EP4452941A1 - Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant - Google Patents

Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant

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Publication number
EP4452941A1
EP4452941A1 EP21847952.5A EP21847952A EP4452941A1 EP 4452941 A1 EP4452941 A1 EP 4452941A1 EP 21847952 A EP21847952 A EP 21847952A EP 4452941 A1 EP4452941 A1 EP 4452941A1
Authority
EP
European Patent Office
Prior art keywords
group
optionally substituted
membered
general formula
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21847952.5A
Other languages
German (de)
English (en)
Inventor
Fabia HENTSCHEL
Bernd Wiedwald
Susanne Paetz
Ulrike Simchen
Michael Backes
Judith MINAKAR
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
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Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP4452941A1 publication Critical patent/EP4452941A1/fr
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

  • the present invention is in the field of flavorings and relates to new representatives of this group, in particular active ingredients with mouthwashing and tingling / tingling effect, the use of these active ingredients and preparations that include them, preferably nutrition, enjoyment, or the Oral hygiene preparations or oral pharmaceutical preparations.
  • the overall organoleptic impression of a product is generally composed of aroma, taste, trigeminal perception and texture.
  • the volatile compounds of the aroma are perceived at the olfactory receptors of the nose.
  • the volatile compounds can be absorbed through the olfactory mucosa of the nose or retronasally, i.e. backwards through the palate.
  • the taste of a product is perceived through the human taste buds.
  • Taste refers to the qualities of sweet, sour, salty, bitter, and umami that are perceived on the tongue with the taste buds.
  • the trigeminal impressions of a product such as mouthwashing, tingling/tingling, numbing, warming, burning, pungent, astringent, biting, stinging, cooling, etc. are caused by substances or active ingredients that stimulate the trigeminal nerve in the face.
  • the stimulus reception takes place in the free sensitive end area of the trigeminal neuron. Free nerve endings that respond to chemical stimuli are found in the eye and in the mucous membranes of the nasal and oral cavities.
  • Substances or active ingredients that stimulate mouthwash or salivation in the mouth have long played an important role in foods, luxury foods, oral hygiene and pharmaceutical preparations. Active ingredients that stimulate saliva are used, for example, to stimulate appetite, to combat pathological dry mouth or to improve oral hygiene by flushing harmful substances or germs out of the oral cavity through the increased flow of saliva.
  • the primary object of the present invention was to identify new substances or active ingredients that cause a trigeminal effect when consumed, preferably active ingredients to stimulate salivation in the mouth and to produce a feeling of tingling in the mouth, but at the same time significantly less off - have notes (aftertaste) and/or off-flavors (off-flavours), such as a bitter taste.
  • these substances or active substances even in low concentrations, should cause a trigeminal effect that begins quickly and immediately and lasts a long time.
  • these substances or active ingredients should have a relatively neutral smell and taste profile in order to be able to be incorporated into preparations, in particular for nutrition, pleasure, preparations serving oral hygiene or oral pharmaceutical preparations.
  • the active ingredients to be specified should ultimately be synthetically easily accessible and stable.
  • the search was primarily for active substances that can impart a particularly rapid and immediate onset and long-lasting trigeminal effect described above.
  • the active ingredients should be efficient, i.e. develop a mouthwashing effect or sensation even in low concentrations.
  • Another object was to provide substances or active ingredients which, in addition to the effects described above, simultaneously reduce or mask off-notes (off-notes or off-flavors). This applies in particular to bitter, astringent, dry, dusty, floury, chalky or metallic, preferably bitter or astringent, ingredients - or aftertaste or off notes.
  • radicals R1 to R5 and R7 can each be the same or different and, independently of one another, have the following meanings:
  • R2 with one of the adjacent radicals R1 or R3, together with the carbon atoms to which they are attached, forms an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring or an optionally substituted four-, five -, Six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or the he teroaryl ring comprises one, two, or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur can; and or
  • R3 with one of the adjacent radicals R2 or R4, together with the carbon atoms to which they are attached, forms an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring or an optionally substituted four-, five -, six- or seven-membered heterocyclyl or heteroaryl ring, where the heterocyclyl or the heteroaryl ring can comprise one, two, or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
  • R4 with one of the adjacent radicals R3 or R5, together with the carbon atoms to which they are attached, forms an optionally substituted four-, five-, six- or seven-membered cycloalkyl or aryl ring or an optionally substituted four-, five -, Six- or seven-membered heterocyclyl or heteroaryl ring, wherein the heterocyclyl or the heteroaryl ring comprises one, two, or more identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur can; and or
  • R7 • an optionally substituted cycloalkyl group
  • an optionally substituted acyl group R(C O)-; optionally one or both nitrogen atom (e) of the saturated six-membered ring in the general formula (I) or the nitrogen atom of the saturated six-membered ring in the general formula (II) or one or both nitrogen atom (e) of the saturated seven-membered ring in the general formula ( III) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) or general formula (II) or the saturated seven-membered ring in general formula (III) is mono- or poly-substituted; wherein the group Q is a radical selected from the group consisting of: halogen, -OY, -SY, -NZZ, -NY, -N-OY, trihalomethyl, -CF 3 , -CN, -OCN, -SON, -NO, -NO2, -NH2, -N3, -S(O) 2Y
  • Y is selected from the group consisting of:
  • Alkyl group in particular Ci to Cw alkyl group, in particular Ci to Ce alkyl group, especially Ci, C2, C3 or C4 alkyl group;
  • Ci-Ce alkoxy group especially optionally substituted Ci, C2, C3 - or C4 alkoxy group;
  • Alkylthio group in particular Ci to Ce alkylthio group, in particular optionally substituted Ci, C2, C3 or C4 alkylthio group;
  • Z represents Y or, alternatively, two Z's together with the nitrogen atom to which they are attached represent a four-, five-, six- or seven-membered heterocyclyl ring or heteroaryl ring, where the heterocyclyl ring or heteroaryl ring may comprise one, two or more same or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; the optionally substituted alkyl group is an optionally substituted one
  • Ci to Cw-alkyl group in particular an optionally substituted Ci to Ce is alkyl group, especially is an optionally substituted Ci, C2, C3 or C4 alkyl group
  • the optionally substituted alkenyl group is an optionally substituted Ci to C alkenyl group, in particular an optionally substituted Ci to Ce alkenyl group, especially an optionally substituted Ci, C2, C3 or C4 alkenyl group is
  • the optionally substituted alkoxy group is an optionally substituted Ci to Cw alkoxy group, in particular an optionally substituted Ci to Ce alkoxy group, especially an optionally substituted Ci, C2, C3 or C4 alkoxy group is
  • the optionally substituted alkylthio group is an optionally substituted Ci to Cw alkylthio group, in particular an optionally substituted Ci to Ce alkylthio group, especially an optionally substituted Ci, C2, C3 or C4 alkylthio group is
  • the active ingredients according to the general formula (I), (II) or (III) according to the invention can be present in the form of pure stereoisomers or as mixtures of different stereoisomers.
  • the structural unit NXR 7 is in the para-position to the nitrogen atom, or optionally to the carbon atom when the nitrogen atom is replaced by a carbon atom, of the six-membered ring in the general formula (I).
  • the structural unit NX-R 7 in the formula (I) can also be arranged in a different position of the six-membered heterocyclic ring in the general formula (I), namely in ortho- or meta- Position on the nitrogen atom or optionally on the carbon atom if the nitrogen atom is replaced by a carbon atom.
  • the structural unit CX-R7 is in the para position to the nitrogen atom, or optionally to the carbon atom when the nitrogen atom is replaced by a carbon atom, of the six-membered ring in general Formula (II).
  • the structural unit CXR 7 in the formula (II) can also be arranged at another position of the six-membered heterocyclic ring in the general formula (II), namely in the ortho or meta position to nitrogen atom or optionally to the carbon atom when the nitrogen atom is replaced by a carbon atom.
  • the structural unit NXR 7 is in the para-position to the nitrogen atom, or optionally to the carbon atom when the nitrogen atom is replaced by a carbon atom, of the seven-membered ring in the general formula (III).
  • the structural unit NXR 7 in the formula (III) can also be arranged at another position of the seven-membered heterocyclic ring in the general formula (III), namely in the ortho or meta position to the nitrogen atom or optionally to the carbon atom when the nitrogen atom is replaced by a carbon atom.
  • active ingredient(s) refers to all compounds encompassed by the structural formulas disclosed herein formula (I), formula (II) or formula (II), and excludes any subgenus and specific compounds within the formula whose structure is disclosed herein.
  • the active ingredients can be identified either by their chemical structure and/or their chemical name. When the chemical structure and chemical name conflict, the chemical structure determines the identity of the compound.
  • the compounds described herein may contain one or more chiral centers and/or double bonds and therefore may exist as stereoisomers such as double bond isomers, i.e. H. geometric isomers, enantiomers or diastereomers. Accordingly, the chemical structures of the general formulas (I) to (III) shown here include all possible enantiomers and diastereomers or stereoisomers.
  • an active ingredient means an active substance, for example in a preparation, as opposed to an excipient.
  • an active substance is a substance or component that has a specific effect or causes a specific reaction.
  • the active ingredients according to the invention are substances that have a trigeminal effect.
  • the active ingredients according to the present invention produce a salivating and/or tingling/tingling effect in the mouth.
  • mouth-watering or tingling / tingling effect in the context of the present invention means that when consuming or applying an active ingredient according to the invention by stimulating the trigeminal nerve, the flow of saliva in the mouth is stimulated, and / or a tingling / tingling feeling in the mouth is triggered.
  • alkyl or alkyl group or alkyl radical used interchangeably, alone or as part of another substituent according to the present invention, refer to a saturated linear or branched monovalent hydrocarbon radical, obtained by removing a hydrogen atom from a single carbon atom of a starting alkane.
  • alkyl group includes saturated linear or branched hydrocarbon radicals having 1 to 10, 1 to 8, 1 to 6 or 1 to 4 carbon atoms.
  • alkylene also refers to a divalent alkyl.
  • -CH2CH3 is an ethyl
  • -CH2CH2- is an ethylene
  • alkylene group alone or as part of another substituent refers to a saturated linear or branched divalent hydrocarbon radical obtained by removing two hydrogen atoms from a single carbon atom or two different carbon atoms of a starting alkane.
  • an alkyl group or an alkylene group comprises 1 to 10 carbon atoms.
  • an alkyl group or alkylene group comprises 1 to 6 carbon atoms.
  • Most preferred is an alkyl group or alkylene group having 1 to 4 carbon atoms.
  • the alkyl group or alkenyl group is most preferably a saturated linear or branched C 1 to C 4 alkyl group or a saturated linear or branched C 1 to C 4 alkylene group.
  • Preferred alkyl groups or alkyl radicals include, without being limited to: Ci to Ce-alkyl, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbut
  • the alkyl group or the alkylene group as defined above is optionally substituted.
  • alkenyl or “alkenyl group” or “alkenyl radical”, used interchangeably, alone or as part of another substituent according to the present invention, refer to an unsaturated linear or branched monovalent hydrocarbon radical having at least one carbon-carbon double bond.
  • the residue can be in either the cis or the trans conformation about the double bond(s).
  • an alkenyl group comprises 1 to 10 carbon atoms. In other preferred variants, an alkenyl group comprises 1 to 6 carbon atoms. In even more preferred variants, an alkenyl group comprises 1 to 4 carbon atoms.
  • the alkenyl group is a mono- or di-unsaturated linear or branched C 1 to C 4 alkenyl group.
  • Preferred alkenyl groups or alkenyl radicals include, but are not limited to, ethenyl, propenyls such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en- 1-yl (allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl, butenyls such as but- 1-en-1-yl, but-1-en-2-yl, 2-methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-1- yl, but-2-en-1- yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl and the like.
  • the alkenyl group as defined above is optionally substituted.
  • alkoxy or "alkoxy group” or “alkoxy radical”, used interchangeably, alone or as part of another substituent according to the present invention, refer to a radical of the formula -O-R, where R is alkyl or substituted alkyl as defined above.
  • an alkoxy group comprises 1 to 10 carbon atoms. In other preferred variants, an alkoxy group comprises 1 to 6 carbon atoms. Most preferred is an alkoxy group having 1 to 4 carbon atoms.
  • the alkoxy group is a saturated linear or branched C 1 to C 4 alkoxy group.
  • alkoxy groups or alkoxy radicals include, without being limited to: C 1 -C 4 alkoxy, including C 1 -C 4 alkoxy, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy , 1-methylpropoxy, 2-methylpropoxy or
  • alkoxy group as defined above is optionally substituted.
  • alkylthio or “alkylthio group” or “alkylthio radical”, used interchangeably, alone or as part of another substituent according to the present invention, refer to a radical of the formula -SR, where R is alkyl or substituted alkyl as defined above.
  • an alkylthio group comprises 1 to 10 carbon atoms. In other preferred variants, an alkylthio group comprises 1 to 6 carbon atoms. Most preferred is an alkylthio group having 1 to 4 carbon atoms.
  • the alkylthio group is a C 1 -C 4 saturated linear or branched alkylthio group.
  • alkylthio group as defined above is optionally substituted.
  • an acyl group includes an alkyl group having 1 to 10 carbon atoms.
  • an acyl group comprises an alkyl group of 1 to 6 carbon atoms.
  • an acyl group includes an alkyl group having 1 to 4 carbon atoms.
  • acyl group is a C 1 to C 4 linear or branched acyl group.
  • acyl group as defined above is optionally substituted.
  • cycloalkyl or “cycloalkyl group” or “cycloalkyl radical”, used interchangeably, alone or as part of another substituent according to the present invention, refer to a saturated non-aromatic cyclic monovalent hydrocarbon radical , in which the carbon atoms are linked together in a ring and which has no heteroatom.
  • the carbon ring may appear as a monocyclic compound having only a single ring or a polycyclic compound having two or more rings.
  • cycloalkyl includes a four- to ten-membered monocyclic cycloalkyl group or a nine- to twelve-membered polycyclic, in particular bicyclic, cycloalkyl group.
  • the cycloalkyl group comprises a five to seven membered monocyclic cycloalkyl group. Most preferred is a monocyclic Cs, Cs, or Cy cycloalkyl group.
  • Preferred cycloalkyl groups include, but are not limited to, saturated carbocyclic radicals having from 4 to 10 carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl; cyclopentyl, cyclohexyl and cycloheptyl are preferred.
  • cycloalkyl or “cycloalkyl group” or “cycloalkyl radical”, which are used side by side, also include cycloalkenyls, ie unsaturated, cyclic C ⁇ C double bonds containing between two carbon atoms of the ring molecule hydrocarbon radicals.
  • cycloalkenyls are compounds with one, two or more double bonds, with the number of possible, mostly conjugated, double bonds in the molecule depending on the ring size.
  • Typical cycloalkenyls include, but are not limited to, cyclopropenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, and the like.
  • Typical cycloalkynes include cyclooctyne.
  • the cycloalkyl group or the cycloalkyl radical can be attached to an atom of the molecule of formula (I), formula (II) or formula (III) via any suitable carbon atom.
  • the cycloalkyl group as defined above is optionally substituted.
  • aryl' or aryl group or “aryl moiety” used interchangeably, alone or as part of another substituent according to the present invention, refer to a monovalent aromatic hydrocarbon radical formed by removal of a hydrogen atom is derived from a single carbon atom of an aromatic ring system.
  • the carbon ring may appear as a monocyclic compound having only a single ring or a polycyclic compound having two or more rings.
  • the term “aryl” includes a four- to ten-membered monocyclic aryl group or a nine- to twelve-membered polycyclic, in particular bicyclic, aryl group.
  • the aryl group comprises a five, six or seven membered monocyclic ryl group. According to the invention, monocyclic Cs, Ce or Cy aryl groups are most preferred.
  • Preferred aryl radicals include, but are not limited to, benzene, phenyl, biphenyl, naphthyl such as 1- or 2-naphthyl, tetrahydronaphthyl, fluorenyl, indenyl, and phenanthrenyl.
  • Typical carboaryl radicals also include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, coronene, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as-indacene, S- Indacene, indan are derived.
  • indene indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene, and the like.
  • preferred aromatic polycyclic aryl radicals or aryl groups include, without being limited to, for example naphthalene, biphenyl, etc.
  • the aryl group or the aryl radical can be attached to an atom of the molecule of formula (I), formula (II) or formula (III) via any suitable carbon atom of the aryl group.
  • the aryl group as defined above is optionally substituted.
  • heterocyclyl or “heterocyclyl group” or “heterocyclyl moiety”, used interchangeably, alone or as part of other substituents, refer to alkyl groups in which one or more of the carbon atom(s) are independently from each other by the same or another Heteroatom have been replaced.
  • the heteroatoms or heteroatomic groups can be located at any internal position of the alkyl group.
  • heterocyclyl alone or as part of another substituent according to the present invention refers to a saturated, non-aromatic, cyclic, monovalent hydrocarbon radical in which one or more carbon atom(s) are independently replaced by the same or another heteroatom or is/are replaced by the same or another heteroatomic group(s).
  • Typical heteroatoms or heteroatomic groups that can replace the carbon atoms include but are not limited to -O-, -S-, -N-, -Si-, -NH-, -S(O)-, -S( O) 2 -, -S(O)NH-, -S(O) 2 NH- and the like and combinations thereof.
  • Typical heterocyclyl groups include, but are not limited to, groups derived from epoxides, azirines, thiiranes, imidazolidine, morpholine, piperazine, piperidine, pyrazolidine, pyrrolidone, quinuclidine, and the like.
  • the heterocyclyl group may appear as a monocyclic compound having only a single ring or a polycyclic compound having two or more rings.
  • heterocyclyl encompasses a four to seven membered saturated heterocyclyl group containing one, two, three or more heteroatoms selected from the group O, N and S.
  • the heteroatom or the Heteroatoms can/can occupy any desired position in the heterocyclyl ring.
  • heterocyclyl encompasses a three- to seven-membered monocyclic heterocyclyl group or a nine- to twelve-membered polycyclic heterocyclyl group.
  • the heterocyclyl group comprises a five, six or seven membered monocyclic heterocyclyl group or a nine to twelve membered bicyclic heterocyclyl group.
  • a monocyclic heterocyclyl group having 5 to 7 ring atoms is most preferred according to the invention.
  • Preferred heterocyclyl groups include, but are not limited to: five- or six-membered saturated heterocyclyl containing one or two nitrogen atoms and/or one oxygen or sulfur atom, or comprising one or two oxygen and/or sulfur atoms as ring members 2-tetrahydrofuranyl,
  • heterocyclyl groups which are derived from the five- or six-membered saturated compounds, including pyrrolidone, tetrahydrofuran, tetrahydrothiophene, piperidine, tetrahydropyran, tetrahydrothiopyran.
  • polycyclic heterocyclyl ring systems particular preference is given in the context of the present invention to benzofuran, benzothiophene, indole, benzopyrrole, benzimidazole, benzoxazole, quinoline, quinazoline, quinoxaline or benzoxazine, 1,3-benzodioxole and benzodioxane.
  • the heterocyclyl group or moiety may be attached to an atom of the molecule of formula (I), formula (II) or formula (III) through any ring carbon atom or ring heteroatom of the heterocyclyl group.
  • heterocyclyl group as defined above is optionally substituted.
  • heteroaryl or “heteroaryl group” or “heteroaryl radical”, used interchangeably, alone or as part of another substituent according to the present invention, refer to a monovalent heteroaromatic radical formed by removal of a hydrogen atom a single atom of a heteroaromatic ring system.
  • Typical heteroaryl radicals or heteroaryl groups include, but are not limited to, those derived from acridine, ß-carboline, chroman, chromium, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochrome, Isoindole, Isoindoline, Isoquinoline, Isothiazole, Isoxazole, Naphthyridine, Oxadiazole, Oxazole, Perimidine, Phenanthridine, Phenanthroline, Phenazine, Phthalazine, Pteridine, Purine, Pyran, Pyrazine, Pyrazole, Pyridazine, Pyridine, Pyrimidine, Pyrrole, Thiazole, Thiophene, Triazole, xanthene and the like.
  • the heteroaryl group may appear as a monocyclic compound having only a single ring or a polycyclic compound having two or more rings.
  • heteroaryl encompasses three- to seven-membered monocyclic heteroaryl radicals containing one, two, three or four heteroatoms selected from the group O, N and S.
  • the heteroatom or heteroatoms can occupy any position in the heteroaryl ring.
  • heteroaryl group encompasses a four- to seven-membered monocyclic heteroaryl group or a nine- to twelve-membered polycyclic heteroaryl group.
  • the heteroaryl group comprises a five, six or seven membered monocyclic heteroaryl group or a nine to twelve membered bicyclic heteroaryl group.
  • a monocyclic Cs to Cy heteroaryl group is most preferred according to the invention.
  • heteroaryl radicals or heteroaryl groups include, but are not limited to, those derived from furan, thiophene, pyrrole, benzothiophene, benzofuran, benzimidazole, indole, pyridine, pyrazole, quinoline, imidazole, oxazole, isoxazole and Pyrazine are derived.
  • Five-membered aromatic heteroaryl radicals containing one, two or three nitrogen atoms or one or two nitrogen atoms and one sulfur or oxygen atom as ring atoms in addition to carbon atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2 -pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl , and 1,3,4-triazol-2-yl.
  • Five-membered aromatic heteroaryl radicals containing one, two, three or four nitrogen atoms as ring atoms include 1-, 2- or 3-pyrrolyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4- imidazolyl, 1,2,3-[1H]-triazol-1-yl, 1,2,3-[2H]-triazol-2-yl, 1,2,3-[1H]-triazole-4 -yl, 1,2,3-[1H]-triazol-5-yl, 1,2,3-[2H]-triazol-4-yl, 1,2,4-[1H]-triazol- 1-yl, 1,2,4-[1H]-triazol-3-yl, 1,2,4-[1H]-triazol-5-yl, 1,2,4-[4H]-triazole -4-yl, 1,2,4-[4H]-triazol-3-yl, [1H]-tetrazol-1-yl, [1H]-t
  • Five-membered aromatic heteroaryl radicals containing one heteroatom selected from oxygen or sulfur and optionally one, two or three nitrogen atoms as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3- or 4- isoxazolyl, 3- or 4-isothiazolyl, 2-, 4- or 5-oxazolyl, 2-, 4 or 5-thiazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl.
  • Six-membered heteroaryl radicals containing one or two or one, two or three nitrogen atoms as ring atoms in addition to carbon atoms include, for. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,2,4-triazin-3-yl ; 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and 1,3,5-triazin-2-yl.
  • heteroaryl radicals derived from the five- or six-membered aromatic compounds, including pyrrole, furan, thiophene, pyridine, pyrylium ion and thiopyrylium ion, pyrazole, imidazole, imidazoline, pyrimidine, oxazole, thiazole and 1,4-thiazine.
  • the heteroaryl group or moiety may be attached to an atom of the molecule of formula (I), formula (II) or formula (III) through any ring carbon atom or ring heteroatom of the heteroaryl group.
  • heteroaryl group as defined above is optionally substituted.
  • salt refers to a salt of a compound or active ingredient according to the present invention.
  • Such salts include: (1) acid addition salts formed with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like; or formed with organic acids such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid , methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-na
  • hydroxynaphthoic acid hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid and the like; or (2) salts formed when an acidic proton present in the starting compound is replaced by a metal ion, e.g., an alkali metal ion, an alkaline earth ion, or an aluminum ion; or coordinates with an organic base such as ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, and the like.
  • a metal ion e.g., an alkali metal ion, an alkaline earth ion, or an aluminum ion
  • organic base such as ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, and the like.
  • substituted in the context of the present invention means that one or more hydrogen atoms of the specified group or radical or radical is/are independently replaced by the same or another, different substituent.
  • substitution in the context of the present invention means that the substitution is optional and not mandatory and denotes the absence or presence of a substituent or a substituent group.
  • optionally substituted XXX group thus means that the XXX group can be unsubstituted but also substituted.
  • optionally substituted alkyl includes both substituted alkyl and unsubstituted alkyl.
  • substituted specifically contemplates one or more, i.e., two, three, four, five, six or more, substitutions conventional in the art. However, it is well known to those skilled in the art that substituents should be chosen so that they do not adversely affect the useful properties of the compound or active ingredient or its function.
  • Y is hydrogen or A;
  • Z is Y or alternatively two Z's together with the nitrogen atom to which they are attached form a four, five, six or seven membered heterocyclyl or heteroaryl ring, the heterocyclyl or heteroaryl ring being one, two, three or four of a kind or various heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur.
  • -NZZ is intended to include -NH 2 , -NH-alkyl, N-pyrrolidinyl and N-morpholinyl.
  • Further specific examples which may be mentioned are: -alkylene-O-alkyl, -alkylene-heteroaryl, -alkylene-cycloheteroalkyl, -alkylene-C(O)OY, -alkylene-C(O)NYY and -CH 2 -CH 2 -C (O)-CH 3 where Y is as defined above.
  • the one or more substituent groups together with the atoms to which they are attached may form a cyclic ring, including cycloalkyl or heterocyclyl.
  • Substituents or substituent groups for substitution of nitrogen atoms in heterocyclyl groups include but are not limited to -A, -OY, -SY, -NZZ, trihalomethyl, -CF 3 , -CN, -OCN, -SCN , -NO, -NO 2 , -S(O) 2 Y, -S(O) 2 OY, -OS(O) 2 Y, -OS(O) 2 OY, -P(O)(OY) 2 , -P(O)(OY)(OY), -C(O)Y, -C(S)Y, -C(NY)Y, -C(O)OY, -C(S)OY, -C( O)NZZ, -C(NY)NZZ, -OC(O)Y, -OC(S)Y, -OC(O)OY, -OC(S)OY, -NYC(O
  • Suitable substituents within the scope of the present invention preferably include halogen groups, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxy groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, aryloxy groups or heteroaryloxy groups, arylalkyl or heteroarylalkyl groups, arylalkoxy or heteroarylalkoxy groups, amino groups, alkyl and dialkylamino groups, carbamoyl groups, Alkylcarbonyl groups, carboxyl groups, alkoxycarbonyl groups, alkylaminocarbonyl groups, dialkylaminocarbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, cycloalkyl groups, cyano groups, Ci to Ce-al
  • Preferred substituents for the above groups or radicals are selected in particular from COOH, COO-alkyl, NH2, NO2, OH, SH, CN, Si, halogens, linear or branched Ci to Ce alkyl groups, linear or branched Ci to Ce alkyloxy groups or linear or branched Ci to Ce alkylthio groups, it being possible for one or more H atoms in the alkyl groups to be replaced by halogen.
  • the substituents used to substitute a particular group, moiety or radical may in turn be further substituted, typically with one or more of the same or different groups or moieties selected from the various groups or moieties listed above and as defined in detail above.
  • the compounds or active ingredients according to the invention have the common property, even in low doses, of stimulating the trigeminal nerve and the active ingredients produce a saliva-promoting and/or tingling/tingling effect when consumed or applied.
  • the saliva-promoting effect is particularly pronounced with the active ingredients according to the invention.
  • a lower dosage of the active ingredient according to the invention or an active ingredient mixture according to the invention is sufficient to produce an intensive mouth-watering and/or tingling effect when it is used or consumed to evoke.
  • the compounds described herein represent particularly efficient active substances.
  • the compounds or active ingredients according to the invention are further characterized in that they are largely tasteless and odorless, so that they are also excellently suited for incorporation into neutral and/or flavored preparations without being perceived as negative, for example as bitter or metallic To create a taste impression or to adversely affect the intended taste impression.
  • the active ingredients according to the invention are characterized in that when they are used or consumed, the trigeminal effect, in particular the mouth-watering effect, sets in quickly and immediately and lasts for a long time.
  • the active ingredients according to the invention are also colorless and do not stain, which is very advantageous in particular for their storage and/or use in the end product.
  • the active ingredients according to the invention are able to eliminate the known taste disadvantages of aromas, especially sweeteners such as steviosides, such as off-notes (off-flavors) and/or off-flavors (off-flavors). to reduce or mask.
  • sweeteners such as steviosides, such as off-notes (off-flavors) and/or off-flavors (off-flavors).
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH or an optionally substituted C 1 , C 2 , C 3 or C 4 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted five- or six-membered cycloalkyl group or an optionally substituted five- or six-membered aryl group or an optionally substituted five- or six-membered heterocyclyl group with one, two or more identical or different he teroatom(s) or an optionally substituted five- or six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated six-membered ring in the general formula (I) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) is mono- or poly-substituted; or wherein in the general formula (II)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH or an optionally substituted C 1 , C 2 , C 3 or C 4 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted five- or six-membered cycloalkyl group or an optionally substituted five- or six-membered aryl group or an optionally substituted five- or six-membered heterocyclyl group with one, two or more identical or different he teroatom(s) or an optionally substituted five- or six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally the nitrogen atom of the saturated six-membered ring in the general formula (II) is replaced by a C atom; optionally the saturated six-membered ring in general formula (II) is mono- or poly-substituted; or wherein in the general formula (III)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH or an optionally substituted C 1 , C 2 , C 3 or C 4 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted five- or six-membered cycloalkyl group or an optionally substituted five- or six-membered aryl group or an optionally substituted five- or six-membered heterocyclyl group with one, two or more identical or different he teroatom(s) or an optionally substituted five- or six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated seven-membered ring in the general formula (III) is/are replaced by a C atom; optionally the saturated seven-membered ring in general formula (III) is mono- or poly-substituted.
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH or an optionally substituted C 1 , C 2 or C 3 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated six-membered ring in the general formula (I) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) is mono- or poly-substituted; or wherein in the general formula (II)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH or an optionally substituted C 1 , C 2 or C 3 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally the nitrogen atom of the saturated six-membered ring in the general formula (II) is replaced by a C atom; optionally the saturated six-membered ring in general formula (II) is mono- or poly-substituted; or wherein in the general formula (III)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents OH or an optionally substituted C 1 , C 2 or C 5 alkoxy group;
  • X stands for an optionally substituted Ci, C2, C3 or C4 alkyl group or an optionally substituted Ci, C2, C3 or C4 alkenyl group or an optionally substituted Ci, C2, C3 or C4 alkoxy group;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated seven-membered ring in the general formula (III) is/are replaced by a C atom; optionally the saturated seven-membered ring in general formula (III) is mono- or poly-substituted.
  • Active ingredients with particularly advantageous properties i.e. a particularly intensive and effective mouthwashing and/or tingling/tingling effect, are regularly found in structures/active ingredients in which the general formula (I) or the general formula (II) or the general Formula (III)
  • R1 , R4 and R5 are each independently H; R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C3 -alkenyl; or
  • R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C4 -alkyl; or
  • R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C3 -alkyl; or
  • R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C2 -alkyl; or
  • R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C1 -alkyl; or
  • R2 and/or R3 are the same or different and each independently represents H or OH or C1 -alkoxy or C2 -alkoxy or C3 -alkoxy and X represents C2 -alkoxy;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (e) of the saturated six-membered ring in the general formula (I) or the nitrogen atom of the saturated six-membered ring in the general formula (II) or one or both nitrogen atom (e) of the saturated seven-membered ring in the general formula ( III) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) or in general formula (II) or the saturated seven-membered ring in general formula (III) is mono- or poly-substituted
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are identical or different and each independently represents H, OH, C1-alkoxy, C2-alkoxy or C3-alkoxy and X represents C2-alkyl, C3-alkyl, C4-alkyl, C3-alkenyl, or C2 alkoxy;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated six-membered ring in the general formula (I) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) is mono- or poly-substituted; or wherein in the general formula (II)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are the same or different and each independently represents H, C1-alkoxy or C2-alkoxy and X represents C3-alkyl;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or one optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally the nitrogen atom of the saturated six-membered ring in the general formula (II) is replaced by a C atom; optionally the saturated six-membered ring in general formula (II) is mono- or poly-substituted; or wherein in the general formula (III)
  • R1 , R4 and R5 are each independently H;
  • R2 and/or R3 are the same or different and each independently represents H, C1-alkoxy or C2-alkoxy and X represents C2-alkyl;
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated seven-membered ring in the general formula (III) is/are replaced by a C atom; optionally the saturated six-membered ring in the general formula (III) is mono- or poly-substituted.
  • R1 , R4 and R5 are each independently H;
  • R2, R3 and X have the following options:
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated six-membered ring in the general formula (I) is/are replaced by a C atom; optionally the saturated six-membered ring in general formula (I) is mono- or poly-substituted; or wherein in the general formula (II) R1 , R4 and R5 are each independently H;
  • R2, R3 and X have the following options:
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally the nitrogen atom of the saturated six-membered ring in the general formula (II) is replaced by a C atom; optionally the saturated six-membered ring in general formula (II) is mono- or poly-substituted; or wherein in the general formula (III)
  • R1 , R4 and R5 are each independently H;
  • R2, R3 and X have the following options:
  • R7 represents an optionally substituted six-membered cycloalkyl group or an optionally substituted six-membered aryl group or an optionally substituted six-membered heterocyclyl group having one, two or more identical or different heteroatom(s) or an optionally substituted six-membered heteroaryl group having one, two or more identical or different heteroatom(s), where the heteroatoms are selected from the group consisting of nitrogen, oxygen and sulfur; optionally one or both nitrogen atom (s) of the saturated seven-membered ring in the general formula (III) is/are replaced by a C atom; optionally the saturated seven-membered ring in general formula (III) is mono- or poly-substituted.
  • the active ingredient of general formula (I) is selected from the group consisting of:
  • Table 2 or the active ingredient of general formula (III) is selected from the group consisting of:
  • the active substance of the general formula (I) is selected from the group consisting of:
  • the active ingredients in particular acid addition salts, with inorganic or organic acids, it being possible for the active ingredients to be present in the form of pure stereoisomers or as mixtures of different stereoisomers.
  • the active ingredient of general formula (I) is selected from the group consisting of:
  • the active ingredients in particular acid addition salts, with inorganic or organic acids, it being possible for the active ingredients to be present in the form of pure stereoisomers or as mixtures of different stereoisomers.
  • the active ingredients of the formula (I), (II) or (III) with particularly advantageous properties i.e. with a particularly intensive trigeminal effect, i.e. with a particularly salivating and/or tingling/tingling effect, are such compounds wherein the active ingredient of general formula (I) is selected from the group consisting of:
  • Table 10 or the active ingredient of general formula (II) is selected from the group consisting of:
  • Table 11 or the active ingredient of general formula (III) is selected from the group consisting of: Table 12: and their salts, in particular acid addition salts, with inorganic or organic acids, it being possible for the active ingredients to be present in the form of pure stereoisomers or as mixtures of different stereoisomers.
  • the active ingredient is selected from the group consisting of the compounds shown in Table 8 below:
  • the active ingredients of the formula (I), (II) or (III) mentioned in Table 13 are characterized by a particularly pronounced trigeminal, ie mouth-watering and/or tingling/tingling effect, with the mouth-watering effect being particularly emphasized.
  • the trigeminal effect of these active ingredients occurs quickly and immediately when they are used or consumed, even in low concentrations, and lasts for a long time.
  • the active ingredients according to the invention can be prepared by standard methods of preparative organic chemistry which are generally known to those skilled in the art. Exemplary synthetic procedures are given in the examples below.
  • Another object of the present invention relates to a flavoring preparation, which comprises or consists of:
  • Table 14 and their salts, in particular acid addition salts, with inorganic or organic acids, it being possible for the active ingredients to be present in the form of pure stereoisomers or as mixtures of different stereoisomers.
  • the present invention comprises the individual active substances or a mixture of two or more active substances or compounds of the general formula (I), formula (II) and formula (III).
  • Flavor preparations according to the invention which comprise not just one but two, three or even more active ingredients according to the invention are particularly advantageous.
  • the particular advantage of such flavoring preparations or active ingredient mixtures is that a combination of several trigeminal effects such as mouthwashing and tingling or a synergistic effect can be achieved.
  • the active ingredients or compounds according to the invention are also suitable for mixing with other active ingredients that are already known, such as aromas or flavorings.
  • the present invention therefore relates to a flavoring preparation which further comprises:
  • Flavor preparations according to the invention which are combinations of one or more active ingredient(s) of the general formula (I), formula (II) or formula (III) which form component (a) with one or more others are particularly advantageous Active ingredient(s) forming component (b) and different from the active ingredient(s) according to the invention.
  • Such a combination can be used, for example, to combine different sensory effects with one another, such as a mouthwashing and warming effect, mouthwashing and cooling effect, etc., or by using them together, another effect, such as a cooling effect, can be enhanced, or a other effect such as an astringent effect can be weakened.
  • Suitable further active ingredients which form component (b) and are different from the active ingredient(s) according to the invention which/which form component (a) are selected from the group consisting of substances that cause a pungent taste or a warmth or heat sensation on the skin or mucous membranes or a tingling or tingling sensation in the mouth or throat, substances with an astringent effect and substances with a physiological cooling effect.
  • the caustic or pungent active ingredients are preferably selected from the group consisting of: paprika powder, chili pepper powder, Extracts of paprika, extracts of pepper, extracts of chili pepper, extracts of ginger roots, extracts of grains of compassion (Aframomum melegueta), extracts of paracress (Jambu oleoresin; Spilanthes acmella, resp.
  • Spilanthes oleracea extracts of Japanese pepper (Zanthoxylum piperitum ), extracts from Kaempferia galanga, extracts from Alpinia galanga, extracts from water pepper (Polygonium hydropiper), capsaicinoids, in particular capsaicin, dihydrocapsaicin or nonivamide; Gingeroids, in particular gingerol [6], gingerol [8], or gingerol [10]; shogaols, in particular shogaol-[6], shogaol-[8], shogaol-[10]; gingerdione, in particular gingerdione-[6], gingerdione-[8] or gingerdione-[10]; paradols, in particular paradol-[6], paradol-[8] or paradol-[10]; dehydrogingerdione, in particular dehydrogingerdione-[6], dehydrogingerdione
  • the active ingredients that can be perceived as stinging or biting are preferably selected from the group consisting of: aromatic isothiocyanates, in particular phenylethyl isothiocyanate, allyl isothiocyanate, cyclopropyl isothiocyanate, butyl isothiocyanate, 3-methylthiopropyl isothiocyanate, 4-hydroxybenzyl isothiocyanate, 4-methoxybenzyl isothiocyanate and mixtures thereof.
  • the active ingredients that cause a tingling sensation are preferably selected from the group consisting of 2E,4E-decadienoic acid-N-isobutylamide (trans-pellitorin), in particular those as described in WO 2004/043906; 2E,4Z-decadienoic acid-N-isobutylamide (cis-pellitorin), in particular those as described in WO 2004/000787; 2Z,4Z-decadienoic acid N-isobutylamide; 2Z,4E-decadienoic acid-N-isobutylamide; 2E,4E-decadienoic acid N-([2S]-2-methylbutyl)amide; 2E,4E-decadienoic acid N-([2S]-2-methylbutyl)amide; 2E,4E-decadienoic acid N-([2R]-2-methylbutylamide); 2E,4Z-decadienoic acid N-(trans-pellitorin), in particular
  • 2E,4E,8Z,11E-tetradecatetraenoic acid N-(2-hydroxy-2-methylpropyl)amide (isobungeanool); 2E,4E,8Z-tetradecatrienoic acid N-(2-hydroxy-2-methylpropyl)amide (dihydrobungeanool) and 2E,4E-tetradecadienoic acid N-(2-hydroxy-2-methylpropyl)amide (tetrahydrobungeanool) and mixtures thereof.
  • Active ingredients with an astringent effect are preferably selected from the group consisting of: catechins, in particular epicatechins, gallocatechins, epigallocatechins and their respective gallic acid esters, in particular epigallocatechin gallate or epicatechin gallate, their oligomers (procyanidins, proanthocyanidins, prodelphinidins, procyanirins, thearubigenins, theogallins) and their C- and O-glycosides; Dihydroflavonoids such as dihydromyricetin, taxifolin and their C and 0 glycosides, flavonols such as myricetin, quercetin and their C and 0 glycosides such as quercetrin, rutin, gallic acid esters of carbohydrates such as tannin, pentagalloyl glucose or their reaction products such as elligatannin, aluminum salts, e.g. alum , and their mixtures.
  • catechins in particular epicatechin
  • the active ingredients with a physiological cooling effect or the so-called cooling agents are those substances that have a cooling sensory effect on the skin or the skin when consumed or applied Cause mucous membranes, although in fact there is no physical cooling such as occurs during evaporation.
  • Such cooling agents are preferably selected from the group consisting of: substances with a physiological cooling effect, selected from the group consisting of: menthol, menthol methyl ether (FEMA GRAS 4054), monomenthyl glutamate (FEMA GRAS 4006), menthoxy-1,2-pro - pandiol (FEMA GRAS 3784), dimethylglutarate (FEMA GRAS 4604), hydroxymethylcyclohexylethanone (FEMA GRAS 4742), 2-(4-ethylphenoxy)-N-(1 H-pyrazol-3-yl)-N-(thiophene- 2-ylmethyl)acetamide (FEMA GRAS 4880), WS-23 (2-isopropyl-N,2,3-trimethylbuty
  • FEMA stands for “Flavor and Extracts Manufacturers Association” and GRAS is defined as “Generally Regarded As Safe”.
  • a FEMA GRAS designation means that the substance so labeled has been tested using standard methods and found to be toxicologically safe. In principle, all known substances with a cooling effect are suitable as component (b). For reasons of food safety, however, preference is given to those compounds which have a FEMA GRAS designation.
  • the flavoring preparations according to the invention as semi-finished goods preferably contain component (a) or alternatively component (a) plus component (b) in an amount of 0.1% by weight to 20% by weight, preferably 1% by weight. to 15% by weight, more preferably from 2% to 10% by weight, most preferably from 3% to 5% by weight.
  • a flavoring preparation as a semi-finished product in the context of the present invention is a product that is later processed into a finished product or a product that is later incorporated into another product to create a ready-to-use product or product. to produce a final formulation.
  • the flavoring preparations according to the invention can contain components (a) and (b) in a weight ratio of about 0.1:99.9 to about 99.0:0.1, preferably about 1:99 to about 99:1, even more preferably 10:90 to about 90:10, more preferably about 25:75 to about 75:25, and especially about 40:60 to 60:40.
  • composition of the flavoring preparation according to the invention is particularly advantageous since it allows the amount of active ingredient(s) in the final formulation or the finished product to be controlled.
  • the flavoring substance preparation according to the invention further comprises (c) at least one aroma or flavoring which differs from the active substance (a) according to general formula (I), general formula (II) or general formula (III) and the active substance (b).
  • new aroma or flavor compositions can be created in which olfactory and/or gustatory (sweet, sour, salty, bitter and umami) effects with trigeminal effects (mouth-watering, tingling) are advantageously combined with one another or be supplemented.
  • a flavoring preparation according to the invention is preferred in which the at least one aroma or flavoring substance, which is different from the active substance (a) according to the invention and the active substance (b), has an unpleasant, in particular bitter taste quality, or an astringent, dry, dusty , floury, chalky and/or metallic note.
  • the one or more flavoring substances contained in the flavoring substance preparation according to the invention is/are selected from the group consisting of: acetophenone, allyl caproate, alpha-ionone, beta-ionone, anisaldehyde, anisyl acetate, anisyl formate, anethole, Benzaldehyde, benzothiazole, benzyl acetate, benzyl alcohol, benzyl benzoate, beta-lonone, butyl butyrate, butyl caproate, butylidenephthalide, carvone, camphene, caryophyllene, cineol, cinnamyl acetate, citral, citronellol, citronellal, citronellyl acetate, cyclohexyl acetate, cymene, damascone, decalactone, dihydrocoumarin, dimethyl anthranilate, dimethyl anthranilate, dodecalact
  • Hedione® Hedione®
  • heliotropin 2-heptanone, 3 -heptanone, 4-heptanone, trans-2-heptenal, cis-4-heptenal, trans-2-hexenal, cis-3-hexenol, trans-2-hexenoic acid, trans-3-hexenoic acid, cis-2-
  • Methyl jasmonate 2-methylmethylbutyrate, 2-methyl-2-pentenolic acid, methyl thiobutyrate, 3,1-methylthiohexanol, 3-methylthiohexyl acetate, nerol, neryl acetate, trans,trans-2,4-nonadienal, 2,4-nonadienol, 2,6- nonadienol, 2,4-nonadienol, nootkatone, delta
  • the flavoring substances can exist as a racemate or as a single enantiomer or as an enantiomerically enriched mixture.
  • Examples of natural raw materials are peppermint oils, spearmint oils, mentha arvensis oils, anise oils, clove oils, citrus oils, cinnamon bark oils, wintergreen oils, cassia oils, davana oils, spruce needle oils, eucalyptus oils, fennel oils, galbanum oils, ginger oils, chamomile oils, caraway oils, rose oils, geranium oil e, Sage oils, parsley oils, yarrow oils, star anise oils, thyme oils, juniper berry oils, rosemary oils, angelica root oils, and the fractions of these oils.
  • the aroma or flavoring substance with an unpleasant taste quality is preferably selected from the group consisting of: xanthine alkaloids, xanthines (caffeine, theobromine, theophylline and methylxanthines), alkaloids (quinine, brucine, strychnine, nicotine), phenolic glycosides (e.g. salicin, arbutin), flavonoid glycosides (e.g.
  • chalcones or chalcone glycosides e.g. phloridzin, phloridzinxylosides
  • hydrolyzable tannins gallic or elagic acid esters of carbohydrates, e.g. pentagalloyl glucose, tannic acids
  • non-hydrolyzable tannins possibly galloylated catechins, gallocatechins, epigallocatechins or epicatechins and their oligomers, e.g.
  • proanthyocyanidins or procyanidins thearubigenin
  • flavones e.g. quercetin, taxifolin, myricetin
  • phenols such as salicin, polyphenols (e.g. gamma-oryzanol, caffeic acid or their esters (e.g. B. chlorogenic acid and isomers)), terpenoid bitter and tannins (e.g.
  • limonoids such as limonin or nomilin from citrus fruits, lupolone and humolone from hops, iridoids, secoiridoids), absinthine from wormwood, amarogentin from gentian, metallic salts (especially potassium, magnesium - and calcium salts, potassium chloride, potassium gluconate, potassium carbonate, potassium sulfate, potassium lactate, potassium glutamate, potassium succinate, potassium malate, sodium sulfate, magnesium sulfate, aluminum salts, zinc salts, tin salts, iron (II) salts, iron (III) salts, chromium (II )-picolinate), active pharmaceutical ingredients (e.g.
  • vitamins e.g. vitamin H, vitamins from the B series such as vitamin B1, B2, B6, B12, niacin, pantothenic acid
  • denatonium benzoate sucralose octaacetate
  • iron salts aluminum salts
  • zinc salts urea
  • unsaturated fatty acids in particular unsaturated fatty acids in emulsions
  • amino acids with a bitter/astringent taste e.g.
  • artificial as well as natural sweeteners and sweetener enhancers can also be used as aroma or flavoring substances. These can be selected from the group consisting of
  • sugar alcohols e.g. erythritol, threitol, arabitol, ribotol, xylitol, sorbitol, mannitol, dulcitol, lactitol
  • sugar alcohols e.g. erythritol, threitol, arabitol, ribotol, xylitol, sorbitol, mannitol, dulcitol, lactitol
  • proteins e.g. miraculin, monellin, thaumatin, curculin, brazzein
  • Synthetic sweeteners e.g. Magap, sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, saccharin sodium salt, aspartame, superaspartame, neotame, alitame, sucralose, stevioside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, monatin, phenylodulcin);
  • Synthetic sweeteners e.g. Magap, sodium cyclamate, acesulfame K, neohesperidin dihydrochalcone, saccharin sodium salt, aspartame, superaspartame, neotame, alitame, sucralose, stevioside, rebaudioside, lugduname, carrelame, sucrononate, sucrooctate, monatin, phenylodulcin);
  • Sweet-tasting amino acids e.g. glycine, D-leucine, D-threonine, D-asparagine, D-phenylalanine, D-tryptophne, L-proline
  • Sweet-tasting low molecular weight substances such as hernandulcin, dihydrochalcone glycosides, glycyrrhizin, glycerrhetinic acid, their derivatives and salts, extracts of licorice (Glycyrrhizza glabra ssp.), Lippia dulcis extracts, Momordica ssp. extracts or
  • Plant extracts such as Momordica grosvenori [Luo Han Guo] and the mogrosides obtained from it, Hydrangea dulcis or Stevia ssp. (e.g. Stevia rebaudiana) extracts or steviosides derived therefrom.
  • active ingredients or flavoring preparations according to the invention can be used in pure form, as solutions or else in specially prepared form and incorporated into ready-to-use products or final formulations.
  • the active ingredient or the flavoring preparation according to the invention is preferably in the form of a solution and therefore comprises at least one solvent as a further component.
  • solvents or solvent systems have proven to be advantageous, the solvent being selected from the group consisting of benzyl alcohol, 2-phenylethanol, benzyl benzoate, diethyl succinate, triethyl citrate, triacetin, ethanol, peppermint oil, anethole, optamint, propylene glycol and mixtures from it.
  • the solvent is preferably present in an amount of from 80% to 99%, preferably from 85% to 99%, even more preferably from 90% to 99% by weight. %, very particularly preferably from 95% by weight to 99% by weight, based on the total weight of the active ingredient preparation or flavoring preparation, with the proviso that components (a) and / or (b) and the solvent together 100 % by weight.
  • the active ingredients or flavoring preparations according to the invention can be bound to a carrier, spray-dried or encapsulated.
  • compounds according to the invention can be bound to or in a carrier, for example common salt, sugar, starches or sugar melts.
  • the spray-dried form is prepared from the liquid compositions by preparing an emulsion with the addition of specified amounts of a carrier, preferably biopolymers such as starch, modified starches, maltodextrin and gum arabic. This emulsion is dried in spray dryers by fine distribution with simultaneous application of temperature. A powder with the desired loading of liquid composition results.
  • the active substance according to the invention or the flavoring preparation is in encapsulated form.
  • Capsules are understood to be spherical aggregates containing at least one solid or liquid core surrounded by at least one continuous shell.
  • the one or more cooling agent(s), or the cooling agent mixture or the aroma preparation is encapsulated with the aid of a coating material/enveloping material and in the process are stored as macrocapsules with diameters of around 0.1 to around 5 mm or microcapsules with diameters of around 0. 0001 to about 0.1 mm.
  • liquid or solid active ingredients and flavoring preparations according to the invention are enclosed in these capsules and can be released by various mechanisms such as application of heat, pH shift or chewing pressure.
  • Suitable coating materials are, for example, starches, including their degradation products and chemically or physically produced derivatives (in particular dextrins and maltodextrins), gelatin, gum arabic, agar-agar, ghatti gum, gellan gum, modified and unmodified celluloses, pullulan, Curdlan, carrageenans, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of these substances.
  • gelatin in particular pork, beef, poultry and/or fish gelatin
  • gelatin which preferably has a swelling factor of greater than or equal to 20, preferably greater than or equal to 24.
  • gelatin is particularly preferred since it is readily available and can be obtained with different swelling factors.
  • capsules made from maltodextrins (particularly based on cereals, especially corn, wheat, tapioca or potatoes), which preferably have DE values in the range from 10 to 20.
  • celluloses e.g. cellulose ethers
  • alginates e.g. sodium alginate
  • carrageenan e.g. beta-, iota-, lambda- and/or kappa-carrageenan
  • gum arabic curdlan and/or agar agar or alginate capsules.
  • the shell of the capsules consists of melamine-formaldehyde resins or coacervation products of cationic monomers or biopolymers (such as chitosan) and anionic monomers such as (meth)acrylates or alginates.
  • the capsules are generally finely dispersed liquid or solid phases coated with film-forming polymers, during the production of which the polymers are deposited on the material to be coated after emulsification and coacervation or interfacial polymerization.
  • molten wax is taken up in a matrix (“microsponge”), which as microparticles can also be coated with film-forming polymers.
  • microsponge molten wax is taken up in a matrix
  • particles are alternately coated with polyelectrolytes of different charges (“layer-by-layer” method).
  • the microscopically small capsules can be dried like powder.
  • multinuclear aggregates also called microspheres, which contain two or more cores distributed in the continuous shell material.
  • Single-core or multi-core microcapsules can also be surrounded by an additional second, third, etc. shell.
  • the shell can come off natural, semi-synthetic or synthetic materials.
  • Natural shell materials are, for example, gum arabic, agar-agar, agarose, maltodextrins, alginic acid or its salts, eg sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides such as starch or dextran, polypeptides, protein hydrolysates, sucrose and waxes.
  • Semi-synthetic casing materials include chemically modified celluloses, in particular cellulose esters and ethers, eg cellulose acetate, ethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethyl cellulose and carboxymethyl cellulose, and starch derivatives, in particular starch ethers and esters.
  • Synthetic shell materials are, for example, polymers such as polyacrylates, polyamides, polyvinyl alcohol or polyvinylpyrrolidone.
  • coating materials/shell materials of the prior art for the production of microcapsules are the following commercial products (the shell material is given in brackets): Hallcrest Microcapsules (gelatine, gum arabic), Coletica Thalaspheres (maritime collagen), Lipotec millicapsules (alginic acid, Agar-Agar), Induchem Unispheres (Lactose, Microcrystalline Cellulose, Hydroxypropyl Methylcellulose); Unicerin C30 (lactose, microcrystalline cellulose, hydroxypropylmethylcellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar-agar) and Kuhs Probiol Nanospheres (phospholipids) as well as Primaspheres and Primasponges (chitosan, alginates) and Primasys (phospholipids) .
  • the encapsulation of the active ingredients or flavoring mixtures according to the invention has the advantage that it protects the sensitive active ingredients and optionally other aromas and flavorings from environmental influences (light, oxygen, moisture) and z. B. slowing down the oxidation. Additionally, the encapsulation allows for hassle-free keeping and storage. In addition, the encapsulation offers a longer shelf life for active ingredients or active ingredient mixtures and prevents undesirable interactions between food components and the corresponding active ingredients. With the encapsulation, a targeted and controlled release can be achieved the active ingredients at the right time. This guarantees the optimal taste experience at the time of consumption.
  • Additives and auxiliaries in particular preservatives, colorants, antioxidants, flow aids, thickeners, etc., can also be added to the active ingredients or flavoring preparations according to the invention.
  • the present invention relates in a further aspect to the use of an active ingredient according to the invention or a flavoring preparation according to the invention as flavoring.
  • the total amount of the active substance according to the invention or the active substance mixture according to the invention or the flavoring or flavoring preparation is such as to produce an oral trigeminal stimulus when consumed or when it is used, preferably a mouth-watering one, in which the flow of saliva in the mouth is stimulated, or produce a tingling/tingling effect in the mouth.
  • the present invention also relates to the use of an active ingredient according to the invention or a flavoring preparation according to the invention, the total amount of the active ingredient according to the invention or the flavoring preparation according to the invention being sufficient to produce a pleasant taste when consumed or when it is used
  • the taste impression being selected from the group consisting of warming, sharp or cooling notes.
  • the present invention also relates to the use of an active ingredient according to the invention or a flavoring preparation according to the invention, the total amount of the active ingredient according to the invention or the invention active ingredients is sufficient to reduce, neutralize or mask the unpleasant taste properties of another active ingredient or flavoring substance, in particular that of a substance contained in the mixture or preparation, when consumed or when it is used, the taste impression being selected from the group composed of astringent, bitter, dry, dusty, mealy, chalky or metallic notes.
  • Known taste disadvantages of aromas for example astringent or bitter notes, especially of sweeteners such as steviosides, can be reduced or eliminated in this way.
  • the pungent, bitter or metallic aftertaste is reduced or masked even when small amounts of active ingredient or active ingredient mixture are added.
  • the active ingredients according to the invention or the flavoring preparations according to the invention with the trigeminal effects described above, in particular mouthwashing, tingling/tingling effects, have a wide field of application, in particular in foods, in food supplements, in cosmetics, in particular in the oral care sector, or in oral pharmaceuticals preparations or animal feed.
  • the active ingredients according to the invention or the flavoring preparations according to the invention are used because of their above-described advantageous properties and/or taste-improving properties for the production of foods, dietary supplements, cosmetic preparations, preferably in the oral care sector, or pharmaceutical preparations or animal feed.
  • Another subject of the present invention is therefore the use of one or more active ingredients according to the invention or a flavoring preparation according to the invention for the production of foods, dietary supplements, cosmetic or pharmaceutical preparations, tobacco products or animal feed.
  • the present invention therefore also includes foodstuffs, dietary supplements, cosmetic or pharmaceutical preparations, tobacco products or animal feedstuffs which comprise/comprise one or more active ingredient(s) according to the invention or a flavoring preparation according to the invention.
  • the content of the active substance or the flavoring preparation depends on the type and use of the aforementioned products, the active substance according to the invention or the active substance mixture according to the invention or the aroma or flavoring preparation according to the invention being present in such a sufficient concentration to have a trigeminal effect or to produce an enhancing or modifying effect as described above.
  • the final formulation or finished product for use or consumption typically contains the active ingredient or flavoring preparation in an amount of from 0.001 ppm to 1000 ppm based on the total weight of the final formulation.
  • a broad range of concentrations typically used to provide the desired level of sensory modulation is preferably from 0.001 ppm to 1000 ppm, more preferably from 0.01 ppm to 500 ppm, more preferably from 0.1 ppm to 200 ppm, am most preferably 1 ppm to about 150 ppm, most preferably 5 ppm to 100 ppm, or 25 ppm to 50 ppm.
  • the product of the invention is a product of the invention.
  • a preparation for nutrition or enjoyment selected from baked goods, confectionery, alcoholic or non-alcoholic beverages, instant beverages, meat products, eggs or egg products, grain products, dairy products, fruit preparations, vegetable preparations, snack foods, fat and oil-based products or emulsions same, others Prepared meals and soups, spices, seasonings, seasonings, semi-finished goods, food supplements; or
  • a preparation for oral hygiene preferably based on a dentifrice, and selected from the group consisting of: toothpaste, toothpaste, toothgel, toothpowder, toothpaste liquid, toothpaste foam, mouthwash, toothpaste and mouthwash as a 2-in-1 product, hard candy, mouth spray, dental floss and dental care chewing gum; or
  • a pharmaceutical preparation wherein the preparation is preferably an oral pharmaceutical preparation, preferably in the form of capsules, tablets, coated tablets, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or than another swallowable or chewable preparation.
  • the foods are preferably baked goods, for example bread, dry biscuits, cakes, other pastries, confectionery (for example chocolate, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (for example coffee, tea, iced tea, wine, wine-based beverages, beer, beer-based beverages, liqueurs, schnapps, brandy, (carbonated) fruit-based lemonades, (carbonated) isotonic drinks, (carbonated) soft drinks, hectare, spritzers, fruit and vegetable juices, fruit - or vegetable juice preparations, instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks, instant fruit drinks), meat products (e.g.
  • ham fresh sausage or raw sausage preparations, seasoned or marinated fresh or cured meat products
  • eggs or egg products dried egg, egg white, egg yolk
  • grain products e.g. breakfast cereals, muesli bars, pre-cooked ready-made rice products
  • dairy products e.g. milk drinks, buttermilk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, whey drinks, butter, buttermilk, partially or fully hydrolyzed milk protein-containing products
  • products made from soy protein or other soybean fractions e.g.
  • soy milk and products made from it fruit drinks with soy protein, preparations containing soy lecithin, fermented products such as tofu or tempe or products made from them), products from other vegetable protein sources, for example oat protein drinks, fruit preparations (for example jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (for example ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, boiled vegetables), snack items (for example baked ones or fried potato chips or potato dough products, corn or peanut based extrudates), fat and oil based products or emulsions thereof (e.g. mayonnaise, tartar sauce, dressings), other prepared meals and soups (e.g. dry soups, instant soups, pre-cooked soups), spices, Seasoning mixtures and, in particular, seasonings that are used, for example, in the snack area.
  • fruit preparations for example jams, fruit ice cream, fruit sauces, fruit fillings
  • vegetable preparations for example ketchup, sauce
  • the above-mentioned foods contain at least one effective amount of at least one active ingredient according to the invention or an active ingredient mixture according to the invention or a flavoring preparation according to the invention.
  • Suitable excipients can be used to produce the preparations according to the invention, such as foodstuffs.
  • Suitable excipients include, but are not limited to, for example, emulsifiers, thickeners, food acids, acidity regulators, vitamins, antioxidants, flavor enhancers, food colors, and the like.
  • Emulsifiers are distinguished by the important property of being soluble both in water and in fat. Emulsifiers usually consist of a fat-soluble and a water-soluble part. They are always used when water and oil are to be brought to a constant, homogeneous mixture.
  • Suitable emulsifiers used in the food processing industry are selected from: ascorbyl palmitate (E 304), lecithin (E 322), phosphoric acid (E 338), sodium phosphate (E 339), potassium phosphate (E 340), calcium phosphate (E 341), magnesium orthophosphate (E 343), propylene glycol alginate (E 405), polyoxyethylene (8) stearate (E 430), polyoxyethylene stearate (E 431), Ammonium phosphatide (E 442), sodium phosphate and potassium phosphate (E 450), sodium salts of fatty acids (E 470 a), mono- and diglycerides of fatty acids (E 471), acetic acid monoglycerides (E 472 a), lactic acid monoglycerides (E 472 b), citric acid monoglycerides ( E 472 c), tartaric acid monoglycerides (E 472 d), diacetyl tartaric acid monoglycerides (
  • Thickeners are substances that are primarily able to bind water. The removal of unbound water leads to an increase in viscosity. Above a concentration that is characteristic for each thickening agent, network effects also occur in addition to this effect, which usually lead to a disproportionate increase in viscosity. In this case, one speaks of the fact that molecules 'communicate' with one another, i.e. intertwine. Most thickeners are linear or branched macromolecules (e.g. polysaccharides or proteins) that can interact with each other through intermolecular interactions such as hydrogen bonding, hydrophobic interactions or ionic relationships.
  • macromolecules e.g. polysaccharides or proteins
  • phyllosilicates bentonite, hectorite
  • hydrated SiO2 particles which are dispersed as particles and can bind water in their solid-like structure or can interact with each other due to the interactions described. Examples are:
  • Food acids can contain carboxylic acids. Acids within the meaning of the invention are preferably acids permitted in foods, in particular those mentioned here: E 260 - acetic acid E 270 - lactic acid E 290 - carbon dioxide E 296 - malic acid E 297 - fumaric acid E 330 - citric acid E 331 - sodium citrate E 332 - potassium citrate E 333 - calcium citrate E 334 - tartaric acid E 335 - sodium tartrate E 336 - potassium tartrate E 337 - sodium potassium tartrate E 338 - phosphoric acid
  • Acidity regulators are food additives that keep the degree of acidity or the basicity and thus the desired pH value of a food constant. These are mostly organic acids and their salts, carbonates, more rarely also inorganic acids and their salts. The addition of an acidity regulator in part increases the stability and firmness of the food, causes a desirable precipitation and improves the action of preservatives. In contrast to acidifiers, they are not used to change the taste of food. Their effect is based on the formation of a buffer system in the food, in which the addition of acidic or basic substances does not change the pH value, or changes it only slightly. Examples are: E 170 - calcium carbonate
  • Vitamins in another embodiment of the present invention, may include vitamins as another optional group of additives.
  • Vitamins have a wide variety of biochemical modes of action. Some act like hormones, regulating mineral metabolism (e.g. vitamin D), or affecting cell and tissue growth and differentiation (e.g. some forms of vitamin A). Others are antioxidants (e.g. vitamin E and, under certain circumstances, vitamin C).
  • the largest number of vitamins e.g. the B vitamins
  • vitamins can sometimes be closely bound to the enzymes, for example as part of the prostetic group: an example of this is biotin, which is part of the enzyme responsible for the synthesis of fatty acids.
  • vitamins can also be less strongly bound and then act as co-catalysts, for example as groups that can be easily cleaved and transport chemical groups or electrons between the molecules.
  • folic acid transports methyl, formyl and methylene groups into the cell.
  • suitable vitamins are substances selected from the group consisting of:
  • Vitamin A retinol, retinal, beta-carotene
  • vitamin B3 niacin, niacinamide
  • Vitamin Bs pantothenic acid
  • Vitamin Be pyridoxine, pyridoxamine, paridoxal
  • Vitamin B9 (folic acid, folinic acid),
  • Vitamin B12 cyanobalamin, hydroxycobalmine, methylcobalmine
  • vitamin C ascorbic acid
  • Vitamin E tocopherols, tocotrienols
  • Vitamin K (phylloquinone, menaquinone).
  • the preferred vitamins are the vitamins of the tocopherol group.
  • antioxidants Both natural and artificial antioxidants are used in the food industry. Natural and artificial antioxidants differ primarily in that the former occur naturally in food and the latter are man-made. Thus, natural antioxidants, if they are to be used as food additives, are obtained from vegetable oils, for example. For example, vitamin E - also known as tocopherol - is often made from soybean oil. Synthetic antioxidants such as propyl gallate, octyl gallate and dodecyl gallate, on the other hand, are obtained through chemical synthesis. The gallates can trigger allergies in sensitive individuals.
  • antioxidants that can be used in compositions of the present invention are: sulfur dioxide (E 220), sulphites sodium sulfite (E 221 ), sodium bisulfite (E 222), sodium bisulfite (E 223), potassium bisulfite (E 224), calcium sulfite (E 226), calcium bisulfite (E 227), potassium bisulfite (E 228), lactic acid (E 270), ascorbic acid (E 300), sodium L-ascorbate (E 301), calcium L-ascorbate (E 302), ascorbic acid ester (E 304), tocopherol (E 306), alpha tocopherol (E 307), gamma tocopherol (E 308), delta tocopherol (E 309), propyl gallate (E 310), octygallate (E 311), dodecyl gallate (E 312), isoascorbic acid (E 315) , sodium isoascorbate (E 316
  • Flavor enhancer The preparations according to the invention, such as foodstuffs for example, can also contain additional flavorings to enhance a salty, possibly slightly acidic and/or Ilmarn i taste impression.
  • the products according to the invention are thus used in combination with at least one further substance which is suitable for enhancing a pleasant taste impression (salty, umami, optionally slightly acidic).
  • salty-tasting compounds and salt-enhancing compounds.
  • Preferred compounds are disclosed in WO 2007/045566.
  • Umam i compounds as described in WO 2008/046895 and EP 1 989 944.
  • Flavorings The preparations according to the invention, such as foods, can also include flavorings to mask bitter and/or astringent taste impressions (flavorings).
  • the (further) taste correctors are selected, for example, from the following list: nucleotides (e.g. adenosine 5'-monophosphate, cytidine 5'-monophosphate) or their pharmaceutically acceptable salts, lactisols, sodium salts (e.g. sodium chloride, sodium lactate, sodium citrate, sodium acetate, sodium gluconoate), other hydroxyflavanes (e.g.
  • hydroxybenzoic acid amides according to DE 10 2004 041 496 (e.g. 2,4-dihydroxybenzoic acid vanillylamide, 2,4-dihydroxybenzoic acid-N-(4- hydroxy-3- methoxybenzyl)amide, 2,4,6-trihydroxybenzoic acid N-(4-hydroxy-3-methoxybenzyl)amide, 2-hydroxy-benzoic acid N-4-(hydroxy-3-methoxybenzyl)amide, 4-Hydroxybenzoic acid N-(4-hydroxy-3-methoxybenzyl)amide, 2,4-Dihydroxybenzoic acid N-(4-hydroxy-3-methoxybenzyl)amide mono sodium salt, 2,4-Dihydroxybenzoic acid N 2-(4-hydroxy-3-methoxyphenyl)ethylamide, 2,4-dihydroxybenzoic acid-N-(
  • gamma-aminobutyric acid according to WO 2005/096841 to reduce or mask an unpleasant taste impression such as bitterness
  • malic acid glycoside according to WO 2006/003107
  • salty-tasting mixtures according to PCT/EP 2006/067120 diacetyl trimers according to WO 2006/058893
  • mixtures of Whey proteins with lecithins and/or bitter-masking substances such as gingerdione according to WO 2007/003527.
  • n-butyl acetate isoamyl acetate, ethyl propionate, ethyl butyrate n-butyl butyrate, isoamyl butyrate, ethyl 3-methylbutyrate, ethyl n-hexanoate, allyl n-hexanoate, n-butyl n-hexanoate, ethyl n-octanoate, ethyl 3-methyl-3-phenylglycidate , ethyl 2-trans-4-cis-decadienoate), 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl- 5-hepten-1 -al, 4-hydroxycinnamic acid, 4-methoxy-3- hydroxycinnamic acid, 3-methoxy-4-hydroxycinnamic acid, 2-hydroxycinna
  • the preparations according to the invention can also include other substances which serve to mask bitter and/or astringent taste impressions.
  • additional flavor correctors are selected, for example, from the following list: from nucleotides (e.g. adenosine 5'-monophosphate, cytidine 5'-monophosphate) or their physiologically acceptable salts, lactisols, sodium salts (e.g.
  • hydroxyflavanones preferably eriodictyol, sterubin (eriodictyol-7-methyl ether), homoeriodictyol, and their sodium, potassium, calcium, magnesium or zinc salts (especially those as described in EP 1258200 A2), hydroxybenzoic acid amides , preferably 2,4-dihydroxybenzoic acid vanillylamide, 2,4-dihydroxybenzoic acid A/-(4-hydroxy-3-methoxybenzyl)amide, 2,4,6-trihydroxybenzoic acid A/-(4-hydroxy-3-methoxybenzyl).
  • Food colorings are food additives for coloring food. Dyes are divided into the groups of natural dyes and synthetic dyes. The nature-identical dyes are also of synthetic origin. The nature-identical dyes are synthetic replicas of naturally occurring coloring substances.
  • Suitable dyes for use in the present composition are selected from: curcumin (E 100), riboflavin (lactoflavin, lactoflavin, vitamin B2, E 101), tartrazine (E 102), quinoline yellow (E 104), yellow orange S (yellow orange RGL, E 110), cochineal (carmine acid, carmine, E 120), azorubine (carmoisine, E 122), amaranth (E 123), cochineal red A (Ponceau 4 R, Victoria scarlet 4 R, E 124), erythrosine (E 127), Allura red AC (E 129), patent blue V (E 131), indigotine (indigo carmine, E 132), brilliant blue FCF (patent blue AE, amido blue AE, E 133), chlorophylls, chlorophyllins (E 140), copper complexes of chlorophylls, copper -Chlorophylline complex (E 141), brilliant acid green (Green S, E 142), caramel (
  • the active ingredients according to the invention or mixtures of active ingredients according to the invention or flavoring preparations are advantageously and preferably used primarily in oral hygiene products.
  • Oral hygiene products according to the invention can be used in a manner known per se, e.g. as toothpaste, toothpaste, tooth gel, tooth powder, tooth cleaning liquid, tooth cleaning foam, aqueous or aqueous-alcoholic oral care products (mouthwash), mouthwash as a 2-in-1 product, hard candy, mouth spray, dental floss and dental care chewing gum.
  • Toothpastes or toothpastes that are flavored with the active ingredients or active ingredient mixtures or flavoring preparations according to the invention are generally gel-like or pasty preparations made of water, thickeners, humectants, abrasives or cleaning agents, surfactants, sweeteners, flavorings, deodorizing active ingredients and active ingredients against Understand oral and dental diseases. All conventional cleaning agents, such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicates, calcium pyrophosphate, finely divided synthetic resins, silicic acids, aluminum oxide and aluminum oxide trihydrate can be used in the toothpastes according to the invention.
  • All conventional cleaning agents such as chalk, dicalcium phosphate, insoluble sodium metaphosphate, aluminum silicates, calcium pyrophosphate, finely divided synthetic resins, silicic acids, aluminum oxide and aluminum oxide trihydrate can be used in the toothpastes according to the invention.
  • Particularly suitable cleaning particles for the toothpastes according to the invention are above all finely divided xerogel silicic acids, hydrogel silicic acids, precipitated silicas, aluminum oxide trihydrate and finely divided alpha aluminum oxide or mixtures of these cleaning particles in quantities of 15 to 40% by weight of the toothpaste.
  • Low molecular weight polyethylene glycols, glycerin, sorbitol or mixtures of these products in amounts of up to 50% by weight are mainly suitable as humectants.
  • thickeners are the thickening, finely divided gel silicic acids and hydrocolloids, such as carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl guar, hydroxyethyl starch, polyvinylpyrrolidone, high molecular weight polyethylene glycol, plant gums such as tragacanth, agar agar, carrageen moss, gum arabic, xantham gum and carboxyvinyl polymers (e.g. Carbopol®- types) suitable.
  • carboxymethyl cellulose hydroxyethyl cellulose, hydroxypropyl guar, hydroxyethyl starch
  • polyvinylpyrrolidone high molecular weight polyethylene glycol
  • plant gums such as tragacanth, agar agar, carrageen moss, gum arabic, xantham gum and carboxyvinyl polymers (e.g. Carbopol®- types) suitable.
  • the oral and dental care products can in particular contain surface-active substances, preferably anionic and nonionic high-foam surfactants, such as the substances already mentioned above, but especially alkyl ether sulfate salts, alkyl polyglucosides and mixtures thereof.
  • surface-active substances preferably anionic and nonionic high-foam surfactants, such as the substances already mentioned above, but especially alkyl ether sulfate salts, alkyl polyglucosides and mixtures thereof.
  • Preservatives and antimicrobials such as methyl, ethyl or propyl p-hydroxybenzoate, sodium sorbate, sodium benzoate, bromochlorophene, phenylsalicylic acid ester, thymol and the like;
  • antitartar agents for example organophosphates such as 1-hydroxyethane-1,1-diphosphonic acid, 1-phosphonopropane-1,2,3-tricarboxylic acid and others, which are known, for example, from US Pat.
  • organophosphates such as 1-hydroxyethane-1,1-diphosphonic acid, 1-phosphonopropane-1,2,3-tricarboxylic acid and others, which are known, for example, from US Pat.
  • Sweeteners such as sodium saccharin, sodium cyclamate, sucrose, lactose, maltose, fructose or Aspartam® (L-aspartyl-L-phenylalanine methyl ester), stevia extracts or their sweetening components, in particular rebaudiosides;
  • pigments such as titanium dioxide
  • Buffer substances such as primary, secondary or tertiary alkali phosphates or citric acid/sodium citrate;
  • Wound-healing and anti-inflammatory substances such as allantoin, urea, azulene, chamomile active ingredients and acetylsalicylic acid derivatives.
  • Hydrotropes such as ethanol, isopropyl alcohol, or polyols can also be used to improve the flow behavior; these substances largely correspond to the carriers described at the outset.
  • Polyols contemplated herein preferably have 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols can also contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are:
  • Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1000 daltons;
  • methylol compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
  • Lower alkyl glucosides especially those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
  • sugars with 5 to 12 carbon atoms such as glucose or sucrose
  • Dialcohol amines such as diethanolamine or 2-amino-1,3-propanediol.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the silver complexes known under the name Surfacine® and other suitable classes of substances known to those skilled in the art.
  • Perfume oils which may be mentioned are those already defined above. Peppermint oil, spearmint oil, anise oil, star anise oil, caraway oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, menthol and the like.
  • a preferred embodiment of the cosmetic preparations are toothpastes in the form of an aqueous, pasty dispersion containing polishing agents, humectants, viscosity regulators and optionally other customary components, and the mixture of menthofuran and menthol compounds in amounts of 0.5 to 2% by weight. .
  • a further preferred embodiment of the invention is a mouthwash in the form of an aqueous or aqueous-alcoholic solution containing the mixture of menthofuran and menthol compounds in amounts of 0.05 to 0.4% by weight.
  • Oral care preparations according to the invention contain, based on the total weight of the composition, preferably 0.1 ppm to 1000 ppm, preferably 1 ppm to 500 ppm, of at least one active ingredient or a mixture of active ingredients or a flavoring preparation according to the present invention.
  • the total content of the active substance or several active substances according to the invention or the flavoring preparation according to the present invention in ready-to-use mouthwashes is preferably 0.01 to 1% by weight, preferably 0.05 to 0.5% by weight, particularly preferably a content of 0.1 to 0.3% by weight, in each case based on the total mouthwash.
  • the total content of the active ingredient(s) according to the invention is 0.1 to 15% by weight, with a content of 0.5 to 8% by weight, particularly preferably 1 to 5% by weight, in each case based on the total mouthwash concentrate.
  • the total content of the or more active ingredients according to the invention is 0.1 to 5% by weight, preferably 0.5 to 2% by weight, particularly preferably 0.8 to 1.5% by weight, in each case based on the total toothpaste.
  • Another positive property of the compounds or active substances according to the invention is their stability in toothpastes based on chalk or bicarbonate, which are difficult to aromatize because of their alkaline pH.
  • the present invention also includes chewing gum that contains one or more cooling agents according to the invention or a cooling agent mixture according to the invention or a flavoring preparation according to the invention.
  • Chewing gums as a further example of oral care preparations flavored with the compositions containing the active substances or active substances according to the invention, generally comprise a chewing gum base, i.e. a chewing base which becomes plastic when chewed, sugars of various types, sugar substitutes, other sweet-tasting Substances, sugar alcohols (especially sorbitol, xylitol, mannitol), cooling agents, taste correctors for unpleasant taste impressions, other taste modulators for other, usually not unpleasant taste impressions, taste-modulating substances (e.g.
  • inositol phosphate nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as monosodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers and stabilizers.
  • Chewing gum compositions typically contain a water-insoluble and a water-soluble component.
  • the water-insoluble base which is also referred to as "gum base” usually includes natural or synthetic elastomers, resins, fats and oils, plasticizers, fillers, dyes and optionally waxes.
  • the proportion of the base in the overall composition is usually 5 to 95% by weight. %, preferably 10 to 50% by weight and in particular 20 to 35% by weight.
  • the basis consists of 20 to 60% by weight synthetic elastomers, 0 to 30% by weight natural elastomers, 5 to 55% by weight plasticizers, 4 to 35% by weight fillers and in minor amounts of additives such as dyes, antioxidants and the like together, with the proviso that they are water-soluble at most in small amounts.
  • elastomers such as polyvinyl acetate (PVA), polyethylene, (low or medium molecular weight) polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymers (butyl rubber), Polyvinyl ethyl ether (PVE), polyvinyl butyl ether, copolymers of vinyl esters and vinyl ethers, styrene-butadiene copolymers (styrene-butadiene rubber, SBR) or vinyl elastomers, for example based on vinyl acetate/inyl laurate, vinyl acetate/inyl stearate or ethylene/inyl acetate , and mixtures of the elastomers mentioned.
  • chewing gum bases include other components such as (mineral) fillers, softeners, emulsifiers, antioxidants, waxes, fats or fatty oils, such as hardened (hydrogenated) vegetable or animal fats, mono-, di- or triglycerides.
  • Suitable (mineral) fillers are, for example, calcium carbonate, titanium dioxide, silicon dioxide, talc, aluminum oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof.
  • plasticizers or detackifiers examples include lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate), triethyl citrate.
  • Suitable waxes are, for example, paraffin wax, candelilla wax, carnauba wax, microcrystalline wax and polyethylene wax.
  • Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and diglycerides of fatty acids, for example glycerol monostearate.
  • Suitable sweeteners are both sugar-containing and sugar-free compounds, which are used in amounts of 5 to 95%, preferably 20 to 80% and in particular 30 to 60% by weight, based on the chewing gum composition.
  • Typical saccharide sweeteners are sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup and mixtures thereof.
  • Possible sugar substitutes are sorbitol, mannitol, xylitol, hardened starch hydrolysates, maltitol and mixtures thereof.
  • HIAS High Intensity Articifical Sweeteners
  • sucralose such as sucralose, aspartame, acesulfame salts, alitame, saccharin and saccharin salts, cyclamic acid and its salts, glycyrrhizin, dihydrochalcone, thaumatin, monellin and the like alone or in mixtures.
  • Suitable synthetic elastomers are, for example, polyisobutylenes with average molecular weights (according to GPC) of 10,000 to 100,000 and preferably 50,000 to 80,000, isobutylene-isoprene copolymers (butyl elastomers), styrene-butadiene copolymers (styrene : butadiene ratio e.g. 1:3 to 3:1), polyvinyl acetates with average molecular weights (according to GPC) of 2,000 to 90,000 and preferably 10,000 to 65,000, polyisoprenes, polyethylene, vinyl acetate-vinyl laurate copolymers and mixtures thereof.
  • GPC polyisobutylenes with average molecular weights
  • suitable natural elastomers are rubbers such as smoked or liquid latex or guayule and natural gums such as Jelutong, Lechi caspi, Perillo, Sorva, Massaranduba balata, Massaranduba chocolate, Nispero, Rosindinba, Chicle, Gutta hang 1 kang and mixtures thereof.
  • the choice of synthetic and natural elastomers and their mixing ratios depends essentially on whether bubble gums are to be produced with the chewing gum or not. Elastomer mixtures containing Jelutong, Chicle, Sorva and Massaranduba are preferably used.
  • esters of resin acids for example esters of lower aliphatic alcohols or polyols with fully or partially hardened, monomeric or oligomeric resin acids.
  • the methyl, glycerol or pentareythritol esters and mixtures thereof are used for this purpose.
  • terpene resins can also be considered, which can be derived from alpha-pinene, beta-pinene, delta-limonene or mixtures thereof.
  • Magnesium or calcium carbonate, ground pumice stone, silicates, especially magnesium or aluminum silicates, clays, aluminum oxides, talc, titanium dioxide, mono-, di- and tricalcium phosphate and cellulosic polymers can be used as fillers or texturing agents.
  • Suitable emulsifiers are tallow, hydrogenated tallow, hydrogenated or partially hydrogenated vegetable oils, cocoa butter, partial glycerides, lecithin, triacetin and saturated or unsaturated fatty acids having 6 to 22 and preferably 12 to 18 carbon atoms and mixtures thereof.
  • Suitable dyes and whitening agents are, for example, the FD and C types approved for coloring foods, plant and fruit extracts, and titanium dioxide.
  • the base masses can contain waxes or be wax-free.
  • chewing gum preparations regularly contain a water-soluble portion, for example softeners, sweeteners, fillers, flavorings, flavor enhancers, emulsifiers, colors, acidifiers, antioxidants and the like are formed, here with the proviso that the components have at least have sufficient water solubility.
  • a water-soluble portion for example softeners, sweeteners, fillers, flavorings, flavor enhancers, emulsifiers, colors, acidifiers, antioxidants and the like are formed, here with the proviso that the components have at least have sufficient water solubility.
  • individual components can therefore belong both to the water-insoluble and to the water-soluble phase.
  • the water-insoluble portion constitutes from 5 to 95% by weight and preferably from 20 to 80% by weight of the formulation.
  • Water-soluble softeners or plasticizers are added to chewing gum compositions to improve chewability and chew feel and are typically present in the mixes at levels of from 0.5% to 15% by weight. present. Typical examples are glycerin, lecithin and aqueous solutions of sorbitol, hardened starch hydrolysates or corn syrup.
  • Suitable sweeteners are both sugar-containing and sugar-free compounds, which are used in amounts of 5 to 95% by weight, preferably 20 to 80% by weight and in particular 30 to 60% by weight, based on the chewing gum composition.
  • Typical saccharide sweeteners are sucrose, dextrose, maltose, dextrin, dried invert sugar, fructose, levulose, galactose, corn syrup and mixtures thereof.
  • Possible sugar substitutes are sorbitol, mannitol, xylitol, hardened starch hydrolysates, maltitol and mixtures thereof.
  • HIAS High Intensity Articifical Sweeteners
  • sucralose aspartame, acesulfame salts, alitame, saccharin and saccharin salts, cyclamic acid and its salts, glycyrrhizin, dihydrochalcone, thaumatin, monellin and the like alone or in mixtures
  • WO 2002 091849 A1 Wrigleys
  • stevia extracts and their active components in particular ribeaudioside A
  • Fillers such as, for example, polydextrose, raftilose, rafitiline, fructooligosaccharides (NutraFlora), palatinose oligosaccharides, guar gum hydrolysates (Sun Fiber) and dextrins are particularly suitable for the production of low-calorie chewing gums.
  • flavorings are practically unlimited and not critical to the essence of the invention.
  • the total amount of all flavorings will range from 0.1% to 15%, and preferably from 0.2% to 5% by weight of the chewing gum composition.
  • suitable flavorings are, for example, essential oils, synthetic flavors and the like, such as aniseed oil, star aniseed oil, caraway oil, eucalyptus oil, fennel oil, lemon oil, wintergreen oil, clove oil, and the like, as they are also used, for example, in oral and dental care products.
  • the total content of the active ingredient or multiple active ingredients or the flavoring preparation according to the present invention is 0.01 to 2.5% by weight, preferably 0.1 to 2.0% by weight, particularly preferably 0. 5 to 1.5% by weight, more preferably 0.8 to 1.0% by weight, based in each case on the chewing gum as a whole.
  • the total content of the active ingredient or several active ingredients or the flavoring preparation according to the present invention is 0.01 to 2.5% by weight, preferably 0.05 to 2.5% by weight, especially preferably 0.07 to 1.0% by weight, even more preferably 0.08 to 0.3% by weight, based in each case on the entire hard candy.
  • oral care products such as. B. mouthwashes and toothpastes, and chewing gum leads to the salivation is stimulated and unpleasant, especially bitter or metallic, taste impressions are partially masked or neutralized, e.g.
  • triclosan by substances such as triclosan, zinc citrate, zinc sulphate, poly- and pyrophosphates, bicarbonates , strontium and potassium salts, tin pyrophosphate, tin chloride, aluminum lactate, hydrogen peroxide, fluorides, vitamins, cetylpyridinium chloride and emulsifiers, such as sodium lauryl sulfate, sodium lauryl sarcosinate and cocamidopropyl betaine in particular, and sweeteners such as aspartame, saccharin, acesulfame-K , sorbitol; xylitol, cyclamates (e.g. sodium cyclamate), sucralose, alitame, neotame, thaumatin, neohesperidin dihydrochalcone, maltitol, lactitol or chewing gum masses.
  • triclosan zinc citrate, zinc sulphate, poly
  • the teaching according to the invention also includes the use of the active ingredients described herein for medical purposes, preferably in pharmaceutical agents for treatment an individual, preferably a mammal, in particular a human, livestock or pet, of dry mouth or xerostomia.
  • a further object of the invention therefore relates to pharmaceutical preparations which contain either an active ingredient according to the invention or an active ingredient mixture according to the invention or a flavoring preparation according to the invention.
  • the present invention therefore relates to a pharmaceutical preparation which comprises either an active ingredient according to the invention or an active ingredient mixture according to the invention or a flavoring preparation according to the invention, for use as a medicament, preferably for use in the prevention and/or treatment of dry mouth or xerostomia .
  • Dry mouth or xerostomia can have various causes: Dry mouth is caused by insufficient salivation (hyposalivation), which is a frequent side effect of drugs such as anticholinergic drugs, diuretics or psychotropic drugs. Causes can also be diseases such as sialladenitis, Sjögren's syndrome, Sicca syndrome or Heerfordt's syndrome. In addition, the removal of salivary glands, radiation therapy, feverish general illnesses, the intake of tetrahydrocannabinol or chronic stress with increased sympathetic tone can lead to dry mouth. Another cause of dry mouth can be increased mouth breathing. The highly viscous saliva produced by dry mouth can cause inflammation in the ducts of the salivary glands; the sublingual salivary gland is particularly affected.
  • Dry mouth can be eliminated or at least reduced with the oral administration of the active substances or mixtures of active substances according to the invention.
  • the active ingredients or active ingredient mixtures are administered in the form of pharmaceutical compositions which comprise a pharmaceutically tolerable excipient with at least one active ingredient according to the invention and optionally other active ingredients. These compositions are preferably administered by the oral route.
  • suitable pharmaceutical formulations or compositions are solid dosage forms such as powder, powder, granules, tablets, lozenges, sachets, cachets, coated tablets, capsules such as hard and soft gelatine capsules, and liquid dosage forms such as solutions, emulsions, especially oil-in -Water emulsions, suspensions, for example lotions, etc., preferably suckable or chewable preparations.
  • Particularly preferred pharmaceutical preparations are non-prescription products and over-the-counter drugs, so-called OTC ("over the counter") preparations.
  • the active ingredient(s) according to the invention or the mixture of active ingredients are usually mixed or diluted with an excipient.
  • Excipients can be solid, semi-solid, or liquid materials that serve as a vehicle, carrier, or medium for the active ingredient.
  • the active ingredient content (of an active ingredient or of several active ingredients according to the invention contained at the same time) can vary within a wide range and is approximately, in each case based on the total weight of the preparation, from about 0.05 ppm to 10% by weight, preferably 0.1 ppm to 10% by weight.
  • Suitable excipients include, for example, lactose, dextrose, sucrose, sorbitol, mannitol, starches, gum acacia, calcium phosphate, alginates, tragacanth, gelatin, calcium silicate, microcrystalline cellulose, polyvinylpyrrolidone, cellulose, water, syrup and methyl cellulose.
  • the formulations may contain pharmaceutically acceptable carriers or usual excipients such as lubricating agents, for example talc, magnesium stearate and mineral oil, wetting agents, emulsifying and suspending agents, preservatives such as methyl and propyl hydroxybenzoates; antioxidants; anti-irritants; chelating agents; panning aids; emulsion stabilizers; film former; gelling agents; odor masking agents; flavor correctors; resins; hydrocolloids; solvents; solubilizer; neutralizing agents; permeation enhancers; pigments; quaternary ammonium compounds; Moisturizing and superfatting agents; ointment, cream or oil bases; silicone derivatives; spreading aids; stabilizers; sterilants; suppository bases; tablet excipients such as binders, fillers, lubricants, disintegrants or coatings; propellant; desiccants; opacifiers; thickeners; waxes; plasticizers; include white
  • compositions according to the invention can also contain cosmetically and/or dermatologically and/or pharmacologically active ingredients in addition to customary additives or auxiliaries.
  • suitable active ingredients include:
  • Cosmetically and/or dermatologically active ingredients are, for example, coloring active ingredients, skin and hair pigmenting agents, tinting agents, tanning agents, bleaching agents, keratin-hardening agents, antimicrobial agents, light filter agents, repellent agents, hyperemising agents , keratolytic and keratoplastic substances, antidandruff active substances, antiphlogistics, keratinizing active substances, antioxidant active substances or active substances as free radical scavengers, skin moisturizing or skin moisturizing substances, moisturizing active substances, antierythematous or antiallergic active substances, branched fatty acids, such as 18-methyleicosanoic acid, and mixtures thereof.
  • Artificial skin tanning agents suitable for tanning the skin without natural or artificial exposure to UV rays are, for example, dihydroxyacetone, alloxan and walnut shell extract.
  • Suitable keratin-hardening substances are usually Active ingredients, such as those used in antiperspirants, such as potassium aluminum sulfate, aluminum hydroxychloride, aluminum lactate, etc.
  • Antimicrobial agents are used to destroy microorganisms or to inhibit their growth. They thus serve both as preservatives and as a substance with a deodorizing effect, which reduces the formation or intensity of body odor. These include, for example, customary preservatives known to those skilled in the art, such as p-hydroxybenzoic acid esters, imidazolidinyl urea, formaldehyde, sorbic acid, benzoic acid, salicylic acid, etc. Such deodorizing substances are, for example, zinc ricinoleate, triclosan, indecylenic acid alkylolamides, triethyl citrate, chlorhexidine, etc.
  • auxiliaries and additives for the production of hair cosmetics or skin cosmetics preparations are known to the person skilled in the art and can be found in cosmetic handbooks, i.e. the relevant specialist literature.
  • the added auxiliaries and additives are preferably cosmetically and/or pharmaceutically acceptable auxiliaries.
  • the excipients that are known to be usable in the field of pharmacy, food technology and related fields are pharmaceutically acceptable, in particular those listed in the relevant pharmacopoeias (e.g. DAB, Ph. Eur., BP, NF) and other excipients whose properties do not conflict with physiological use.
  • Suitable auxiliaries may be: lubricants, wetting agents, emulsifying and suspending agents, preservatives, antioxidants, anti-irritants, chelating agents, emulsion stabilizers, film formers, gelling agents, odor masking agents, hydrocolloids, solvents, solubilizers, neutralizing agents, permeation accelerators, pigments, quaternary ammonium compounds, moisturizing agents - and superfatting agents, ointment, cream or oil bases, silicone derivatives, stabilizers, sterilants, propellants, drying agents, opacifiers, thickeners, waxes, plasticizers, white oil.
  • a configuration in this regard is based on expert knowledge, as can be found in the relevant technical literature.
  • Suitable additives are selected from perfume oils, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light stabilizers, bleaches, care products, coloring agents, tinting agents, tanning agents, dyes, consistency enhancers, humectants, moisturizing agents, collagen, protein hydrolysates, Lipids, antioxidants, defoamers, antistatic agents, emollients, plasticizers, peroxide decomposers.
  • the present invention also relates to tobacco products.
  • the active ingredients according to the invention i.e. the mouthwashing and/or tingling/tingling active ingredient according to the invention, or the active ingredient mixture according to the invention or the flavoring preparation according to the invention, can advantageously also be used for the production of tobacco products.
  • tobacco products include cigars, cigarettes, pipe tobacco, chewing tobacco, and snuff.
  • manufacture of tobacco products which are supplemented with additives that have a cooling effect is known per se.
  • the active ingredients according to the invention were prepared using synthetic methods such as are described in more detail below and are known to those skilled in the art of organic synthesis.
  • the active ingredients according to the invention are synthesized as follows
  • R 1 is H, ethoxy, methoxy, methylethoxy, propoxy, hydroxy
  • R2 is H, ethoxy, methoxy, methylethoxy, propoxy, hydroxy
  • R4 stands.
  • Method A The benzoic acid derivative A was placed in toluene, thionyl chloride was added and the mixture was stirred under reflux for 1 h. The mixture was allowed to cool to about 50° C. and the batch was concentrated. The residue B is used in the 2nd stage. The piperazine derivative C was submitted with triethylamine and toluene. The residue B from FIG. Stage was entered and stirred at room temperature for 4 to 16 h.
  • Method B The benzoic acid derivative A was placed in dichloromethane. Oxalyl chloride was added dropwise. After the evolution of gas had ended, the mixture was stirred at reflux for 30 min and under reflux for 30 min. After cooling, the batch was concentrated and the residue is used in the 2nd stage.
  • the piperazine derivative C was introduced with triethylamine in dichloromethane.
  • the residue B from the 1st stage was dissolved in dichloromethane and added dropwise.
  • the mixture was stirred at room temperature for 24 h.
  • the batch was washed twice with NaHCOs solution and concentrated.
  • the residue was chromatographed on silica gel.
  • the piperazine derivative C was presented in 1% sodium hydroxide solution. Acetone was added until the mixture was a single phase. The residue B of the 1 . Stage was dissolved in acetone and added dropwise. The batch was concentrated, extracted twice with dichloromethane or ethyl acetate and then concentrated. The residue was chromatographed over silica gel.
  • the numbering of the examples does not necessarily correspond to the numbering of the compounds according to the preceding tables.
  • the sensory tasting of the active ingredients according to the invention was carried out as follows: (1) The active ingredients were each prepared in a 5% sugar solution or in an unflavored standard fondant mass.
  • Fondant is the name for a soft, pasty mass of sugar that is used to make various confectionery products.
  • Fondant is made from water and sucrose as well as glucose syrup, invert sugar cream and/or sugar alcohols (e.g. sorbitol or manniz).
  • the mass is boiled and then processed into a soft paste by vigorous kneading and rapid cooling.
  • test samples were tested by a panel of sensory experts under practical conditions. For the tasting, the oral cavity of 3 to 7 testers was rinsed with approx. 5 ml of the sugar solution and the solution spat out again.
  • the mouthwatering (mouthwatering) and/or tingling/tingling (tingling) effect was assessed on a scale of 1 (very weak) to 10 (very strong) and the profile was evaluated.
  • the compounds Nm. 16, 17, 18, 21, 23, 25, 28, 35, 36, 39, 42 or 44 according to Table 15 a mouthwashing, tingling/tingling effect, which was rated with an average intensity of 3 to 4.
  • the compounds Nos. 22, 27 and 39 according to Table 15 showed a mouthwashing, tingling/tingling effect, which was rated with an average intensity of 4 to 5.
  • the comma as the decimal separator is replaced by a period.
  • Application example 1.1 Typically hot aroma compositions containing the active ingredients according to the invention
  • the components are dissolved in a mixture of ethanol and demineralized water and then spray dried.
  • Application example 1.4 Production of flavors with a peppermint flavor using substances according to the invention
  • Example 1.5 Reduced alcohol beverage—production of a beer mix beverage with reduced alcohol content or without alcohol.
  • Example 1.6 Applications in a toothpaste ('Silica opaque')
  • Example 1.7 Use in a toothpaste (calcium carbonate base)
  • Example 1.8 Application in a sugar-free chewing gum
  • the parts A to D are mixed and kneaded intensively.
  • the raw mass obtained can then be processed into ready-to-eat chewing gum, e.g. in the form of thin strips.
  • Example 1.9 Mouthwash (“ready to use” without alcohol)
  • Example 1.11 Use in combination with a pungent plant extract as an alcohol booster
  • Version B Liqueur base 5.5% vol + 0.075% of a 10% solution of a
  • Version C Liqueur base 5.5%vol + 0.075% of a 10% solution of a grains of paradise extract in ethanol + 0.015% of a solution of (4-ethoxyphenyl)-[4-(2-phenylethyl)piperazin-1-yl]methanone (37/46 ) 1% in ethanol (corresponds to 1.5 ppm)
  • phases A and B are heated separately from one another to about 80.degree. Stir phase B into phase A with homogenization. Cool to approx. 40 °C while stirring, add phases C and D and briefly homogenize. Cool to room temperature while stirring.
  • Example 1.14 Seasoning mixture, “pepper” type
  • Application example 1.16 Application in a green tea beverage
  • the green tea concentrate is diluted with the 1% solution of (3,4-diethoxyphenyl)-[4-(2-phenoxyethyl)piperazin-1-yl]methanone (8/13) in propylene glycol and in the case of beverage B mixed with the 1% solution of [4-(2-cyclohexylethyl)-piperazin-1-yl]-phenyl-methanone (9/19) in propylene glycol. It is then filled up with demineralised water and thoroughly mixed again. The product is then filtered, packaged ready for use and sterilized at 118°C. A panel of trained test persons rated the taste of drinks A and B as clearly preferable to the unflavored green tea concentrate. The bitterness and astringency are reduced by the addition of the compounds according to the invention.
  • Example 1.17 Use in an iced tea drink (black tea)
  • the active ingredients according to the invention were each 10% or 1% pre-dissolved in ethanol.
  • Black tea extract was dissolved in water and stirred in a glass beaker together with sugar, a flavoring preparation (peach flavor) and the ethanolic solutions of the amides according to the invention.
  • Example 1.20 Instant soup, type chicken soup with noodles
  • Example 1.21 production of dark chili chocolates using the substances according to the invention
  • concentration of the compound or mixture used according to the invention can also be easily varied by a person skilled in the art.
  • product-specific further components in the respective application example can also be exchanged for or supplemented by other product-typical components in a way that is easy for the person skilled in the art to understand.
  • a variety of such product specific ingredients are disclosed in the above specification.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
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  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne le domaine des arômes et plus précisément de nouveaux représentants de ce groupe, en particulier des ingrédients actifs présentant un effet sialagogue. L'invention concerne également l'utilisation de ces ingrédients actifs et des préparations les comprenant, de préférence des préparations nutritionnelles ou stimulantes ou des préparations de soins bucco-dentaires, ou des préparations pharmaceutiques orales.
EP21847952.5A 2021-12-23 2021-12-23 Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant Pending EP4452941A1 (fr)

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WO2023117119A1 (fr) 2023-06-29

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