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(12) Patent Application Publication (10) Pub. No.: US 2016/0263023 A1 KARAVAS Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2016/0263023 A1 KARAVAS Et Al US 20160263023A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0263023 A1 KARAVAS et al. (43) Pub. Date: Sep. 15, 2016 (54) PRESERVATIVE FREE PHARMACEUTICAL Publication Classification COMPOSITIONS FOR OPHTHALMC ADMINISTRATION (51) Int. Cl. A619/00 (2006.01) (71) Applicant: PHARMATHEN S.A., Pallini Attikis A 6LX3/55.75 (2006.01) (GR) A647/02 (2006.01) A647/10 (2006.01) (72) Inventors: EVANGELOS KARAVAS, PALLINI A613 L/65 (2006.01) ATTIKIS (GR); EFTHIMIOS KOUTRIS, PALLINIATTIKIS (GR): A 6LX3/5377 (2006.01) VASILIKI SAMARA, PALLINI A63L/382 (2006.01) ATTIKIS (GR): IOANNA KOUTRI, A647/12 (2006.01) PALLINIATTIKIS (GR): ANASTASIA A647/38 (2006.01) KALASKANI, PALLINIATTIKIS A619/08 (2006.01) (GR); ANDREAS KAKOURIS, A647/26 (2006.01) PALLINIATTIKIS (GR); GEORGE (52) U.S. Cl. GOTZAMANIS, PALLINIATTIKIS CPC ................. A61 K9/0048 (2013.01); A61 K9/08 (GR) (2013.01); A61 K3I/55.75 (2013.01); A61 K 47/02 (2013.01); A61 K47/10 (2013.01); A61 K (73) Assignee: PHARMATHEN S.A., 47/26 (2013.01); A61 K3I/5377 (2013.01); PALLINI-ATTIKIS (GR) A61 K3I/382 (2013.01); A61K47/12 (2013.01); A61 K47/38 (2013.01); A61 K (21) Appl. No.: 15/028,685 3 1/165 (2013.01) (22) PCT Fled: Oct. 14, 2014 (57) ABSTRACT (86) PCT NO.: PCT/EP2014/002767 S371 (c)(1), (2) Date: Apr. 11, 2016 The present invention relates to a preservative-free, aqueous Solution in the form of eye drops packed in a container that (30) Foreign Application Priority Data ensures stability of the product, ideal eye drop volume and reduced drop volume variability and provides efficient dis Oct. 15, 2013 (EP) ................... PCT/EP2013/003102 pensing. US 2016/0263023 A1 Sep. 15, 2016 PRESERVATIVE FREE PHARMACEUTICAL tration, there still remains the need in the art for alternative COMPOSITIONS FOR OPHTHALMC formulations providing as well adequate chemical and physi ADMINISTRATION cal characteristics and improved patient compliance. In par ticular, there is a need for formulations that are free from TECHNICAL FIELD OF THE INVENTION preservatives to be provided in a multiple use container and 0001. The present invention relates to aqueous preserva provide efficient dosing of the solution to the patient, without tive-free formulations for ophthalmic administration packed Wastage. in container that ensures physical and chemical stability of the product and provides efficient dispensing. SUMMARY OF THE INVENTION 0010. The present invention aims at developing aqueous BACKROUND OF THE INVENTION pharmaceutical formulations for ophthalmic administration 0002 Ocular administration of drugs is primarily associ that overcome the disadvantages of and provide significant ated with the need to treat ophthalmic diseases. The eye is the improvement over the prior art formulations. most easily accessible site for topical administration of a 0011. It is, therefore, an object of the present invention to medication. Ophthalmic preparations are sterile products provide an efficient ophthalmic product that contains no anti essentially free from foreign particles, Suitably compounded microbial preservatives. Such product is as effective in terms and packaged for instillation into the eye. They are easily of therapy as products available with preservatives. administered by the nurse or the patient himself, they have 0012 Another object of the present invention is to provide quick absorption and effect, less visual and systemic side an ophthalmic product that is stable over time at ambient effects, increased shelf life and better patient compliance. temperature. 0003 Drugs may be delivered to the eye through the appli 0013. A further object of the present invention is to pro cation of four primary modes of administration: Systemic, vide an aqueous pharmaceutical formulation for ophthalmic topical, intravitreal, and periocular. Topical administration is use that effectively addresses issues related to physiological generally considered the preferred route for the administra acceptability by patient. tion of ocular drugs due to its convenience and affordability. 0014. A further approach of the present invention is to Drugs applied in this manner can be in multiple forms, includ provide ophthalmic Solutions that are easily administrable in ing solutions, ointments and Suspensions. drop form. 0004 Drug absorption occurs through corneal and non 0015. In accordance with the above objects of the present corneal pathways. Most non-corneal absorption occurs via invention, eye drops with ideal volume are provided by con the nasolacrimal duct and leads to non-productive systemic trolling Surface tension of the ophthalmic solution and pack uptake, while most drug transported through the cornea is ing the product in container with appropriate design. taken up by the targeted intraocular tissue. Unfortunately, 0016 A further aspect of the present invention is to pro corneal absorption is limited by drainage of the instilled solu vide reduced drop volume variability in order to obtain higher tions, lacrimation, tear turnover, metabolism, tear evapora degree of accuracy and better treatment outcomes. tion, non-productive absorption/adsorption, limited corneal 0017. Other objects and advantages of the present inven area, poor corneal permeability, binding by the lacrimal pro tion will become apparent to those skilled in the artin view of teins, enzymatic degradation. the following detailed description. 0005. The objective of ocular medication delivery is maxi mizing the amount of medication that reaches the ocular site DETAILED DESCRIPTION OF THE INVENTION of action in Sufficient concentration to produce a beneficial 0018 For the purposes of the present invention, a pharma therapeutic effect. This is determined by the dynamics of ceutical composition comprising an active ingredient is con ocular pharmacokinetics: absorption, distribution, metabo sidered to be “stable' if said ingredient degrades less or more lism and excretion. slowly than it does on its own and/or in known pharmaceuti 0006 Aqueous solutions are most commonly used for the cal compositions. eye. They are the least expensive medications and interfere 0019 Antimicrobial preservatives are added to aqueous least with vision. Some commonly used ocular medications preparations that are required to be sterile, Such as in oph are topical anesthetics, mydriatics and cycloplegics, medica thalmic Solutions. The use of preservatives in topical oph tions used to treat glaucoma, anti-infectives, corticosteroids thalmic treatments is ubiquitous for any product that is to be and non-steroidal anti-inflammatory drugs. used more than once by the patient as they prevent any 0007 EP 0999825 B1 discloses atopical ophthalmic com microbes that may enter into the product after its first use from position comprising one or more galactomannan(s) and one allowing those microbes to grow and infect the patient on a or more borate compound(s), wherein the galactomannan and later use of the product. Antimicrobial preservatives are not the borate compound are contained in the composition in found in single use vials of ophthalmic Solutions since they concentrations effective to create a gel or partial gel when the are manufactured aseptically or are sterilised and the products composition is administered to an eye. are used once and the dispenser is thrown away. Although 0008 U.S. Pat. No. 7491383 B2 discloses compositions providing effective biocidal properties with well tolerated comprising a therapeutic component and an efficacy enhanc short-term use at low concentrations, preservatives can cause ing component that enhances the pharmacokinetic disposi serious inflammatory effects on the eye with long-term use in tion of the therapeutic component. The therapeutic compo chronic conditions, such as glaucoma or potentially ocular nent and the efficacy enhancing component may form a allergies. complex. 0020. As the incorporation of preservatives in topical oph 0009. Although each of the patents above represents an thalmic solutions becomes more common, sensitization attempt to provide stable Solutions for ophthalmic adminis toward them is increasing. For example, the salts of benza US 2016/0263023 A1 Sep. 15, 2016 Ikonium have been classified as being moderately allergic 0027 Tonicity refers to the osmotic pressure exerted by whereas mercurial products are strongly allergic. Thimerosal salts in aqueous Solution. An ophthalmic Solution is isotonic may cause ocular delayed hypersensitivity. Chlorhexidine with another solution when the magnitudes of the colligative may cause corneal endothelium damage. Parabens are properties of the Solutions are equal. An ophthalmic Solution capable of producing immunologically mediated, immediate is considered isotonic when its tonicity is equal to that of systemic hyperSensitivity reactions. 0.9% sodium chloride solution (290 mOsm). If the tonicity 0021. As the use of preservative containing eye drops has deviates too far from this value, the pain produced evokes a been implicated in the development or worsening of ocular reflex tearing that washes the drug from the eye. Conse Surface disease, there is a tendency to limit their use by quently, a certaintonicity agent must be added so that the total reducing their concentration as much as possible in eye drops. osmotic pressure is the same as the body fluid. Sodium chlo The present invention provides completely preservative-free ride, mannitol, dextrose, glycerine, potassium chloride are ophthalmic formulations. Such formulations are packed in typical tonicity agents. Isotonicity
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