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Delrto Ndrrl .7 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (43) International Publication Date (10) International Publication Number 26 May 2006 (26.05.2006) PCT WO 2006/054315 Al (51) International Patent Classification: AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, A61K9108 (2006.01) A61K4700 (2006.01) CO, CR, CU, CZ, DE, DK, DM, DZ, EC, FE, EU, ES, H, A61K31119 (2006.01) C07C 229142 (2006.01) GB, GD, GE, Gi, GM, HR, IJR, ID, IL, IN, IS, JP, KE, A61K 311216 (2006.01) C07C 57138 (2006.01) KG, KM, KP, KR, KZ, LC, LK, LR, LS, LI, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, MI, NO, (21) International Application Number: NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, PCT/IN2005/000339 SL, SM, SY, TJ, TM, TN, IR, T, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. (22) International Filing Date: 19 October 2005 (19.10.2005) (84) Designated States (unless otherwise indicated, for every (25) Filing Language: English kind of regional protection available): ARIPO (BW, Gi, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (26)GM, (26)Pubicatonangage:Engish ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), (30) Priority Data: European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, H, I, L, LU, LV, MC, NL, PL, PT, 2332/DEL/2004 2332DEL20022Novmber200(2211.00422 November 2004 (22.11.2004) ININIS, RO, SE, SI, SK, IR), OAPI (BE, BJ, CF, CG, CI, CM, GA, (71) Applicant (for all designated States except US): VENUS GN, GQ, GW, ML, MR, NE, SN, ID, TG). REMEDIES LIMITED [IN/IN]; S.C.O. 39, Sector 26, Madhya Marg, Chandigarh 160 019 of inventorship (Rule 4.17(D)), (72) Inventor; and (75) Inventor/Applicant (for US only): CHAUDHARY, B D Mau [IN/IN]; 51-52, Industrial Area, Phase-M,Panchkula with internationalP search report 134 113, aryana (IN). with amendedM claims and statement (74) Agent: DUBEY, Rajkumar; Dubey & Partners - Advo- Date of publication of the amended claims and statement: cates, 310 New Delhi House, 27 Barakhamba Road, New 17 August 2006 Delhi 110 001 (IN). For two-letter codes and other abbreviations, refer to the "Guid GMIE S W MNSS, Z Z G M (81) Designated States (unless otherwise indicated, for every dance Notes on Codes andAbbreviations"appearing at the be gin kind of nationalprotection available): AE, AG, AL, AM, ning ofZWErsa each regular issueA, ofZ the FCTY G Gazette. Z MRTT) Euoen(T E BCCCDE K E S I - (54) Title: NONAQUEOUS LIQUID PARENTERAL ACECLOFENACFR0B FORMULATION R U E S T T U V C L L T RO0E I K ROP BF J F G I M A - (57) Abstract: A nonaqueous liquid parenterally deliverable pharmaceuticalGN0Q formulation, W andL moreRNSTT) particularly a nonaqueous liquid -parenteral Aceclofenac formulation comprising the selective NSAID Aceclofenac, is disclosed. A process of preparing Aceclofenac formulation, the therapeutic dosage form and storage of dose, and theDelrto method of treatingndrRl a subject.7 having a condition or a disorder ___wherein treatment with NSAID is indicated, are also disclosed. Diclofenac formed by conversion of Aceclofenac is solubilized by the nonaqueous solubilizer(s), which are substantially inert with respect to such conversion. The composition has Aceclofenac salt stabilizing means for inhibiting precipitation of Aceclofenac. The compositions disclosed in the present invention are stable upon i storage at room temperature and at refrigerated temperatures. Compositions disclosed in the present invention, whether ready-to-use -or requiring dilution prior to administration, can be prepared by inexpensive processes disclosed herein. WO 2006/054315 PCT/IN2005/000339 Title: NON AQUEOUS LIQUID PARENTERAL ACECLOFENAC FORMULATION FIELD OF INVENTION 5 The present invention generally relates to nonaqueous liquid parenterally deliverable pharmaceutical formulation and more particularly to nonaqueous liquid parenteral Aceclofenac formulation comprising the selective NSAID Aceclofenac and still more particularly to pharmaceutically acceptable salts of 10 Aceclofenac. The invention also relates to a process of preparing Aceclofenac formulation, the therapeutic dosage form and storage of dose, and the method of treating a subject having a condition or a disorder wherein treatment with NSAID is indicated. 15 BACKGROUND OF INVENTION The non-steroidal anti-inflammatory drug (NSAID) has a wide range and it is available both in non-prescription and prescription mode. The major groups of NSAID are as follows: 20 a. Salicyclic acid group: aspirin (acetyl salicyclic acid), Choline magnesium trisalicylate, diflunisal and salsalate. b. Propionic acid group: fenoprofen, flurbiprofen, ibuprofen, ketoprofen, naproxen, and oxaprozin. 25 c. Acetic and acid group: diclofenac, aceclofenac, indomethacin, sulindac, and tolmetin. d. Enolic acid group: meloxicam and piroxicam. e. Fenamic acid group: meclofenamate and mefenamic acid. f. Napthylalkenone group: nabumetone. 30 g. Pyarnocarboxylic acid group: etodalac. h. Pyrrole group: Keterolac. i. COX-2 inhibitor group: Celecoxib, valdecoxib and rofecoxib. SUBSTITUTE SHEET (RULE 26) WO 2006/054315 PCT/IN2005/000339 Some of different NSAIDs are available in one or more forms like tablets, injections, and dry powder for injection form. The present invention relates to "ready to use injection of aceclofenac." 5 The disadvantages of other NSAIDs as compared to the present invention are given below. 1) Dry powder injectable NSAID needs to be lyophilized and then reconstituted before use. The process is costly and cumbersome. 10 2) Injection form is more advantageous over oral form as serum concentration of oral NSAID is lesser because of intestinal metabolism of the drug. 3) Serum concentration of oral NSAID is unpredictable. 4) The frequency of administration of oral NSAID is higher. 15 5) Diclofenac has more side-effects than Aceclofenac. 6) NSAID's injections such as indometacin have lesser tolerability than Aceclofenac. 7) Ketoprofen is less stable than Aceclofenac. 20 Parenteral drug formulations have become a very important component in the arsenal of available drug delivery options, particularly for drugs having analgesic effect. Parenteral routes of administration, including subcutaneous, intramuscular and intravenous injection, offer numerous benefits over oral delivery in particular situations, for a wide variety of drugs. For example, 25 parenteral administration of a drug typically results in attainment of a therapeutically effective blood serum concentration of the drug in a shorter time than is achievable by oral administration. This is especially true of intravenous injection, whereby the drug is placed directly in the bloodstream. Parenteral administration can also result in more predictable blood serum concentrations of 30 a drug, because losses in the gastrointestinal tract due to metabolism, binding to food and other causes are eliminated. For similar reasons, parenteral administration often permits dose reduction. Parenteral administration is generally the preferred method of drug delivery in emergency situations, and is also useful in treating subjects who are uncooperative, unconscious, or 2 SUBSTITUTE SHEET (RULE 26) WO 2006/054315 PCT/IN2005/000339 otherwise unable or unwilling to accept oral medication, and where a faster relief is required in lesser time, specially in acute and chronic painful condition. If a parenteral drug formulation is to be prepared, it is preferable from patient 5 convenience and safety standpoints that such a formulation be a ready-to-use formulation, i.e. one that does not require dilution or mixing immediately prior to use (as opposed to a reconstitutable formulation). Ready-to-use and dilutable liquid parenteral formulations can also be advantageous from a manufacturing standpoint by avoiding expensive lyophilization and/or other similar 10 manufacturing steps. Aceclofenac is a phenyl acetic acid derivative which inhibits interleukini1p induced prostaglandin E2 production but has poor COX-l inhibitor effect in oral form. This formulation converts it to the Diclofenac, the COX-1 and COX-Il 15 inhibitor, following administration to a subject, itself shows enhanced inhibitory activity against both COX-1 and COX-2. Because Diclofenac has very poor gastrointestinal (GI) tolerability ,it is not particularly well suited for formulation. By contrast, because of the better GI 20 tolerability of aceclofenac and lesser side effects than diclofenac, Aceclofenac has been proposed by the inventor for liquid formulation. Unfortunately, attempts to formulate Aceclofenac as a ready-to-use solution for injection have heretofore been complicated by the fact that Aceclofenac , when 25 in solution and especially in presence of certain excipients, is unstable, and undergoes degradation which may precipitate out making injection unsuitable for use. One potential solution to this problem is to provide a dry reconstitutable 30 Aceclofenac formulation which is mixed with a liquid vehicle just prior to administration but this too is not stable for longer period. However, in many situations it is particularly advantageous to provide a liquid formulation, more especially a ready-to-use formulation, as indicated above. 3 SUBSTITUTE SHEET (RULE 26) WO 2006/054315 PCT/IN2005/000339 If a liquid parenterally deliverable formulation of Aceclofenac or a pharmaceutically acceptable salt thereof, particularly such a formulation that is ready-to-use, that is storage stable at room temperature could be prepared, a 5 significant advance in treatment of COX-2 mediated conditions
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