WO2022190082A1 - Compositions biphasiques pour le traitement d'indications de la peau - Google Patents

Compositions biphasiques pour le traitement d'indications de la peau Download PDF

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Publication number
WO2022190082A1
WO2022190082A1 PCT/IL2022/050223 IL2022050223W WO2022190082A1 WO 2022190082 A1 WO2022190082 A1 WO 2022190082A1 IL 2022050223 W IL2022050223 W IL 2022050223W WO 2022190082 A1 WO2022190082 A1 WO 2022190082A1
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WO
WIPO (PCT)
Prior art keywords
composition
composition according
cannabinoid
amount
previous
Prior art date
Application number
PCT/IL2022/050223
Other languages
English (en)
Inventor
Nir Avram
Original Assignee
Innocan Pharma 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 Innocan Pharma Ltd. filed Critical Innocan Pharma Ltd.
Publication of WO2022190082A1 publication Critical patent/WO2022190082A1/fr

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Classifications

    • 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
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/886—Aloeaceae (Aloe family), e.g. aloe vera
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • A61P23/02—Local anaesthetics
    • 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
    • A61K31/05—Phenols
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
    • A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine

Definitions

  • biphasic topical compositions for treatment of skin conditions.
  • Pruritus is an uncomfortable, itching sensation of the skin.
  • causes of pruritus include dry skin, eczema, psoriasis, scabies, burns, scars, insect bites, hives, nerve disorders, psychiatric diseases or exposure to skin irritants or sources of allergic reaction.
  • Allergic reaction of the skin may be caused by exposure to allergens such as chemicals, natural substances, or insect bites. Itchy skin may sometimes be accompanied with visible changes to the skin such as a rash, redness, bumps, spots or scaly skin.
  • biphasic compositions for topical administration, to relieve pruritis.
  • the pruritis may be associated with insect bites, rash, cuts or bums.
  • the compositions comprise a cannabinoid and at least one anesthetic agent.
  • the compositions are biphasic compositions comprising an aqueous phase and an oil-based phase. The two phases may be contained in a single container and mixed, for example, by shaking, before administration of the composition to the skin of the patient.
  • compositions comprising a pharmaceutically effective amount of a cannabinoid and at least one anesthetic ingredient.
  • the anesthetic agent may be an amino-ester anesthetic or a pharmaceutically acceptable salt thereof described in table 1.
  • Table 1 :
  • the anesthetic may be an amino-amide anesthetic described in table 2 or a pharmaceutically acceptable salt thereof.
  • a preferable anesthetic agent is lidocaine.
  • Cannabinoid is a chemical compound that acts on cannabinoid receptors in cells in mammals, including in humans.
  • Cannabinoids can be manufactured synthetically or obtained from various parts of the genus Cannabis, in particular, from the species Cannabis Sativa.
  • Cannabinoids from the cannabis plant are referred to as phytocannabinoids.
  • Two preferred cannabinoids according to various embodiments are (-)-trans-A 9 - tetrahydrocannabinol, and/or isomers thereof (THC) and cannabidiol (CBD).
  • a cannabinoid may be in the form of cannabis extract.
  • a cannabinoid may be in the form of a synthetic cannabinoid.
  • Compositions described herein may comprise one cannabinoid or multiple cannabinoids, such as a combination of CBD and THC.
  • Pruritis Itching of the skin.
  • compositions which are biphasic mixtures, having an aqueous phase and an oil-based phase, which are packaged together in the same receptacle, but exist primarily as two separate phases.
  • the phases combine, as determined by visual examination, and can then be applied to an affected area of a patient suffering from pruritis. It is suggested that such compositions will be advantageous relative to currently available compositions by providing effective treatment without providing an unaesthetic appearance and without causing irritation to the skin.
  • the composition comprises a combination of water- soluble and water-insoluble active ingredients.
  • the composition may optionally comprise an aqueous phase and a non-aqueous phase.
  • the biphasic composition may be shaken or stirred, or shaken, not stirred, by the user before administration.
  • the aqueous phase comprises the anesthetic agent.
  • the non-aqueous phase comprises the cannabinoid.
  • both phases mix and do not separate for at least 10 seconds, preferably at least 30 seconds.
  • compositions according to embodiments described herein may comprise a cannabinoid or a plurality of cannabinoids selected from the group consisting of CBD and THC.
  • the cannabinoid is CBD.
  • the cannabinoid may be present in an amount of between 0.001 and 10%, preferably 0.1 and 2 percent, by weight, of the compositions.
  • the cannabinoid is present in an amount of 0.87% by weight.
  • the composition may comprise an additional active ingredient which is selected from the group consisting of, a soothing agent, or a topical analgesic.
  • a soothing agent or a topical analgesic.
  • the soothing agent or topical analgesic is selected from the group consisting of: Aloe Barbadensis leaf juice, and menthol.
  • the composition comprises hemp oil in the oil phase of the composition.
  • hemp oil is present in the composition in an amount of between 0.25 and 10% of the composition.
  • hemp oil is present in an amount of 0.5% of the composition.
  • the hemp oil may act as a solubilizer for a cannabinoid.
  • the cannabinoid may be present naturally in the hemp oil, or a cannabinoid may be added to the hemp oil.
  • the composition has less than 1% emulsifier by weight. According to an embodiment, the composition is free of emulsifier.
  • Emulsifier has a soap-consistency and may cause an unpleasant feeling on the skin.
  • An emulsifier may cause components of the water phase to mix with the oil phase and thereby cause a lack of stability of the biphasic composition.
  • An emulsifier may cause some of the active components of the composition to lose their activity over time.
  • the ratio by weight of aqueous to non-aqueous phase to oil-based phase is between 10:90 and 90:10.
  • the viscosity of the composition is preferably in the range of between 0.5 and 200 centipoise (cps) at 25°C.
  • the determination of viscosity is performed immediately after shaking.
  • the viscosity is under 100 cps.
  • the composition may be in the form of a liquid, provided in a bottle for spraying onto an affected area.
  • the composition may be in an aerosol spray or a pump spray.
  • the pump spray may be a bottle equipped with a button spray or a trigger spray.
  • the compositions may be packaged in a packaging and provided with instructions to shake before use.
  • compositions described herein may further comprise at least one inert ingredient.
  • the inert ingredient may be selected from the group consisting of: water, a solvent, an emollient, a moisturizer, a pH adjustment agent, a polymer, a humectant, an occlusive agent, a preservative, a thickener, an anti-irritation agent, a conditioning agent, a buffer, a vitamin, an extract, a natural oil, a wax, a penetration enhancer, a peptide, a sugar derivative, a fatty acid, a fatty alcohol, a silicone, a polyethyl-glycol, a fragrance, a pigment, an ester, a triglyceride, an antioxidant and an absorbing powder.
  • the composition comprises an aqueous phase and an oil- based, non-aqueous phase.
  • the biphasic composition may be shaken or stirred by the user before administration.
  • the non-aqueous phase comprises the cannabinoid.
  • both phases mix and do not separate for at least 10 seconds, preferably at least 30 seconds.
  • a biphasic composition may provide stability to the composition in that the water-soluble active ingredient is contained in an aqueous environment and the cannabinoid is contained in a non-aqueous environment.
  • Biphasic compositions when stored, are separated into two phases. Before use, the patient is instructed to shake the container in which the composition is stored and from which the composition is dispensed for a number of seconds between 2 and 5 times. The phases of the biphasic composition then combine, as determined by visual inspection, and the composition can be applied, preferably by spraying, onto the skin of the patient in need.
  • Phase separation happens in preferably greater than 30 seconds from the shaking of the biphasic composition.
  • phase separation happens after two minutes from shaking of the biphasic composition.
  • the cannabinoid is dissolved in an oil.
  • the oil may be hemp oil, olive oil, or an essential oil.
  • the oil is an ester, a triglyceride, a hydrocarbon, a fatty alcohol, mineral oil, silicon oil, ethoxylate alcohol, or vegetable oil.
  • the pH of the composition after shaking is between 6 and 8.
  • the pH electrode is calibrated at pH of 4 and pH of 7, then immediately immersed in the composition after shaking.
  • an acid or base is added to the composition until the composition has pH of between 6 and 8.
  • Additional embodiments relate to methods for treatment of a condition of the skin such as pruritis, comprising administering to a patient in need thereof, a pharmaceutical composition via the topical route comprising a cannabinoid and an anesthetic agent.
  • the composition may comprise two phases, an aqueous and an oil-based phase.
  • Treatment of pmruitis may involve treatment of symptoms of pruritis including one or more than one of the following symptoms: irritation, cuts, bums, insect bites, rashes, itchy, red and / or inflamed skin.
  • the symptoms may be associated with exposure to an allergen such as poison ivy, poison oak or poison sumac.
  • the composition may be applied daily, optionally, between 1 and 4 times daily.
  • the composition is applied and left on the patient’s skin.
  • the composition may be applied in an amount of between about 0.05 milliliter (ml) and about 1 ml per spray (per pump release).
  • the composition may be applied in an amount between 0.1 ml and 0.25 ml per spray.
  • the composition may be applied via a single spray burst or multiple spray bursts to cover an affected area.
  • the composition may further comprise a solubilizer.
  • the solubilizer may be selected from the group consisting of: Polysorbate-20, Polysorbate-80, PEG-40 Hydrogenated Castor oil.
  • a biphasic pharmaceutical composition comprising an aqueous phase and an oil-based phase, wherein the composition comprises an anesthetic agent and at least one cannabinoid, and wherein the composition is free of emulsifier.
  • the cannabinoid is selected from the group consisting of full spectrum cannabis, CBD and THC.
  • the cannabinoid is CBD.
  • the cannabinoid is present in an amount between 0.001% and 10% by weight of the composition, preferably, in an amount between 0.05% and 2% by weight of the composition, most preferably in an amount of 0.87% by weight.
  • the composition has a viscosity of between 0.5 and 200 centipoise at 25°C when measured immediately after shaking.
  • the anesthetic agent is lidocaine or a pharmaceutically acceptable salt thereof, optionally, lidocaine HC1.
  • the anesthetic agent is present in an amount of between 1% and 10%, by weight, of the composition, preferably in an amount of between 3% and 5%, by weight, of the composition.
  • the composition further comprises an additional active agent.
  • the additional active agent is a soothing agent or a topical analgesic.
  • the additional active agent is selected from the group consisting of: Aloe Barbadensis leaf juice and menthol.
  • both phases mix and do not separate for at least 10 seconds and up to two minutes.
  • compositions use in treatment of pruritis, by administering to a patient in need thereof a therapeutically effective amount of a biphasic pharmaceutical composition comprising an aqueous phase and an oil-based phase, wherein the composition comprises an anesthetic agent and at least one cannabinoid.
  • the treatment is for irritation, cuts, burns, insect bites, rashes, itchy, red and / or inflamed skin.
  • the composition is administered by spraying in an amount between 0.05 ml and 1 ml per spray.
  • the composition is administered between once and 4 times daily.
  • the use in treating further comprises shaking the composition before administering the composition topically.
  • the composition is administered to the skin of a patient via an aerosol spray or pump spray.
  • a method for treatment or pruritis comprising topically administering to a patient in need thereof, a composition comprising a therapeutically effective amount of a biphasic pharmaceutical composition comprising an aqueous phase and an oil- based phase, wherein the composition comprises an anesthetic agent and at least one cannabinoid.
  • the treatment is for irritation, cuts, bums, insect bites, rashes, itchy, red and / or inflamed skin.
  • the composition is administered by spraying in an amount of between 0.05 ml and 1 ml per spray.
  • the composition is administered between once and 4 times daily.
  • the method further comprises shaking the composition before administering the composition topically.
  • the composition is administered to the skin of a patient via an aerosol spray or pump spray.
  • a spray for treatment of pruritis of the skin was prepared using the ingredients described in table 3: Table 3:
  • Bottles of pump spray were filled. After shaking, phase separation occurs in longer than 30 seconds.
  • the composition formed was a low-viscosity yellowish lotion having a viscosity of less than 100 cps.
  • compositions having a cannabinoid and another active ingredient, conveniently, to the affected area comprise allowing a patient in need to apply the composition having a cannabinoid and another active ingredient, conveniently, to the affected area. After administration, much of the water-phase of the composition evaporates and does not leave an oily residue on a patient’s skin. After administration, the aqueous and oil-based layers separate, providing additional stability to the composition.
  • a spray for treatment of pruritis of the skin was prepared using the ingredients described in table 4, using the process described in Example 1.
  • Bottles of pump spray were filled. After shaking, phase separation occurs in longer than 30 seconds.
  • the composition formed was a low-viscosity yellowish lotion having a viscosity of less than 100 cps.
  • a spray for treatment of pmritis of the skin was prepared using the ingredients described in table 5. Table 5:
  • Bottles of pump spray were filled. After shaking, phase separation occurs in longer than 7 minutes.
  • the composition formed was a low-viscosity white-yellow lotion having a viscosity of less than 100 cps.
  • compositions having a cannabinoid and another active ingredient comprise allowing a patient in need to apply the composition having a cannabinoid and another active ingredient, conveniently, to the affected area. After administration, much of the water-phase of the composition evaporates and does not leave an oily residue on a patient’s skin. After administration, the aqueous and oil-based layers (in the bottle) separate, providing additional stability to the composition.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Botany (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Medical Informatics (AREA)
  • Biotechnology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Dispersion Chemistry (AREA)
  • Anesthesiology (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mycology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des compositions biphasiques pour une administration topique, destinées à soulager le prurit. Le prurit peut être associée à des piqûres d'insectes, des éruptions, des coupes ou des brûlures. Les compositions comprennent un cannabinoïde et au moins un agent anesthésique. Les compositions sont des compositions biphasiques comprenant une phase aqueuse et une phase huileuse. Les deux phases peuvent être contenues dans un récipient unique et mélangées, par exemple, par agitation, avant l'administration de la composition sur la peau du patient. L'invention concerne en outre des procédés de traitement du prurit comprenant l'administration, à une personne qui en a besoin, d'une composition comprenant une quantité pharmaceutiquement efficace d'un cannabinoïde et d'au moins un ingrédient anesthésique.
PCT/IL2022/050223 2021-03-09 2022-03-01 Compositions biphasiques pour le traitement d'indications de la peau WO2022190082A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163158370P 2021-03-09 2021-03-09
US63/158,370 2021-03-09

Publications (1)

Publication Number Publication Date
WO2022190082A1 true WO2022190082A1 (fr) 2022-09-15

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150290267A1 (en) * 2013-09-26 2015-10-15 Ronald D. Sekura Topical treatments incorporating cannabis sp. derived botanical drug product
WO2020012480A1 (fr) * 2018-07-11 2020-01-16 Innocan Pharma Ltd. Compositions topiques soulageant la douleur
WO2020051047A2 (fr) * 2018-09-04 2020-03-12 Babak Ghalili Compositions et procédés faisant appel à des cannabinoïdes et à des anesthésiques
WO2020194308A1 (fr) * 2019-03-28 2020-10-01 Innocan Pharma Ltd. Compositions antiprurigineuses

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150290267A1 (en) * 2013-09-26 2015-10-15 Ronald D. Sekura Topical treatments incorporating cannabis sp. derived botanical drug product
WO2020012480A1 (fr) * 2018-07-11 2020-01-16 Innocan Pharma Ltd. Compositions topiques soulageant la douleur
WO2020051047A2 (fr) * 2018-09-04 2020-03-12 Babak Ghalili Compositions et procédés faisant appel à des cannabinoïdes et à des anesthésiques
WO2020194308A1 (fr) * 2019-03-28 2020-10-01 Innocan Pharma Ltd. Compositions antiprurigineuses

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "Caprylyl/Capryl glucoside", NATURALLYTHINKING (ONLINE SHOP), 21 January 2021 (2021-01-21), XP055964965, Retrieved from the Internet <URL:https://naturallythinking.com/caprylyl-capryl-glucoside#> *
BARRETT-HILL F.: "EMULSIFIERS IN SKIN CARE: PURPOSES, PROPERTIES & DISADVANTAGES", INTERNATIONAL ASSOCIATION FOR APPLIED CORNEOTHERAPY, 19 October 2015 (2015-10-19), XP055964964 *
DIETRICH KEPPLER: "Drug Transporters - Part of the Handbook of Experimental Pharmacology book series (HEP, volume 201) ISSN 0171-2004", vol. 226, 30 December 2015, SPRINGER VERLAG , BERLIN, DE , ISBN: 978-3-642-14540-7, ISSN: 0171-2004, article LESLIE TABI, GREAVES MALCOLM, YOSIPOVITCH GIL, COWAN ALAN: "Current topical and systemic therapies for itch", pages: 337 - 356, XP009539416, DOI: 10.1007/978-3-662-44605-8_18 *

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