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Zubereitungen Zur Oralen Aufnahme

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Zubereitungen Zur Oralen Aufnahme (19) TZZ ¥Z__T (11) EP 2 730 178 A1 (12) EUROPÄISCHE PATENTANMELDUNG (43) Veröffentlichungstag: (51) Int Cl.: 14.05.2014 Patentblatt 2014/20 A23L 1/314 (2006.01) A23L 2/385 (2006.01) A23L 2/56 (2006.01) A23L 1/226 (2006.01) (2006.01) (2006.01) (21) Anmeldenummer: 12192171.2 A61K 8/37 A61Q 11/00 A61K 47/14 (2006.01) (22) Anmeldetag: 12.11.2012 (84) Benannte Vertragsstaaten: • Krammer, Gerhard AL AT BE BG CH CY CZ DE DK EE ES FI FR GB 37603 Holzminden (DE) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Ley, Jakob PL PT RO RS SE SI SK SM TR 37603 Holzminden (DE) Benannte Erstreckungsstaaten: • Reichelt, Katharina BA ME 37603 Holzminden (DE) (71) Anmelder: Symrise AG (74) Vertreter: Fabry, Bernd 37603 Holzminden (DE) IP2 Patentanwalts GmbH Schlossstrasse 523 (72) Erfinder: 41238 Mönchengladbach (DE) •Obst,Katja 37603 Holzminden (DE) (54) Zubereitungen zur oralen Aufnahme (57) Vorgeschlagen werden Zubereitungen zur ora- dessen Stereoisomere oder deren Mischungen, len Aufnahme, enthaltend (b) mindestens einen Stoff mit bitterem, adstringieren- (a) Milchsäure-1-menthylester der allgemeinen Formel dem und/ odermetallischem Geschmackseindrucksowie (I), gegebenenfalls (c) weitere Aromastoffe. Ebenfalls offenbart ist die Verwendung von Milch- säure-1-menthylestern der Formel (I) zur Maskierung von unangenehmen Geschmackseindrücken bei Zube- reitungen zur oralen Aufnahme. EP 2 730 178 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 730 178 A1 Beschreibung Gebiet der Erfindung 5 [0001] Die Erfindung befindet sich auf dem Gebiet der Aromastoffe und betrifft den Einsatz von speziellen Milchsäu- reestern zur Maskierung von unangenehmen Geschmacksnoten. Stand der Technik 10 [0002] Nahrungs- und Genussmittel enthalten häufig eine Vielzahl verschiedener Bitterstoffe, die zwar einerseits in bestimmten Lebensmitteln in Maßen erwünscht sind und zu deren charakteristischen Geschmack beitragen (z.B. Coffein in Tee oder Kaffee, Chinin in so genannten Bitter-Lemon-Getränken, Bitterstoffe aus Hopfen in Bier), andererseits den Wert aber auch stark mindern können. Dazu gehören z.B. Flavonoidglycoside und Limonoide in Zitrus-Säften, der bittere Nachgeschmack vieler hochintensiver Süßstoffe wie Aspartam, Cyclamat, Acesulfam K, Rebaudiosid A, Glyccyrhizin- 15 säure oder Saccharin sowie der unangenehme Geschmack, den hydrophobe Aminosäuren und Peptide in Käse verur- sachen können. [0003] Bittergeschmack wird regelmäßig durch einzelne Stoffe verursacht, die an spezielle Bitterrezeptoren auf Ge- schmackszellen, die in den so genannten Geschmacksknospen auf der Zunge zu finden sind, binden und über neuro- chemische Kaskaden ein Signal an das Gehirn senden, dass eine Abwehrreaktion und einen negativen Geschmack- 20 seindruck verursacht (vgl. Meyerhof, Reviews of Physiology, Biochemistry and Pharmacology 2005, 154, 37-72 ). [0004] Adstringierender Geschmack wird in der Regel durch Fällung von Prolin-reichen Proteinen im Speichel durch Adstringentien, z.B. Metallsalze, Polyphenole wie (Gallo-)Catechine, Proanthocyanidine, andere Flavonoide oder Tan- nine, verursacht. Der normalerweise als "Schmiermittel" dienende homogene Speichel enthält dann denaturierte Pro- teine, die die Gleitfähigkeit herabsetzen und dadurch ein raues oder trockenes, auch als adstringierend empfundenes 25 Gefühl im Mund hinterlassen (vgl. Am. J. Clin. Nutr. 2005, 81, 330S-335S). [0005] Insbesondere zur Senkung des natürlichen Gehalts an Adstringentien ist dementsprechend oft eine nachträg- liche Behandlung nötig, beispielsweise durch einen zu verwerfenden Voraufguss bei grünem Tee zur Entfernung von Catechinen,oder enzymatisch, z.B. Behandlung von Tee mit zersetzenden Enzymen zurZerstörung deradstringierenden Polyphenole, wie in WO 2003 022065 A1 (Unicafe) oder JP 2007 135481 A1 (Kikkoman) beschrieben, oder Einsatz von 30 speziellen Peptidasen bei der Reifung von Käse. [0006] Diese Behandlungen zur Senkung des natürlichen Gehalts an Adstringentien sind belastend für das Produkt, erzeugen Abfallstoffe und bedingen z.B. auch Lösungsmittelreste und andere Rückstände (Enzyme) in den Produkten. [0007] Daher ist es wünschenswert, Stoffe zu finden, die unangenehme Geschmackseindrücke, insbesondere ad- stringierende, trockene, mehlige, staubige, kalkige und/oder metallische Geschmackseindrücke, in kleinsten Konzent- 35 rationen wirkungsvoll unterdrücken, oder zumindest vermindern können. [0008] Besonders wichtig ist die Unterdrückung unangenehmer Geschmackseindrücke auch bei vielen pharmazeu- tischen Wirkstoffen, da dadurch die Bereitschaft der Patienten, insbesondere bei Kindern, die den Wirkstoff enthaltende Zubereitung oral zu sich zu nehmen, deutlich erhöht werden kann. Viele pharmazeutische Wirkstoffe, beispielsweise Aspirin, Salicin, Paracetamol, Ambroxol oder Chinin, um nur eine sehr kleine Auswahl zur Verdeutlichung zu nennen, 40 haben einen ausgeprägten adstringierenden und/oder metallischen Geschmack und/oder Nachgeschmack. [0009] Klassischerweise werden als Gegenmittel für Adstringentien Fettemulsionen verwendet, deren Verwendung in vielen Fällen aber nicht angezeigt ist, so z.B. in fettfreien Getränken oder gesundheitsbewussten fettarmen Produkten. [0010] In JP 2000 287630 A1 (Shiga) und WO 2006 013930 A1 (Suntory) wird eine Methode beschrieben, den ad- stringierenden Geschmack von Polyphenolen in Teegetränken unter Verwendung von Zucker und bestimmten Amino- 45 säuren zu mindern. Dabei werden die Aminosäuren im Bereich von 0,04 bis 0,1 % eingesetzt. [0011] In JP 2001 046037 A1 (Kikkoman) wird die Minderung des adstringierenden Geschmacks von Polyphenolen mit Stärke und Proteinen erreicht. Dieses Verfahren birgt jedoch den Nachteil, dass insbesondere Proteine und Stärken großen Einfluss auf die rheologischen Eigenschaften der Produkte haben. [0012] In JP 2003 128664 A1 (Nagaoka) wird die Reduktion der Adstringenz durch Salzbildung der Polyphenole 50 erreicht. Leider wird dadurch in vielen Fällen die Stabilität dieser Verbindungen gemindert und die Oxidationsanfälligkeit derselben gesteigert. [0013] In JP 2004 315 441 A1 (Taisho) wird beschrieben, dass man den adstringierenden Geschmack von Eisensalzen mit speziellen Aminosäuren wie γ-Aminobuttersäure reduzieren kann. Durch den notwendigen Einsatz extrem hoher Konzentrationen (1 % und mehr) erhält das Produkt bzw. die Zubereitung jedoch einen sauren Geschmack. 55 [0014] Spezielle Zucker wie Palatinose, auch in Kombination mit Süßstoffen, wurden zur Maskierung der Adstringenz von Sojagetränken in der WO 2004 062385 A1 (Mitsui) vorgeschlagen, allerdings sind auch hier sehr große Mengen erforderlich. In WO 2005 016031 A1 (Cargill) werden nichtreduzierende Disaccharide wie Trehalose als Adstringenz- Maskierer vorgeschlagen. In JP 2004 337132 A1 (Mitsui) wird die Maskierung mit Cyclofructanen beschrieben, die die 2 EP 2 730 178 A1 adstringierenden Stoffe durch Komplexierung maskieren. Gemäß JP 2005 145933 A1 (Taiyo) sind größere Konzentra- tionen (> 0,1 %) Pektin oder Alginate ebenfalls in der Lage, die Adstringenz von Polyphenolen z.B. aus Traubenkern- extrakten zu reduzieren. Gallat-Catechine, wie sie z.B. in Grüntee vorkommen, wurden ebenfalls mit dieser Methode maskiert (vgl. N. Hayashi et al. in: Biosci. Biotechnol. Biochem. 2005, 69 (7), 1306-1310 ). 5 [0015] In EP 2058297 A1 (Symrise) wird die Verwendung von ungesättigten Alkamiden wie z.B. Pellitorin oder Mi- schungen solcher ungesättigten aliphatischen Alkamide wie Spilanthol und Pellitorin zur Minderung der adstringierenden Eigenschaften von oral konsumierbaren Zubereitungen beschrieben; dabei ist aber durch die notwendige wirksame Konzentration auch der trigeminale Effekt, insbesondere der als Kribbeln oder "Tingling" beschriebene trigeminale Effekt, noch deutlich ausgeprägt und kann die Anwendung als Adstringenzmaskierung stören. 10 [0016] DE 102010049708 A1 (Hexal) beschreibt die Verwendung von Mischungen enthaltend bestimmte monocycli- sche Monoterpene (1-(2,6,6-Trimethylcyclohexenyl)-2-buten-1-on, N-Ethyl-2-(isopropyl)-5-methyl-cyclohexancarboxa- mid, Menthyllactat, Mentholethylenglycolcarbonat und Mentholpropylenglycolcarbonat), anorganische oder organische Salze, sowie einen oder mehrere Süßstoffe zur Maskierung bitter schmeckender Arzneimittel (z.B. Cetrizidin, in einer pharmazeutischen Filmformulierung. Aufgrund der hohen Dosierung der auch als physiologische Kühlwirkung auslö- 15 senden Monoterpene von 0,01 - 10% ist jedoch eine starke Kühlwirkung wahrzunehmen, die für den angestrebten Einsatz als Maskierer in Lebensmittel störend wirkt. [0017] Teilweise werden auch Süßstoffe zur Reduktion der Adstringenz eingesetzt, wie z.B. in JP 2007 135481 A1 (Kikkoman) beschrieben. Dabei erhält man aber grundsätzlich nur süße Applikationen. [0018] Bei den oben erwähnten, bekannten Verfahren besteht neben den bereits genannten Nachteilen regelmäßig 20 ein weiterer Nachteil darin, dass die Maskierungsmittel in erheblichen Mengen (> 0,05 %-Bereich) eingesetzt werden sollten, was zu höheren Kosten und im Falle der polymeren Kohlenhydrate oder Proteine auch zu Anwendungsproblemen führt. [0019] Die komplexe Aufgabe, die der vorliegenden Erfindung zugrunde liegt, hat daher darin bestanden, Stoffe zu finden, die gleichzeitig in sehr geringen Mengen zur Maskierung oder Verminderung des unangenehmen Geschmack- 25 seindrucks unangenehm schmeckender Stoffe geeignet sind und insbesondere einen Adstringenz-maskierenden Effekt gegen eine Vielzahl von Adstringentien zeigen, breit anwendbar sowie leicht zugänglich sind und im Idealfall natürlich vorkommen. Beschreibung der Erfindung 30 [0020] Gegenstand
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