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WO2000051549A1 - Compositions dermatologiques contenant un excipient de cristaux liquides et procede de preparation de celles-ci - Google Patents

Compositions dermatologiques contenant un excipient de cristaux liquides et procede de preparation de celles-ci Download PDF

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Publication number
WO2000051549A1
WO2000051549A1 PCT/SK1999/000017 SK9900017W WO0051549A1 WO 2000051549 A1 WO2000051549 A1 WO 2000051549A1 SK 9900017 W SK9900017 W SK 9900017W WO 0051549 A1 WO0051549 A1 WO 0051549A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
amount
homogenizer
active substance
emulsifying
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.)
Ceased
Application number
PCT/SK1999/000017
Other languages
English (en)
Inventor
Olga SÁKOVÁ
Ružena SOCHOROVÁ
Ivan Varga
Ľuboslav RÁZUS
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.)
Zentiva KS
Original Assignee
Slovakofarma AS
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 Slovakofarma AS filed Critical Slovakofarma AS
Priority to PL350141A priority Critical patent/PL198485B1/pl
Publication of WO2000051549A1 publication Critical patent/WO2000051549A1/fr
Priority to BG105852A priority patent/BG65442B1/bg
Anticipated expiration legal-status Critical
Priority to LV010141A priority patent/LV12781B/xx
Ceased 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
    • A61K8/18—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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K8/0295—Liquid crystals
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic 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
    • A61K8/42—Amides
    • 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
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1274—Non-vesicle bilayer structures, e.g. liquid crystals, tubules, cubic phases or cochleates; Sponge phases
    • 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
    • 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

Definitions

  • the invention relates to the field of production of dermatological compositions using liquid crystals of the lyotropic phase.
  • the intracellular substance in the stratum comeum of the superficial layer of the skin is arranged in a lamellar manner and is also sometimes designated as a liquid crystal structure.
  • Prior macrogol vehicles polyethyleneglycols
  • Hygroscopicity and osmotic activity of these vehicles results in withdrawal of water from the skin, which is undesirable, as controlled release of the active substances from vehicles and their transport into the skin require formation of an equilibrium between the vehicle and water which is withdrawn from epidermal cells.
  • a technological drawback is great dependence of their viscosity on temperature.
  • Vehicles consisting of emulsifying cetyl stearyl alcohol, liquid paraffin and white vaseline have been broadly used, but have a great drawback in incompatibility of the anionic emulsifier with compounds of ionic nature.
  • a chemical reaction may create insoluble compounds of the active substance or salts, which damage the solvating envelope, followed by decomposition of the emulsion.
  • Such vehicles include also those containing non-ionic emulsifiers (Milan Chalabala et al.: Technologie lek ⁇ , Galen®, 1997). Some producers use this type of vehicles for compositions containing urea.
  • Creams and lotions are often complex systems which comprise several different surface active substances having higher values of hydrophilic-lipophilic balance (HLB) and fatty amphiphilic compounds.
  • HLB hydrophilic-lipophilic balance
  • Fatty amphiphilics such as long chain alcohols, acids, monoglycerides, some other fatty acid esters and the like, are often dominant emulsifiers, but they are too lipophilic to stabilize oil-in-water emulsions.
  • Liquid crystals can serve for controlled release of active substances by preventing rapid release of the pharmaceutical dissolved in the oil phase of the emulsion (Tyle P., Dissertation University Microfilms International, 1985). In a liquid crystal emulsion, release was 1000 times lower than in other emulsions (Friberg S., J.Soc. Cosmet.Chem., 1979).
  • a drawback of prior art methods of production of dermatological compositions based on liquid crystals is technological difficulty of the manufacturing process of the liquid crystal vehicle itself and of the lamellar phase thereof.
  • the invention provides dermatological compositions containing a liquid crystal vehicle and a method for the preparation thereof.
  • Use of the lamellar phase of liquid crystals as vehicle improves release of the active substance from the vehicle and at the same time the moisturizing effect of the vehicle itself is utilized, thus improving not only subjective skin feel, but also objective softening and smoothing of the skin.
  • the lamellar phase of the liquid crystals consists of bilayers formed by a surface active substance in which the hydrocarbon chains occur in an unordered state, similarly to paraffin in the liquid state.
  • the bilayers are separated by aqueous layers.
  • Such phase is relatively liquid even in high concentrations of the surfactant such that the lamellas can easily slide one on another.
  • Creams and lotions are often complex systems which comprise several different higher HLB surfactants and fatty amphiphilic compounds.
  • Fatty amphiphilics such as long chain alcohols, acids, monoglycerides, some other fatty acid esters and the like, are often dominant emulsifiers, but they are too lipophilic to stabilize oil-in-water emulsions.
  • fatty amphiphilics are dispersed in water in the presence of a surfactant having higher HLB, a lamellar phase is obtained.
  • the lamellar liquid crystal phase is obtained by the method of this invention by specific mixing of fatty amphiphilic materials and surfactants which form micellar solutions of very low concentrations.
  • liquid crystals as the vehicle has an advantage of increased stability of the emulsion. Multiple layers around oil droplets act as a rheological barrier against coalescence. In addition, Van der Waals attractive forces between two oil droplets become extremely low.
  • Lamellar liquid crystal phases comprise swollen aqueous layers. Fifty per cent of the total water content of an oil-in-water emulsion may be bound in these structures. Said water is then less rapidly exposed to evaporation, undergoes evaporation less rapidly and provides a long-term effect.
  • the dermatological compositions of this invention are composed of an active substance and organic and inorganic filters in an amount of 0.5 to 25 % by weight, a disinfectant in the amount of 0.3 % by weight and adjuvants.
  • the specific method of this invention works the adjuvants up into a liquid crystal system in an oil-in-water emulsion with an anisotropic lamellar phase such that the aqueous phase and oil layer is separated with another water layer, which is entrapped at the phase interface of the emulsifying system and thus a lamella is formed. Due to their structure, the formed liquid crystals can be monitored similarly as true crystals by means of X-ray diffraction polarized light microscopy (see Fig. 2).
  • compositions of this invention are important in that by means of the starting materials and the method of the invention compositions are obtained in which it is possible to coordinate controlled delivery of moisture and of active substances into the skin.
  • the invention solves a method of preparing the vehicle - liquid crystals - and, subsequently, a method of preparing the dermatological compositions themselves.
  • adjuvants are charged into a sterilizing kettle and under continuous stirring the contents of the sterilizing kettle is heated to a temperature of 80 + 5 °C.
  • the prepared disinfectant is added to the resulting emulsifying liquid.
  • the prescribed amount of water is charged into a homogenizer.
  • Propyleneglycol is added under continuous stirring and the contents of the homogenizer is heated at 70 ⁇ 5 °C, followed by addition of the active substance. At this temperature the aqueous phase is emulsified with the emulsifiying liquid preheated to 80 ⁇ 5 °C very slowly for 20 to 30 minutes using a low-speed agitator dependent of the homogenizer used.
  • adjuvants are charged into a sterilizing kettle and under continuous stirring the contents of the sterilizing kettle is heated to a temperature of 75 to 95 °C.
  • the active substances and prepared disinfectant are added to the resulting emulsifying liquid.
  • the prescribed amount of water is charged into a homogenizer.
  • Propyleneglycol and sodium gluconate are added under continuous stirring.
  • the contents of the homogenizer is heated at 70 ⁇ 5 °C. At this temperature the aqueous phase is emulsified with the emulsifiying liquid preheated to 80 ⁇ 5 °C very slowly for 20 to 30 minutes using a low-speed agitator dependent of the homogenizer used.
  • the contents of the homogenizer are homogenized for exactly 1 minute.
  • Agitators of anchor and spiral type, or an anchor agitator and dissolver, and homogenizers are set to operation and at the same time, heating of the homogenizer is stopped. After homogenizing, under agitators running, cooling is started and the mixture is cooled down to a temperature of 27 to 28 °C.
  • This process provides a dermatological composition based on liquid crystals in an oil-in-water emulsion with an anisotropic lamellar phase, characterized by higher activity in delivery of moisture, progressive diffusion of active substances based on the requirements of the skin, prolonged activity and which improves bioavailability.
  • dermatological compositions of the invention may be indicated for use as emollients and protectives, antimycotics or protective creams with UV filter.
  • Adjuvants steareth-21 , steareth-2, PPG-15 stearyl ether and isohexadecane are charged into a sterilizing kettle, followed by cetyl stearyl alcohol, stearic acid and Cera alba. Under continuous stirring the contents of the sterilizing kettle is heated to a temperature of 80 ⁇ 5 °C. In a container of a class 17 material the disinfectant is triturated in dimethicone and added to the emulsifying liquid in the sterilizing kettle. The prescribed amount of purified water is vacuum sucked into a jacketed homogenizer. Propyleneglycol is added under continuous mixing by means of an opening in the homogenizer, destined for sucking of liquid materials.
  • the contents of the homogenizer is heated at 70 ⁇ 5 °C. At this temperature, the active substance is added under continuous mixing by means of an opening in the homogenizer, destined for sucking of powdery materials.
  • the aqueous phase with the active substance is emulsified with an emulsifiying liquid preheated to 80 ⁇ 5 °C very slowly for 20 to 30 minutes using a low-speed agitator depending of the homogenizer used. After emulsifying, the contents of the homogenizer are homogenized for exactly 1 minute.
  • Agitators of anchor and spiral type 500 rpm homogenizer
  • an anchor agitator and a dissolver Fryma
  • a 2900 to 3000 rpm homogenizer a 2900 to 3000 rpm homogenizer
  • the process of the preparation is the same as in Example 1 except the fact that the active substance is a part of the emulsifying liquid, which is heated to 75 to 85 °C.
  • the temperature of the aqueous phase is 75 ⁇ 5 °C.
  • Titanium dioxide 1.0-5.0 % by weight
  • the invention is useful in the pharmaceutical industry in the manufacture of dermatological and cosmetic compositions and protective working creams, in which it enables coordination of controlled delivery of moisture and active substances.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dispersion Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Dermatology (AREA)
  • Inorganic Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

L'invention a trait à des compositions dermatologiques topiques comportant des cristaux liquides comme excipient, qui contiennent comme substance active de l'urée, du bifonazole, du lactate de sodium, des filtres organiques et inorganiques, du gluconate de sodium, un désinfectant et des adjuvants ; et à un procédé de préparation qui comporte l'étape consistant à former dans une émulsion huile dans l'eau un système de cristaux liquides qui présente une phase anisotrope lamellaire, de sorte que la couche de phase d'eau et d'huile est séparée par une autre couche d'eau, cette dernière étant piégée à l'interface de phases du système émulsifiant et formant ainsi une lamelle. L'originalité consiste dans le procédé de préparation et l'utilisation de la phase lamellaire des cristaux liquides comme excipient dans des compositions dermatologiques, de manière à tirer profit de leurs propriétés physiques et chimiques pour améliorer les performances des substances actives contenues dans l'excipient donné.
PCT/SK1999/000017 1999-03-03 1999-12-28 Compositions dermatologiques contenant un excipient de cristaux liquides et procede de preparation de celles-ci Ceased WO2000051549A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PL350141A PL198485B1 (pl) 1999-03-03 1999-12-28 Kompozycja do zastosowania miejscowego zawierająca nośnik ciekłokrystaliczny i sposób jej wytwarzania
BG105852A BG65442B1 (bg) 1999-03-03 2001-08-29 Дерматологични състави, съдържащи течен кристал, като носител и метод за получаването им
LV010141A LV12781B (lv) 1999-03-03 2001-10-02 Skidro kristalu pildvielu saturosas dermatologiskas kompozicijas un metode to iegusanai

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SKPV0288-99 1999-03-03
SK288-99A SK283697B6 (sk) 1999-03-03 1999-03-03 Dermatologické prípravky s tekutými kryštálmi ako vehikulom a spôsob ich prípravy

Publications (1)

Publication Number Publication Date
WO2000051549A1 true WO2000051549A1 (fr) 2000-09-08

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ID=20433382

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SK1999/000017 Ceased WO2000051549A1 (fr) 1999-03-03 1999-12-28 Compositions dermatologiques contenant un excipient de cristaux liquides et procede de preparation de celles-ci

Country Status (8)

Country Link
BG (1) BG65442B1 (fr)
CZ (1) CZ295212B6 (fr)
HU (1) HUP0200101A3 (fr)
LT (1) LT4910B (fr)
LV (1) LV12781B (fr)
PL (1) PL198485B1 (fr)
SK (1) SK283697B6 (fr)
WO (1) WO2000051549A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10241541A1 (de) * 2002-09-05 2004-03-18 Nguyen-Petersen, Chanh-Dinh, Dr.med. Creme für kosmetische Zwecke
EP1468668A3 (fr) * 2000-02-15 2005-02-02 Dija Zeist B.V. Emulsion huile-dans-l'eau et préparation à libération controllée pour la peau
WO2016026527A1 (fr) * 2014-08-20 2016-02-25 Amantin Experts Compositions et procédés pour une humidification et une libération contrôlées de principes actifs

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456460A2 (fr) * 1990-05-10 1991-11-13 Unilever Plc Composition cosm˩tique
WO1995003781A1 (fr) * 1993-07-03 1995-02-09 The Procter & Gamble Company Composition de nettoyage destinees aux personnes
EP0710478A1 (fr) * 1994-10-24 1996-05-08 L'oreal Produit pour application topique contenant une lipase et un precurseur d'actif

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0456460A2 (fr) * 1990-05-10 1991-11-13 Unilever Plc Composition cosm˩tique
WO1995003781A1 (fr) * 1993-07-03 1995-02-09 The Procter & Gamble Company Composition de nettoyage destinees aux personnes
EP0710478A1 (fr) * 1994-10-24 1996-05-08 L'oreal Produit pour application topique contenant une lipase et un precurseur d'actif

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1468668A3 (fr) * 2000-02-15 2005-02-02 Dija Zeist B.V. Emulsion huile-dans-l'eau et préparation à libération controllée pour la peau
DE10241541A1 (de) * 2002-09-05 2004-03-18 Nguyen-Petersen, Chanh-Dinh, Dr.med. Creme für kosmetische Zwecke
WO2016026527A1 (fr) * 2014-08-20 2016-02-25 Amantin Experts Compositions et procédés pour une humidification et une libération contrôlées de principes actifs
US11191704B2 (en) 2014-08-20 2021-12-07 Amantin Experts Compositions and methods for controlled moisturizing and release of active ingredients

Also Published As

Publication number Publication date
SK28899A3 (en) 2000-09-12
CZ295212B6 (cs) 2005-06-15
BG105852A (en) 2002-04-30
HUP0200101A3 (en) 2006-07-28
LV12781B (lv) 2002-04-20
PL350141A1 (en) 2002-11-04
PL198485B1 (pl) 2008-06-30
LT2001079A (en) 2002-02-25
SK283697B6 (sk) 2003-12-02
LT4910B (lt) 2002-04-25
BG65442B1 (bg) 2008-08-29
CZ20013092A3 (cs) 2002-01-16
LV12781A (en) 2002-01-20
HUP0200101A2 (en) 2002-06-29

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