US20100047357A1 - Compositions for topical application comprising a peroxide and retinoid - Google Patents

Compositions for topical application comprising a peroxide and retinoid Download PDF

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Publication number
US20100047357A1
US20100047357A1 US12/525,329 US52532908A US2010047357A1 US 20100047357 A1 US20100047357 A1 US 20100047357A1 US 52532908 A US52532908 A US 52532908A US 2010047357 A1 US2010047357 A1 US 2010047357A1
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US
United States
Prior art keywords
composition
metal oxide
particulate matter
coated
active ingredient
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.)
Abandoned
Application number
US12/525,329
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English (en)
Inventor
Ofer Toledano
Hanan Sertchook
Natalia Loboda
Haim Bar-Simantov
Leora Shapiro
Raed Abu-Reziq
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.)
Sol Gel Technologies Ltd
Original Assignee
Sol Gel Technologies Ltd
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 Sol Gel Technologies Ltd filed Critical Sol Gel Technologies Ltd
Priority to US12/525,329 priority Critical patent/US20100047357A1/en
Assigned to SOL-GEL TECHNOLOGIES LTD. reassignment SOL-GEL TECHNOLOGIES LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ABU-REZIQ, RAED, SHAPIRO, LEORA, BAR-SIMANTOV, HAIM, LOBODA, NATALIA, SERTCHOOK, HANAN, TOLEDANO, OFER
Publication of US20100047357A1 publication Critical patent/US20100047357A1/en
Assigned to SOL-GEL TECHNOLOGIES LTD. reassignment SOL-GEL TECHNOLOGIES LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ABU-REZIQ, RAED, SHAPIRO, LEORA, BAR-SIMANTOV, HAIM, LOBODA, NATALIA, SERTCHOOK, HANAN, TOLEDANO, OFER
Abandoned legal-status Critical Current

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    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts 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
    • A61K31/327—Peroxy compounds, e.g. hydroperoxides, peroxides, peroxyacids
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation

Definitions

  • Sol-Gel process has been used to encapsulate various active ingredients, thus isolating the active ingredient from the environments.
  • FIG. 1 depicts the irritation test results performed according to Example 6.
  • the mean size of a side may be in the range 0.3 to 80 microns, preferably 0.3 to 40 microns, more preferably 0.8 to 40, even more preferably 4 to 15 microns.
  • the microparticles (coated particulate matter) have a diameter (d90) of 0.5 to 100 ⁇ m or preferably the diameter of the microparticles is in the range of 1 to 50 ⁇ m and most preferably in the range of 5 to 30 ⁇ m. It is appreciated that the microparticles of the present invention are composed of distinct regions of the metal oxide layer in the core material (i.e. the water insoluble particulate matter).
  • microparticles are preferably characterized in that the core material is substantially free of the metal oxide and further in that the metal oxide layer is substantially free of said core material, e.g. either as particle dispersion (in the nano-metric range of below 0.1 ⁇ m) of the particulate matter or as molecular dispersion of said particulate matter.
  • said coated form of the active ingredient is second microparticles comprising a solid particulate matter of the active ingredient coated by a metal oxide layer.
  • said peroxide is in the form of first microparticles comprising solid particulate matter of peroxide coated by a metal oxide layer and said retinoid is in the form of second microparticles comprising a solid particulate matter of the retinoid coated by a metal oxide layer.
  • the final form of the composition may be any of the above forms, mentioned with respect to the carrier, where the microparticles are dispersed in the carrier.
  • the final form of the composition may also be in the form of a wash or cleanser.
  • said first microparticles are prepared by deposition of metal oxide on the surface of the solid particulate matter.
  • the deposition of metal oxide on the surface of the particulate matter may be performed by precipitation of a metal oxide salt onto the surface of the particulate matter, forming a metal oxide layer thereon as will be described below or by a spray drying method.
  • the first microparticles are prepared by a process comprising:
  • the solid, water-insoluble particulate matter refers to the peroxide or retinoid.
  • the process described may also be used to coat additional active ingredients (e.g. antibiotics) which may be incorporated into the composition described in the present invention.
  • step (b2) subjecting the particulate matter obtained in step (b1) to a coating procedure as in step (b);
  • step (c) is repeated 3 to about 1000 times.
  • step (c) is repeated 3 to about 300 times, and more preferably 3 to about 100 times. This means that preferably steps (b1) and (b2) are repeated as indicted above with respect to step (c).
  • the cationic surfactant selected from monoalkylquaternary ammonium salts, dialkyl quaternary ammonium salts, and mixtures thereof.
  • the ionic additive may be an anionic surfactant.
  • the weight ratio of the further processed coated particulate matter (e.g. in the repeated steps described in step (c)) to the second cationic additive is in the range of about 25,000/1 to about 50/1, more preferably about 5,000/1 to about 100/1, most preferably about 2000/1 to about 200/1.
  • the surface chemical modification preferably comprises modifying the metal oxide surface with organic groups, preferably hydrophobic groups.
  • the halo group may be for example chloro, bromo, iodo, fluoro. Most preferably the halo groups are chloro and bromo.
  • the positive zeta potential in step (a) is less than +150 mV, more preferably zeta potential in the range +60 mV to +130 mV.
  • the preferred zeta potential in step (d) is less than +150 mV, more preferably in the range +5 mV to +130 mV, and most preferably +10 mV to +100 mV. This is the preferred zeta potential also in the further, optional, processing steps.
  • the monoalkylquaternary ammonium salt is cetyltrimethylammonium chloride.
  • the weight ratio of the second cationic additive to the further processed coated particulate matter is in the range 1:1000-1:10, more preferably 1:200-1:50, most preferably about 1:100.
  • the first microparticles may also prepared by spray drying as described for example in:
  • the side effects are selected from irritation, erythema, stringing, itching, scaling, dryness, and combinations thereof.
  • the aging step The coated BPO suspension at pH 6.5 was kept for aging at room temperature under gentle agitation for 24 hrs.
  • the aging step The coated ATRA suspension at pH 4.5 was kept for aging at room temperature under gentle agitation for 24 hrs.
  • ATRA All-trans-Retinoic acid

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Toxicology (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
US12/525,329 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid Abandoned US20100047357A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/525,329 US20100047357A1 (en) 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US89870107P 2007-02-01 2007-02-01
US12/525,329 US20100047357A1 (en) 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid
PCT/IL2008/000140 WO2008093346A2 (en) 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/IL2008/000140 A-371-Of-International WO2008093346A2 (en) 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/495,701 Continuation US8617580B2 (en) 2007-02-01 2012-06-13 Compositions for topical application comprising a peroxide and retinoid

Publications (1)

Publication Number Publication Date
US20100047357A1 true US20100047357A1 (en) 2010-02-25

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US12/525,329 Abandoned US20100047357A1 (en) 2007-02-01 2008-02-03 Compositions for topical application comprising a peroxide and retinoid
US13/495,701 Active US8617580B2 (en) 2007-02-01 2012-06-13 Compositions for topical application comprising a peroxide and retinoid

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Application Number Title Priority Date Filing Date
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Country Status (11)

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US (2) US20100047357A1 (es)
EP (1) EP2109445B1 (es)
JP (2) JP2010517996A (es)
KR (1) KR20090125243A (es)
AU (1) AU2008211553B2 (es)
BR (1) BRPI0808163A2 (es)
CA (1) CA2677184C (es)
EA (1) EA200970724A1 (es)
ES (1) ES2912051T3 (es)
MX (1) MX2009008250A (es)
WO (1) WO2008093346A2 (es)

Cited By (7)

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US20100016443A1 (en) * 2007-02-01 2010-01-21 Sol-Gel Technologies Ltd. Method for preparing particles comprising metal oxide coating and particles with metal oxide coating
US20130095185A1 (en) * 2011-06-29 2013-04-18 Medicis Pharamaceutical Corporation Stabilized topical formulations containing core-shell microcapsules
US9687465B2 (en) 2012-11-27 2017-06-27 Sol-Gel Technologies Ltd. Compositions for the treatment of rosacea
US9868103B2 (en) 2005-08-02 2018-01-16 Sol-Gel Technologies Ltd. Metal oxide coating of water insoluble ingredients
US10512796B2 (en) 2009-12-31 2019-12-24 Sol-Gel Technologies Ltd. Core stabilized microcapsules, method of their preparation and uses thereof
US10653899B2 (en) 2009-12-31 2020-05-19 Sol-Gel Technologies Ltd. Core stabilized microcapsules, method of their preparation and uses thereof
US11071878B2 (en) 2009-12-31 2021-07-27 Sol-Gel Technologies Ltd. Core stabilized microcapsules, method of their preparation and uses thereof

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EP2263788B1 (en) 2003-07-31 2018-07-25 Sol-Gel Technologies Ltd. A process for the preparation of microcapsules filled with active ingredients
MX2011000682A (es) 2008-07-31 2011-03-25 Sol Gel Technologies Ltd Microcapsulas que comprenden ingredientes activos y una cubierta de oxido de metal, un metodo para su preparacion y usos de las mismas.
BRPI1006011A2 (pt) * 2009-01-05 2016-04-05 Sol Gel Technologies Ltd sistema tópico de múltiplos componentes, métodos para tratar, melhorar a aparência de ou evitar uma doença ou condição da pele ou de uma membrana de mucosa, para tratar lesões da pela, para tratar comedões de pele, e para tratar acne, uso de um sistema, e, kit.
AU2010273261B2 (en) * 2009-07-16 2013-07-25 Stiefel Laboratories, Inc. Tazarotene derivatives
WO2011154421A1 (de) * 2010-06-09 2011-12-15 Basf Se Wirkstoff enthaltende mikrokapseln mit einer metalloxid-haltigen schale
US9572880B2 (en) 2010-08-27 2017-02-21 Sienna Biopharmaceuticals, Inc. Ultrasound delivery of nanoparticles
EP3210591B1 (en) 2010-08-27 2019-01-02 Sienna Biopharmaceuticals, Inc. Compositions and methods for targeted thermomodulation
MX2015004524A (es) 2012-10-11 2015-09-25 Nanocomposix Inc Metodos y composiciones de nanoplacas de plata.
JP6423355B2 (ja) * 2012-11-27 2018-11-14 ソル − ゲル テクノロジーズ リミテッド 酒さの治療のための組成物
WO2015092602A1 (en) * 2013-12-17 2015-06-25 Ranbaxy Laboratories Limited Topical pharmaceutical composition of a retinoid
WO2015161179A1 (en) 2014-04-18 2015-10-22 Pilant Gregory P Methods and compositions for topical delivery for skin care
WO2017029665A1 (en) 2015-08-20 2017-02-23 Sol-Gel Technologies Ltd. Compositions for topical application comprising benzoyl peroxide and adapalene
CA3016436A1 (en) * 2016-03-04 2017-09-08 Arkema Inc. Encapsulation of peroxides for skin applications
CA3069359C (en) 2017-07-12 2023-01-10 Sol-Gel Technologies Ltd. Compositions comprising encapsulated tretinoin
JP2020527143A (ja) 2017-07-12 2020-09-03 ソル − ゲル テクノロジーズ リミテッド ざ瘡の治療のための方法および組成物
US20190015368A1 (en) * 2017-07-12 2019-01-17 Sol-Gel Technologies Ltd. Method of acne treatment by concomitant topical administration of benzoyl peroxide and tretinoin
JP6811213B2 (ja) * 2018-07-03 2021-01-13 ソル − ゲル テクノロジーズ リミテッド 酒さの治療のための組成物
WO2020044344A1 (en) * 2018-08-29 2020-03-05 Sol-Gel Technologies Ltd Compositions comprising ozenoxacin
US10933046B2 (en) * 2019-02-19 2021-03-02 Sol-Gel Technologies, Ltd. Method for treatment of rosacea in patients aged 65 years and older
JP7241967B2 (ja) 2020-03-27 2023-03-17 三菱電機株式会社 空気調和機
KR20230027073A (ko) * 2020-05-22 2023-02-27 솔-겔 테크놀로지스 리미티드 안정화된 마이크로캡슐, 그의 제조 방법 및 그의 용도
WO2023105227A1 (en) * 2021-12-08 2023-06-15 Nanexa Ab New injectable combination formulation

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