012002268 A BR 112012002268A BR 112012002268 A BR112012002268 A BR 112012002268A BR 112012002268 A2 BR112012002268 A2 BR 112012002268A2
- Authority
- BR
- Brazil
- Prior art keywords
- photostabilization
- retinoids
- alkoxycrylene compounds
- alkoxycrylene
- compounds
- Prior art date
Links
Classifications
-
- 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
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/533,598 US8070989B2 (en) | 2007-08-09 | 2009-07-31 | Photostabilization of retinoids with alkoxycrylene compounds |
PCT/US2010/042227 WO2011014371A2 (en) | 2009-07-31 | 2010-07-16 | Photostabilization of retinoids with alkoxycrylene compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
BR112012002268A2 true BR112012002268A2 (pt) | 2016-06-14 |
Family
ID=43416815
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112012002268A BR112012002268A2 (pt) | 2009-07-31 | 2010-07-16 | fotoestabailização de retinóides com compostos de alcóxicrileno |
Country Status (5)
Country | Link |
---|---|
US (3) | US8070989B2 (pt) |
EP (1) | EP2459157A2 (pt) |
JP (1) | JP2012533520A (pt) |
BR (1) | BR112012002268A2 (pt) |
WO (1) | WO2011014371A2 (pt) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8263051B2 (en) * | 2007-08-09 | 2012-09-11 | Hallstar Innovations Corp. | Photostabilization of resveratrol with alkoxycrylene compounds |
US8257687B2 (en) * | 2007-08-09 | 2012-09-04 | Hallstar Innovations Corp. | Photostabilization of coenzyme Q compounds with alkoxycrylene compounds |
US7964245B2 (en) * | 2008-06-27 | 2011-06-21 | Hallstar Innovations Corp. | UV-absorbing and photostabilizing polymers |
DE102012205526A1 (de) | 2012-04-04 | 2013-10-10 | Beiersdorf Ag | Stabile kosmetische Zubereitung mit hohem Pigmentgehalt |
JP7178781B2 (ja) * | 2014-10-10 | 2022-11-28 | ハイ フォース リサーチ リミテッド | 蛍光合成レチノイド |
BR112020025923A2 (pt) | 2018-06-18 | 2021-04-06 | Elc Management Llc | Compostos fotoestabilizantes, composições e métodos |
US11484485B2 (en) | 2018-06-18 | 2022-11-01 | Elc Management Llc | Photostabilizing compounds, compositions, and methods |
KR102531948B1 (ko) | 2018-06-18 | 2023-05-12 | 이엘씨 매니지먼트 엘엘씨 | 광안정화 화합물, 조성물, 및 방법 |
Family Cites Families (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2623060A (en) * | 1949-11-04 | 1952-12-23 | Sharp & Dohme Inc | Alkylidenecyanoacetates and improved process for preparation thereof |
DE1222926C2 (de) | 1960-03-09 | 1976-07-15 | General Aniline & Filme Corporation, New York, N.Y. (V.St.A.) | Schuetzen organischer stoffe gegen uv-strahlung |
NL126306C (pt) * | 1960-03-09 | |||
US3215724A (en) * | 1961-09-18 | 1965-11-02 | Gen Aniline & Film Corp | alpha-cyano-beta, beta-diphenyl acrylic acid esters |
FR2350095A1 (fr) * | 1976-05-03 | 1977-12-02 | Oreal | Compositions destinees a la coloration de la peau a base de derives de la pyridine |
DE2816819A1 (de) * | 1978-04-18 | 1979-10-31 | Bayer Ag | Lichtschutzmittel |
US4396240A (en) * | 1978-06-16 | 1983-08-02 | Henson Artel R | Storage system |
US4307240A (en) * | 1980-05-30 | 1981-12-22 | General Electric Company | Alkoxysilanes and method for making |
US4562278A (en) * | 1984-10-12 | 1985-12-31 | Dow Corning, Ltd. | Organosilicon compounds and preparation and use thereof |
US4617374A (en) * | 1985-02-15 | 1986-10-14 | Eastman Kodak Company | UV-absorbing condensation polymeric compositions and products therefrom |
SU1273360A1 (ru) | 1985-05-21 | 1986-11-30 | Ордена Ленина институт элементоорганических соединений им.А.Н.Несмеянова | @ -Фурфурилиден- @ -цианоацетаты в качестве ингибиторов радикальной полимеризации непредельных соединений при их хранении |
US4707537A (en) * | 1986-09-30 | 1987-11-17 | Eastman Kodak Company | UV-absorbing condensation polymeric compositions and products therefrom |
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. |
IT1255729B (it) | 1992-05-19 | 1995-11-15 | Giuseppe Raspanti | Derivati di s-triazina come agenti fotostabilizzanti |
DE4237132C1 (de) * | 1992-11-03 | 1994-07-07 | Siemens Ag | UV-aktiviert thermisch härtendes einkomponentiges Reaktionsharzsystem |
US5393862A (en) | 1993-08-09 | 1995-02-28 | Eastman Chemical Company | Naphthalenedicarboxylic acid containing polymer compositions having reduced fluorescence |
US5663213A (en) | 1994-02-28 | 1997-09-02 | Rohm And Haas Company | Method of improving ultraviolet radiation absorption of a composition |
EP0711803B1 (en) | 1994-11-08 | 2000-01-19 | Teijin Limited | Method for preventing emission of fluorescence from polyalkylenenaphthalene-2,6-dicarboxylate |
JP3423827B2 (ja) | 1994-12-09 | 2003-07-07 | 帝人株式会社 | ポリエチレンナフタレート成形体の蛍光防止方法 |
US5783307A (en) * | 1996-11-04 | 1998-07-21 | Eastman Chemical Company | UV stabilized multi-layer structures with detectable UV protective layers and a method of detection |
US5738842A (en) * | 1996-11-29 | 1998-04-14 | 3V Inc. | Sun protecting cosmetic compositions comprising derivatives of dibenzoylmethane, of diphenylcyanoacrylic acid and of triazine |
US6117973A (en) * | 1997-02-24 | 2000-09-12 | Georgia Tech Research Corp. | PNA monomers with electron donor or acceptor |
US6001952A (en) | 1997-06-18 | 1999-12-14 | Eastman Chemical Company | Polyester containing benzylidene having reduced fluorescence |
US5989528A (en) * | 1998-07-30 | 1999-11-23 | The Procter & Gamble Company | Sunscreen compositions |
FR2785540B1 (fr) | 1998-11-10 | 2002-09-20 | Oreal | Procede de photostabilisation de filtres solaires derives de 1,3,5-triazine |
US7064114B2 (en) * | 1999-03-19 | 2006-06-20 | Parker Hughes Institute | Gel-microemulsion formulations |
US6113931A (en) * | 1999-03-25 | 2000-09-05 | The C.P. Hall Company | Clear formulations containing diesters or polyesters of naphthalene dicarboxylic acid |
US5993789A (en) * | 1999-03-25 | 1999-11-30 | The C.P. Hall Company | Photostable sunscreen compositions containing dibenzoylmethane derivative, E.G., parsol® 1789, and diesters or polyesters of naphthalene dicarboxylic acid photostabilizers and enhancers of the sun protection factor (SPF) |
US6353029B1 (en) * | 2000-08-24 | 2002-03-05 | Bristol-Myers Squibb Company | Storage stable tretinoin and 4-hydroxyanisole containing topical composition |
DE10058290A1 (de) | 2000-11-23 | 2002-05-29 | Basf Ag | Verfahren zur Stabilisierung von Polyolefinen |
US20020127192A1 (en) * | 2001-01-04 | 2002-09-12 | John Murphy | Lipstick with translucent or transparent region |
US6905525B2 (en) * | 2001-04-02 | 2005-06-14 | Ciba Specialty Chemicals Corporation | Candle wax stabilized with piperazinones |
DE10117336A1 (de) * | 2001-04-06 | 2002-10-10 | Max Planck Gesellschaft | Neuartige Lichtschutz- und Hautpflegemittel durch stabilisierte Lichtschutz-Komponenten und Verminderung schädigender Photoprodukte |
US6551605B2 (en) * | 2001-04-06 | 2003-04-22 | Haarmann & Reimer | Diesters or polyesters of naphthalene dicarboxylic acid as solubilizer/stabilizer for retinoids |
US6518451B2 (en) * | 2001-04-26 | 2003-02-11 | Haarmann & Reimer | Diesters of naphthalene dicarboxylic acid |
DE10141474A1 (de) * | 2001-08-29 | 2003-03-20 | Beiersdorf Ag | Stabilisierung UV-empfindlicher Wirkstoffe |
JP4152732B2 (ja) * | 2001-12-27 | 2008-09-17 | 株式会社トクヤマ | 樹脂組成物 |
US6485713B1 (en) * | 2002-03-05 | 2002-11-26 | The C. P. Hall Company | Sunscreen compositions and methods and materials for producing the same |
US6537529B1 (en) * | 2002-03-05 | 2003-03-25 | The C.P. Hall Company | Sunscreen compositions and methods and materials for producing the same |
US20040047817A1 (en) * | 2002-09-06 | 2004-03-11 | Bonda Craig A. | Photostabilization of a sunscreen composition with low levels of an alpha-cyano-beta,beta-diphenylacrylate compound |
US6890521B2 (en) * | 2002-09-06 | 2005-05-10 | The C.P. Hall Company | Photostabilization of a sunscreen composition with low levels of an α-cyano-β, β-diphenylacrylate |
US6800274B2 (en) * | 2002-09-17 | 2004-10-05 | The C.P. Hall Company | Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition |
US6919473B2 (en) * | 2002-09-17 | 2005-07-19 | Cph Innovations Corporation | Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition |
DE10333675A1 (de) | 2003-07-24 | 2005-03-03 | Aventis Pharma Deutschland Gmbh | Perfusionsverfahren für die Produktion von Erythropoietin |
US7292156B2 (en) * | 2003-10-07 | 2007-11-06 | Underground Solutions Technologies Group, Inc. | Remote tapping method and system for internally tapping a conduit |
JP2005139263A (ja) | 2003-11-05 | 2005-06-02 | Fuji Photo Film Co Ltd | セルロース溶液、セルロースフイルム、偏光板および液晶表示装置 |
DE102004003478A1 (de) * | 2004-01-22 | 2005-08-18 | Basf Ag | Retinoid-haltige Zubereitungen |
US7534420B2 (en) * | 2004-02-25 | 2009-05-19 | Hallstar Innovations Corp. | Compounds derived from polyanhydride resins with film-forming, UV-absorbing, and photostablizing properties, compositions containing same, and methods of using the same |
US7235587B2 (en) * | 2004-07-01 | 2007-06-26 | Cph Innovations Corporation | Diesters containing two crylene or fluorene moieties, sunscreen compositions containing the same, and methods of photostabilizing a sunscreen compositions containing the same |
DE602004014127D1 (de) * | 2004-07-02 | 2008-07-10 | Silikon-modifiziertes Protein enthaltende Sonnenschutzzubereitung | |
US7449698B2 (en) * | 2005-02-18 | 2008-11-11 | American Dye Source, Inc. | Method for encoding materials with a luminescent tag and apparatus for reading same |
US8158678B2 (en) * | 2005-04-07 | 2012-04-17 | Cph Innovations Corp. | Photoabsorbing, highly conjugated compounds of cyanoacrylic esters, sunscreen compositions and methods of use |
US20100135917A1 (en) * | 2005-08-11 | 2010-06-03 | Basf Aktiengesellschaft | Cosmetically used cross-linked methyl methacrylate-copolymer |
JP2008106041A (ja) * | 2006-09-28 | 2008-05-08 | Mizusawa Ind Chem Ltd | 光安定性が改善された薬剤 |
US20080286217A1 (en) * | 2007-05-14 | 2008-11-20 | Chaudhuri Ratan K | Sunscreen compositions and methods |
EP2185126B1 (en) | 2007-08-07 | 2017-06-21 | Symrise AG | Use of troxerutin to quench the fluorescence of disodium phenyl dibenzimidazole tetrasulfonate |
US8263051B2 (en) * | 2007-08-09 | 2012-09-11 | Hallstar Innovations Corp. | Photostabilization of resveratrol with alkoxycrylene compounds |
US7597825B2 (en) * | 2007-08-09 | 2009-10-06 | Hallstar Innovations Corp. | Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositions |
US7754191B2 (en) * | 2007-08-09 | 2010-07-13 | Hallstar Innovations Corp. | Method of quenching electronic excitation of chromophore-containing organic molecules photoactive compositions |
US7588702B2 (en) * | 2007-08-09 | 2009-09-15 | Hallstar Innovations Corp. | Method of quenching electronic excitation of chromophore-containing organic molecules in photoactive compositions |
-
2009
- 2009-07-31 US US12/533,598 patent/US8070989B2/en active Active
-
2010
- 2010-07-16 BR BR112012002268A patent/BR112012002268A2/pt not_active Application Discontinuation
- 2010-07-16 WO PCT/US2010/042227 patent/WO2011014371A2/en active Application Filing
- 2010-07-16 EP EP10738073A patent/EP2459157A2/en not_active Withdrawn
- 2010-07-16 JP JP2012516391A patent/JP2012533520A/ja active Pending
-
2011
- 2011-02-22 US US13/032,215 patent/US8268294B2/en active Active
- 2011-10-27 US US13/282,667 patent/US8278332B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
US8268294B2 (en) | 2012-09-18 |
US20110142771A1 (en) | 2011-06-16 |
EP2459157A2 (en) | 2012-06-06 |
WO2011014371A3 (en) | 2013-04-04 |
US20120065232A1 (en) | 2012-03-15 |
US8070989B2 (en) | 2011-12-06 |
WO2011014371A2 (en) | 2011-02-03 |
US8278332B2 (en) | 2012-10-02 |
US20090324570A1 (en) | 2009-12-31 |
JP2012533520A (ja) | 2012-12-27 |
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Legal Events
Date | Code | Title | Description |
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B11A | Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing | ||
B11Y | Definitive dismissal acc. article 33 of ipl - extension of time limit for request of examination expired |