WO2021261930A1 - 디쿠아포솔을 포함하는 점안 조성물 - Google Patents

디쿠아포솔을 포함하는 점안 조성물 Download PDF

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Publication number
WO2021261930A1
WO2021261930A1 PCT/KR2021/007922 KR2021007922W WO2021261930A1 WO 2021261930 A1 WO2021261930 A1 WO 2021261930A1 KR 2021007922 W KR2021007922 W KR 2021007922W WO 2021261930 A1 WO2021261930 A1 WO 2021261930A1
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Prior art keywords
composition
diquafosol
polysorbate
eye drop
ophthalmic composition
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Ceased
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PCT/KR2021/007922
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English (en)
French (fr)
Korean (ko)
Inventor
이준엽
류상록
한병현
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Taejoon Pharmaceutical Co Ltd
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Taejoon Pharmaceutical Co Ltd
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Priority to CN202180047268.9A priority Critical patent/CN115996705A/zh
Priority to JP2022575737A priority patent/JP7812807B2/ja
Publication of WO2021261930A1 publication Critical patent/WO2021261930A1/ko
Anticipated expiration legal-status Critical
Ceased 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • 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
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • 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
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P27/02—Ophthalmic agents
    • A61P27/04—Artificial tears; Irrigation solutions

Definitions

  • the present invention relates to an ophthalmic composition comprising diquafosol, and specifically to an ophthalmic composition comprising diquafosol, polysorbate and dexpanthenol.
  • Diquafosol is a P2Y 2 purine receptor agonist and is used in the treatment of dry eyes.
  • Diquas® is commercially available.
  • the eye drop is an eye drop administered 6 times a day containing diquafosol sodium at a concentration of 3 w/v%, and there is a disadvantage that the patient needs to administer the drug several times because of the large number of administration.
  • eye drops have disadvantages such as short residence time in the eye and low drug delivery rate due to their characteristics.
  • diquafosol it is important to effectively disperse in the water and mucus layers of the tear layer. It has low permeability to the lipid layer, so the absorption rate and durability are low. Therefore, it is necessary to develop a new eye drop that increases the drug delivery rate by increasing the permeability of the drug into the lipid layer.
  • the present invention provides an ophthalmic composition comprising diquafosol, polysorbate and dexpanthenol.
  • the present inventors completed the present invention by confirming that a composition containing diquafosol, polysorbate and dexpanthenol can improve the permeability of diquafosol as a result of earnest efforts to develop new eye drops with improved drug permeability. did
  • the present invention provides an ophthalmic composition
  • the eye drop composition may improve the permeability of daquafosol and exhibit a continuous dry eye treatment effect, thereby improving patient convenience.
  • Diquafosol (Diquafosol) refers to a compound represented by the following Chemical Formula 1, and is generally usefully used for the treatment of dry eye syndrome.
  • composition of the present invention includes diquafosol or a pharmaceutically acceptable salt thereof as an active ingredient, and specifically may include diquafosol sodium, but is not limited thereto.
  • diquafosol may refer to all of the compound represented by Formula 1 as well as pharmaceutically acceptable salts thereof.
  • the diquafosol or a pharmaceutically acceptable salt thereof may be contained in the eye drop composition in a therapeutically effective amount for the prevention, improvement or treatment of dry eye syndrome.
  • diquafosol or a pharmaceutically acceptable salt thereof may be included in an amount of 0.1 w/v% to 18 w/v% of the total eye drop composition, and more specifically, 2 w/v% to 18 w/v% , 1 w/v% to 10 w/v%, 4 w/v% to 10 w/v%, 4.5 w/v% to 10 w/v%, 3 w/v% to 6 w/v%, or In a content of 5 w/v% to 10 w/v%, more specifically, it may be included in a content of 4.5 w/v% to 5 w/v% or 5 w/v%, but is not limited thereto.
  • the diquafosol is 0.1 w/v% or more, 1 w/v% or more, 2 w/v% or more, 3 w/v% or more, more specifically 4 w/v% or more, more specifically, of the total eye drop composition As may be included in an amount of 4.5 w/v% or more or 5 w/v% or more.
  • the diquafosol may be included in an amount of 18 w/v% or less, 10 w/v% or less, or 6 w/v% or less of the total ophthalmic composition.
  • composition of the present invention can be usefully used for prevention, improvement or treatment of dry eye syndrome or related symptoms (eg, keratoconjunctival epithelial disorder), etc. .
  • dry eye syndrome or related symptoms eg, keratoconjunctival epithelial disorder
  • MMD obstructive meibomian gland dysfunction
  • the dry eye syndrome or symptoms related thereto may include symptoms such as dry eyes, eye discomfort, eye fatigue, dullness, and eye pain.
  • the eye drop composition of the present invention may be used for treating dry eye syndrome.
  • composition of the present invention comprises polysorbate.
  • the polysorbate may specifically be at least one selected from the group consisting of polysorbate 20, polysorbate 40, polysorbate 60 and polysorbate 80, and more specifically, polysorbate 20 or polysorbate It may be 80, but is not limited thereto.
  • the polysorbate may be included in an amount of 0.01 w/v% to 5 w/v% of the total ophthalmic composition, specifically 0.01 w/v% to 1 w/v%, 0.1 w/v% to 1 w/v% It may be included in a content of v%, 0.1 w/v% to 0.5 w/v%, or 0.2 w/v% to 0.3 w/v%, more specifically 0.2 w/v%, but is limited thereto no.
  • the polysorbate may be included in an amount of 0.01 w/v% or more, 0.1 w/v% or more, 0.2 w/v% or more, 0.3 w/v% or more of the total eye drop composition.
  • the polysorbate may be included in an amount of 5 w/v% or less, 1 w/v% or less, 0.5 w/v% or less, 0.3 w/v% or less, or 0.2 w/v% or less of the total ophthalmic composition.
  • Polysorbate may be included in the above content range to relieve irritation during instillation.
  • composition of the present invention comprises dexpantenol.
  • the dexpanthenol may be included in an amount of 0.001 w/v% to 1 w/v% of the total ophthalmic composition, specifically 0.001 w/v% to 0.1 w/v%, 0.001 w/v% to 0.05 w/v %, or in a content of 0.001 w/v% to 0.01 w/v%, more specifically, in a content of 0.01 w/v%, but is not limited thereto.
  • the dexpanthenol may be included in an amount of 0.001 w/v% or more and 0.01 w/v% or more of the total ophthalmic composition.
  • the dexpanthenol may be included in an amount of 1 w/v% or less, 0.1 w/v% or less, 0.05 w/v% or less, or 0.01 w/v% or less of the total ophthalmic composition.
  • composition of the present invention may further include at least one selected from the group consisting of polyvinyl alcohol (PVA), povidone (PVP) and polyethylene glycol (PEG).
  • PVA polyvinyl alcohol
  • PVP povidone
  • PEG polyethylene glycol
  • the components may be included for the viscosity of the composition, the stability of the composition, and the effect of delaying the release of the active ingredient.
  • the polyvinyl alcohol may be included in an amount of 0.01 w/v% to 1.8 w/v% of the total eye drop composition, specifically 0.03 w/v% to 1.4 w/v%, or 0.03 w/v% to 0.28 w As a content of /v%, more specifically, it may be included in a content of 0.1 w/v%, but is not limited thereto.
  • the povidone may be included in an amount of 0.01 w/v% to 4 w/v% of the total eye drop composition, specifically 0.01 w/v% to 1.8 w/v%, 0.04 w/v% to 0.6 w/v% Alternatively, it may be included in a content of 0.04 w/v% to 0.12 w/v%, more specifically, in a content of 0.12 w/v%, but is not limited thereto.
  • the polyethylene glycol may be included in an amount of 0.01 w/v% to 2 w/v% of the total eye drop composition, specifically 0.1 w/v% to 2 w/v%, or 1 w/v% to 2 w/v% As a content of v%, more specifically, it may be included in a content of 1 w/v%, but is not limited thereto.
  • composition of the present invention may further comprise Xanthan Gum.
  • the xanthan gum may be specifically included in an amount of 0.15 w/v% to 0.6 w/v% of the total ophthalmic composition, more specifically 0.2 w/v% to 0.4 w/v%, 0.2 w/v% to 0.25 w /v%, or in a content of 0.22 w/v% to 0.25 w/v%, more specifically, may be included in a content of 0.225 w/v% to 0.24 w/v%, but is not limited thereto.
  • composition of the present invention may further include an additive.
  • composition of the present invention may further include one or more additives selected from a pH adjusting agent, a buffering agent, a tonicity agent, a viscosity adjusting agent, a solubilizing agent, a stabilizer, and a preservative.
  • additives selected from a pH adjusting agent, a buffering agent, a tonicity agent, a viscosity adjusting agent, a solubilizing agent, a stabilizer, and a preservative.
  • pH adjusting agent sodium hydroxide, hydrochloric acid, etc. may be used, and a necessary amount may be added by a method known to those skilled in the art to obtain an appropriate pH.
  • the buffer includes acetic acid and/or salts thereof, citric acid and/or salts thereof, phosphoric acid and/or salts thereof (eg sodium hydrogen phosphate and/or hydrates thereof, sodium dihydrogen phosphate and/or hydrates thereof), boric acid And/or salts thereof may be used, and specifically, phosphate, citric acid and/or salts thereof, or mixtures thereof may be used, but the present invention is not limited thereto.
  • glycerol glycerol, mannitol, sorbitol, sodium chloride, potassium chloride, boric acid, and the like may be used.
  • alginic acid or a salt thereof, carbomer, bentonite, hydroxypropyl methyl cellulose, methyl cellulose, carboxymethyl cellulose, etc. may be used, and in order to obtain an appropriate viscosity, a required amount may be added by a method known to those skilled in the art.
  • the solubilizing agents include benzoalkonium chloride, sodium lauryl sulfate, sorbitan monopalmitate, nonoxynol 10, oxynol 9, tyloxapol, poloxamers, diethylene glycol monoethyl ether, polyethylene glycols, polyoxyl 15 hydrogenated stearic acid and the like can be used.
  • the stabilizer includes sodium edetate, aminocaproic acid, carnitine, vitamin E and/or derivatives (eg tocopherol acetate, etc.), sorbitol, ascorbic acid, hydroxypropyl methylcellulose, methylcellulose, carboxymethylcellulose, poloxamer, poly Propylene glycol, guar gum, carbomer, alginic acid and salts, gellan gum, carrageenan, chitosan and the like can be used.
  • the preservative includes quaternary ammonium compounds including benzalkonium chloride, benzethonium chloride, cetalkonium chloride, polyquaternium-1 (eg, polyquad) and the like; guanidine-based compounds including PHMB and chlorhexidine; chlorobutanol; mercury preservatives including thimerosal, phenylmercury acetate and phenylmercury nitrate; And a stabilized oxychloro complex (eg, furite), an oxidizing preservative including an alkyl para-hydroxy acid (eg, methyl para-hydroxy acid (PM), etc. may be used.
  • quaternary ammonium compounds including benzalkonium chloride, benzethonium chloride, cetalkonium chloride, polyquaternium-1 (eg, polyquad) and the like
  • guanidine-based compounds including PHMB and chlorhexidine
  • chlorobutanol mercury preservatives including thimeros
  • composition of the present invention can reduce the number of administration by improving the permeability of diquafosol.
  • composition of the present invention can improve transmittance while maintaining excellent eye drop.
  • composition of the present invention may be administered up to 4 times a day, specifically 3 times a day or less, 2 times a day or less, more specifically 2 to 4 times a day, even more specifically 3 times a day It may be administered in a circuit, but is not limited thereto.
  • composition of the present invention improves the transmittance of diquafosol ( FIGS. 1 to 3 ).
  • single administration may mean one instillation.
  • composition of the present invention can increase medication compliance by reducing the number of administration.
  • composition of the present invention exhibits physical and chemical properties (eg, viscosity, pH, osmotic pressure, etc.) suitable for application to eye tissue.
  • the viscosity of the composition of the present invention may be 1 mPa ⁇ s to 450 mPa ⁇ s when measured using a single cylindrical rotational viscometer and a spindle S61, and specifically, 10 mPa ⁇ s to 450 mPa ⁇ s, 20 mPa ⁇ s to 450 mPa ⁇ s, 10 mPa ⁇ s to 200 mPa ⁇ s, more specifically 20 mPa ⁇ s to 70 mPa ⁇ s, but is not limited thereto.
  • the pH of the composition of the present invention may be 5 to 9, specifically 6 to 8, but is not limited thereto.
  • the osmotic pressure of the composition of the present invention may be 250 mOsmol/kg to 500 mOsmol/kg, specifically, 270 mOsmol/kg to 330 mOsmol/kg, but is not limited thereto.
  • composition of the present invention is specially formulated for topical application, and may be administered topically by formulations such as solutions, emulsions, suspensions, gels, or ointments.
  • the present invention provides a method for preventing or treating dry eye, comprising administering the above-described eye drop composition to a subject.
  • the present invention provides a method for preventing or treating dry eye, comprising administering to a subject an eye drop composition comprising diquafosol or a pharmaceutically acceptable salt thereof, polysorbate and dexpanthenol.
  • the present invention also provides the use of the above-mentioned eye drop composition for the preparation of a medicament for the prevention or treatment of dry eye syndrome.
  • the present invention provides the use of an ophthalmic composition comprising diquafosol or a pharmaceutically acceptable salt thereof, polysorbate and dexpanthenol for the manufacture of a medicament for the prevention or treatment of dry eye syndrome.
  • the present invention also provides the use of the above-mentioned eye drop composition for the prevention or treatment of dry eye syndrome.
  • the present invention provides the use of an ophthalmic composition comprising diquafosol or a pharmaceutically acceptable salt thereof, polysorbate and dexpanthenol for the prevention or treatment of dry eye syndrome.
  • the "individual” may refer to all animals, including humans, who have been diagnosed with dry eye syndrome or are likely to be diagnosed with dry eye syndrome.
  • the animal may be a mammal, such as a cow, a horse, a sheep, a pig, a goat, a camel, an antelope, a dog, or a cat, in need of treatment for symptoms similar to those of a human as well as humans, but is not limited thereto.
  • the "administration" means introducing the eye drop composition of the present invention to a patient by any suitable method, and the route of administration of the present invention may be topical administration to the eye due to the nature of the composition as an eye drop.
  • the method for treating dry eye syndrome of the present invention includes administering the eye drop composition of the present invention in a therapeutically effective amount.
  • the composition of the present invention can be administered in a pharmaceutically effective amount.
  • the pharmaceutically effective amount means an amount sufficient to treat a disease with a reasonable benefit/risk ratio applicable to medical treatment and not to cause side effects, and the effective dose level is determined by the patient's health condition, disease type, severity, The activity of the drug, the sensitivity to the drug, the administration method, administration time, administration route and excretion rate, treatment period, factors including drugs used in combination or concurrently, and other factors well known in the medical field may be determined according to factors. Specifically, according to the judgment of the doctor or pharmacist, it may be administered in divided doses from once to several times a day at regular time intervals, and 0.01 ml to 0.1 ml may be administered per one administration, but is not limited thereto.
  • composition of the present invention has excellent eye drop, improves the permeability of diquafosol, exhibits a lasting effect, and improves medication compliance, so it can be usefully used for prevention or treatment of dry eye syndrome or related symptoms.
  • Example 1 is a graph showing the transmittance of diquafosol of Example 1, Example 2 and Comparative Example 1.
  • Example 2 is a graph showing the transmittance of diquafosol of Example 3 and Comparative Example 1.
  • Example 3 is a graph showing the transmittance of diquafosol of Example 4 and Comparative Example 2.
  • a composition was prepared according to the components and contents of Table 1 below. Diquafosol sodium, polysorbate 20 (Example 1 only), polysorbate 80 (Example 2 only), dexpanthenol (Examples 1 and 20 only), buffer, and sodium chloride were dissolved in sterile purified water, and then 0.2 The composition was prepared by filtration through a ⁇ m membrane filter. The pH of the prepared solution is about 7.2 ⁇ 0.2, and the osmotic pressure is 300 ⁇ 30 mOsmol/kg.
  • Examples 1, 2 and Comparative Example 1 were put in a semi-permeable membrane (Float A lyzer) and put into an eluator (SOTAXTM) containing a STF (Simulated Tear Fluid) solution to measure the release amount of the active ingredient using a liquid chromatogram. was used for evaluation.
  • SOTAXTM eluator
  • STF Simulated Tear Fluid
  • a composition was prepared according to the components and contents of Table 2 below. Diquafosol sodium, polysorbate 80 (Example 3 only), dexpanthenol (Example 3 only), buffer, and sodium chloride were dissolved in sterile purified water, and then filtered through a 0.2 ⁇ m membrane filter to prepare a composition.
  • the pH of the prepared solution is about 7.2 ⁇ 0.2, and the osmotic pressure is 300 ⁇ 30 mOsmol/kg.
  • Example 3 As shown in FIG. 2 , it can be seen that the transmittance of diquafosol was high in Example 3 containing polysorbate and dexpanthenol.
  • a composition was prepared according to the components and contents of Table 3 below. Specifically, polyvinyl alcohol, xanthan gum, and povidone were hydrated in sterile purified water at a high temperature (eg, 60 to 70 ° C. or higher), polyethylene glycol was dissolved, and then a solution was prepared by high-temperature and high-pressure sterilization. Dissolve diquafosol sodium, polysorbate 20 (Example 4 only), dexpanthenol (Example 4 only), buffer, and tonicity agent in sterile purified water, then filter through a 0.2 ⁇ m membrane filter, and mix with the solution prepared above to prepare a composition. The pH of the prepared solution is about 7.2 ⁇ 0.2.
  • Example 4 and Comparative Example 2 were put in a semi-permeable membrane (Float A lyzer) and put into an eluator (SOTAXTM) containing a STF (Simulated Tear Fluid) solution, and the release amount of the active ingredient over time was measured using a liquid chromatogram and evaluated.
  • SOTAXTM semi-permeable membrane
  • STF Simulated Tear Fluid
  • Example 4 exhibited excellent diquafosol transmittance.
  • composition of the present invention has improved diquafosol transmittance.

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PCT/KR2021/007922 2020-06-23 2021-06-23 디쿠아포솔을 포함하는 점안 조성물 Ceased WO2021261930A1 (ko)

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CN202180047268.9A CN115996705A (zh) 2020-06-23 2021-06-23 包含地夸磷索的眼用组合物
JP2022575737A JP7812807B2 (ja) 2020-06-23 2021-06-23 ジクアホソルを含む点眼組成物

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KR10-2020-0076574 2020-06-23
KR20200076574 2020-06-23

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CN115887356A (zh) * 2022-11-21 2023-04-04 山东诺明康药物研究院有限公司 一种地夸磷索钠离子敏感型凝胶剂及其制备方法

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