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WO 2010/092468 Al (12) INTERNATIONALAPPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date 19 August 2010 (19.08.2010) WO 2010/092468 Al (51) International Patent Classification: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A61K 31/015 (2006.01) A61P 1/04 (2006.01) HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, A61K 47/36 (2006.01) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (21) International Application Number: NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, PCT/IB20 10/000275 SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, (22) International Filing Date: TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. 12 February 2010 (12.02.2010) (84) Designated States (unless otherwise indicated, for every (25) Filing Language: English kind of regional protection available): ARIPO (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, (26) Publication Language: English ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (30) Priority Data: TM), European (AT, BE, BG, CH, CY, CZ, DE, DK, EE, PCT/IB2009/000254 ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, 13 February 2009 (13.02.2009) IB MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (72) Inventor; and ML, MR, NE, SN, TD, TG). (71) Applicant : GHISALBERTI, Carlo [BR/BR]; Rua Luis Dias 85/61, ITAIM - BIBI, BR-04542-080 Sao Paulo - Published: SP (BR). — with international search report (Art. 21(3)) (81) Designated States (unless otherwise indicated, for every — before the expiration of the time limit for amending the kind of national protection available): AE, AG, AL, AM, claims and to be republished in the event of receipt of AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, amendments (Rule 48.2(h)) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, (54) Title: COMPOSITION COMPRISING ALGINATES AND D-LIMONENE TO TREAT GERD AND DYSPEPSIA (57) Abstract: The invention refers to nutritional and pharmaceutical compositions for the use in the treatment and relief of GERD and dyspepsia in mammals, including humans The compositions comprise a combination of alginates of low and high molecular weight and d-limonene in microdispersed form. This combination can be further improved with an antacid or an essen tial oil with high cholinesterase inhibitory activity. COMPOSITION COMPRISING ALGINATES AND D-LIMONENE T O TREAT GERD AND DYSPEPSIA FELD OF THE INVENTION The invention relates to a composition comprising alginates and d-limonene in micrαdispersed form to treat gastroesophageal reflux disease (GERD) add dyspepsia. Preferably the composition also comprises an antacid to improve heartburn symptoms, or the d-limonene is further admixed with an essential oil to enhance the. cholincsterase inhibitory action. BACKGROUND GERD and dyspepsia are common ailments in the upper gastro-intesltinal (Gl) tract. Stress directly affect the digestive tract and aggravate bad digestion and GERD, with more than 25% of the population in Western Countries experiencing heartburn once or more times per month, while just 11% in Eastern Asia have at least a monthly heartburn episode. The symptoms include difficulty swallowing, regurgitation of stomach acid and/or food, hoarseness, coughing and irritation of larynx, throat and/or esophagus, whilst the untreated disorders may seriously aggravate, e.g. leading to gastroesophageal cancer. Current therapies in GERD and dyspepsia aim at suppress gastric acid secretion or enhance the gastro-intestinal motility to limit the exposure of the esophagus to acidic gastric contents. Common drugs thus include proton pump inhibitors* histamine H2- blockers, prostaglandin analogues, sulphated polysaccharides, and antacids. A non-prescription approach is provided in U.S. Pat. No. 6,420,435 which discloses a method of treating GERD and related conditions with limonene, presently marketed as EsophaGuard™ by WRC Laboratories, Inc, (Galvesto π, TX, USA). U.S. Pat. No. 2008248136 aims to improve limonene by the combination with antacids, while U.S. Pat. No. 2008292693 combines limonene with Aloe v, hydrocollois. Hydrocolioids are used to reduce the symptoms of heartburn and GERD, as disclosed by G B 2349570; WO 01/661 19; and EP 1859786. Among hydrocolloids, alginates are well-known for their efficacy in GERD therapy. The performance of alginates in GERD was first claimed by Reclcitt Colmann Prod. Inc., presently Reckitt Benckiser Healthcare (UK) in US 4,140,760 an in several other patent applications. The combinations of alginates and antacids such as Gaviscon™, Algicon™, Rennie™, Topaal™ provide an efficient symptomatic relief of OERD (World J Gastroenterol. 2006; 12(5):747-54). Actually, a meta-analysis ranked the alginate formulations as the mosij efficient among the non-prescription treatments of GERD (Tran, Lowry, El-Serag; Alilment Pharmacol Ther, 2007, 25(2): 143-53). Although alginate-based raft products are often categorized among antacids, they are indeed different. Unlike traditional antacids which chemically neutralize gastric acid, or histamine H2-receptor antagonists which pharmacologically reduce acid secretion, alginate rafting products appear to act primarily by a physical, rather than a chemical or pharmacological means. This action provides the rapid onset of action of conventional antacids and a longer effective duration. Although some alginate formulations provide significant neutralization capacity, there does not appear to be a stringent requirement to neutralize bulk gastric contents to achieve efficacy. However, the formulations comprising alginates have a limitation in term of the time needed for the gastric emptying after meal. In fact, the average residence time for Gaviscon at fast is around 3 hours (Beckloff et al. J Clin Pharmacol. 1972; 12:1 1-21). Therefore, there is still a request to ameliorate the therapeutic approach by improving the gastric coating effect while fastening meal transit, so to alleviate the discomfort associated with GERD 1, dyspepsia (indigestion), heartburn and similar QJI disorders. SUMMARY The invention provides an efficient composition for treating GERD and dyspepsia comprising alginate in combination with microdispersed d-lϊmonenet to improve the coating effect onto the internal/distal mucosa while adding a proki etic action, i.e. fasten the gastric emptying. The invention also provides a comprising a mixture of high and low molecular weight alginates in combination with microdispersed d-limonene. The invention also provides a composition as described above to treat GERD and dyspepsia further comprising an antacid. The invention further provides a composition as described above to treat GERD and dyspepsia, wherein d-limonene is blended with an essential ail having high cholinesterase inhibitory activity. The invention furthermore provides a method for the treatment of GERD and dyspepsia in a subject in need thereof by administering a compositions comprising a mixture of high and low molecular weight alginate and microdispersed d-limoneπe, which may be further improved with the addition of an antacid and/υr an essential oil with high cholinesterase inhibitory activity. DETAILED DESCRIPTION In accordance with the present application, the efficacy of alginates ahd d-limonene in the treatment of GERD and dyspepsia can be enhanced by their combined used in a single nutritional/ pharmaceutical composition. In a preferred embodiment, the invention provides a composition to treat GERD and dyspepsia comprising alginates and microdispersed d-limonene. d-Limonene is the major component of citrus rind oil thereto obtained by a press out process, optionally refined by a steam extraction. The collected oil is separated, distilled to recover certain flavor and fragrances, and the collected to recover a food-grade 95% d-limonene. A further distillation affords a high-grade d-limonene, since the material to be used i the invention preferably has purity greater then 95%, more preferably greater than 98%. The high purity d-limonene is required to limit the presence of residual (fragrance) aldehydes and acids of which may impart a strong flavour to the composition and/or deteriorate by oxidation. Such d-limonene is supplied, e.g., by Florida Chemical Comp. Co (Winter Haven, FL, USA) as high purity, food-grade d-limonene (98+%). The microdispersed d-limonene is capable to afford the gastric coating on the internal and distal stomach mucosae while it help in fastening the meal transit, therefore with an improve of the discomfort associated with dyspepsia. Differently from simethicone which were added to several alginate formulations (e.g. Sedomag™), d-Iimonene has limited defoaming properties, so that the formation of the alginate raft is preserved. The expression "microdispersed" herein is equivalent to "microemulsionated" or "microencapsulated" or "microabsorbed" or any lingual variation thereof refers herein to a solid or liquid droplet or granule of any shape with a size below 1 mm, preferably below 100 µm which is capable of holding therein a substantial amount of d-limonene. Microemulsionated d-Iimonene can be obtained by emulsification of d-limonene in water or in a hydroalcoholic solution (e.g. ethanol-water) in the presence of food-grade surfactants including nonionic such as ethoxylated sorbitan esters, polyglycerol esters, sugar ester; and/or anionic such as K or Na oleate, bis(2-ethylhexyl) sodium sulfosuccinate, and phosphatidylcholine; as well as co-emulsifiers such as polyols (e.g. propylene glycol and glycerol), moπoglycerides; and mixture thereof. Microincapsulated d-limonene can be obtained by coacervation, e.g. as in WO 051 05290, to afford gelatine microcapsules with 30% to 65% of d-iimo ene content. Microabsorbed d-limonene can be obtained by physical absorption onto a colloidal granulated (porous) silica, e.g. VP Aereoperl™ 300 Pharma or Sipernat™ 2200 from Degussa (Germany) to afford adsorbed microparticules with 20% to 50% d-Hmonene.
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