CA2233108A1 - Complex of y-cyclodextrin and retinol or retinol derivatives, processes for their preparation and their use - Google Patents

Complex of y-cyclodextrin and retinol or retinol derivatives, processes for their preparation and their use

Info

Publication number
CA2233108A1
CA2233108A1 CA002233108A CA2233108A CA2233108A1 CA 2233108 A1 CA2233108 A1 CA 2233108A1 CA 002233108 A CA002233108 A CA 002233108A CA 2233108 A CA2233108 A CA 2233108A CA 2233108 A1 CA2233108 A1 CA 2233108A1
Authority
CA
Canada
Prior art keywords
retinol
cyclodextrin
processes
preparation
complex
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.)
Granted
Application number
CA002233108A
Other languages
French (fr)
Other versions
CA2233108C (en
Inventor
Jens-Peter Moldenhauer
Marlies Regiert
Thomas Wimmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of CA2233108A1 publication Critical patent/CA2233108A1/en
Application granted granted Critical
Publication of CA2233108C publication Critical patent/CA2233108C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0212—Face masks
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/07—Retinol compounds, e.g. vitamin A
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A61K31/724—Cyclodextrins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/738—Cyclodextrins
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • A61Q19/004—Aftersun preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • 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
    • 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
    • A61K2800/56—Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
    • 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
    • A61K2800/59—Mixtures
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • 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

Abstract

Complexes of .gamma.-cyclodextrin and retinol or retinol derivatives, along with processes for their preparation and compositions for their use. The complexes are useful in cosmetic formulations and in pharmaceutical formulations.
CA002233108A 1997-03-27 1998-03-20 Complex of y-cyclodextrin and retinol or retinol derivatives, processes for their preparation and their use Expired - Fee Related CA2233108C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19713092.5 1997-03-27
DE19713092A DE19713092A1 (en) 1997-03-27 1997-03-27 Complexes of gamma-cyclodextrin and retinol or retinol derivatives, as well as processes for their preparation and their use

Publications (2)

Publication Number Publication Date
CA2233108A1 true CA2233108A1 (en) 1998-09-27
CA2233108C CA2233108C (en) 2005-07-26

Family

ID=7824924

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002233108A Expired - Fee Related CA2233108C (en) 1997-03-27 1998-03-20 Complex of y-cyclodextrin and retinol or retinol derivatives, processes for their preparation and their use

Country Status (7)

Country Link
US (1) US5985296A (en)
EP (1) EP0867175B1 (en)
JP (1) JP3010435B2 (en)
KR (1) KR100304382B1 (en)
CA (1) CA2233108C (en)
DE (2) DE19713092A1 (en)
HU (1) HUP9800688A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113244157A (en) * 2021-06-04 2021-08-13 何平蓉 Anti-darkness makeup powder cake and preparation method thereof

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KR100560188B1 (en) * 1997-11-27 2006-03-13 가부시키가이샤 시세이도 Face pack
DE19847633C1 (en) * 1998-10-15 2000-03-02 Wacker Chemie Gmbh Preparation of retinol-gamma cyclodextrin complex useful in skin care cosmetic or dermatological compositions comprises using retinol as solution in polysorbate, giving quantitative conversion to stable complex
DE19943678A1 (en) * 1999-09-13 2001-03-15 Beiersdorf Ag Active substance combinations of surface-active citric acid esters and inclusion compounds of cyclodextrins and retinoids and cosmetic and dermatological preparations containing such mixtures
CA2414406A1 (en) * 2000-06-26 2002-01-03 The Regents Of The University Of Michigan Use of egf-r protein tyrosine kinase inhibitors for preventing photoaging in human skin
KR100402576B1 (en) * 2000-07-05 2003-10-22 동아제약 주식회사 Cosmetic composition containing retinol by multiple stabilization
IT1317911B1 (en) * 2000-09-28 2003-07-15 Idi Irccs COSMETIC FORMULATION.
KR100437102B1 (en) * 2001-01-11 2004-06-23 (주)케비젠 New retinol derivatives, the method of preparations and the uses thereof
BR0207663A (en) * 2001-02-27 2005-10-25 Univ Michigan Use of natural egfr inhibitors to prevent side effects due to therapy with retinoids, soaps and other stimuli that activate the epidermal growth factor receptor.
DE10141682A1 (en) * 2001-08-25 2003-03-06 Beiersdorf Ag Cyclodextrin is used in production of cosmetic and dermatological compositions to give improved filler distribution on the skin
DE10151245A1 (en) * 2001-10-17 2003-05-15 Beiersdorf Ag Cosmetic and / or dermatological combination of active ingredients
EP1304161B1 (en) * 2001-10-19 2007-02-28 Pacific Corporation Thermotropic liquid crystal polymer microcapsules, a method for preparing the same, and cosmetic compositions containing the same
JP4528903B2 (en) * 2002-03-11 2010-08-25 石川県 Method for producing cyclodextrin inclusion product of plant-containing active ingredient
DE10224298A1 (en) * 2002-05-31 2003-12-18 Beiersdorf Ag Combinations of cyclodextrins, retinoids and/or bioquinones and selected polymers useful in cosmetic or dermatological compositions
US20030232091A1 (en) * 2002-06-17 2003-12-18 Adi Shefer Stabilized retinol for cosmetic dermatological, and pharmaceutical compositions, and use thereof
FI20030426A (en) * 2003-03-24 2004-09-25 Tomi Jaervinen cyclodextrin complexes
US20060177405A1 (en) * 2005-02-04 2006-08-10 Morrissey Maureen S Moisturizing compositions
CN101223183A (en) * 2005-06-13 2008-07-16 嘉吉公司 Cyclodextrin inclusion complexes and methods of preparing same
WO2006137958A1 (en) * 2005-06-13 2006-12-28 Cargill Incorporated Cyclodextrin inclusion complexes and methods of preparing same
CN101431980B (en) * 2006-05-02 2012-08-01 株式会社东洋发酵 Fermented product composition, cosmetic composition and method of producing the same
EP2027136A4 (en) * 2006-06-13 2011-08-03 Cargill Inc Large-particle cyclodextrin inclusion complexes and methods of preparing same
JP5253171B2 (en) * 2006-09-22 2013-07-31 株式会社クラベ PTFE porous body, PTFE mixture, method for producing PTFE porous body, and electric wire / cable using PTFE porous body
JP2010514794A (en) * 2006-12-27 2010-05-06 カーギル インコーポレイテッド Cyclodextrin-encapsulated complex and method for preparing the complex
US20080283693A1 (en) * 2007-05-15 2008-11-20 Evans Michael J F Propulsion apparatus and system
DE102007051614A1 (en) * 2007-10-24 2009-04-30 Coty Prestige Lancaster Group Gmbh Retinol-containing cosmetic product
DE102008022041A1 (en) * 2008-04-29 2009-11-05 Coty Prestige Lancaster Group Gmbh Cosmetic product with delayed retinol release
US8410079B2 (en) 2010-08-06 2013-04-02 Island Kinetics Chirally correct retinal cyclodextrin hemiacetals for clarifying skin complexion
US20130251644A1 (en) * 2012-03-22 2013-09-26 Precision Dermatology, Inc. Cyclodextrin-Based Microemulsions, and Dermatological Uses Thereof
WO2014055532A2 (en) * 2012-10-02 2014-04-10 Allergan, Inc. Dermal filler hydrogels with vitamin a/cyclodextrin inclusion complexes
CN105611909B (en) 2013-03-12 2020-09-15 普莱玛疗法公司 Dental compositions comprising chelating agents and bases
KR101503301B1 (en) * 2013-07-22 2015-03-17 주식회사 웰코스 Retinylpalmitate stabilized formulations
EP3290026A1 (en) 2016-09-06 2018-03-07 Athenion AG Method for solubilizing poorly water-soluble dietary supplements and pharmaceutically active agents
EP3421096A1 (en) 2017-06-30 2019-01-02 Athenion AG Method for solubilizing poorly water-soluble cosmetic agents
WO2019150087A1 (en) * 2018-01-30 2019-08-08 Olusola Clement Idowu Mangiferin as a protective agent against mitochondrial dna damage and skin-care compositions comprising same
CN112294693B (en) * 2019-07-26 2021-07-20 珀莱雅化妆品股份有限公司 Supermolecule preparation of retinol and derivatives thereof and preparation method thereof
CN110623859A (en) * 2019-10-25 2019-12-31 广州市博之越精细化工有限公司 Preparation method of hydroxypropyl cyclodextrin inclusion retinol
KR102297632B1 (en) * 2021-04-19 2021-09-06 주식회사 라파스 Composition for manufacturing microneedle including cyclodextrin for stablilzing retinol, and microneedle manufactured with the same composition
CN113181078A (en) * 2021-05-21 2021-07-30 何平蓉 Moistening and astringing type deep cleaning mask powder
CN113318027A (en) * 2021-06-15 2021-08-31 何平蓉 Mild oil-control acne-removing facial cleansing composition and preparation method thereof
CN114869797B (en) * 2022-03-22 2023-07-21 深圳市美莲达生物科技有限公司 Essence containing retinol and rhizoma polygonati polysaccharide and application thereof
CN114652659B (en) * 2022-05-10 2023-07-14 广州兰蝶生物科技有限公司 Moisturizing gel containing aloe and rose hydrosol
CN115381732B (en) * 2022-08-01 2023-05-12 广州市博之越精细化工有限公司 Preparation method of hydroxypropyl cyclodextrin inclusion retinol

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Publication number Priority date Publication date Assignee Title
CN113244157A (en) * 2021-06-04 2021-08-13 何平蓉 Anti-darkness makeup powder cake and preparation method thereof

Also Published As

Publication number Publication date
US5985296A (en) 1999-11-16
HUP9800688A3 (en) 1999-04-28
JP3010435B2 (en) 2000-02-21
HUP9800688A2 (en) 1999-02-01
KR19980080135A (en) 1998-11-25
EP0867175B1 (en) 2000-08-09
EP0867175A1 (en) 1998-09-30
DE19713092A1 (en) 1998-10-01
JPH10279504A (en) 1998-10-20
KR100304382B1 (en) 2002-04-24
DE59800221D1 (en) 2000-09-14
CA2233108C (en) 2005-07-26

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Effective date: 20150320

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Effective date: 20150320