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(12) Patent Application Publication (10) Pub. No.: US 2011/0269724 A1 KRANTZ (43) Pub

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(12) Patent Application Publication (10) Pub. No.: US 2011/0269724 A1 KRANTZ (43) Pub US 20110269724A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0269724 A1 KRANTZ (43) Pub. Date: Nov. 3, 2011 (54) COMBINATION THERAPY WITH Publication Classification NON-SELECTIVE COXINHIBITORSTO (51) Int. Cl. PREVENT COX-RELATED GASTRIC A6II 3/44 (2006.01) INURES A6II 3/66 (2006.01) A613/60 (2006.01) (75) Inventor: Alexander KRANTZ, (US) A613/618 (2006.01) A613/603 (2006.01) A6IP 7/06 (2006.01) (73) Assignee: Cortria Corporation, Needham, A6IP II/06 (2006.01) MA (US) A6IP 9/02 (2006.01) A6IP 25/06 (2006.01) (21) Appl. No.: 13/100,204 A6IP 7/06 (2006.01) A6IP 9/10 (2006.01) A6IP 9/08 (2006.01) (22) Filed: May 3, 2011 A6II 3/545 (2006.01) A6IP 29/00 (2006.01) Related U.S. Application Data (52) U.S. Cl. ......... 514/161; 514/356; 514/355; 514/352: 514/226.5 (62) Division of application No. 1 1/715,660, filed on Mar. (57) ABSTRACT 8, 2007. The present invention is directed to nicotinamide, nicotina mide derivatives and prostaglandin mimetics, alone or in (60) Provisional application No. 60/780.264, filed on Mar. combination with an NSAID, and their use in treating pain, 8, 2006. inflammation, and/or gastrointestinal toxicty, US 2011/0269724 A1 Nov. 3, 2011 COMBINATION THERAPY WITH began marketing Arthrotec for the treatment of arthritis in NON-SELECTIVE COXINHIBITORSTO patients at risk for developing GI ulcers. This product con PREVENT COX-RELATED GASTRIC tains misoprostol (a cytoprotective prostaglandin) and the INURES NSAID diclofenac. Although patients administered Arthro tecTM do have a lower risk of developing ulcers, they may RELATED APPLICATION experience a number of other serious side effects such as diarrhea, severe cramping and, in the case of pregnant 0001. This application claims priority to U.S. Provisional women, potential damage to the fetus. Application No. 60/780.264, Attorney Docket No. PRI-004 0006 Another approach has been to produce enteric 1, filed Mar. 8, 2006, titled “COMBINATION THERAPY coated NSAID products. However, even though these have WITH NON-SELECTIVE COX INHIBITORS TO PRE shown modest reductions in gastroduodenal damage in short VENT COX-RELATED GASTRIC INJURIES” which is term studies (Scand. J. Gastroenterol. 20: 239-242 (1985) and incorporated herein by reference in its entirety. Additionally, Scand. J. Gastroenterol. 25:231-234 (1990)), there is no con the contents of any patents, patent applications, and refer sistent evidence of a long term benefit during chronic treat ences cited throughout this specification are hereby incorpo ment. rated by reference in their entireties. 0007 Overall, it may be concluded that the risk of gas trointestinal toxicity in the form of gastritis, peptic erosions, BACKGROUND OF THE INVENTION ulcerations, GI bleeds, etc., is a recognized problem associ 0002. Non-steroidal anti-inflammatory drugs (NSAIDs), ated with the administration of NSAIDs and that, despite including compounds such as ibuprofen, ketoprofen and considerable effort, an ideal solution has not yet been found. diclofenac, have anti-inflammatory actions and are effective on pair; associated with the release of prostaglandins and SUMMARY OF THE INVENTION other mediators of inflammation. For example, diclofenac is 0008. In one aspect, the invention provides a pharmaceu considered to be extremely potent and effective as an analge tical composition comprising an NSAID and a prostaglandin sic and anti-inflammatory agent. Diclofenac is approved in mimetic. In one embodiment, the prostaglandin mimetic is the United States for the long-term symptomatic treatment of selected from the group consisting of genistein, daidzein, rheumatoid arthritis, osteoarthritis and alkylosing spondyli tamoxifen, tetrandrine, thapsigargin and a compound of for tis. It is also considered to be useful for the short-term treat mula (I): ment of acute musculoskeletal injury, acute painful shoulder, postoperative pain and dysmenorrhea. Furthermore, NSAIDs have been widely used in arthritis therapy for several years. (I) 0003. Although NSAIDs are widely accepted as effective R5 6 agents for controlling pain, their administration can lead to the development of gastroduodenal lesions, e.g., ulcers and erosions, in Susceptible individuals. It has been Suggested Cor that, a major factor contributing to the development of these lesions is the presence of acid in the stomach and upper Small (CH3) (X), intestine of patients. This view is supported by clinical studies demonstrating an improvement in NSAID tolerability when patients are also taking, independent doses of acid inhibitors whereinnis 0 or 1: R is H. For Cl; Risazido, C(O)CHN (Dig. Dis. 12:210-222 (1994); Drug Safety 21:503–512 - N(H)C(O)NH, -N(H)C(O)H, -C(O)R or the following (1999); Aliment. Pharmacol. Ther. 12:135-140 (1998); Am. J. 5-membered heterocycle: Med. 104(3A):67S-74S (1998); Clin. Ther. 17:1159-1173 (1995)). Other major factors contributing to NSAID-associ ated gastropathy include a local toxic effect of NSAIDs and inhibition of protective prostaglandins (Can. J. Gastroenterol. 13:135-142 (1999) and Pract. Drug Safety 21:503-512, (1999)), which may also make some patients more Suscep tible to the ulcerogenic effects of other noxious stimuli. 0004 Attempts to develop NSAIDs that are inherently less toxic to the gastrointestinal tract have met with only limited wherein R is NR'R' or OR; R and Reach, independently, Success. For example, the recently developed cyclooxyge are hydrogen or Calkyl; R is hydrogen, Calkyl or nase-2 (COX-2) inhibitors show a reduced tendency to pro CHOH: W and Zare, independently, C(H) or N: A is O.S or duce gastrointestinal ulcers and erosions, but a significant risk NH; and X is a physiologically suitable counter-anion.” is still present, especially if the patient is exposed to other 0009. In another embodiment, the prostaglandin mimetic ulcerogens (JAMA 284:1247-1255 (2000): N. Eng. J. Med. is a prostacyclin mimetic. In yet another embodiment, the 343:1520-1528 (2000)). In addition, the COX-2 inhibitors prostaglandin mimetic is a prostaglandin agonist. In still may not be as effective as other NSAIDs at relieving some another embodiment, prostaglandinagonist is selected from a types of pain and have been associated with significant car PGI2 agonist or a PGE agonist. In another embodiment, the diovascular problems (JADA 131: 1729-1737 (2000); SCRIP agonist is selected from the group consisting of U46619, 2617, pg. 19, Feb. 14, 2001). I-BOP, STA, BW245C, L-644698, ZK110841, 13, 15-dihy 0005. Other attempts to produce an NSAID therapy with dro-15-keto-PGD, indomethacin, 15-R-methyl-PGD, 15d less gastrointestinal toxicity have involved the concomitant PGJ, ONO-KI-004, iloprost, 17-phenyl-trinor PGE, sulpro administration of a cytoprotective agent. In 1998, Searle stone, butaprost, 11-deoxy PGE, AH13205, ONO-AEI-259, US 2011/0269724 A1 Nov. 3, 2011 sulprostone, MB28767, misoprostol, SC46275, ONO-AE cet's syndrome, polymyositis, hyperSensitivity, conjunctivi 249, PGE-OH, ONO-AEI-329, cicaprost, carbacyclin, flu tis, gingivitis, Swelling occurring after injury and myocardial prostenol, latanoprost, travoprost, bimatoprost, beraprost, ischemia. In yet another embodiment, the arthritis is selected cloprostenol sodium, eicosopentanoic acid, docosohexanoic from rheumatoid arthritis, spondyloarthopathies, gouty acid, ceramide, Sodium butyrate and aluminum fluoride. arthritis, Systemic lupus erythematosus, osteoarthritis and 0010. In another embodiment, the invention provides use juvenile arthritis. In still another embodiment, the inflamma of the pharmaceutical composition of the invention, for the tory disorders of the skin are selected from the group consist treatment or prevention of deleterious effects associated with ing of psoriasis, eczema, burns and dermatitis. In another NSAID administration in a subject. In one embodiment, the embodiment, the gastrointestinal conditions are selected deleterious effects associated with NSAID administration in from the group consisting of inflammatory bowel syndrome, a Subject is related to a decrease in one or more prostaglandins Crohn's disease, gastritis, irritable bowel syndrome and anywhere in the gastrointestinal tract. In another embodi ulcerative colitis. In yet another embodiment, the pain is ment, the deleterious effects associated with NSAID admin selected from the group consisting of menstrual pain, low istration in a subject is related to a decrease in one or more back pain, neck pain, skeletal pain, post-partum pain, head prostaglandins in the stomach. In still another embodiment, ache, pain associated with migraine, toothache, sprains, the prostaglandins are PGE and/or PGI. In another embodi strains, arthritis, degenerative joint diseases, gout, ankylosing ment, the deleterious effect associated with NSAID adminis spondylitis, bursitis, burns, including radiation and corrosive tration in a Subject is GI toxicity. In yet another embodiment, chemical injuries, Sunburns, bone fracture, immune and the GI toxicity is selected from the group consisting of gas autoimmune diseases, cellular neoplastic transformations or tritis, peptic erosions, ulceration, gastric lesions and GI metastic tumor growth, and pain following Surgical and den bleeds. tal procedures. In another embodiment, the arthritis is 0011. In another embodiment, the NSAID for use in the selected from rheumatoid arthritis, spondyloarthopathies, invention is selected from the group consisting of aspirin, gouty arthritis, systemic lupus erythematosus, osteoarthritis indomethacin, Voltaren, naprosyn,
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