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(12) United States Patent (10) Patent No.: US 9,072,750 B2 Garrigue Et Al

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(12) United States Patent (10) Patent No.: US 9,072,750 B2 Garrigue Et Al US00907275OB2 (12) United States Patent (10) Patent No.: US 9,072,750 B2 Garrigue et al. (45) Date of Patent: Jul. 7, 2015 (54) USE OF PROSTAGLANDINSF2ALPHIA AND (56) References Cited ANALOGUES FOR THE HEALING OF CORNEAL AND CONUUNCTIVAL LESIONS U.S. PATENT DOCUMENTS 4,599,353 A 7, 1986 Bito et al. ..................... 514,530 (75) Inventors: Jean-Sébastien Garrigue, Verrieres le 4,684,633. A 8/1987 Imagawa et al. ................ 514,78 Buisson (FR); Frédéric Lallemand, 5,321,128 A * 6/1994 Stjernschantz et al. ....... 514/530 5,496,811 A 3/1996 Aviv et al. ....................... 514,78 Fresnes (FR); Philippe Daull, 5,510,383 A 4/1996 Bishop et al. ...... 514,530 Soisy-sur-Seine (FR); Christophe 5,588,559 A 12/1996 Vallet Maset al. ............. 222/92 Baudouin, Paris (FR) 5,688,819 A 11/1997 Woodward et al. ........... 514/357 5,767,153 A 6/1998 Bowman et al. ....... 514,530 5,849,792 A 12/1998 Schneider et al. 514,530 (73) Assignee: SANTEN SAS, Evry (FR) 6,007,826 A 12/1999 Benita et al. ....... ... 424/401 6,011,062 A 1/2000 Schneider et al. 514,530 Notice: Subject to any disclaimer, the term of this 6,225.348 B1 5, 2001 Paulsen et al. ..... 514,530 (*) 6,342,524 B1 1/2002 Hellberg et al. ... 514,530 patent is extended or adjusted under 35 6,344,477 B1 2/2002 Sharif et al. ....... 514,530 U.S.C. 154(b) by 559 days. 7,064,109 B2 6/2006 Luyckx et al. .................. 514, 29 8,273,362 B2 9/2012 Philips et al. .. ... 424/400 8,697,751 B2 4/2014 Sakai et al. .... 514,573 (21) Appl. No.: 13/510,884 2002/0136771 A1 9, 2002 Parr et al. .... ... 424/488 2004/0082660 A1 4/2004 Ueno et al. ..... 514,573 (22) PCT Fled: Nov. 19, 2010 2004/O115234 A1 6/2004 Gewirtz et al. ... 424/401 2004/0198829 A1 10/2004 Sponsel et al. ... 514,573 2005, 0124699 A1 6/2005 Akiba et al. ... 514,573 (86) PCT NO.: PCT/EP2010/067846 2008/0268020 A1 10/2008 Philips et al. ...... ... 424/427 2009/0298956 All 12/2009 Chowhan et al. .. 514,785 S371 (c)(1), 2011 0118349 A1 5/2011 Garrigue et al. .............. 514,530 (2), (4) Date: May 18, 2012 (Continued) (87) PCT Pub. No.: WO2O11AO61298 FOREIGN PATENT DOCUMENTS PCT Pub. Date: May 26, 2011 CN 101.0566.15 A 10/2007 CN 1.01282714 A 10, 2008 (65) Prior Publication Data (Continued) US 2012/O225939 A1 Sep. 6, 2012 OTHER PUBLICATIONS Baudouin et al., “In vitro studies of antiglaucomatous prostaglandin Related U.S. Application Data analogues: Travoprost with and without benzalkonium chloride and preserved latanoprost', IOVS, vol. 48, No. 9, Sep. 2007. (60) Provisional application No. 61/262,664, filed on Nov. Bell et al., “A new ophthalmic irrigating solution'. American Journal 19, 2009. of Ophthalmology, vol. 34, No. 9, Sep. 1951, pp. 1321-1322. Dilly, P.N. et al., "Surface changes in the anaesthetic conjunctiva in (30) Foreign Application Priority Data man, with special reference to the production of mucus from a non goblet-cell source', British Journal of Ophthalmology, vol. 65, No. May 28, 2010 (EP) ..................................... 1O164376 12, Dec. 1981, pp. 833-842. Erb. C. et al., “German register for glaucoma patients with dry eye I. Basic outcome with respect to dry eye'. Graefe's Archive for Clinical (51) Int. C. and Experimental Ophthalmology, vol. 246, No. 11, Nov. 2008, pp. A 6LX3/55.75 (2006.01) 1593-1601. A6 IK3I/26 (2006.01) (Continued) A6 IK9/00 (2006.01) A 6LX 9/07 (2006.01) Primary Examiner — Raymond Henley, III A6 IK 45/06 (2006.01) (74) Attorney, Agent, or Firm — Norton Rose Fulbright US A6 IK 47/10 (2006.01) LLP A6 IK 47/8 (2006.01) A6 IK 47/26 (2006.01) (57) ABSTRACT (52) U.S. C. The invention relates to a composition for use in treating CPC ........... A61 K3I/55.75 (2013.01); A61 K 3 1/216 corneal and conjunctival lesions, wherein the composition (2013.01); A61 K9/0048 (2013.01); A61 K comprises a prostaglandin F2alpha or analogue, in a thera 9/107 (2013.01); A61K 45/06 (2013.01); A61 K peutic amount, said composition being in a form suitable for 47/10 (2013.01); A61 K47/183 (2013.01); topical application on the ocular Surface and is free of delete A61K4726 (2013.01) rious preservative; the invention also relates to a method for (58) Field of Classification Search treating Surface ocular conditions in a patient in need thereof, CPC ......................... A61K 31/5575; A61K 31/216 comprising administering a composition of the invention. USPC .................................................. 514/530,573 See application file for complete search history. 18 Claims, 10 Drawing Sheets US 9,072,750 B2 Page 2 (56) References Cited International Search Report, dated Jul. 3, 2007, from PCT/EP2006/ 0097.83 (WO2007/042262). U.S. PATENT DOCUMENTS International Search Report, dated Aug. 20, 2010, from the applica tion PCT/EP2010/052740 (WO2010/100217). 2011/0313038 A1 12/2011 Lallemand et al. ........... 514,530 International Search Report, dated Sep. 6, 2011, from the application 2011/0319488 A1 12/2011 Lallemand et al. ........... 514,530 PCT/EP2010/052741 (WO2010/100218). Landreville, S. et al., “Expression of Phospholipases A2 and C in FOREIGN PATENT DOCUMENTS Human Corneal Epithelial Cells'. Investigative Ophthalmology & CN 101516332. A 8, 2009 Visual Science, vol. 45, No. 11, Nov. 2004, pp. 3997-4003. CN 102341094 2, 2012 Leung, E. W. et al., “Prevalence of Ocular Surface Disease in Glau EP O423697 10, 1990 coma Patients”, Journal of Glaucoma, vol. 17, No. 5, Aug. 2008, pp. EP O6964.52 7, 1995 350-355. EP 1532.981 8, 2003 McCarey et al. “In vivo corneal epithelial permeability following EP 15475.99 9, 2003 treatment with prostaglandin analoges with or without benzalkonium EP 1681059 10, 2004 chloride'. Journal of ocular pharmacology and Therapeutics, vol. 23. EP 1655.021 11, 2004 EP 1994.933 3, 2007 No. 5, Oct. 2007, pp. 445-451, XP002607567. EP 1985298 4/2007 Mietz, H. et al., “Latanoprost Stimulates Secretion of Matrix Metal EP 1972334 9, 2007 loproteinases in Tenon Fibroblasts Both InVitro and InVivo”. Inves EP 2127638 5, 2008 tigative Ophthalmology & Visual Science, vol. 44, No. 12, Dec. 2003, JP HT-504848 9, 1993 pp. 5182-5188. KR 2003/0046553 4/2007 Nagai et al., “Comparison of corneal wound healing rates afetrinstil MX af2010/012987 5, 2008 lation of commercially available latanoprost and travoprost in rat WO 93.18852 9, 1993 debrided corneal eputhelium”, Journal of Oleo Science, 2010, vol. WO O3053405 T 2003 59, No. 3, pp. 135-141. WO 2005/044276 5, 2005 Satoshi Ogawa et al., “Production and Characterization of O/W WO 2006/050836 5, 2006 emulsions containing cationic droplets stabilized by lecithin WO 2006/050838 5, 2006 WO 2007/042262 4/2007 chitosan membranes'. Journal of Agricultural and Food Chemistry, WO 2007/0899.31 8, 2007 2003, pp. 2806-2812, vol. 51 American Chemical Society. WO 2008/O12367 1, 2008 Shunmugaperumal Tamilvanan et al., “The potential of lipid emul WO 2008/036847 3, 2008 sion for ocular delivery of lipophilic drugs'. European Journal of WO 2008.074885 6, 2008 Pharmaceuticals and Biopharmaceuticals, 2004, pp. 357-368, vol. WO 2009, 145356 12/2009 58, Elsevier B. V. WO 2010/100218 9, 2010 Wei Xu et al., “FP Prostanoid Receptor-Mediated Induction of the Expression of Early Growth Response Factor-1 by Activation of a OTHER PUBLICATIONS Ras/Raf Mitogen-Activated Protein Kinase Signaling Cascade'. European Search Report, dated Oct. 2010, from the application Molecular Pharmacology, vol. 73, No. 1, Jan. 2008, pp. 111-118. EP10164376. Wen-Cheng Chung et al., “CREB Mediates Prostaglandin F2C-In Gary Ott et al., “A cationic sub-micron emulsion (MF59/DOTAP) is an effective delivery system for DNA vaccines”, Journal of Con duced MUC5AC Overexpression”, Journal of Immunology, vol. 182, trolled Release, 2002, pp. 1-5, vol. 79, Elsevier Ltd. No. 4, Feb. 2009, pp. 2349-2356. Greiner, J. V. et al., “Mucus Secretory Vesicles in Conjunctival Wilde, P. J. et al., “Interfaces: their role in foam and emulsion Epithelial Cells of Wearers of Contact Lenses”. Archives of Ophthal behaviour'. Current Opinion in Colloid & Interface Sciences, vol. 5, mology, vol. 98, No. 10, Oct. 1980, pp. 1843-1846. No. 3-4, Jul. 2000, pp. 176-181. Gronert, K., "Lipid Autacoids in Inflammation and Injury Responses: Woo-Jeong Choi et al., “Low toxicity of cationic lipid-based emul A Matter of Privilege'. Molecular Interventions, vol. 8, No. 1, Feb. sion for gene tranfer'. Biomaterials, 2004, pp. 5893-5903, vol. 25. 2008, pp. 28-35. Elsevier Ltd. International Search Report, dated May 24, 2007, from the applica tion PCTEP2005/011648. * cited by examiner U.S. Patent Jul. 7, 2015 Sheet 2 of 10 US 9,072,750 B2 PBS Latanoprost Xalatan O.02% BAK Emulsion w & S------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- * , p<0.05 when compared to Xalatan(E) or 0.02% BAK. Figure 2. U.S. Patent Jul. 7, 2015 Sheet 3 of 10 US 9,072,750 B2 PBS Xalatan O.O2% BAK Latanoprost Emulsion SSass R F8F sississionis: a assists S. & S. as Sistasig signs, RS: 5.83 SSSSSS 3. SSSSS S 8: SS RSS SS SR S s 8,385.8 Cotes Sixts it. 28828. Estis Sk8es S. &KS, CS sissississia:S :: SSSSSS 38: 88 SS rarer Figure 3. U.S. Patent Jul. 7, 2015 Sheet 4 of 10 US 9,072,750 B2 PBS Latanoprost Emulsion Š , , , , , , , , Figure 4. U.S. Patent Jul. 7, 2015 Sheet 5 of 10 US 9,072,750 B2 PBS Latanoprost Xalatan O.02% BAK Emulsion Figure 5.
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