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WO2024142116A1 - Composition pharmaceutique stable contre l'otite externe - Google Patents

Composition pharmaceutique stable contre l'otite externe Download PDF

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Publication number
WO2024142116A1
WO2024142116A1 PCT/IN2023/051247 IN2023051247W WO2024142116A1 WO 2024142116 A1 WO2024142116 A1 WO 2024142116A1 IN 2023051247 W IN2023051247 W IN 2023051247W WO 2024142116 A1 WO2024142116 A1 WO 2024142116A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
density polyethylene
present
stored
stable
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/IN2023/051247
Other languages
English (en)
Inventor
Yashwant GUPTA
Sukhjeet Singh
Deepak Bahri
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.)
Sentiss Pharma Pvt Ltd
Original Assignee
Sentiss Pharma Pvt 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 Sentiss Pharma Pvt Ltd filed Critical Sentiss Pharma Pvt Ltd
Priority to AU2023420407A priority Critical patent/AU2023420407A1/en
Publication of WO2024142116A1 publication Critical patent/WO2024142116A1/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
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • 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
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • 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
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
    • A61K9/0046—Ear
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals

Definitions

  • the present invention is related to a pharmaceutical composition comprising fluoroquinolone antibiotic, corticosteroid along with one or more pharmaceutically acceptable excipients, which is stable when stored in high-density polyethylene container
  • the said composition is useful for the treatment of otitis externa.
  • the present invention is also related to a method of increasing the stability of pharmaceutical composition by packaging the pharmaceutical composition in high- density polyethylene container.
  • a pharmaceutical composition is considered unstable when the potency of the active ingredient(s) is lost.
  • the potency of a drug product may decline over time during storage due to various reasons, such as degradation of the active ingredient(s), reaction of the active ingredient(s) with excipients or container materials, leaching of the active ingredient(s) through the container wall, and absorption/adsorption of the active ingredient(s) into/to the container wall.
  • the purity of a medicinal preparation may also change during storage due to leaching of chemicals into the drug preparation from the container materials, from the labels on the containers, or from the environment where the packaged medicinal product is stored.
  • the solvent of the composition may also permeate the container wall, which will increase the concentration of the active ingredient and of the other components of the composition.
  • Preservatives may also permeate the container wall and as a result, their preservative value is diminished, and the medicinal preparation may no longer meet preservative specifications.
  • the containers used for packaging medicinal preparations can significantly affect the stability and purity of the preparations contained therein.
  • Containers commonly used for medicinal products include glass containers, polyolefin containers such as polypropylene containers, polyethylene containers and polyethylene terephthalates (PET) containers.
  • PET polyethylene terephthalates
  • glass containers are also not preferred due to the disadvantages associated with them.
  • CIPRO® HC which contains ciprofloxacin hydrochloride and hydrocortisone. It is indicated for the treatment of acute otitis externa in adult and pediatric patients, one year and older, due to susceptible strains of Pseudomonas aeruginosa, Staphylococcus aureus, and Proteus mirabilis.
  • Ciprofloxacin hydrochloride 0.1 to 0.5 wt% of Ciprofloxacin hydrochloride
  • Hydrocortisone 0.1 to 2 wt% of Hydrocortisone; and one or more pharmaceutically acceptable excipients.
  • Another aspect of the present invention provides stable pharmaceutical composition comprising fluoroquinolone antibiotic, corticosteroid and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition exhibits reduced sorption of preservative when stored in high-density polyethylene container.
  • Yet another aspect of the present invention provides stable pharmaceutical composition wherein the pharmaceutical composition exhibits reduced sorption of preservative when stored in high- density polyethylene container as compared to when stored in low-density polyethylene container.
  • Yet another aspect of the present invention provides stable pharmaceutical composition
  • pharmaceutical composition comprising ciprofloxacin hydrochloride, hydrocortisone and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition is stored for at least 3 months at a temperature of 40°C and relative humidity not more than 25%.
  • Yet another aspect of the present invention provides stable pharmaceutical composition comprising ciprofloxacin hydrochloride, hydrocortisone and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition is stored for at least 6 months at a temperature of 40°C and relative humidity not more than 25%.
  • Yet another aspect of the present invention provides a stable pharmaceutical composition comprising ciprofloxacin hydrochloride, hydrocortisone and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition exhibits less than 30% sorption of preservative when stored in high-density polyethylene container for at least 6 months at a temperature of 40°C and relative humidity not more than 25%.
  • Yet another aspect of the present invention provides a stable pharmaceutical composition comprising:
  • Ciprofloxacin hydrochloride 0.1 to 0.5 wt% of Ciprofloxacin hydrochloride
  • Hydrocortisone 0.1 to 2 wt% of Hydrocortisone; and one or more pharmaceutically acceptable excipients wherein the pharmaceutical composition exhibits less than 20% sorption of preservative when stored in high-density polyethylene container for 3 months at a temperature of 40 °C and relative humidity not more than 25%.
  • Ciprofloxacin hydrochloride 0.1 to 0.5 wt% of Ciprofloxacin hydrochloride
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition
  • the suitable polymers include, but are not limited to natural and synthetic polymers, polysaccharides, gums, cellulose derivatives, dextran, hyaluronate, polyvinyl alcohol, polyvinyl pyrrolidone, hydroxypropyl methyl cellulose, hydroxyethyl cellulose, carbopol, polycarbophil, polystyrene sulfonate and/or combinations thereof.
  • composition comprises one or more solvents or co-solvents.
  • the pharmaceutically acceptable solvents may be selected from a group of purified water, alcohols, such as alcohols having 2 or 3 hydroxyl groups, ethanol, and glycols such as ethylene glycol, propylene glycol, polyethylene glycol, glycofurol and the like.
  • Polysorbate, acetic acid, sodium acetate, and/or sodium hydroxide or hydrochloric acid Polysorbate, acetic acid, sodium acetate, and/or sodium hydroxide or hydrochloric acid.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the pharmaceutical composition is packed in polyolefin container.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the pharmaceutical composition exhibits reduced sorption of preservative when stored in high-density polyethylene container as compared to when stored in low-density polyethylene container.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the pharmaceutical composition of the present invention is stable when stored for at least 3 months at a temperature of 40°C and relative humidity of not more than 25%.
  • the pharmaceutical composition of the present invention is stable when stored for at least 6 months at a temperature of 40°C and relative humidity not more than 25%.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the pharmaceutical composition of the present invention exhibits reduced sorption of preservative when stored in high-density polyethylene container as compared to when stored in low-density polyethylene container.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the pharmaceutical composition exhibits less than 20% sorption of preservative when stored in high-density polyethylene container for 3 months at a temperature of 40 °C and relative humidity not more than 25%.
  • the pharmaceutical composition exhibits less than 20% sorption of preservative when stored in high-density polyethylene container.
  • the pharmaceutical composition exhibits less than 10% sorption of preservative when stored in high-density polyethylene container.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition, wherein the composition is used for the treatment of diseases like otitis externa.
  • the pharmaceutical composition as per the present invention is used for otic administration to treat otitis externa.
  • Yet another aspect of the present invention provides a stable pharmaceutical composition comprising:
  • Hydrocortisone and one or more pharmaceutically acceptable excipients wherein the pharmaceutical composition exhibits less than 20% sorption of preservative when stored in high-density polyethylene container for 3 months at a temperature of 40 °C and relative humidity not more than 25%.
  • Yet another aspect of the present invention provides a stable pharmaceutical composition comprising:
  • Ciprofloxacin hydrochloride 0.1 to 0.5 wt% of Ciprofloxacin hydrochloride
  • composition 0.1 to 2 wt% of Hydrocortisone; and one or more pharmaceutically acceptable excipients wherein the pharmaceutical composition exhibits less than 20% sorption of preservative when stored in high-density polyethylene container for 3 months at a temperature of 40 °C and relative humidity not more than 25%.
  • a stable pharmaceutical composition comprising:
  • Hydrocortisone and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition exhibits less than 30% sorption of preservative when stored in high-density polyethylene container for 6 months at a temperature of 40 °C and relative humidity not more than 25%.
  • Ciprofloxacin hydrochloride 0.1 to 0.5 wt% of Ciprofloxacin hydrochloride
  • Hydrocortisone 0.1 to 2 wt% of Hydrocortisone; and one or more pharmaceutically acceptable excipients, wherein the pharmaceutical composition exhibits less than 30% sorption of preservative when stored in high-density polyethylene container for 6 months at a temperature of 40 °C and relative humidity not more than 25%.
  • Yet another embodiment of the present invention provides a method of increasing the stability of pharmaceutical composition comprising ciprofloxacin hydrochloride, hydrocortisone and pharmaceutically acceptable excipients wherein the method comprises packaging the pharmaceutical composition in high-density polyethylene container.
  • Yet another embodiment of the present invention provides a stable pharmaceutical composition which is used for the treatment of diseases like otitis externa.
  • Yet another embodiment of the present invention provides a method of increasing the stability of pharmaceutical composition which is used for the treatment of diseases like otitis externa. While the present invention is disclosed generally above, additional aspects are further discussed and illustrated with reference to the examples below. However, the examples are presented merely to illustrate the invention and should not be considered as limitations thereto.
  • Example 1 A stable pharmaceutical composition comprising the components thereof is provided in Table 1 below.
  • Table 1 A stable pharmaceutical composition of the present invention.
  • composition of the present invention is synthesized by the following method.

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

Abstract

La présente invention concerne une composition pharmaceutique comprenant un antibiotique fluoroquinolone, un corticostéroïde conjointement avec au moins un excipient acceptable sur le plan pharmaceutique. La présente invention concerne également la composition pharmaceutique qui présente une sorption réduite de conservateur lorsqu'elle est stockée dans un récipient en polyéthylène haute densité par rapport à un stockage dans un récipient en polyéthylène basse densité. La présente invention concerne en outre un procédé destiné à augmenter la stabilité de la composition pharmaceutique, ce procédé consistant à mettre sous emballage la composition pharmaceutique dans un récipient en polyéthylène haute densité. La présente invention est utilisée dans le traitement de maladies telles que l'otite externe.
PCT/IN2023/051247 2022-12-29 2023-12-29 Composition pharmaceutique stable contre l'otite externe Ceased WO2024142116A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2023420407A AU2023420407A1 (en) 2022-12-29 2023-12-29 Stable pharmaceutical composition for otitis externa

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN202211076860 2022-12-29
IN202211076860 2022-12-29

Publications (1)

Publication Number Publication Date
WO2024142116A1 true WO2024142116A1 (fr) 2024-07-04

Family

ID=91716882

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2023/051247 Ceased WO2024142116A1 (fr) 2022-12-29 2023-12-29 Composition pharmaceutique stable contre l'otite externe

Country Status (2)

Country Link
AU (1) AU2023420407A1 (fr)
WO (1) WO2024142116A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843930A (en) * 1995-06-06 1998-12-01 Bayer Corporation Method of treating otitis with ciprofloxacin-hydrocortisone suspension
US20020037884A1 (en) * 2000-07-26 2002-03-28 Alcon Universal Ltd. Topical composition comprising ciprofloxacin and hydrocortisone
US20020037883A1 (en) * 2000-07-26 2002-03-28 Alcon Universal Ltd. Process for manufacturing compositions containinig ciprofloxacin and hydrocortisone

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843930A (en) * 1995-06-06 1998-12-01 Bayer Corporation Method of treating otitis with ciprofloxacin-hydrocortisone suspension
US20020037884A1 (en) * 2000-07-26 2002-03-28 Alcon Universal Ltd. Topical composition comprising ciprofloxacin and hydrocortisone
US20020037883A1 (en) * 2000-07-26 2002-03-28 Alcon Universal Ltd. Process for manufacturing compositions containinig ciprofloxacin and hydrocortisone

Also Published As

Publication number Publication date
AU2023420407A1 (en) 2025-07-31

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