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WO 2010/120253 Al (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 21 October 2010 (21.10.2010) WO 2010/120253 Al (51) International Patent Classification: Tarcan Sokak No:5/1, Gayrettepe ISTANBUL 34349 A61K 31/704 (2006.01) A61K 31/5415 (2006.01) (TR). A61K 45/06 (2006.01) A61K 31/542 (2006.01) (74) Agent: KAYACAN, Vidan; Kirkkonaklar Mh. 327. Sk. A61P 19/00 (2006.01) No: 13/13, Qankaya ANKARA 06610 (TR). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/TR2009/000137 kind of national protection available): AE, AG, AL, AM, (22) International Filing Date: AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, 4 November 2009 (04.1 1.2009) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (25) Filing Language: English HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (26) Publication Language: English KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (30) Priority Data: NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, 2009/03036 17 April 2009 (17.04.2009) TR SE, SG, SK, SL, SM, ST, SV, SY, TJ, TM, TN, TR, TT, (71) Applicant (for all designated States except US): TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. MUSTAFA NEVZAT ILAC SANAYII A.S. [TR/TR]; (84) Designated States (unless otherwise indicated, for every Pak Is Merkezi, Prof. Dr. Bϋlent Tarcan Sok. 5/1, 80290 kind of regional protection available): ARIPO (BW, GH, Gayrettepe, Istanbul (TR). GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (72) Inventors; and ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (75) Inventors/Applicants (for US only): PISAK, Ibrahim TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, Mustafa Iskender [TR/TR]; Pak Is Merkezi; Prof.Dr.Bϋ- ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, lent Tarcan Sokak No:5/1, Gayrettepe ISTANBUL 34349 MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, (TR). SELAMOGLU, Mehmet Levent [TR/TR]; Pak Is TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Merkezi; Prof.Dr.Bulent Tarcan Sokak No: 5/1, Gayrette ML, MR, NE, SN, TD, TG). pe ISTANBUL 34349 (TR). BINGOL, Semra [TR/TR]; Published: Pak Is Merkezi; Prof.Dr.Bulent Tarcan Sokak No:5/1, Gayrettepe ISTANBUL 34349 (TR). SERBETCIOGLU, — with international search report (Art. 21(3)) Marie Brunet [TR/TR]; Pak Is Merkezi; Prof.Dr.Bulent (54) Title: THIOCOLCHICOSIDE AND NON-STEROIDAL ANTI-INFLAMMATORY DRUG COMBINATIONS (57) Abstract: This invention relates to pharmaceutical compositions and unit dosage forms containing in combination: the mus- cle relaxant thiocolchicoside or a salt of thereof or any therapeutically active stereoisomer thereof, substantially free of its other stereoisomers; a non-steroidal anti-inflammatory drug (NSAID). Thiocolchicoside and non-steroidal anti-inflammatory drug combinations This invention relates to pharmaceutical compositions and unit dosage forms containing in combination: i. the muscle relaxant thiocolchicoside or a salt of thereof or any therapeutically active stereoisomer therof, substantially free of its other stereoisomers; ii. a non-steroidal anti-inflammatory drug (NSAID). The pharmaceutical compositions are useful for the treatment of musculo-skelatal disorders and the treatment of pain and inflammation in mammalian organism, especially for the treatment of low back pain. Thiocolchicoside is a glycosulfurated analogue of colchicine and is a well known centrally acting muscle relaxant used in the treatment of musculo-skelatel disorders. Its chemical structure is shown in the Formula 1. Formula 1 The chemical name of thiocolchicoside is N-[3-(β-D-glucopyranosyloxy)-l,2- dimethoxy-10-(methylthio)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide. The usual initial dose is 16 mg daily by oral administration in the form of capsules or tablets. It is also used for intramuscular administration in doses up to 8 mg per day or for topical application as cream, ointment, gel or aerosol. The non-steroidal anti-inflammatory drugs have been utilized in the treatment of pain and inflammation, as well as for a variety of disorders including rheumatoid and osteoarthritis. They vary widely in their chemical structure and biological profiles as analgesics, anti-inflammatory agents and antipyretic agents. They present a superior analgesic and anti-inflammatory activity compared to aspirin and paracetamol but also less side effects like gastrointestinal ulcerations and bleeding experienced with aspirin or hepatic toxicity with large doses of paracetamol. Centrally acting skeletal muscle relaxants are generally prescribed either as single agents or as components of combination products. Several commercial combinations of a muscle relaxant and aspirin have been approved by the US FDA and are marketed in the USA like carisoprodol + aspirin (Soma Compound, Meda Pharms), carisoprodol + aspirin + codeine (Soma Compound W/ Codeine), methocarbamol + aspirin (Methocarbarbamol and Aspirin, Ivax Pharms) and orphenadrine + aspirin + caffeine (Norgesic Forte, Graceway). However, few combinations of the muscle relaxant thiocolchicoside with NSAID have been described in the past and none of the descriptions includes the combinations disclosed in the present invention. French patent FR 2725134 Bl (Laboratoire Lederle), filed on 04.10.1994, describes a new combination comprising ibuprofen or a pharmaceutically acceptable salt thereof and thiocolchicoside or a pharmaceutically salt salt thereof in a weight ratio generally comprising between approximately 1:50 and approximately 1:200 for oral administration in a form of a capsule, a tablet or granules. European patent EP 0837684 Bl (Sanofi-Synthelabo), filed on 12.06.1996, describes a new combination comprising a diclofenac salt and thiocolchicoside with at least one pharmaceutically acceptable excipient and provided in a solid form which is stable over time. European patent EP 1992333 Al (Sanovel) describes a composition comprising flurbiprofen and an alpha-2 adrenergic receptor agonist or a gamma-aminobutiric acid receptor agonist, in particular tizanidine and thiocolchicoside. The physicochemical compatibility of the injectable mixture of thiocolchicoside and other drugs frequently used in association, like anti-inflammatory drugs or vitamins, have been shown for a period of three hours at room temperature in solution (Farmaco. 2002 Nov; 57(1 1):925-30). The addition of thiocolchicoside to NSAID standard treatment has shown more effective results for the treatment of low back pain than the NSAID alone. In addition, the combination was well tolerated and produced no more adverse reactions than the NSAID alone (J Orthopaed Traumatol (2002) 3-103-108). The present invention describes new combinations of thiocolchicoside and NSAID in unit dosage form which is stable over time. The present invention relates to a combination of the muscle relaxant thiocolchicoside and its pharmaceutically acceptable salts with at least one non-steroidal anti¬ inflammatory drug and at least one pharmaceutically acceptable non-toxic carrier adapted for unit dose administration. The muscle relaxant for use in the pharmaceutical compositions and methods of use of the present invention is thiocolchicoside. The invention includes any pharmaceutically acceptable salt of thiocolchicoside and any therapeutically active stereoisomer of thiocolchicoside, substantially free of its other stereoisomers. The amount of thiocolchicoside useful in the practice of the present invention may vary from 4 mg to 16 mg depending on the mode of administration. The preferred amount of thiocolchicoside is selected from a range 4 to 8 mg per unit for parenteral administration. The preferred amount of thiocolchicoside is selected from a range 8 to 16 mg per unit for oral administration. The NSAID for use in the pharmaceutical compositions and methods of use of the present invention may be chosen from the group consisting of, but not limited to, the oxicams, the fenamic acid derivatives, the acetic acid derivatives, the propionic acid derivatives, the coxibs and other NSAIDs. They include all their pharmaceutically acceptable salts of thereof or therapeutically active stereoisomers therof, substantially free of their other stereoisomers. These compounds are well known to those skilled in art and described in various literature reference sources like the Merck Index for their chemical structures, pharmacological activities, side effects, normal dosage ranges, etc. The preferred oxicams for use in the present invention include, but are not limited to, lornoxicam, tenoxicam, meloxicam and piroxicam. The preferred fenamic acid derivatives for use in the present invention include, but are not limited to, mefenamic acid and etofenamate. The preferred acetic acid derivatives for use in the present invention include, but are not limited to, etodolac, acemetacin and indometacin. The preferred propionic acid derivatives for use in the present invention include, but are not limited to, tiaprofenic acid, naproxen and oxaprozin. The preferred coxibs for use in the present invention include, but are not limited to, celecoxib, rofecoxib, lumiracoxib and valdecoxib. The preferred other NSAID' s for use in the present invention include, but are not limited to, nimesulide. The preferred unit dose for the preferred compounds mentionned hereinabove are listed in Table 1. Compound Preferred
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