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WO2016157112A1 - Compositions de pulvérisation topiques de furoate de mométasone - Google Patents

Compositions de pulvérisation topiques de furoate de mométasone Download PDF

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Publication number
WO2016157112A1
WO2016157112A1 PCT/IB2016/051827 IB2016051827W WO2016157112A1 WO 2016157112 A1 WO2016157112 A1 WO 2016157112A1 IB 2016051827 W IB2016051827 W IB 2016051827W WO 2016157112 A1 WO2016157112 A1 WO 2016157112A1
Authority
WO
WIPO (PCT)
Prior art keywords
topical spray
composition
spray composition
mometasone furoate
aqueous
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/IB2016/051827
Other languages
English (en)
Inventor
Lalatendu Panigrahi
Alok Ranjan SAMAL
Uma Sowjanya Asapu
Sunil Kumar GHOSH
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.)
Dr Reddys Laboratories Ltd
Original Assignee
Dr Reddys Laboratories 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 Dr Reddys Laboratories Ltd filed Critical Dr Reddys Laboratories Ltd
Priority to CN201680029218.7A priority Critical patent/CN107613987A/zh
Priority to EA201792173A priority patent/EA201792173A1/ru
Publication of WO2016157112A1 publication Critical patent/WO2016157112A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K9/08—Solutions
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7015—Drug-containing film-forming compositions, e.g. spray-on

Definitions

  • the present invention relates to a rapid drying, non-aqueous topical spray composition of mometasone furoate. Methods of preparing such compositions are also provided.
  • Topical corticosteroids are a class of compounds that demonstrate anti-inflammatory, anti-pruritic and vasoconstrictive actions. They are generally used to relieve the redness, skin edema (swelling), itching, crusting, flaking, cracking, oozing, psoriasis, atopic dermatitis (atopic eczema) and other pathologies of the skin like contact dermatitis, seborrheic dermatitis, eczema, dermatitis herpetiformis, neurodermatitis or autoeczematization.
  • Mometasone furoate is a synthetic corticosteroid with anti-inflammatory activity.
  • the chemical name of mometasone furoate is 9a, 21 -dichloro-1 1 ⁇ , 17-dihydroxy-16a- methylpregna-1 ,4-diene-3,20-dione 17-(2-furoate), with the empirical formula C27H30CI2O6, a molecular weight of 521 .4 and following structural formula:
  • Mometasone furoate is a white to off-white powder practically insoluble in water, slightly soluble in octanol, and moderately soluble in ethyl alcohol. Mometasone furoate is commercially available as various topical dosage forms such as cream, ointment and lotion. It is marketed under the brand name ELOCON ® and indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid- responsive dermatoses in patients 2 years of age or older.
  • US4775529 discloses topical lotion compositions containing corticosteroids in a hydro- alcoholic base containing propylene glycol.
  • US4808610 discloses topical cream compositions comprising mometasone furoate, hexylene glycol, water, white wax, white petrolatum and other ingredients.
  • EP1886686 (B1 ) discloses topical pharmaceutical compositions comprising mometasone furoate, water and a combination of at least an aromatic alcohol and at least a solvent selected from two different groups, and optionally further additives.
  • the compositions include solution, microemulsion, gel, lotion, cream or ointment.
  • EP2575822 discloses topical pharmaceutical compositions comprising mometasone furoate, hexylene glycol, water, and oil phase.
  • the composition is preferably formulated in the form of a cream.
  • topical corticosteroids in the form of cream and ointment are greasy, and hence are unpleasant to apply on large areas of the skin.
  • some conventional cream and ointment bases are irritating to the skin, particularly over the long exposure that is frequently required for efficacy, and the fluidity of lotions often makes the physical application difficult to control over a desired area.
  • Several commercially available topical formulations are primarily incapable of providing the much needed soothing effect to the affected areas, particularly in conditions such as psoriasis and other skin disorders. Such formulations do not promote patient compliance. Therefore, a spray composition, which increases the ease of use for the patient is often preferred.
  • WO2000045795 discloses a topical medicinal spray composition
  • a topical medicinal spray composition comprising one or more medicaments in a volatile vehicle, and one or more film-forming polymers. When sprayed on to a topical site, the composition forms a stable, breathable film from which the medicaments are transdermal ⁇ available.
  • WO201 1026076 discloses a propellant free sprayable topical composition comprising steroids, emulsifying agents, polymer, water, water immiscible substance and penetration enhancer.
  • compositions which are stable, provide occlusive film, provide longer duration of action, have improved patient compliance, and exhibit efficacy comparable to mometasone furoate compositions currently available in the market.
  • the compositions of the present invention provide rapid drying after application on to the skin. Such compositions are effective in the treatment of psoriasis, atopic dermatitis (atopic eczema) and other skin disorders or diseases.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition of mometasone furoate and its process for preparation.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising: (i) mometasone furoate,
  • composition forms a stable occlusive film.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification provides a stable, rapid drying, nonaqueous topical spray composition of mometasone furoate.
  • the present specification relates to use of rapid drying, nonaqueous topical spray composition of mometasone furoate for the treatment of psoriasis, atopic dermatitis (atopic eczema) and other skin disorders or diseases.
  • Figure: 1 Comparative pharmacokinetic study between the present invention (Example 2) and commercially available ELOCON ® ointment.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition of mometasone furoate and its process for preparation.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • composition forms a stable occlusive film.
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the present specification relates to a rapid drying, non-aqueous topical spray composition
  • a rapid drying, non-aqueous topical spray composition comprising:
  • the term "rapid drying” means that the composition dries rapidly after application on to the skin.
  • the topical spray compositions have a drying time of less than ten minutes, preferably less than five minutes, e.g. less than two minutes.
  • non-aqueous means that the composition is substantially free of water.
  • the composition being substantially free of water means that: the composition is free of water; or, if the composition contains water, the level of water is very low.
  • the level of water, if included, is 5 % or less, preferably 3 % or less, more preferably 2 % or less, still more preferably 1 % or less, even more preferably 0.5% by weight of the composition.
  • mometasone includes mometasone or any pharmaceutically acceptable salts or esters or derivatives thereof, e.g. mometasone furoate.
  • the amount of mometasone furoate employed in the composition is in the range of 0.01 % to 5% (w/w), 0.01 % to 1 % (w/w) of total composition, e.g. 0.1 % (w/w).
  • solubilizers refer to components that help in solubilization of mometasone furoate.
  • Suitable solubilizers include hexylene glycol, propylene glycol, polyethylene glycol or mixtures thereof.
  • Preferred solubilizers include hexylene glycol.
  • the amount of solubilizers employed in the composition is in the range of 1 % to 20% (w/w) of total composition, e.g. 3% (w/w), 5% (w/w).
  • solvents refer to components that aid in the dissolution of the drug in the formulation. The solvents are typically volatile in nature.
  • Suitable volatile solvents may be selected from non-aqueous solvents.
  • the volatile non-aqueous solvents may be selected from ethanol, ethyl acetate, isopropyl alcohol, acetone, ethyl formate, methyl acetate, methyl ethyl ketone, cyclomethicone, dimethiconol, hexamethyldisiloxane or mixtures thereof.
  • the amount of solvents employed in the composition is in the range of 50% to 99% (w/w) of total composition, e.g. more than 70%, 75% or 80%.
  • the topical spray compositions of the present specification may further comprise co- solvents.
  • the co-solvents are added to improve the solubilization of mometasone furoate in the volatile solvents.
  • Suitable co-solvents include alkyl benzoates, benzyl alcohol, isopropyl palmitate, isopropyl myristate, diisopropyl adipate, diethylene glycol monoethyl ether, N-methyl pyrrolidone, or mixtures thereof.
  • the amount of co-solvents employed in the composition is in the range of 1 % to 20% (w/w) of total composition, e.g. 3% (w/w), 5% (w/w).
  • film former refers to a substance that provides a smooth uniform thin occlusive film after evaporation of solvents. The film firmly adheres to the skin and thereby is able to retain on the skin for a suitable period of time.
  • the film formers include but are not limited to acrylic polymers or copolymers, including methacrylic polymers and copolymers such as non-ionic copolymer of methyl methacrylate and butyl methacrylate (Plastoid® B), a copolymer of dimethylamine ethyl methacrylate and a neutral methacrylic acid ester (Eudragit® E100), ammonio methacrylate copolymer type B (Eudragit® RS), ammonio methacrylate copolymer type A (Eudragit® RL), methacrylic acid copolymer type A (Eudragit® LlOO), methacrylic acid copolymer type B (Eudragit® S100), Acrylates / Octylacrylamide copolymer (Dermacryl ® ), urethanes polymers or copolymers, polyvinyl acetate, polyvinyl alcohol, povidone, alkylated polyvinylpyrroli
  • the amount of film former employed in the composition is in the range of 1 % to 15% (w/w), 1 % to 10% (w/w), 1 % to 5% (w/w) of total composition, e.g. 2% (w/w), 5% (w/w).
  • emollient refers to a substance that softens and soothes the skin. Emollients are used to correct dryness, scaling of the skin and also provide an occlusive barrier. Suitable emollients include, for example, stearyl alcohol, glyceryl monooleate, glyceryl monoricinoleate, glyceryl monostearate, cetyl alcohol, ispropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, cetyl palmitate, dimethylpolysiloxane, di-n-butyl sebacate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol,
  • the amount of emollient employed in the composition is in the range of 1 % to 20% (w/w), 1 % to 10% (w/w), 5% to 15% (w/w), e.g. 5% (w/w), or 10 % (w/w).
  • the topical spray compositions of the present specification may include an acidifying agent.
  • Various useful acidifying agents include but are not limited to citric acid, citric acid anhydrous, citric acid monohydrate, DL-lactic acid, DL-malic acid, DL-tartaric acid, fumaric acid, L-malic acid, L-tartaric acid, salicylic acid, glycol acid, potassium acid tartrate, potassium citrate, potassium DL-bitartarate, potassium gluconate, sodium lactate, sodium L-tartrate, sodium citrate, ascorbic acid, and mixtures thereof.
  • the topical spray compositions of the present specification may include one or more antioxidants.
  • the antioxidant may be selected from DL-alpha-tocopherol, butylhydroxy toluene (BHT), butylhydroxy anisole (BHA), ascorbyl palmitate, ascorbic acid, propyl gallate, or mixtures thereof.
  • the amount of antioxidant employed in the composition is in the range of 0.01 to about 0.5% (w/w) of total composition, e.g. 0.07% (w/w), or 0.09% (w/w).
  • the topical spray compositions of the present specification may contain additional ingredients to improve the composition. Such ingredients include plasticizers, surfactants, penetration enhancers, humectants, coloring agents, chelating agents. Examples of such ingredients are well known in the art.
  • topical spray compositions of present specification may be prepared by any suitable conventional process.
  • the topical spray compositions may be prepared by the process steps comprising dissolving mometasone furoate in solubilizers and adding the resulting mixture to one or more non-aqueous volatile solvents. Subsequently, the film formers, emollients, other excipients are added sequentially and mixed well until clear solution is formed.
  • the topical spray compositions of present specification may be applied onto the skin by using a sprayable dispensing device.
  • the dispensing device provides either a fixed or variable metered dose application such as a stored-energy metered dose pump or a manual metered dose pump.
  • the topical spray compositions of present specification form a stable occlusive film onto the skin after drying.
  • the occlusive film is resistant to water and it does not get washed off easily and is retained on the skin for longer duration.
  • the film can be removed easily by rubbing with a cotton plug after use.
  • topical spray compositions of present specification may be used for the treatment or prevention of psoriasis or atopic dermatitis (atopic eczema) and other skin disorders or diseases.
  • the psoriasis could be chronic plaque psoriasis or palmoplantar psoriasis.
  • Mometasone furoate was dissolved in hexylene glycol and the mixture was added to isopropyl myristate and ethanol mixture.
  • Ammonio methacrylate copolymer type B and ammonio methacrylate copolymer type A were added to the solution prepared in step 1 and stirred well until clear solution was formed.
  • Mometasone furoate was dissolved in hexylene glycol and the mixture was added to isopropyl alcohol and isopropyl myristate mixture.
  • Mometasone furoate was dissolved in hexylene glycol and the mixture was added to isopropyl alcohol and isopropyl myristate mixture.
  • Mometasone furoate was dissolved in hexylene glycol and the mixture was added to isopropyl alcohol and isopropyl myristate mixture.
  • compositions of present specification were evaluated through accelerated stability studies. Two compositions were prepared according to the formula and process of example 3 and 6, and the compositions were subjected to stability study at various temperature and humidity conditions. The compositions were found to be stable at accelerated conditions. Table 2 represents the study result data. Table 2:
  • compositions prepared in accordance with Example 2 and 3 were evaluated in a double blinded, non-comparative, multicentric study on palmoplantar psoriasis subjects. Total 30 subjects (includingl 9 males and 1 1 females), aged between 18 and 65 years, having mild to moderate psoriasis on both palms were included. The compositions were applied by spraying at an approximate distance 10 to 15 cm, 3-4 times on each palm uniformly. Safety of the compositions were assessed by the dermatologist, through the grading on the both palms of defined clinical signs (observed by the dermatologist) and functional signs (felt by the subjects and reported to the dermatologist), at TO, T immediate after product application, T+15 to 20 minutes after product application.
  • Table 1 represents the physical characteristics of spray compositions and Table 2 represents the study assessment protocol and Observation by dermatologists. The compositions were dried within 2-3 minutes and formed smooth uniform film. No increase in the clinical and functional signs from baseline (TO) is observed 15-20 minutes after product application. Table 1 :
  • Table 2 occurrence of oedema and tingling was recorded by the dermatologist for the test site, on average, on the whole panel.
  • a 0.1 % mometasone furoate topical spray composition is prepared in accordance with Example 2.
  • the composition is applied by spraying on to the skin of male rat.
  • a commercial 0.1 % mometasone furoate topical ointment product, ELOCON ® ointment is applied in same manner and concentration similar to the spray composition.
  • the rat skin is collected at 2 hours and 8 hours after application and the amount of mometasone is measured in the skin for both groups.
  • Pharmacokinetic analyses indicate that mean mometasone concentration in the skin is superior in spray composition prepared in accordance with Example 2 as compared to the commercially available ELOCON ® ointment ( Figure 1 ).

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention se rapporte à des compositions topiques non aqueuses, à séchage rapide et stables de furoate de mométasone sous la forme de pulvérisation, la composition comprenant un ou plusieurs agents de solubilisation, un ou plusieurs solvants volatils non aqueux et des émollients ou agents filmogènes. L'invention porte également sur des procédés de préparation de telles compositions. La présente invention concerne en outre l'utilisation de compositions de pulvérisation topiques de furoate de mométasone pour le traitement du psoriasis, de la dermite atopique (eczéma atopique) et d'autres troubles ou maladies de la peau.
PCT/IB2016/051827 2015-03-31 2016-03-31 Compositions de pulvérisation topiques de furoate de mométasone Ceased WO2016157112A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201680029218.7A CN107613987A (zh) 2015-03-31 2016-03-31 糠酸莫米松的局部喷雾组合物
EA201792173A EA201792173A1 (ru) 2015-03-31 2016-03-31 Композиции спрея фуроата мометазона для местного применения

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1670CH2015 2015-03-31
IN1670/CHE/2015 2015-03-31

Publications (1)

Publication Number Publication Date
WO2016157112A1 true WO2016157112A1 (fr) 2016-10-06

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PCT/IB2016/051827 Ceased WO2016157112A1 (fr) 2015-03-31 2016-03-31 Compositions de pulvérisation topiques de furoate de mométasone

Country Status (3)

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CN (1) CN107613987A (fr)
EA (1) EA201792173A1 (fr)
WO (1) WO2016157112A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019224035A1 (fr) * 2018-05-24 2019-11-28 Almirall, S.A. Compositions pharmaceutiques topiques comprenant un corticostéroïde
EP4108234A1 (fr) * 2021-06-25 2022-12-28 RaDes GmbH Formulation pharmaceutique topique
WO2025034936A3 (fr) * 2023-08-09 2025-04-03 Virpax Pharmaceuticals, Inc. Formulation et procédé de pulvérisation d'ains

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000045795A2 (fr) * 1999-02-05 2000-08-10 Cipla Limited Sprays topiques
US6231875B1 (en) * 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011026076A2 (fr) * 2009-08-31 2011-03-03 Dr. Reddy's Laboratories Ltd. Compositions topiques contenant un stéroïde

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6231875B1 (en) * 1998-03-31 2001-05-15 Johnson & Johnson Consumer Companies, Inc. Acidified composition for topical treatment of nail and skin conditions
WO2000045795A2 (fr) * 1999-02-05 2000-08-10 Cipla Limited Sprays topiques

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019224035A1 (fr) * 2018-05-24 2019-11-28 Almirall, S.A. Compositions pharmaceutiques topiques comprenant un corticostéroïde
EP4108234A1 (fr) * 2021-06-25 2022-12-28 RaDes GmbH Formulation pharmaceutique topique
EP4108235A1 (fr) * 2021-06-25 2022-12-28 RaDes GmbH Formulation pharmaceutique topique
US12447161B2 (en) 2021-06-25 2025-10-21 Rades Gmbh Topical pharmaceutical formulation
WO2025034936A3 (fr) * 2023-08-09 2025-04-03 Virpax Pharmaceuticals, Inc. Formulation et procédé de pulvérisation d'ains

Also Published As

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EA201792173A1 (ru) 2018-04-30
CN107613987A (zh) 2018-01-19

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