WO2022201032A1 - Collyre ophtalmique triple - Google Patents

Collyre ophtalmique triple Download PDF

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Publication number
WO2022201032A1
WO2022201032A1 PCT/IB2022/052617 IB2022052617W WO2022201032A1 WO 2022201032 A1 WO2022201032 A1 WO 2022201032A1 IB 2022052617 W IB2022052617 W IB 2022052617W WO 2022201032 A1 WO2022201032 A1 WO 2022201032A1
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WO
WIPO (PCT)
Prior art keywords
present
acid
pharmaceutical composition
oil
composition
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Application number
PCT/IB2022/052617
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English (en)
Inventor
Ana Cecilia GONZÁLEZ VILLEGAS
Luis Alberto HERRERA MENDOZA
Jesus RIVERA HERNÁNDEZ
Original Assignee
Laboratorios Grin S. A. De C. V.
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.)
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Application filed by Laboratorios Grin S. A. De C. V. filed Critical Laboratorios Grin S. A. De C. V.
Publication of WO2022201032A1 publication Critical patent/WO2022201032A1/fr

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Classifications

    • 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
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • 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
    • A61K47/26—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
    • A61K47/36—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
    • 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
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin

Definitions

  • the invention relates to an ophthalmic composition that can be used in the treatment of dry eye disease, providing the 3 types of components that the natural tear contains: lipid component, aqueous component and mucoid component.
  • the ocular surface, tear film, lacrimal glands, and eyelids act as a functional unit to preserve the quality of the refractive surface of the eye and to resist injury and protect the eye against changing bodily and environmental conditions.
  • the tear film is the most dynamic structure of the functional unit, and is essential for maintaining the health of the ocular surface.
  • the tear film is reported to be composed of three layers: the mucin or mucous layer, aqueous layer, and lipid layer.
  • the mucin or mucous layer is the innermost and is the one in continuous contact with the cornea.
  • the aqueous layer is the middle layer and is what is made mainly by the tear gland.
  • the lipid layer is the outermost and is produced by the Meibomian glands. A dysfunction of any of these layers can result in dry eye disease.
  • Dry eye disorder e.g., dry eye syndrome
  • dry eye syndrome is a common eye disease. It is the condition of having dry eyes. Some common symptoms of dry eye disorders include e.g., irritation, redness, discharge, inflammation, easily fatigued eyes, and blurred vision. In some severe cases, scarring of the cornea may occur. An option for the treatment of dry eye disease is artificial tears.
  • the invention relates to an ophthalmic composition that can be used in the treatment of dry eye disease, providing the 3 types of components that the natural tear contains: lipid component, aqueous component and mucoid component.
  • the objective of present invention is to provide an ophthalmic composition that helps in a) Improvement in the aqueous part through its hydration properties. b) Improvement in the lipid layer that prevents aqueous evaporation and improves hyperosmolarity. c) Improvement in the mucidic part that is damaged by loss of microvilli and glycocalyx. d) Avoid possible corneal deposits with chronic use because it does not contain phosphates (free of phosphates). e) Avoid damage or death of corneal epithelial cells with chronic use because it does not contain a preservative (preservative free).
  • This invention relates to a pharmaceutical nano-emulsion ophthalmic compositions comprising biopolysaccharide, sodium hyaluronate and omega fatty acid and process of preparing the same.
  • This disclosure is related to compositions and methods for treating dry dye disorders.
  • the present disclosure provides methods of treating or alleviating symptoms of a dry eye disorder, asthenopia, impaired vision, blurred vision, photophobia, astigmatism, and/or blepharitis.
  • the methods involve identifying a subject having the dry eye disorder, asthenopia, impaired vision, blurred vision, photophobia, astigmatism, and/or blepharitis; and administering to the subject in need thereof an effective amount of a pharmaceutical composition comprising arabinogalactan, hyaluronate and omega fatty acid alone and/or in combination with other ingredients.
  • the present invention relates to use of components proposed to meet the attributes regarding hydration, mucidic-adhesive component and lipidic part that it has also anti-inflammatory properties: a) Hydration: Sodium hyaluronate. b) Mucidic/Adhesion: biopolysaccharides, preferentially arabinogalactan or xanthan gum. c) Lipidic and Anti-inflammatory: Omega fatty acid like polyunsaturated omega-3 fatty acids, polyunsaturated omega-6 fatty acids, and mono- and / or polyunsaturated omega-9 fatty acids, preferentially oleic acid.
  • the invention relates to a pharmaceutical nano-emulsion ophthalmic composition
  • a pharmaceutical nano-emulsion ophthalmic composition comprising biopolysaccharides; a hyaluronic acid or a salt thereof; and omega fatty acids and process of preparing the same.
  • the invention further relates to a pharmaceutical nano-emulsion ophthalmic compositions comprising biopolysaccharides; a hyaluronic acid or a salt thereof; and omega fatty acids optionally in combination with other inactive ingredients and process of preparing the same.
  • the present invention is described with respect to biopolysaccharides; a hyaluronic acid or a salt thereof; and omega fatty acids, the invention is not limited thereto.
  • the present invention can further comprise active ingredients selected from the group of corticosteroid, anti inflammatory agent, beta-adrenergic receptor agonist, beta-blocker, prostaglandin, carbonic anhydrase inhibitor, alpha 2 adrenergic receptor agonist, antibiotic, antibacterial, antihistaminic/ mast cell stabilizer alone or in combinations thereof.
  • biopolysaccharides that can be used are like but not limited to natural or semisynthetic polymers such as xanthan gum, arabinogalctan, gelatin, acacia gum, and tragacanth gum.
  • Arabinogalactan (AG) is a polysaccharide abundant in most plants but it is usually obtained from the bark of the Larch trees (Larix occidentalis, L. decidua) of Larix species.
  • Xanthan gum is an anionic polysaccharide that is obtained by fermentation process of the Xanthomonas Campestris bacteria. Its mucoadhesion property and ability to improve ocular bioavailability has already been examined.
  • biopolysaccharides are used to impart their mucoadhesive property that would be adequate to achieve a longer contact time between the drop of the solution and the surface of the cornea, where the microvilli of the mucidic layer are found.
  • biopolysaccharides used are xanthan gum or arbinogalactan.
  • bio-polysaccharides used in the pharmaceutical ophthalmic compositions according to the present invention are in the range of about 0.02% to 5% w/v of composition; preferably 0.01, 0.5, 0.75, 1, 2, 3, 4 or 5% w/v of composition or intermediate fraction thereof.
  • arabinogalactan is present in the concentration of 0.5 % w/v.
  • the concentration of arabinogalactan or xanthan gum in the pharmaceutical ophthalmic composition is in the range of about 0.02% to 5% w/v of composition; preferably 0.01, 0.5, 0.75, 1, 2, 3, 4 or 5% w/v of composition or intermediate fraction thereof.
  • arabinogalactan is present in the concentration of 0.5 % w/v.
  • Hyaluronic acid or salt because of its chemical structure it has a high affinity for water.
  • hyaluronic acid or salt thereof is used as a hydrating agent.
  • hyaluronic acid can be used alone or in combination of salts thereof.
  • hyaluronic acid salt used is sodium hyaluronate.
  • Hyaluronic acid or salts thereof have important water retention properties, with an affinity of 1000 times their own weight. This increases the wettability of the ocular surface and reduces friction of the cornea from blinking in dry eye.
  • the concentration of the hyaluronic acid or salt present in the pharmaceutical ophthalmic compositions according to the present invention is in the range of about 0.02% to 5% w/v of composition; preferably 0.01, 0.5, 0.75, 0.1, 0.2, 0.3, 0.4 or 0.5% w/v of composition or intermediate fraction thereof.
  • hyaluronic acid or its salt is present in the concentration of about 0.2% w/v.
  • sodium hyaluronate is present in the concentration of about 0.2% w/v.
  • Omega fatty acids are used in ophthalmic compositions as a lipid lubricant or an emollient vehicle.
  • omega fatty acid is a fatty acid, a component of the oil or lipid type. Its fatty or oily properties can repair the deficiency of the lipid layer of dry eye, working like a lid of a pot that prevents the aqueous part of the tear from evaporating.
  • omega fatty acid used may be omega-3 fatty acid, omega-6 fatty acid or omega-9 fatty acid alone or in combinations thereof.
  • omega-3 fatty acids are selected from the group consisting of, but not limited to, a-linolenic acid (ALA), eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA).
  • ALA a-linolenic acid
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • omega-6 fatty acids are selected from the group consisting of, but not limited to linoleic acid (LA); gamma-linolenic acid (GLA) ; calendic acid; eicosadienoic acid; fihomo-gamma-linolenic acid (DGLA); arachidonic acid (AA, ARA); docosadienoic acid; adrenic acid; osbond acid; tetracosatetraenoic acid or tetracosapentaenoic acid.
  • LA linoleic acid
  • GLA gamma-linolenic acid
  • DGLA fihomo-gamma-linolenic acid
  • ARA arachidonic acid
  • docosadienoic acid adrenic acid
  • osbond acid tetracosatetraenoic acid or tetracosapentaenoic acid.
  • omega-9 fatty acids are selected from the group consisting of, but limited to hypogeic acid; oleic acid; elaidic acid; gondoic acid; mead acid; erucic acid; nervonic acid; or ximenic acid.
  • Omega-9 fatty acid is Oleic acid.
  • Omega-9 fatty acid oleic acid can be used in eye drops to treat dry eye because it can act as a lipid lubricant and as an emollient vehicle.
  • the concentration of the omega fatty acid in the pharmaceutical ophthalmic compositions according to the present invention is in the range of about 0.02% to 5% w/v of composition; preferably 0.01, 0.5, 0.75, 0.1, 0.2, 0.3, 0.4 or 0.5% w/v of composition or intermediate fraction thereof.
  • Omega fatty acid is present in the concentration of 0.1% w/v.
  • the omega- 9/oleic is present in the concentration of 0.1% w/v.
  • an emulsion refers to a liquid-liquid dispersion system in which at least one liquid is dispersed in another liquid with which it is immiscible, and the emulsion generally has a size distribution ranging from 0.1 to several tens of nanometers.
  • the water is continuous phase and an oil is dispersed phase i.e. oil globules dispersed in the water.
  • nano-emulsions are oil-in-water emulsions, the oil globules of which have a very fine particle size, i.e. a mean globule size of 10 nm to 30 nm.
  • the globule size was measured using— LitesizerTM 500 Particle Analyzer from Anton Paar.
  • the nano-emulsion has a pH between 5 and 8 and an osmolality between 250 and 600 mOsm/kg.
  • the oil that forms part of the emulsion may be selected from vegetable oil, animal oil, mineral oil, fatty acids, medium chain triglyceride, fatty alcohols alone or any combinations of these oils and/or oily substances that are well tolerated in the eye.
  • the preferred oils are medium chain triglycerides, vegetable oils, olive oil, sunflower seed oil, sesame seed soil with an acid value less than 0.5, castor oil, mineral oil and glyceryl monostearate (GMS) or combinations thereof.
  • the more preferred oils are castor oil, mineral oil and glyceryl monostearate (GMS) or combination thereof.
  • oil is present in concentration preferably between 0.1% and 25% w/v of composition. In a preferred embodiment the oil is present in 0.2% w/v to 20% w/v of composition. In most preferred embodiment oil component is present in 0.5% w/v to 1.0% w/v of composition.
  • the aqueous phase includes water or water and glycerin mixture.
  • surfactants used in the emulsion.
  • surfactants are selected from the group consisting of, but not limited to, sorbitan esters (such as Span or Arlacel), glycerol esters (such as glycerin monostearate), polyethylene glycol esters (such as polyethylene glycol stearate), block polymers (such as poloxamers (Pluronics®)), acrylic polymers (such as Pemulen®), ethoxylated fatty esters (such as polyoxyl 35 castor oil ,Cremophor® RH-40), ethoxylated alcohols (such as Brij®), ethoxylated fatty acids (such as polysorbate 80, Tween or Tween 20), monoglycerides, silicon based surfactants alone or in combinations thereof.
  • sorbitan esters such as Span or Arlacel
  • glycerol esters such as glycerin monostearate
  • polyethylene glycol esters such as polyethylene glyco
  • surfactants polyoxyl 35 castor oil and polysorbate 80 are used in combination.
  • the ratio of surfactants is 1:2, 1:1.5, 1:1, 1.5:1, 2:1, 2.5:1, 3:1 or fractions in between.
  • the ratio of primary to secondary surfactant is 1:1.
  • each surfactant is present in concentration of about 50 mg/mL to about 150 mg/mL.
  • the composition comprises a buffer.
  • composition may optionally further comprise of one or more of the following components; isotonizing agents, stabilizers, buffers, preservatives, and antioxidants.
  • composition of the present invention may include an isotonizing agent such as mannitol, glycerin, glycerol, sorbitol, glucose alone or combinations thereof.
  • an isotonizing agent such as mannitol, glycerin, glycerol, sorbitol, glucose alone or combinations thereof.
  • the isotonizing agent is selected from glycerin, glycerol alone or combination thereof.
  • composition of present invention may contain stabilizers such as sodium edatate, citric acid alone or combination thereof; buffers such as tris(hydroxymethyl)aminomethane, sodium phosphate and potassium phosphate, sodium citrate, sodium carbonate and sodium bicarbonate alone or combinations thereof.
  • stabilizers such as sodium edatate, citric acid alone or combination thereof
  • buffers such as tris(hydroxymethyl)aminomethane, sodium phosphate and potassium phosphate, sodium citrate, sodium carbonate and sodium bicarbonate alone or combinations thereof.
  • composition of present invention may contain preservatives such as quaternary ammonium compound like benzalkonium chloride, chlorobutanol, sodium perborate alone or combinations thereof.
  • preservatives such as quaternary ammonium compound like benzalkonium chloride, chlorobutanol, sodium perborate alone or combinations thereof.
  • the preservative used is benzalkonium chloride.
  • composition of the present invention may be preservative free.
  • the compositions of the present invention may be sterilized by filtration or they may be obtained by sterilization of the aqueous phase and the oily phase and subsequently mixing and emulsifying in aseptic conditions.
  • an embodiment of the present invention discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising: biopolysaccharides; an oil phase dispersed in an aqueous phase; wherein oil phase comprises of at least one omega fatty acid; and a hyaluronic acid or a salt thereof.
  • an embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising; arabinogalactan or xanthan gum alone or in combination thereof; an oil phase dispersed in an aqueous phase; wherein oil phase comprises of at least one omega fatty acid; and a hyaluronic acid or a salt thereof.
  • Another embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising; arabinogalactan or xanthan gum alone or in combination thereof; a hyaluronic acid or a salt thereof; an oil phase dispersed in an aqueous phase; wherein oil phase comprises of at least one omega fatty acid; and wherein the oil phase includes oil globules having a mean globule size of less than 30 nm.
  • Another embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising; arabinogalactan or xanthan gum alone or in combination thereof; a hyaluronic acid or a salt thereof; a primary and/or a secondary surfactant selected from the group comprising of polyoxyl 35 castor oil, polysorbate 80 alone or combination thereof; wherein about 0.1%-25% w/v of oil phase dispersed in an aqueous phase, wherein oil phase comprises of at least one omega fatty acid or combination thereof; wherein the oil phase includes oil globules having a mean globule size of less than 30 nm.
  • Another embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising; arabinogalactan or xanthan gum alone or in combination thereof; a hyaluronic acid or a salt thereof; a primary and a secondary surfactant; wherein primary and secondary surfactant are polyoxyl 35 castor oil, polysorbate 80; wherein about 0. l%-25% w/v of oil phase dispersed in an aqueous phase; wherein oil phase comprises of at least one omega fatty acid or combination thereof; wherein the oil phase includes oil globules having a mean globule size of less than 30 nm.
  • Another embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising;
  • oil phase dispersed in an aqueous phase, wherein the oil phase selected from the group comprising of at least one omega fatty acid or combination thereof; a primary and/or a secondary surfactant selected from the group comprising of polyoxyl 35 castor oil, polysorbate 80 alone or combination thereof; and wherein the oil phase includes oil globules having a mean globule size of less than 30 nm; wherein the emulsion is characterized by having a negative zeta potential.
  • Another embodiment discloses a pharmaceutical nano-emulsion ophthalmic compositions comprising;
  • Viscosity of the nano-emulsion was determined by Brookfield Rheometer DV3T. The rotation speed was 250 rpm and the viscosity was determined in centipoise from rheogram plotted using shear stress (dyn/cm 2 ) and shear rate (1/s).
  • the viscosity of the present invention is 5cps to 500cps. In preferred embodiment of the present invention viscosity of the present invention is 5cps to lOOcps. In preferred embodiment of present invention, the viscosity of present invention is 20cps to 30cps.
  • the nano-emulsion was prepared by using following method: Oil phase: In a container of adequate capacity, add Polysorbate 80, Cremophor EL® and super refined castor oil. Mix until completely incorporated. Add oleic acid (Omega-9) to the mixture from step 1, mix until completely dissolved. Aqueous phase: In a second container equipped with a stirrer, add 60% water of the total quantity to be prepared from the batch. Dissolve with stirring, in the aqueous phase of step 3, sodium borate and once completely dissolved, add boric acid. Shake until completely dissolved. Maintaining the agitation, add the amount of Sodium hyaluronate to the container in point 4 and dissolve completely.
  • Oil phase In a container of adequate capacity, add Polysorbate 80, Cremophor EL® and super refined castor oil. Mix until completely incorporated. Add oleic acid (Omega-9) to the mixture from step 1, mix until completely dissolved.
  • Aqueous phase In a second container equipped with a stirrer,
  • Nano-emulsion Formation Add the aqueous phase to the container containing the oil phase. 8. Shake, if necessary, increase the speed of the stirrer until the nano-emulsion is formed (only one phase must be observed).
  • Test 4 - Test 8 which comprised of two surfactants had better stability than Test 1 to Test 3 formulations.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Ophthalmology & Optometry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne une composition ophtalmique qui peut être utilisée dans le traitement du syndrome de l'oeil sec, fournissant 3 types de composants que les larmes naturelles contiennent : un composant lipidique, un composant aqueux et un composant mucoïde.
PCT/IB2022/052617 2021-03-22 2022-03-22 Collyre ophtalmique triple WO2022201032A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
MX2021003369A MX2021003369A (es) 2021-03-22 2021-03-22 Lágrima ocular triple.
MXMX/A/2021/003369 2021-03-22

Publications (1)

Publication Number Publication Date
WO2022201032A1 true WO2022201032A1 (fr) 2022-09-29

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060251685A1 (en) * 2003-03-18 2006-11-09 Zhi-Jian Yu Stable ophthalmic oil-in-water emulsions with Omega-3 fatty acids for alleviating dry eye
WO2010106571A2 (fr) * 2009-03-19 2010-09-23 Medivis S.R.L. Compositions ophtalmiques à base d'acides gras oméga-3 et oméga-6 polyinsaturés
US20100305045A1 (en) * 2009-06-02 2010-12-02 Abbott Medical Optics Inc. Omega-3 oil containing ophthalmic emulsions
WO2014189251A1 (fr) * 2013-05-20 2014-11-27 주식회사태준제약 Composition de goutte oculaire de nano-émulsion contenant de la cyclosporine et son procédé de préparation
US20160166601A1 (en) * 2002-04-30 2016-06-16 Sifi S.P.A. Re-epithelializing pharmaceutical compositions comprising xanthan gum

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160166601A1 (en) * 2002-04-30 2016-06-16 Sifi S.P.A. Re-epithelializing pharmaceutical compositions comprising xanthan gum
US20060251685A1 (en) * 2003-03-18 2006-11-09 Zhi-Jian Yu Stable ophthalmic oil-in-water emulsions with Omega-3 fatty acids for alleviating dry eye
WO2010106571A2 (fr) * 2009-03-19 2010-09-23 Medivis S.R.L. Compositions ophtalmiques à base d'acides gras oméga-3 et oméga-6 polyinsaturés
US20100305045A1 (en) * 2009-06-02 2010-12-02 Abbott Medical Optics Inc. Omega-3 oil containing ophthalmic emulsions
WO2014189251A1 (fr) * 2013-05-20 2014-11-27 주식회사태준제약 Composition de goutte oculaire de nano-émulsion contenant de la cyclosporine et son procédé de préparation

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