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(12) Patent Application Publication (10) Pub. No.: US 2007/0280995 A1 Rabinovich-Guilatt Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2007/0280995 A1 Rabinovich-Guilatt Et Al US 20070280995A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2007/0280995 A1 Rabinovich-Guilatt et al. (43) Pub. Date: Dec. 6, 2007 (54) USE OF A STEROID PRODRUG FOR THE Related U.S. Application Data TREATMENT OF DISEASE OF THE POSTERIOR SEGMENT OF THE EYE (62) Division of application No. 1 1/444,337, filed on Jun. 1, 2006. (75) Inventors: Laura Rabinovich-Guilatt, (30) Foreign Application Priority Data Kadima (IL); Gregory Lambert, Chatenay-Malabry (FR) Jun. 1, 2006 (EP) .................................. O629O902.3 Publication Classification Correspondence Address: YOUNG & THOMPSON (51) Int. Cl. A 6LX 3/57 (2006.01) 745 SOUTH 23RD STREET, 2ND FLOOR A6IR 9/00 (2006.01) ARLINGTON, VA 22202 A6IP27/02 (2006.01) (73) Assignee: NOVAGALI PHARMA SA, (52) U.S. Cl. ......................... 424/427: 514/169; 514/177 EVRY (FR) (57) ABSTRACT Use of a composition comprising at least one prodrug of a (21) Appl. No.: 11/806,554 steroid, preferably of a corticosteroid, for the preparation of an ophthalmic composition intended for the treatment of an (22) Filed: Jun. 1, 2007 ocular condition or disease of a human being or an animal. US 2007/0280995 A1 Dec. 6, 2007 USE OF A STEROID PRODRUG FOR THE 0009. The need to administrate the corticosteroids the TREATMENT OF DISEASE OF THE most locally possible, therefore selectively in the disease POSTERIOR SEGMENT OF THE EYE site, in effective quantities, was then clear. 0010. The effectiveness of the treatment is in particular related to the presence of the active compound and hence to the half life of the drug. A known corticosteroid, the dex 0001. The present invention relates to the field of the amethasone has a half life of 3.5 hours when injected treatment of the ophthalmic diseases, in particular of the intraocularly (Kwak, Arch Opthalmol, 1992). Thus, the intraocular diseases of a human being or an animal, by at injections must be repeated to maintain a therapeutic effect. least one steroid, and in particular by at least one corticos 0011. However, repeated injections are difficult to cope teroid. with for the patients Suffering of long or chronic diseases. 0002 The invention particularly focuses on ophthalmic Moreover, repeated injections are likely to increase harmful compositions or devices, preferably ophthalmic emulsions, side effects such as retina detachment, endophtalmy, and comprising at least one steroid, preferably a corticosteroid. Cataracts. The invention also relates to the administration of such 0012. In view of the additional side effects caused by ophthalmic compositions, and in particular to their admin repeated injections, intraocular implants of steroids have istration intraocularly. The invention relates also to the been developed: controlled release of therapeutic active agents, in particular (0013 RETISERTTM (fluocinolone acetonide intravitreal of corticosteroids intraocularly, in particular in the posterior implant, Bausch & Lomb) 0.59 mg is a sterile implant segment of the eye. designed to release fluocinolone acetonide locally to the 0003) A posterior ocular condition is a disease which posterior segment of the eye. RETISERTTM was recently primarily affects a posterior ocular site Such as choroid or approved by the FDA and is indicated for the treatment of Sclera, vitreous, vitreous chamber, retina, optic nerve, and chronic non-infectious uveitis affecting the posterior seg blood vessels and nerves which vascularize or innervate a ment of the eye. However, clinical trials of this implant posterior ocular site. systematically results in a raise of the intraocular pressure 0004 Steroids are already largely used to treat oph (IOP) and cataracts as main adverse effects. Holekamp et al. thalmic diseases affecting the posterior chamber of the eye, found that after long-term follow-up, high-dose intraocular in particular central retinal vein occlusion (CRVO), branch fluocinolone acetonide results in significant complications retinal vein occlusion (BRVO), choroidal macular edema rate, with 100% of the eyes developing elevated IOP and (CME), diabetic macular edema (DME), diabetic macular 30% showing nonischemic central retinal vein occlusion. retinopathy, uveitis, and age related macular degeneration These complications required the implant removal in almost (ARMD). These treatments generally imply their systemic 60% of the eyes (Am J Opthalmol 2005). Implantation of administration, causing known side effects, which are sig 0.59 mg or 2.1 mg fluocinolone acetonide in noninfectious nificant, regarding the ophthalmic diseases to treat. These posterior uveitis patients results in a 5-fold augmentation of side effects singularly decrease the interest of the treatment the need of IOP lowering agents (Jaffe, Opthalmology, of these ophthalmic diseases by Systemic administration of 2005). In a randomized clinical trial of 0.59 mg fluocinolone steroids. acetonide intravitreal implant in patients with diabetic macu lar edema, the most common adverse included serious 0005. Other modes of administration, topic, suprachoroi cataract progression (43.1%) and a serious intraocular pres dal, subconjunctival, retrobulbar, and intravitreal were sure rise (8.6%) (Pearson, ISOPT communication, Berlin, searched. Regarding topical application, dexamethasone 2006). Based on clinical trials with RETISERT, within 34 penetration into the vitreous humour after repeated topical weeks post-implantation, approximately 60% of patients application is negligible (less than 2 ng/ml after 1 drop of will require IOP lowering medications to control intraocular 0.1% dexamethasone phosphate drops hourly for 10 hours) pressure. Within an average postimplantation period of (Weitens, Opthalmology, 2002). In comparison, serum and approximately 2 years, approximately 32% of patients are vitreous levels of 60 and 5 ng/ml respectively are observed expected to require filtering procedures to control intraocu following a single oral administration of 7.5 mg dexametha lar pressure. Moreover, within an average post-implantation sone (Weitens, Am J Opthalmol, 1998). period of approximately 2 years, nearly all phakic eyes are 0006. It was also shown that the subretinals concentra expected to develop cataracts and require cataract Surgery tions of dexamethasone after subconjunctival or peribulbar (source Bausch & Lomb). injection were 120 and 13-fold more elevated than after oral 0014 Posurdex is another intraocular device being devel administration (Weitens et al. Opthalmology, 2000). The oped by Allergan containing 700 micrograms of dexametha local intraocular administration is thus highly preferred. Sone which are released during the first month post implan 0007. However, the injection of steroids in significant tation. Its efficacy has been evaluated among others in cases amounts in the eye, implies a Sudden and massive increase of persistent macular edema (Williams, ISOPT communi in their concentration in all ocular structures, and can also cation, 2006) and for anti-inflammatory effects after cataract lead to undesirable and consequent local ocular side effects, surgery (Tan, Opthalmology, 2004). However, a safety and in particular a significant increase in the intraocular pressure efficacy clinical study of 700 micrograms dexamethasone possibly leading to the development of glaucoma, or to the implant for the treatment of macular edema showed signifi appearance or the development of cataracts. cant increases in IOP (to 225 mm Hg) in 15% of patients 0008. It was notably noticed that the presence of corti (Williams, ISOPT communication, Berlin, 2006). costeroids in the anterior segment of the eye was in particu 0015 The off-label use of triamcinolone acetonide (Ke lar related to the appearance of these side effects, and was nalog 40TM, Bristol Myers Squib) intraocularly results indi thus undesirable. rectly in the slow-release of the drug, as the insoluble steroid US 2007/0280995 A1 Dec. 6, 2007 precipitates following injection in the vitreous cavity and is fewer side effects occasioned by the therapeutic agent are only gradually solubilized. Therefore, it can be considered expected to be observed. The drug would be release at the as well as a Sustained release steroidal formulation. How very location of the disease, resulting in a decrease of ever, this formulation which was not originally developed unwanted adverse effects in other ocular structures where for intraocular use can cause serious complications such as the prodrug is not hydrolyzed. The invention also permits infectious endophthalmitis and sterile endophthalmitis, reti maintaining the desired effect in the ocular condition for an nal toxicity and crystalline retinal deposits. Nevertheless, it extended period of time during which an amount of the has been used intravitreally to treat ocular inflammation as prodrug is present at the ocular site such that it allows the well as macular edema due to numerous causes. In addition, retrospective analysis of Subtenon triamcinolone acetonide release of an effective amount of the active drug for an cases also reveals intraocular pressure rise in 21% of the extended period of time, which is preferably at least one patients (Bui Quoc, J. Fr Ophtalmol, 2002). month. Thus, the present invention also relates to a method 0016 Other steroid-containing devices being developed of personalized treatment of a patient in need of a steroid in research are triamcinolone acetonide/polycaprolactone intraocular treatment: each patient, as of he/she is adminis implants (Beeley, J Biomed Mater Res A,
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