WO2014087421A2 - Composition soluble en milieu hydrophile et son utilisation - Google Patents

Composition soluble en milieu hydrophile et son utilisation Download PDF

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Publication number
WO2014087421A2
WO2014087421A2 PCT/IN2013/000515 IN2013000515W WO2014087421A2 WO 2014087421 A2 WO2014087421 A2 WO 2014087421A2 IN 2013000515 W IN2013000515 W IN 2013000515W WO 2014087421 A2 WO2014087421 A2 WO 2014087421A2
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WO
WIPO (PCT)
Prior art keywords
composition
group
component
hydrophilic
hydrophilic medium
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PCT/IN2013/000515
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English (en)
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WO2014087421A3 (fr
Inventor
Vishal Joshi
Milind Vaidya
Vivek RAJE
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Dow Corning India Private Limited
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Publication of WO2014087421A2 publication Critical patent/WO2014087421A2/fr
Publication of WO2014087421A3 publication Critical patent/WO2014087421A3/fr

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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
    • A61K8/494—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
    • A61K8/4953—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 containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to a stable hydrophilic medium-soluble composition of a hydrophobic physiologically active ingredient comprising (A) hydrophobic physiologically active ingredient; (B) silicone compound having specific hydrophilic group (preferably polyether group); and (C) silane having specific hydrophilic group (preferably, having at least two or more polyether group in a silane molecule).
  • Insoluble hydrophobic physiologically active ingredient are stabilized by a combination of said component (B) and (C) in the hydrophilic medium selected from water, alcohols and a mixture thereof without crystallization.
  • the obtained clear hydrophilic medium-soluble composition is useful as a cosmetic raw material or quasi-drug raw material in the personal and health care industries.
  • the hydrophobic physiologically active ingredient is hair-growing agent (ex. Minoxidil), and the hydrophilic medium-soluble composition is applied as a raw material for hair cosmetics or quasi-drugs for human skin of the head.
  • Minoxidil (6-piperidin-l-ylpyrimidine-2, 4-diamine 3-oxide) or other water-insoluble hair growing agent is a vasodilator medication known for its ability to slow or stop hair loss and promote hair re-growth. It is available over the counter for treatment of androgenic alopecia, among other baldness treatments. Then, Minoxidil needs to be applied once or twice daily for the hair gain to be maintained. For maximum effect, the solution should be in contact with the scalp for four hours before being washed out.
  • DHT dihydro testosterone
  • 5-alpha reductase the enzyme responsible for its accumulation around the hair follicle
  • Minoxidil solution in highly-concentrated form.
  • Minoxidil has poor solubility in water or other hydrophilic medium. For this, it is difficult to increase the concentration of physiologically active ingredient to 5 or more % in the solution. Furthermore, during its storage term, insoluble active ingredients are precipitated in the product and caused a heavy crystallization. Furthermore, the obtained Minoxidil solution appears to be unclear and its acceptable usage is fairly limited in a personal-care and/or health-care product. Additionally, Minoxidil products involve contact with hair strands, which may cause problems with hair styling since minoxidil must be in an alcohol solution and on evaporation minoxidil is crystallized and on light exposure, converts to dark brown material. This is one of the biggest challenges for formulators to keep minoxidil in soluble form after applications.
  • WO2009/101497 discloses a fixed topical composition which contains minoxidil, aminexil, siloxanes, and silicone elastomers.
  • WO03055454A1 teaches to the use of lipophillic components selected from fatty acids comprising 14-20 carbon atoms and dimethyl polysiloxane (mixtures thereof).
  • US6740318 teach an efficacy-enhancing additive (specific silicone based compound) for hair growing agent and a hair growing agent composition containing it.
  • the additive is capable to secure the hair growing effect, even if the content of the pharmaceutically active components is reduced from that of the conventional hair growing agent composition, hence the side-effect thereof could be reduced, and to the hair growing agent composition containing it.
  • hydrophobic physiologically active ingredient is effectively stabilized by using a combination of specific hydrophilic silicone and specific hydrophilic silane in a clear solution. Furthermore, with said combination of three components, hydrophilic medium-soluble composition with high-content of bioactive ingredient is easily obtained by conventional method for personal-care and/or health care products. The obtained composition appears to be clear and stable after storage without any crystallization of bioactive ingredients.
  • the invention is for a stable hydrophilic medium-soluble composition of a hydrophobic physiologically active ingredient comprising:
  • r is a number ranging from 1 to 6,
  • W represents a hydrogen atom or an Ci-C 20 alkyl group
  • (C) at least one silane having a hydrophilic group which binds to a silicone atom via a linkage group with two or more valences and comprise at least one hydrophilic unit selected from hydrophilic units represented by said structural formulae (1) to (4).
  • said components (A) to (C) are dispersed into (D) hydrophilic medium selected from water, alcohols and a mixture thereof in the composition.
  • the preferred component (A) is water-insoluble hair-growing agent (ex. Minoxidil)
  • the preferred component (B) is polyether-modified silicone represented by specific structural formulae
  • the preferred component (C) is polyether-modified silane having two or more polyether groups in a silane molecule.
  • the composition further comprises (E) an organic acid to adjust its pH into acidic state.
  • the amount of component (A) is 0.5 to 30 % by weight of total amount of the composition
  • the amount of component (B) is 1.0 to 30 % by weight of total amount of the composition
  • the amount of component (C) is 0.1 to 10 % by weight of total amount of the composition.
  • the amount of component (A) is increased to 5.0 or more % by weight of total amount of the composition.
  • Most preferable weight range of component (A) is from 7.5 to 15.0 % by weight of total amount of the composition.
  • the present invention relates to a stable hydrophilic medium-soluble composition of a hydrophobic physiologically active ingredient comprising:
  • (B) at least one silicone compound having a hydrophilic group which binds to a silicone atom via a linkage group with two or more valences and comprise at least one hydrophilic unit selected from hydrophilic units represented by the following structural formulae (l) to (4):
  • r is a number ranging from 1 to 6,
  • W represents a hydrogen atom or an Ci-C 2 o alkyl group
  • (C) at least one silane compound having a hydrophilic group which binds to a silicone atom via a linkage group with two or more valences and comprise at least one hydrophilic unit selected from hydrophilic units represented by said structural formulae (l) to (4).
  • Component (A) is at . least one of water-insoluble hair-growing agent.
  • component A is Minoxidil.
  • hair-growing agent can be exemplified by water-insoluble hair-growing agents such as mononitroguaiacol, resorcinol, g-aminobutyric acid, benzethonium chloride, mexiletine hydrochloride, auxin, female hormones, cantharis tincture, cyclosporine, zinc pyrithione, hydrocortisone, polyoxyethylene sorbitan monostearate, peppermint oil, and sasanishiki extract.
  • two or more hair-growing agents may be used in combination for advantageous hair-growing effect on human scalp.
  • Component (B) is a silicone compound having a hydrophilic group such as polyether-modified silicones, mono- or polyvalent alcohol-modified silicones, monoglycerol-modified silicones, diglycerol-modified silicones, polyglycerol-modified silicones, sugar-alcohol modified silicones, polysiloxane-polyoxyalkylene block copolymers.
  • a hydrophilic group such as polyether-modified silicones, mono- or polyvalent alcohol-modified silicones, monoglycerol-modified silicones, diglycerol-modified silicones, polyglycerol-modified silicones, sugar-alcohol modified silicones, polysiloxane-polyoxyalkylene block copolymers.
  • polyether-modified silicone (B2) is represented by the following structural formulae (5):
  • Q represents polyether group represented by following formula (6):
  • each of tl and t2 is independently a number of 0 or more
  • tl+t2 is a number ranging from 4 to 50, preferably 6 to 30,
  • W represents a hydrogen atom or an Ci-C 2 o alkyl group, preferably a hydrogen atom or methyl group,
  • R is a group selected from R 1 , Q and -OH,
  • n is a number ranging from 1 to 50, preferably 1 to 30, more preferably 1 to 20.
  • Component (C) is a silane compound having a hydrophilic group.
  • the silane compound has two or more defined hydrophilic group in a molecule.
  • Other groups binding to Si atom may be selected from Ci-C 20 alkyl group, phenyl group, hydroxyl (- OH) group, C1-C4 alkoxy group and Chloride.
  • Hydrophilic group of component (C) is preferably selected from polyether-group, mono- or polyvalent alcohol- group, monoglycerol- group, diglycerol- group, polyglycerol- group and sugar-alcohol group.
  • Component C may be a polyether-modified silane.
  • the silane has two or more defined hydrophilic group in a molecule and represented as following:
  • tl and t2 is independently a number of 0 or more
  • tl+t2 is a number ranging from 4 to 50, preferably 6 to 30,
  • r is a number of 1 to 6, preferably 2 to 3,
  • p is a number of 2 to 4, preferably 2 to 3, most preferably 2,
  • R 2 independently represents Ci-C 20 alkyl group, phenyl group, hydroxyl(-OH) group, d- C4 alkoxy group or Chloride, Preferably R 2 independently represents methyl group or ethyl group,
  • W represents a hydrogen atom or an C1-C20 alkyl group, preferably a hydrogen atom or methyl group.
  • the hydrophilic medium-soluble composition Component (D) is a hydrophilic medium selected from water, alcohols and a mixture thereof.
  • water, ethanol, isopropanol, 1,3-butylene glycol, sorbitol, dipropylene glycol, glycerol, and polyethylene glycol may be used as component (D) that are able to increase the stability of the inventive composition.
  • water, 1,3-butylene glycol, sorbitol, dipropylene glycol, glycerol, and polyethylene glycol may be used as component (D) as they additionally have a moisturizing effect.
  • the water should be clean and free of components toxic to humans and can be exemplified by tap water, purified water, and mineral water.
  • the hydrophilic medium-soluble composition may further comprise Component (E) which is preferably organic acids.
  • the organic acid may be selected from the group consisting of acetic acid, lactic acid, citric acid, ascorbic acid, malic acid, tartaric acid, and so forth.
  • the pH should be adjusted, preferably in the ranges from 2 to 7 (acidic) to stabilize component (A).
  • Component (A) is much stable at lower pH.
  • the weight ratio of component (A), (B), and (C) in the composition preferably ranges from 0.5 to 30 % by weight of total amount of the composition, from 1.0 to 30 % by weight of total amount of the composition, and from 0.1 to 10 % by weight of total amount of the composition, respectively.
  • composition of the present invention has the capability to be used in personal-care and/or health-care products.
  • the composition of the present invention can comprise any combination of the aforementioned components (A) to (D) and at least any one of the following components; oil agents (including fats and oils, higher fatty acids, higher alcohols, fluorine-based oils and the like); other surfactants (at least one type selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and semi-polar surfactants); water-soluble polymers; thickening and/or gelling agents; powders; solid silicone resins or crosslinking organopolysiloxanes; UV-ray protective components; oxidation hair dyes; direct dyes; organic resins, moisture- retaining agents, preservative, anti-microbial agents, perfumes, salts, oxidants or antioxidants, pH adjusting agents, chelating agents, algefacients, anti-inflammatory agents, physiologically active components (such as whitening
  • the most preferred form of using the composition is when the composition comprises Minoxidil in high concentration and is applied to human hair or human scalp as cosmetic or a quasi-drug for scalp treatment.
  • the forms of the cosmetic or quasi-drug of the present invention are not particularly restricted, and may be in the form of liquids, creams, solids, pastes, gels, powders, lamellas, mousses, sprays, sheets, and the like.
  • the cosmetic or quasi-drug of the present invention can be exemplified by hair-restoring agents, hair growth agents, hair tonics, hair oil, skin ageing inhibitors, scalp-care oils, scalp soap, scalp cleansing agents, scalp treatment agents, ointments, shampoos, rinses, hair- treatments and the like but are not limited to the preceding.
  • Example 1 Preparation of Minoxidil-comprising composition
  • Table 1 shows the effect of solubility of Minoxidil in various component (a) or (b) and crystallization and degradation observations.
  • SPE (bl) is PEG-12 Dimethicone represented by bellow formula:
  • Ql represents - (C 2 H 4 0)i 2 H
  • SPE (b2) is polyether-modified silicone represented by bellow formula:
  • Q2 represents - (C 2 H 4 0)i 2 (C 3 H 6 0)i 2 -H
  • SAW (cl) is Bis-PEG(18) mehyl ethyl Dimethyl silane.
  • Example 2 Formulation for 10% Minoxidil Gel
  • Carbopol 940TM 2% solution was prepared in water to obtain Phase A.
  • Phase B was prepared by first mixing Minoxidil, Benzyl alcohol, Propylene glycol, Ethanol and water together. The mixture was stirred till clear solution was obtained. SPE (bl) and SAW (cl) were added in the mixture and stirred. All other ingredients were added to obtain a clear gel.
  • Example 3 Formulation for 10% Minoxidil foam
  • Phase A was prepared by mixing Minoxidil, Benzyl alcohol, Propylene glycol, Ethanol and water together. The mixture is stirred till a clear solution is obtained. SPE (bl) and SAW (cl) were added in the same and stirred. All other ingredients were added to get a clear solution. Phase B was prepared and added to Phase A slowly and packed with tetra fluroethene to get a stable foam. [0032] Example 4 : Formulation for 10% Minoxidil Solution (hydrous)
  • Phase A All the ingredients of Phase A, Phase B, and Phase C were mixed in a separate beaker.
  • Phase B was added to Phase A solution and stirred till a clear solution was obtained.
  • Phase C was added to Phase A-Phase B mixture and stirred till a clear solution is obtained. This solution was heated for about 40-45°C and the temperature was maintained. Minoxidil was added to the above solution slowly, while continuously stirring it for 20 minutes till a clear solution is obtained. The clarity must be checked to ensure complete dissolution of the drug.
  • Example 5 Formulation for 10% Minoxidil solution (anhydrous)
  • Phase A All the ingredients of Phase A, Phase B, and Phase C were mixed in a separate beaker.
  • Phase B was added to Phase A solution and stirred till a clear solution was obtained.
  • This solution was heated for about 40-45°C and the temperature was maintained.
  • Minoxidil was added to the above solution slowly, while continuously stirring it for 20 minutes till a clear solution is obtained. The clarity must be checked to ensure complete dissolution of the drug.
  • Example 6 Formulation for 10% Minoxidil solution (anhydrous)
  • Phase A All the ingredients of Phase A, Phase B, and Phase C were mixed in a separate beaker.
  • Phase B was added to Phase A solution and stirred till a clear solution was obtained.
  • This solution was heated for about 40-45°C and the temperature was maintained.
  • Minoxidil was added to the above solution slowly, while continuously stirring it for 20 minutes till a clear solution is obtained. The clarity must be checked to ensure complete dissolution of the drug.
  • the instant invention relates to a stable hydrophilic medium-soluble composition of a hydrophobic physiologically active ingredient having excellent compatibility with hydrophilic medium and maintains a clear appearance after storage at a high concentration of said active ingredient.
  • the said composition may be used as a raw material for cosmetic or quasi-drug application.
  • component (A) to (C) in the composition a stable composition with higher concentration of bioactive ingredients is easily obtained by conventional method for personal-care and/or health care products.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention porte sur une composition soluble en milieu hydrophile comprenant (A) un principe physiologiquement actif hydrophobe (de préférence du minoxidil) ; (B) un composé silicone ayant un groupe hydrophile particulier (de préférence un groupe polyéther) ; et (C) un silane ayant un groupe hydrophile particulier (de préférence un groupe polyéther). Le principe physiologiquement actif hydrophobe insoluble est stabilisé par une association dudit constituant (B) et dudit constituant (C) dans le milieu hydrophile choisi parmi l'eau, les alcools et un mélange de ceux-ci, sans cristallisation. La composition soluble en milieu hydrophile transparente obtenue est utile comme matière première de produit cosmétique ou matière première de quasi-médicament.
PCT/IN2013/000515 2012-12-04 2013-08-26 Composition soluble en milieu hydrophile et son utilisation WO2014087421A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN3429MU2012 2012-12-04
IN3429/MUM/2012 2012-12-04

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WO2014087421A2 true WO2014087421A2 (fr) 2014-06-12
WO2014087421A3 WO2014087421A3 (fr) 2014-12-24

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1112136A (ja) 1997-06-27 1999-01-19 Taisho Pharmaceut Co Ltd ミノキシジル配合エアゾール剤
JP2000313808A (ja) 1999-04-28 2000-11-14 Shiseido Co Ltd 可溶化組成物
JP2001302543A (ja) 2000-04-27 2001-10-31 Lion Corp 髪質改善剤
WO2003055454A1 (fr) 2001-12-21 2003-07-10 Ponsus Pharma Ab Nouvelle composition permettant de prevenir la chute des cheveux et/ou de stimuler la croissance des cheveux
US6740318B2 (en) 2000-04-04 2004-05-25 Nippon Unicar Company Limited Additive for hair growing agent and hair growing agent composition
WO2009101497A2 (fr) 2008-02-11 2009-08-20 Glenmark Pharmaceuticals Limited Association pharmaceutique topique comprenant du minoxidil et de l'aminexil

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6403067B1 (en) * 2000-05-19 2002-06-11 Colgate-Palmolive Company Stable emulsions for cosmetic products
US20040034094A1 (en) * 2002-08-16 2004-02-19 Gupta Shyam K. Vitamin C stabilized topical formulation
DE102004048987B3 (de) * 2004-10-04 2005-12-15 Coty Deutschland Gmbh Kühlende kosmetische Zusammensetzung und deren Verwendung
KR101444689B1 (ko) * 2008-02-25 2014-09-26 (주)아모레퍼시픽 피부 미백용 화장료 조성물
DE102008035834A1 (de) * 2008-07-31 2010-02-04 Coty Prestige Lancaster Group Gmbh Verfahren zur Herstellung von Liposomkomplexen mit unterschiedlichen Wirkstoffen und damit hergestellte Produkte, insbesondere kosmetische Produkte
WO2011017274A2 (fr) * 2009-08-06 2011-02-10 Peter Thomas Roth Labs, Llc Compositions pour favoriser un aspect sain de la peau
KR20120019409A (ko) * 2010-08-25 2012-03-06 주식회사 엘지생활건강 고형 성상의 수분 공급용 화장료 조성물
WO2013080717A1 (fr) * 2011-12-01 2013-06-06 株式会社資生堂 Préparation cosmétique aqueuse destinée à la peau

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1112136A (ja) 1997-06-27 1999-01-19 Taisho Pharmaceut Co Ltd ミノキシジル配合エアゾール剤
JP2000313808A (ja) 1999-04-28 2000-11-14 Shiseido Co Ltd 可溶化組成物
US6740318B2 (en) 2000-04-04 2004-05-25 Nippon Unicar Company Limited Additive for hair growing agent and hair growing agent composition
JP2001302543A (ja) 2000-04-27 2001-10-31 Lion Corp 髪質改善剤
WO2003055454A1 (fr) 2001-12-21 2003-07-10 Ponsus Pharma Ab Nouvelle composition permettant de prevenir la chute des cheveux et/ou de stimuler la croissance des cheveux
WO2009101497A2 (fr) 2008-02-11 2009-08-20 Glenmark Pharmaceuticals Limited Association pharmaceutique topique comprenant du minoxidil et de l'aminexil

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