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Modified Release Formulations of Emoxypine

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Modified Release Formulations of Emoxypine (19) & (11) EP 2 241 310 A2 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 20.10.2010 Bulletin 2010/42 A61K 9/20 (2006.01) A61K 31/44 (2006.01) A61K 9/28 (2006.01) A61K 9/28 (2006.01) (21) Application number: 10160217.5 (22) Date of filing: 16.04.2010 (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Toksöz, Ahmet HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL 34398, Istanbul (TR) PT RO SE SI SK SM TR • Cifter, Ümit Designated Extension States: 34398, Istanbul (TR) AL BA ME RS • Türkyilmaz, Ali 34398, Istanbul (TR) (30) Priority: 17.04.2009 TR 200903013 28.05.2009 TR 200904159 (74) Representative: Sevinç, Erkan Istanbul Patent & Trademark Consultancy Ltd. (71) Applicant: Sanovel Ilac Sanayi ve Ticaret A.S. Plaza-33, Büyükdere cad. No: 33/16 34398 Istanbul (TR) Sisli 34381 Istanbul (TR) (54) Modified release formulations of emoxypine (57) The present invention is related to a modifed a rate controlling polymer, with at least one pharmaceu- release pharmaceutical formulations comprising emox- tically acceptable excipient. ypine or a pharmaceutically acceptable salt thereof and EP 2 241 310 A2 Printed by Jouve, 75001 PARIS (FR) 1 EP 2 241 310 A2 2 Description ing intraocular hemorrhage, myopic chorioretinal dystro- phies, congenital retinal dystrophies, retinal burns and Technical Aspect prevention of injury in lasercoagulation. [0007] A conventional tablet formulation of emoxypine [0001] The present invention is related to modifed re- 5 succinate (Mexidol ®) is described in PCT application WO lease pharmaceutical formulations comprising emox- 96/02238 A1, Aktsionernoe Obschestvo Zakrytogo Tipa ypine or a pharmaceutically acceptable salt thereof and ’Olvik’, 15.07.1994. The proposed neurotropic and sed- a rate controlling polymer, with at least one pharmaceu- ative formulation contains emoxypine and auxiliary tically acceptable excipient. agents in core and a coating layer. The auxiliary agents 10 in the core comprise kaolin, potato starch, calcium stea- Background of the Invention rate, stearic acid, talc and methyl cellulose. The coating layer contains titanium dioxide and serge 80. [0002] Emoxypine is a heteroaromatic antioxidant [0008] It is desirable in the treatment of a number of which has a membranoprotective, nootropic and seda- diseases, to provide the active pharmaceutical ingredient tive action. Its aromatic activity range is very wide such 15 ina modified release form. Desirably the modified release as increasing the stress resistance of organism. It acts provides a generally uniform and constant rate of release as the anxiolytic which doesn’t cause the sleepiness and over a modified period of time which achieves desired myorelaxant effect; its nootropic properties allow to pre- plasma level of the active ingredient without the need for vent and reduce learning and memory defects in patients frequent administration of the medicament. of old age under pathogenic factors. One of the activities 20 [0009] Accordingly, a need rises for modified release of emoxypine is its anticonvulsant action which shows formulations of emoxypine or pharmaceutically accept- antioxidant and antihypoxic properties. It increases the able salt, which overcomes the above described prob- attention concentration and capacity for work and de- lems and minimizes the adverse effects and provides a creases the alcohol toxic affect. It inhibits peroxide oxi- comperable drug plasma concentration which is equiva- dation of lipids, increases the superoxidoxidase activity 25 lent to or better than the immediate release tablet or in- and elevates the ratio of lipid-protein. Also, provides a jectable formulations currently used. The formulation of higher dopamine concentration in brain. this invention represents a novel modified release formu- [0003] Its chemical name is ethyl-2- 6-methyl-3-hy- lation previously undisclosed in the prior art. droxypyridine and its chemical structure is shown in the [0010] The modified relase formulation of this inven- Formula I. 30 tion further provides the advantageous property of allow- ing the active medicament to be administered less fre- quently, e.g. once-a-day or twice-a- day, while achieving comparable plasma levels to immediate release forms. 35 Description of the invention [0011] The main embodiment of the present invention is to provide a novel modified release formulation com- prising emoxypine or a pharmaceutically acceptable salt 40 thereof and a rate controlling polymer, with at least one pharmaceutically acceptable excipient which overcomes the above described problems in prior art and have an additive advantages over them. [0004] Emoxypine is marketed under the brand name [0012] "Modified release dosage forms" are defined as MEXIDOL® and it is administered orally in a therapeutic 45 those whose drug release characteristics of time course dose from 125 mg to 250 mg, three times a day and it and/or location are chosen to accomplish therapeutic or has injectable formulations containing 50mg/ml in 2 ml convenience objectives not offered by conventional and 5ml ampules in IV/IM forms. forms. A modified release dosage form potentially pro- [0005] In prior art, emoxypine is widely used as inject- vides greater effectiveness in the treatment of chronic able preparations but it can not provide enough nootropic 50 conditions; greater convenience; reduces side effects activity over a prolonged period in enjectable prepara- and provides higher levels of patient compliance or ther- tions. It has to be used in higher dosage ranges and long- apeutic performance due to a simplified dosage sched- er time periods such as between 30 to 95 days which is ule, compared with those of immediate-release drugs. not very suitable for the patient compliance and for the Modified release pharmaceutical products are formulat- therapeutic activity ranges of emoxypine. 55 ed to release the drug’s active ingredient gradually and [0006] US patent no 4,486,440 in 17.08.1983, disclos- predictably over a 12-hour to 24-hour period. es injectable solutions and drops containing 1% of emox- [0013] The USP (United States Pharmacopeia) con- ypine HCl by weight. It is used as retinoprotector for treat- siders that the terms controlled release; prolonged re- 2 3 EP 2 241 310 A2 4 lease extended release and sustained release is inter- tion. Preferably, the amount of rate controlling polymer changeable with modified release. Accordingly, the is from about 5.0% to about 70.0% by weight of the for- terms "modified-release", controlled-release", "prolon- mulation. Most preferably, the amont of the rate control- ged-release", "extended-release", and "sustained-re- ling polymer is from about 10.0% to about 60.0% by lease" are used interchangeably herein. 5 weight of the formulation. [0014] One of the advantages of modified release for- [0020] According to another embodiment of this inven- mulation of this invention for the outpatient is reduced tion, the modified release formulation comprises emox- dosage regimens convenience and, more importantly, ypine or a pharmaceutically acceptable salt in an amount better assurance of compliance. For example, the reduc- of about 1.0% to 80.0% by weight of total formulation, tion of a dose regimen from four times a day to three10 preferably about 20.0% to 75.0% by wieght, the most times a day allows the patient to take the prescribed drug preferably about 45.0% to 70.0% by weight. Emoxypine during waking hours. Reduction of a dose regimen to is preferably in the form of succinate or HCl salt. twice a day allows the patient to take the prescribed drug [0021] In a further aspect, the present invention relates in the morning and in the evening, which provides greater to the modified release formulations comprising emox- convenience; e.g., the patient is not required to carry an 15 ypine or a pharmaceutically acceptable salt thereof, in additional one when away from home. Of course, the an amount of 1 mg to 1000mg. Preferably 50 mg to 800 most convenient dosage form is a once daily dose regi- mg, the most preferably 125 mg to 750 mg. men. This also reduces the risk of the omitted tablets. [0022] The modified release formulation of this present [0015] The other advantage of modified release for- invention is administered in the form of a once-a-day or mulations is to make the plasma concentration level sta- 20 twice-a-day dosage regimen. ble by maintaining the drug in the blood stream for a [0023] It has surprisingly found that in this modified longer time period. In this manner, the formulation of this release formulation having a weight ratio of emoxypine invention is designed as modified release to prevent the or a pharmaceutically acceptable salt to rate controlling changes in drug plasma concentration levels and can be polymer between the ranges of about 1:10 to 10: 1 (w/w) administered only once ortwice a day for drugs thatwould 25 has a synergistic effect over the dissolution rate. otherwise have to be taken more frequently to maintain [0024] Another advantageof this invention isto provide required blood levels. Also modified release oral dosage a modified release formulation with a rate controlling pol- forms may help to treat with reduced dosage regimens. ymer, wherein the maximum 30% of total amount of Using lower dosages of active ingredients provide great- emoxypine or a pharmaceutically acceptable salt is re- er convenience and reduced side effects and toxicity. 30 leased in 2 hours and 40-65% in 6 hours and at least [0016] Another advantage of this modified release for- 85% between in a period of 16 to 20 hours. mulations of this invention is to prevent dose dumping. [0025] Rate controlling polymers can be used to form Dose dumping is one of the most important disadvantag- a matrix in which an active substance is dispersed, the es of modified release dosage forms.
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