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Ep 2328426 B1 (19) TZZ ¥ _T (11) EP 2 328 426 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A23L 1/236 (2006.01) A23L 1/09 (2006.01) 01.10.2014 Bulletin 2014/40 (86) International application number: (21) Application number: 09803591.8 PCT/US2009/052258 (22) Date of filing: 30.07.2009 (87) International publication number: WO 2010/014813 (04.02.2010 Gazette 2010/05) (54) COMPOSITIONS COMRPISING SWEETNESS ENHANCERS AND METHODS OF MAKING THEM ZUSAMMENSETZUNGEN MIT SÜSSKRAFTVERSTÄRKERN UND HERSTELLUNGSVERFAHREN DAFÜR COMPOSITIONS COMPRENANT DES EDULCORANTS ET LEURS PROCEDES DE PREPARATION (84) Designated Contracting States: • WARD, Jennifer AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Spring Valley HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL CA 91977 (US) PT RO SE SI SK SM TR • ALATORRE, Ana San Diego (30) Priority: 31.07.2008 US 85228 P CA 92110 (US) • LEBIEN, Thitiwan (43) Date of publication of application: Carlsbad 91016, (US) 08.06.2011 Bulletin 2011/23 (74) Representative: Leissler-Gerstl, Gabriele (73) Proprietor: Senomyx, Inc. Hoefer & Partner San Diego, CA 92121 (US) Patentanwälte Pilgersheimer Strasse 20 (72) Inventors: 81543 München (DE) • SHIGEMURA, Rhondi Encinitas (56) References cited: CA 92024 (US) WO-A2-2008/154221 US-A1- 2002 025 366 • PODGURSKI, Carolyn US-A1- 2005 196 503 US-A1- 2006 045 953 San Diego US-A1- 2006 257 543 US-A1- 2007 003 680 CA 92129 (US) • KITISIN, Boriruck Carlsbad CA 92010 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 328 426 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 328 426 B1 Description FIELD OF THE INVENTION 5 [0001] This invention relates to solid and liquid compositions comprising 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6] thiadiazin-5-yloxy)-2,2’-dimethyl-N-propylpropanamide, or salts, and/or solvates thereof, and one or more sweeteners, methods of making such compositions, and methods of making ingestible products comprising such compositions. BACKGROUND OF THE INVENTION 10 [0002] Low calorie or diabetic foods can be prepared by replacing some or all of the natural sweetener (e.g., sucrose, fructose, corn syrup, etc.) with low calorie sweeteners such as saccharin, aspartame, or acesulfame potassium. However, artificial sweeteners such as saccharin and acesulfame potassium can have bitter and/or metallic aftertastes, and high intensity sweeteners such as sucralose and aspartame, although providing a level of sweetness similar to sugar without 15 bitter or metallic aftertastes, can have "sweetness delivery" problems, e.g., different rates and time periods for the onset and linger of the sweet taste. As a result, it is difficult to formulate low calorie diabetic foods with reduced natural sweete ner levels, having the same sweetness characteristics as "regular" non-dietetic products sweetened with e.g., sucrose and/or fructose. [0003] Sweetness enhancers (for example those described in publication Nos. US 2008-0306093A1, US 20 2008-0306053A1, and WO 2008/154221) are compounds which enhance the perceived sweetness of various natural and artificial sweeteners. Thus, low calorie foods containing sweetness enhancers can be formulated with acceptable sweetness characteristics, yet significantly lower levels of sweeteners. However, formulating foods containing sweetness enhancers can be challenging, due to the high potency and/or low solubility of some sweetness enhancers. For example, highly potent sweetness enhancers require precise and uniform mixing of low levels of the sweetness enhancer in the 25 food to avoid batch-to-batch variability in the perceived sweetness of the food. Accordingly, low solubility sweetness enhancers may require special processing methods to permit formulation of reduced/low calorie foods in a commercially acceptable manner. [0004] US2007/003680A1 discloses man-made bi-aromatic amide compounds that, when contacted with comestible food or drinks or pharmaceutical compositions at concentrations preferably on the order of about 100 ppm or lower, 30 serve as sweet taste modifiers, sweet flavoring agents, or sweet flavor enhancers, for use in foods, beverages, and other comestible products, or orally administered medicinal products or compositions, optionally in the presence of or in mixtures with conventional flavoring agents such as known natural saccharide sweeteners and previously known artificial sweeteners. [0005] US2006/045953A1 discloses non-naturally occurring amide compounds that are capable, when contacted with 35 comestible food or drinks or pharmaceutical compositions at concentrations preferably on the order of about 100 ppm or lower, of serving as savory ("umami") or sweet taste modifiers, savory or sweet flavoring agents and savory or sweet flavor enhancers, for use in foods, beverages, and other comestible or orally administered medicinal products or com- positions, optionally in the presence of or in mixtures with conventional flavoring agents such as monosodium glutamate or known natural and artificial sweeteners. 40 [0006] The present invention is directed to improved compositions comprising sweetness enhancers, and methods for preparing such compositions. SUMMARY OF THE INVENTION 45 [0007] The present invention is defined in the claims. [0008] In one embodiment, the present invention is directed to a composition comprising a plurality of solid particles, each particle comprising a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c] [1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates thereof, as described in claim 1. [0009] In another embodiment, the present invention is directed to a solution or suspension comprising a sweetness 50 enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dime- thyl-N-propylpropanamide, or salts and/or solvates thereof; and at least one food grade solvent, as described in claim 5. [0010] In another embodiment, the present invention is directed to a composition comprising a plurality of solid particles, each particle comprising a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c] [1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates thereof prepared by spray drying, 55 precipitation, crystallization, or spin band entrapment. [0011] In another embodiment, the present invention is directed to a solution or suspension comprising a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dime- thyl-N-propylpropanamide, or salts and/or solvates thereof prepared by spray drying, precipitation, crystallization, or 2 EP 2 328 426 B1 spin band entrapment. [0012] In another embodiment, the present invention is directed to an ingestible composition comprising a plurality of solid particles, each particle comprising a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2- dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates thereof in 5 combination with at least one edible ingredient, as described in claim 11. [0013] In another embodiment, the present invention is directed to a method of making a composition comprising a plurality of solid particles, each particle comprising a sweetness enhancer, wherein the sweetness enhancer is 3-(4- amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates said method comprising spray drying a solution comprising 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5- 10 yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates thereof, and a solvent, as described in claim 34. [0014] In another embodiment, the present invention is directed to a method of making an ingestible composition said method comprising combining solid particles of a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino- 2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or solvates with at least one edible ingredient, as described in claim 35. 15 [0015] In another embodiment, the present invention is directed to a method of making an ingestible composition said method comprising combining a solution or suspension of a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dimethyl-N-propylpropanamide, or salts and/or sol- vates thereof with at least one edible ingredient, as described in claim 36. [0016] In another embodiment, the present invention is directed to a method of reducing the amount of sweetener in 20 a sweetener-containing ingestible composition, comprising replacing the sweetener in the sweetener-containing ingest- ible composition with an effective amount of sweetener and a composition comprising solid particles of a sweetness enhancer, wherein the sweetness enhancer is 3-(4-amino-2,2-dioxide-1H-benzo[c][1,2,6]thiadiazin-5-yloxy)-2’,2’-dime- thyl-N-propylpropanamide, or salts and/or solvates thereof, as described in claim 37. 25 BRIEF DESCRIPTION OF THE DRAWINGS [0017] Figure 1 is a graph showing the sweetness enhancing effect of Compound A for one embodiment of a sweetener. 30 Figure 2 is a graph showing the sweetness enhancing effect of Compound A for one embodiment of a sweetener when Compound A is at different concentrations. Figure 3 is a graph showing the sweetness enhancing effect of Compound A when the sweetener is at different concentrations.
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