EP3687311A1 - Amide destiné à produire un effet trigéminal - Google Patents

Amide destiné à produire un effet trigéminal

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Publication number
EP3687311A1
EP3687311A1 EP17784872.8A EP17784872A EP3687311A1 EP 3687311 A1 EP3687311 A1 EP 3687311A1 EP 17784872 A EP17784872 A EP 17784872A EP 3687311 A1 EP3687311 A1 EP 3687311A1
Authority
EP
European Patent Office
Prior art keywords
prop
formula
acid
thiomorpholino
compound
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
EP17784872.8A
Other languages
German (de)
English (en)
Inventor
Jekaterina ONGOUTA
Fabia HENTSCHEL
Michael Backes
Jakob Peter Ley
Thomas Riess
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
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP3687311A1 publication Critical patent/EP3687311A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • 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
    • C07D211/18—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • 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
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic 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
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to the use of a compound of formula (I) as described herein as a flavoring agent.
  • the invention further relates to novel compounds of the formula (I) as described herein or mixtures comprising one or more different compounds of the formula (I) as described herein or consisting of several different compounds of the formula (I) as described herein.
  • compositions comprising or consisting of a compound of formula (I) as described herein or mixtures thereof as described herein, pharmaceutical preparations, nutrition, oral hygiene or pleasure-providing preparations comprising a compound of formula (I ) as described herein or mixtures thereof as described herein or flavoring compositions as described herein, and methods of making a pharmaceutical preparation, nutritional, oral hygiene or pleasure preparation as described herein.
  • Capsaicin [N- (4-hydroxy-3-methoxybenzyl) -8-methyl- (6E) -nonoic acid amide] and other capsaicinoids such as nonivamide ([N- (4-hydroxy-3-methoxybenzyl) nonanoic acid amide) are known to be pungent and heat-producing flavors from various Capsicum species, especially chilli pepper, have long been known. With a correspondingly low dosage of the capsaicinoids a neutral sharpness and a warm sensation in the mouth is perceived, whereby the threshold to the painful sharpness and heat sensation is exceeded very fast.
  • capsaicin in food is not allowed in the European Union and was deleted from the Community Flavoring List in 2004 as the genotoxic potential of the compound was assessed as negative (European Food Safety Authority (EFSA), P., Italy, Opinion of the Scientific Committee on Food on Capsaicin, European Comission 2002, (SDF / CS / FLAV / FLAVOR / 8 ADD1 Final)).
  • EFSA European Food Safety Authority
  • SDF / CS / FLAV / FLAVOR / 8 ADD1 Final European Comission 2002
  • the use in food is often difficult because capsaicin has a very low taste threshold and high potency as Scharfstoff (about 16,000,000 Scoville heat units (SHU)).
  • Capsaicin is, also due to the high price of the pure substance, also used almost exclusively in the form of a capsicum extract, which contains, in addition to other pungent remains of other, after Capsicum tasting or smelling flavors and is therefore only partially suitable for widespread use.
  • a capsicum extract which contains, in addition to other pungent remains of other, after Capsicum tasting or smelling flavors and is therefore only partially suitable for widespread use.
  • the piperine (1-piperoylpiperidine) occurring in white pepper also causes a strong sharp impression (Römpp Lexikon Naturstoffchemie, Thieme 1997, p. 500), it shows a relative sharpness of only about 1% in comparison to capsaicin.
  • piperine has an intense taste that is pronounced of pepper, so that the application can be limited in many preparations.
  • n 1 or 2
  • X O or NCH.
  • R linear or branched C1-C5 alkyl radical
  • Radicals R-R 4 are described with substituents, among which also R and R 2 bridged together with OCH 2 0 is included. Furthermore, the radicals R 5 and Q are defined as separate alkyl or alkylphenyl side chains with the additional substituents R 6 -R 9 , but no cyclic amide side chains have been described.
  • the substituent hAr is an optionally substituted heteroatom five-membered ring (N, O, S) and R is another side chain. Not included in the described general formula (IV) direct cyclic amide side chains. A sharp taste impression is also not described.
  • the primary object is to provide less lipophilic, sensory quickly onset and not long-lasting pungent, which cause a warming taste sensation.
  • R 1 is H or O and R 2 is a branched or unbranched alkoxy radical having 1 to 6 C atoms or OH, or
  • X 1 and X 2 each represent C atoms linked via a single bond, a double bond or via a cyclopropane ring, and represents, where
  • Y ⁇ CHCH 2 OH is > or a physiologically acceptable salt thereof (in particular a sodium, potassium, ammonium, calcium, magnesium and / or zinc salt), the phenolic hydroxy group, if present, in formula (I) deprotonated, or a mixture comprising one or more different compounds of formula (I) and / or physiologically acceptable salts thereof (in particular sodium, potassium, ammonium, calcium, magnesium and / or zinc salts), wherein each of the phenolic Hydroxy group, if present, deprotonated in formula (I), or consisting of several different compounds of formula (I) and / or physiologically acceptable salts thereof (especially sodium, potassium, ammonium, calcium, magnesium and / or Zinc salts), wherein in each case the phenolic hydroxy group, if present, is deprotonated in formula (I), as a flavoring agent.
  • a physiologically acceptable salt thereof in particular a sodium, potassium, ammonium, calcium, magnesium and / or zinc salt
  • Particularly advantageous is therefore a use as described herein, as a flavoring or sharp material with a heat and / or sharpness-generating effect (ie as a substance (mixture) that sensory creates a heat impression) and / or as a flavoring for reducing or masking a unpleasant taste impression, preferably selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic (further details on this will be apparent from the comments below), and / or as a flavoring agent for enhancing a pleasant taste impression, preferably selected from the group consisting of warming, hot and cool (further details on this can be found in the comments below).
  • a flavoring or sharp material with a heat and / or sharpness-generating effect ie as a substance (mixture) that sensory creates a heat impression
  • a flavoring for reducing or masking a unpleasant taste impression preferably selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic (fur
  • the compound of the formula (I) or one, several or all compounds of the formula (I) is / are selected from the group consisting of
  • R represents H and R 2 represents a branched or unbranched Alkoyxrest having 1 to 5, preferably 1 to 4 C-atoms,
  • X 1 and X 2 each represent C atoms which are linked via a double bond
  • an unpleasant taste impression preferably selected from the group consisting of astringent, bitter, dry, dusty, floury, calcareous and metallic, to diminish or mask (further details of which will become apparent from the discussion below), and / or
  • (c) to enhance a pleasant taste impression preferably selected from the group consisting of warming, pungent and cooling (further details on this can be found in the statements below), preferably wherein the total amount of compound (s) of the formula (I) and / or salt (s) thereof is insufficient in the preparation to produce a warming and / or sharp effect on the tongue or in the oral cavity, but sufficient to mask or reduce an unpleasant taste impression of an unpleasant tasting substance or mixture.
  • a further aspect of the present invention relates to a compound of the formula (I) or a physiologically acceptable salt thereof (in particular sodium, potassium, ammonium, calcium, magnesium and / or zinc salts), where the phenolic hydroxy group, if present, deprotonated in formula (I), or a mixture comprising one or more different compounds of formula (I) and / or one or more physiologically acceptable salts thereof (in particular sodium, potassium, ammonium, calcium, magnesium and / or or zinc salts), wherein the phenolic hydroxy group, if present, in each case deprotonated in formula (I), or consisting of several different compounds of formula (I) and / or physiologically acceptable salts thereof (in particular sodium, potassium, ammonium, calcium, Magnesium and / or zinc salts), the phenolic hydroxy group, if present, in each case being deprotonated in formula (I),
  • a physiologically acceptable salt thereof in particular sodium, potassium, ammonium, calcium, magnesium and / or zinc salts
  • R is H or OMe and R 2 is a branched or unbranched alkoxy radical having 1 to 6 C atoms or OH, or
  • X 1 and X 2 each represent C atoms linked via a single bond, a double bond or via a cyclopropane ring, and
  • R 1 is H or O and R 2 is a branched or unbranched alkoxy radical having 1 to 5 C atoms,
  • X 1 and X 2 each represent C atoms linked via a single bond, a double bond or via a cyclopropane ring, and particularly preferred RH and R 2 represent a branched or unbranched Alkoyxrest having 1 to 5, preferably 1 to 4 C-atoms,
  • Preferred is a compound or mixture according to the invention as described herein, wherein the compound of formula (I) or one, several or all compounds of formula (I) is selected in the mixture or are selected from the group consisting of
  • a further aspect of the present invention relates to an aroma composition (A) comprising or consisting of a compound or mixture according to the invention (as described herein), preferably wherein the total amount of compound (s) of formula (I) and / or salt (s) thereof in the aroma composition, based on the total weight of the aroma composition, is in the range of 500 to 100,000 mg / kg, preferably in the range of 1,000 to 40,000 mg / kg, more preferably in the range of 1,000 to 15,000 mg / kg, and / or
  • (B) comprising a compound of formula (I) as defined herein or a physiologically acceptable salt thereof as defined herein or comprising or consisting of a mixture as defined herein, preferably wherein the total amount of compound (s) of formula (II) I) and / or salt (s) thereof in the aroma composition, based on the total weight of the aroma composition, in the range of 500 to 100,000 mg / kg, preferably in the range of 1,000 to 40,000 mg / kg, particularly preferably in the range of 1,000 to 15,000 mg / kg.
  • an aroma composition according to the invention as described herein additionally comprises one or more further flavorings not corresponding to formula (I), preferably selected from the group consisting of a) heat-causing or pungent substances, preferably selected from the group consisting of: capsaicinoids, such as, for example Capsaicin, dihydrocapsaicin or nonivamide; Gingerols, such as gingerol [6], gingerol [8], or Gingerol- [10]; Shogaols such as Shogaol [6], Shogaol [8], Shogaol [10]; Gingerdions such as gingerdione [6], gingerdione [8] or gingerdione [10]; Paradoxes such as paradole [6], paradole [8] or paradole [10]; Dehydrogenation diones, such as dehydrogenatedione [6], dehydrogenatedione [8] or dehydrogenated dione [10]; piperine; piperidine derivatives;
  • Tetradecapentaenoic acid N- (2-hydroxy-2-methylpropyl) -amide (gamma-hydroxyisosanshool); 2E, 4E, 8Z, 10E, 12E-tetradecapentaenoic acid N- (2-methyl-2-propenyl) amide (gamma-dehydrosanhool); 2E, 4E, 8Z, 10E, 12E-
  • Tetradecapentaenoic acid N- (2-methylpropyl) amide (gamma-sanshool); 2E, 4E, 8Z, 11Z-tetradecatetraenoic acid N- (2-hydroxy-2-methylpropyl) amide (Bungeanool); 2E, 4E, 8Z, 1 1E-tetradecatetraenoic acid N- (2-hydroxy-2-methylpropyl) amide (isobungeanool); 2E, 4E, 8Z-tetradecatrienoic acid N- (2-hydroxy-2-methylpropyl) amide (dihydrotungeanool) and 2E, 4E-tetradecadienoic acid N- (2-hydroxy-2-methylpropyl) amide (tetrahydrobungseanol);
  • Substances having a physiological cooling effect preferably selected from the following list: menthol and menthol derivatives (eg L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthyl ether (eg (L-menthoxy) -1, 2-propanediol, ( L-menthoxy) -2-methyl-1,2-propanediol, L-menthyl methyl ether), menthyl ester (eg menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl - (2-methoxy) acetate, menthyl (2-methoxyethoxy) acetate, menthyl pyroglutamate), menthyl carbonates (eg menthyl propylene glycol
  • L-menthone-glycerol ketal 2,3-dimethyl-2- (2-propyl) -butanoic acid derivatives (eg 2,3-dimethyl-2- (2-propyl) butanoic acid N-methylamide [WS23]), isopulegol or its esters (l - (-) - isopulegol, I- (-) - isopulegol acetate), menthane derivatives (eg p-menthane-3,8-diol), cubebol or synthetic or natural mixtures containing cubebol, pyrrolidone derivatives of cycloalkyldione derivatives (eg 3-methyl -2 (1-pyrrolidinyl) -2-cyclopenten-1-one) or tetrahydropyrimidin-2-one (eg icilin or related compounds as described in WO 2004/026840), other cooling agents as described in WO201 1061330, in particular derivatives different substituted cinnamic and 2-
  • Substances having an astringent effect preferably selected from the following list: catechols such as epicatechins, gallocatechins, epigallocatechins and their respective gallic acid esters, eg epigallocatechin gallate or epicatechingallate, their oligomers (procyanidins, proanthocyanidins, prodelphinidines, procyanirins, thearubigenins, theogallins) and their C- and O-glycosides; Dihydroflavonoids such as Dihydromyricetin, Taxifolin, and their C- and O-glycosides, flavonols such as myricetin, quercetin and their C- and O-glycosides such as quercetrin, rutin, gallic acid esters of carbohydrates such as tannin, pentagalloylglucose or their reaction products such as Elligatannin, aluminum salts, eg alum ,
  • compounds of formula (I) or their salts or mixtures thereof advantageously often have no significant other or undesirable flavor effects than those described herein. They can therefore be used particularly well in many different types of aromatics.
  • Flavor compositions according to the invention which are particularly advantageous are the combinations of compounds of the formula (I) or their salts with one or more other trigeminal (sharp, warming, pungent, biting, scratching, cooling, anesthetic, tingling, astringent) substances whose trigeminal (main) effect can be advantageously modulated by compounds of the formula (I) or salts thereof according to the invention.
  • trigeminal (main) effect can be advantageously modulated by compounds of the formula (I) or salts thereof according to the invention.
  • a warming, sharp or cooling effect can be enhanced, while an astringent effect can be attenuated.
  • an aroma composition according to the invention as described herein moreover comprising one or more non-formula (I) substances with unpleasant, especially bitter taste quality, or an astringent, bitter, dry, dusty, floury, calcareous and / or metallic note, preferably selected from the group consisting of: f) xanthine alkaloids, xanthines (caffeine, theobromine, theophylline and methylxanthines), alkaloids (quinine, brucine, strychnine, nicotine), phenolic glycosides (eg salicin, arbutin), flavonoid glycosides (eg neohespereidin, hesperidin, naringin , Quercitrin, rutin, hyperoside, quercetin-3-O-glucoside, myricetin-3-O-glycosides), chalcone or chalcone glycosides (eg phloridzin, p
  • terpenoid bitter and tannin eg limonoids such as limonin or nomiline from citrus fruits, lupolones and humolones from hops, iridoids, Secoiridoide
  • Absinthe from vermouth 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
  • pharmaceutical agents eg, fluoroquinolone antibiotics, paracetamol, aspirin, beta-lactam antibiotics, ambroxol, propylthiouracil [PROP], guaifenesin
  • vitamins for example,
  • Soy aspirins, isoflavonoids esp. Genistein, daidzein, genistin, daidzin, their glycosides and acylated glycosides
  • Substances having a non-unpleasant primary taste for example sweet, salty, spicy, sour
  • a non-unpleasant primary taste for example sweet, salty, spicy, sour
  • potassium salts especially potassium chloride, potassium gluconate, potassium carbonate, potassium sulfate, potassium lactate, potassium glutamate, Potassium succinate, potassium malate
  • aspartame acesulfame K, neotame, superaspartame, saccharin, sucralose, tagatose, monellin, stevioside, rebaudioside, rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside X, rubusoside, hernandulci
  • Another aspect of the present invention relates to a pharmaceutical preparation comprising nutrition, oral hygiene or pleasure preparation
  • (A) a compound or mixture of the invention (as described herein), preferably wherein the total amount of compound (s) of the formula (I) and / or salt (s) thereof in the preparation, based on the total weight of the preparation, in the range of 0.05 to 500 mg / kg, preferably in the range of 0, 1 to 200 mg / kg, more preferably in the range of 1 to 50 mg / kg, and / or
  • Preparation in the range of 0.05 to 500 mg / kg, preferably in the range of 0, 1 to 200 mg / kg, more preferably in the range of 1 to 50 mg / kg, and / or
  • Salt (s) thereof in the preparation based on the total weight of the preparation, in the range of 0.05 to 500 mg / kg, preferably in the range of 0, 1 to 200 mg / kg, particularly preferably in the range of 1 to 50 mg / kg.
  • an unpleasant taste impression preferably another substance contained in the preparation, in particular a taste impression selected from the group consisting of astringent, bitter, dry, dusty, floury, chalky and metallic, to reduce or mask, and / or
  • (C) a pleasant taste impression, preferably another substance contained in the preparation, in particular a taste impression selected from the group consisting of warming, hot and cooling to reinforce.
  • nutrition or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), confectionery (for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages.
  • baked goods eg bread, dry biscuits, cakes, other pastries
  • confectionery for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum
  • alcoholic or non-alcoholic beverages are, for example, baked goods (eg bread, dry biscuits, cakes, other pastries), confectionery (for example chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages.
  • alcoholic beverages eg cocoa, coffee, green tea, black tea, (green, black) tea extracts enriched with green, black tea, rooibos tea, other herbal tea, wine, wine-based beverages, beer, beer-containing Beverages, liqueurs, schnapps, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (Eg ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or pickled meat products), eggs or egg products (dry egg, egg white, egg yolk), Get rice products (eg breakfast cereals, granola bars, pre-cooked finished rice products), dairy products (eg full-fat or reduced-fat milk drinks, rice pudding, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dried milk powder, whey, butter, buttermilk, partly or completely hydrolyzed milk protein) containing products),
  • Pharmaceutical preparations comprise a pharmaceutically active substance.
  • Advantageous pharmaceutical agents are, for example, corticosteroids steroidal anti-inflammatory substances such.
  • Hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone.
  • non-steroidal pharmaceutical active ingredients are, for example, anti-inflammatory agents such as oxicams such as piroxicam or tenoxicam; Salicylates such as Aspirin® (acetylsalicylic acid), disalcide, solprin or fendosal; Acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin, or clindanac; Fenamates such as Mefenamic, Meclofenamic, Flufenamic or Niflumic; Propionic acid derivatives such as ibuprofen, naproxen, flurbiprofen, benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone.
  • oxicams such as piroxicam or tenoxicam
  • Salicylates such as Aspirin® (acetylsalicylic acid), disalcid
  • Particularly preferred pharmaceutical preparations are non-prescription products and over-the-counter drugs, so-called OTC (over-the-counter) preparations containing active ingredients such as paracetamol, acetylsalicylic acid or ibuprofen, vitamins (for example vitamin H, B-series vitamins such as vitamin B1, B2, B6, B12, niacin, pantothenic acid, preferably in the form of (effervescent) tablets or capsules), minerals (preferably in the form of (effervescent) tablets or capsules) such as iron salts, zinc salts, selenium salts, products containing active substances or extracts of ribwort (eg in cough syrup) or St. John's wort.
  • active ingredients such as paracetamol, acetylsalicylic acid or ibuprofen
  • vitamins for example vitamin H, B-series vitamins such as vitamin B1, B2, B6, B12, niacin, pantothenic acid, preferably in the form of (effervescent
  • the preparations according to the invention may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, Dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowable or chewable preparations and as a preparation with functional ingredients, as dietary supplements or as balanced diets.
  • the oral care preparations according to the invention are in particular oral and / or dental care such as toothpastes, tooth gums, tooth powder, mouthwash, chewing gum and other oral care products.
  • Dentifrices (as a base for oral care preparations) generally comprise an abrasive system (abrasives or abrasives) such as silicas, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites, surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine.
  • abrasive system abrasives or abrasives
  • silicas such as silicas, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites
  • surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine.
  • Humectants such as glycerol and / or sorbitol, thickening agents, such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or Laponite®, sweeteners, such as saccharin, other flavoring agents for unpleasant taste sensations, taste-correcting agents for further, generally not unpleasant taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as monosodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, menthol derivatives (eg L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketone le, menthane carboxylic acid amides), 2,2,2-trialkylacetic acid amides (eg 2,2-diisopropylpropionic acid methylamide), methylenedioxycinn
  • Chewing gums (as another example of oral care preparations) generally comprise a chewing gum base, ie chewing gum that becomes plastic upon chewing, sugars of various types, sugar substitutes, sweeteners, sugar alcohols, other taste senses for unpleasant taste sensations, taste scores for others, as a rule unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), the cooling agents, humectants, thickeners, emulsifiers, flavors and stabilizers or odor precursors mentioned in the previous section.
  • taste modulating substances eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • the cooling agents eg inositol phosphat
  • customary bases, auxiliaries and additives for preparations according to the invention are mixtures of fresh or processed, vegetable or animal raw materials or raw materials (for example raw, roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, Fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose, glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose), sugar alcohols (eg sorbitol ), natural or hydrogenated fats (eg tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (eg sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate), proteinogenic or not proteinogenic amino acids and related compounds (eg taurine), peptides, native or processed proteins (
  • taste modulating substances eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • emulsifiers eg lecithins, diacylglycerols
  • stabilizers eg carageenan, alginate
  • preservatives eg benzoic acid, sorbic acid
  • antioxidants eg tocopherol, ascorbic acid
  • chelators eg citric acid
  • organic or inorganic acidulants eg Malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid, lactic acid
  • additional bitter substances eg quinine, caffeine, limonin, am
  • a further aspect of the present invention relates to a process for preparing a pharmaceutical preparation, a nutrition, oral hygiene or pleasure preparation, preferably a preparation as described herein, comprising the following steps: i) providing
  • (A) a compound or mixture according to the invention (as described herein), preferably wherein the total amount of compound (s) of formula (I) and / or salt (s) thereof is selected such that the total amount in the preparation to be prepared, based on the total weight of the preparation is in the range of 0.05 to 500 mg / kg, preferably in the range of 0.1 to 200 mg / kg, more preferably in the range of 1 to 50 mg / kg, and / or
  • (B) a compound of formula (I) as defined herein or a physiologically acceptable salt thereof as defined herein or a mixture as defined herein, preferably wherein the total amount of compound (s) of formula (I) and / or Salt (s) thereof is selected such that the total amount in the preparation to be prepared, based on the total weight of the preparation, is in the range from 0.05 to 500 mg / kg, preferably in the range from 0.1 to 200 mg / kg, more preferably in the range of 1 to
  • an aroma composition according to the invention (as described herein), preferably wherein the total amount of compound (s) of formula (I) and / or salt (s) thereof is selected such that the total amount in the preparation to be prepared, based on the total weight the preparation is in the range of 0.05 to 500 mg / kg, preferably in the range of 0, 1 to 200 mg / kg, more preferably in the range of 1 to 50 mg / kg, ii) providing one or more further components of and iii) contacting or mixing the further constituents provided in step ii) with the constituent (s) provided in step i), preferably in a sensorially effective amount.
  • the described preparations according to the invention are preferably prepared by reacting one or more compounds of formula (I) according to the invention or mixtures according to the invention as described herein or one (or more) flavoring composition (s) according to the invention as described herein as a solid or as a solution in one of Nutrition, oral care or pleasure or oral pharmaceutical base preparation are incorporated.
  • preparations according to the invention which are present as a solution may also be used, for example. be converted by spray drying in a solid preparation.
  • a further aspect of the present invention relates to a composition
  • a composition comprising or consisting of a compound or mixture according to the invention as described herein and one or more compound (s) of the formula (I)
  • R is H or OMe and R 2 is a branched or unbranched alkoxy radical having 1 to 6 C atoms or OH, or
  • X 1 and X 2 are each C atoms which are linked via a single bond, a double bond or via a cyclopropane ring,
  • R and R 2 independently represent a hydrogen atom or an alkyl radical having 1-2 carbon atoms
  • R 3 and R 4 independently represent a hydrogen atom or a linear or branched alkyl radical having 1 to 5 carbon atoms, a phenyl radical, an alkylphenyl radical or a phenylalkyl radical or a linear or branched alkenyl radical having 2 to 4 carbon atoms or an alkenylphenyl radical or a phenylalkenyl radical, or
  • R and R 3 together with the carbon atoms linking them form a cyclohexyl ring which is optionally substituted by an additional radical R 5 , where R 5 is an alkyl radical having 1-2 carbon atoms,
  • R 2 represents a hydrogen atom or an alkyl radical having 1-2 carbon atoms
  • R 4 is a hydrogen atom or a linear or branched alkyl radical having 1 to 5 carbon atoms, a phenyl radical, an alkylphenyl radical or a phenylalkyl radical or a linear or branched alkenyl radical having 2 to 4 Represents carbon atoms or an alkenylphenyl radical or a phenylalkenyl radical, or a physiologically acceptable salt thereof,
  • compositions according to the invention described above in turn, the statements made above in connection with uses according to the invention or compounds of the formula (I) according to the invention or mixtures thereof or aroma compositions, preparations or processes according to the invention apply correspondingly.
  • Triethylamine (5.7 mL, 41.2 mmol, 4.0 eq.) And appropriate amine (1.1 g, 10.3 mmol, 1.0 eq.) Were dissolved in CH 2 Cl 2 (50 mL) and cooled to 0 ° C. The crude product was dissolved in CH 2 Cl 2 (10 mL) and slowly added dropwise to the solution. The reaction mixture was stirred at RT for 16 h. The reaction was stopped by the addition of NaHCO 3 solution. The aqueous phase was extracted with CH 2 Cl 2 (3 *), the combined organic phase dried over Na 2 S0 4 and concentrated in vacuo. The clean product was obtained after purification by column chromatography.
  • Example 3 Isointensity of amides according to the invention in comparison to nonivamide and a capsicum extract
  • the substance to be tasted was dissolved in ethanol and the ethanolic solution was then diluted with 5% sugar solution (final concentration: 10 ppm).
  • capsicum extract containing 1,000,000 SHU (0.3-10 ppm) and nonivamide (0.1-1 ppm) in 5% sugar solution in ascending concentration were prepared.
  • the oral cavity was rinsed by 4 examiners each with approx. 5 mL of the tasting solution and the solution was spit out again and evaluated against the reference series.
  • Example 4 Threshold values of amides according to the invention The threshold values were determined according to the method ASTM E 679-91 ("Standard Practice for Determination of Odor and Key Thresholds by a Forced-Choice Ascending Concentration Series Method of Limitsl"). It is the respective Flavor Threshold on Vittel ® water.
  • the threshold of (E) -3- (4-isopropoxyphenyl) -1-thiomorpholino-prop-2-en-1-one (16) in water is 660 ppb.
  • the threshold of (E) -3- (4-isobutoxyphenyl) -1-thiomorpholinoprop-2-en-1-one (14) in water is 707 ppb.
  • Example 5 Sharpness profile of (E) -3- (4-isopropoxyphenyl) -1-thiomorpholino-prop-2-en-1-oo (16) as compared to nonivamide, ethyl 2- (4-hydroxy-3-methoxy - phenyl) acetate (19) and 3-phenylpropyl-2- (4-hydroxy-3-methoxy-phenyl) -acetate (20)
  • Example 6 Warming effect of inventive or inventively used amides compared to vanillyl butyl ether
  • Test solutions containing 1.5 ppm of the amides according to the invention in a 5% sugar solution were evaluated by sensors and compared with a test solution of 10 ppm of vanillyl butyl ether.
  • (E) -3- (4-Ethoxyphenyl) -1-thiomorpholinoprop-2-en-1-one (17) and (E) -3- (4-ethoxyphenyl) -1-morpholino-prop-2-en-1 -one (18) had a milder heat effect compared to vanillyl butyl ether.
  • (E) -3- (4-isobutoxyphenyl) -1-thiomorpholinoprop-2-en-1-one (14) had a clearer thermal effect than vanillyl butyl ether.
  • the two components are dissolved in a mixture of ethanol and demineralized water and then spray dried.
  • Beer non-alcoholic, 0%
  • Grapefruit flavor 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20
  • Titanium (IV) oxide 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50
  • Application example 7 Application in a toothpaste (calcium carbonate base) All data, unless otherwise stated, in% by weight.
  • Parts A to D are mixed and kneaded intensively.
  • the raw mass obtained can then be processed for example in the form of thin strips to ready-to-eat chewing gum.
  • Sorbitol 70% 10 10 10 10 10 10 10 10 10 10 10 10 10 10
  • Green dye (1% in water) 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50 0.50
  • Version B Liqueur base 5.5% vol + 0.075% of a 10% solution of a paradise grain extract in ethanol + 0.02% of a solution of (E) -3- (4-isobutoxyphenyl) -1-thiomorpholinoprop-2-en-1-one (14 ) 1% in ethanol (equivalent to 2 ppm).
  • Version C Liqueur Base 5.5% vol + 0.075% of a 10% solution of a Paradise Grain Extract in ethanol + 0.015% of a solution of (E) -3- (4- isopropoxyphenyl) -1-thiomorpholino-prop-2-en-1-one (16) 1% in ethanol (equivalent to 1.5 ppm).
  • Version A and the comparison sample are very sensory-like.
  • Preparation Heat the components of phases A and B separately from each other to approx. 80 ° C. Stir phase B into phase A while homogenizing. Cool with stirring to approx. 40 ° C, add phases C and D and briefly post-homogenize. Cool to room temperature while stirring.
  • Palatinit was mixed with water. The mixture was then melted at 165 ° C and then cooled to 1 15 ° C. Then, the peppermint flavor and the aroma preparation (Use Example 1) were added. After mixing, the mixtures were poured into molds, removed from the molds after solidification and then individually packaged.
  • Grease powder 1 1.00 1 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00
  • Aroma Type "Pizza” 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20 1.20
  • Wort extract oil 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20
  • Application Example 16 Application in a green tea beverage
  • the green tea concentrate is in the case of drink A with the 1% solution of (E) -3- (4-lsobutoxyphenyl) -1-thiomorpholinoprop-2-en-1-one (14) in propylene glycol and in the case of beverage B with the 1% solution of (E) -3- (4-isopropoxyphenyl) -1-thiomorpholino-prop-2-en-1-one (16) in propylene glycol. Then it is filled up with demineralized water and thoroughly mixed again. Then the product is filtered, packed ready for use and sterilized at 1 18 ° C.
  • the taste of drinks A and B is evaluated by a panel of trained panelists as clearly preferred over the unflavoured green tea concentrate. The bitterness and astringency is reduced by the addition of the compounds of the invention.
  • the amides according to the invention were in each case pre-dissolved in ethanol at 10% or 1%.
  • Black tea extract was dissolved in water and stirred together with sugar, a flavoring preparation (peach flavor), and the ethanolic solutions of the amides according to the invention in a beaker.
  • Aroma preparation (peach type) 0.67 0.67 0.67 0.67 0.67
  • Citric acid (crystalline) 1.20 1.20 1.20 1.20
  • Application Example 21 Preparation of dark chilli chocolates using the substances according to the invention.

Abstract

La présente invention concerne l'utilisation d'un composé de formule (I), tel que décrit dans la description, en tant que substance aromatique. L'invention concerne en outre de nouveaux composés de formule (I) tel que décrits dans la description ou des mélanges comprenant un ou plusieurs composés différents de formule (I) tels que décrits dans la description ou constitués de plusieurs composés différents de formule (I) tel que décrits dans la description. Selon d'autres aspects, la présente invention concerne en outre des compositions aromatiques comprenant ou constituées d'un composé de formule (I) tel que décrit dans la description ou des mélanges de ces dernières tels que décrits dans la description, des préparations pharmaceutiques, des préparations servant à l'alimentation, à l'hygiène buccale ou à la consommation, comprenant un composé de formule (I) tel que décrit dans la description ou des mélanges de ces dernières tels que décrits dans la description ou des compositions aromatiques tels que décrites dans la description, et un procédé destiné à produire une préparation pharmaceutique, une préparation servant à l'alimentation, à l'hygiène buccale ou à la consommation telle que décrite dans la description.
EP17784872.8A 2017-09-27 2017-09-27 Amide destiné à produire un effet trigéminal Pending EP3687311A1 (fr)

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BR112022004348A2 (pt) 2019-09-30 2022-05-31 Givaudan Sa Aperfeiçoamentos em ou relacionados a compostos orgânicos
WO2023117119A1 (fr) * 2021-12-23 2023-06-29 Symrise Ag Ingrédients actifs présentant un effet sialagogue et un effet de picotement et de vertige et préparations les contenant
WO2024083615A1 (fr) 2022-10-21 2024-04-25 Givaudan Sa Compositions et procédés pour masquer des arrière-goûts dans des produits de consommation

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EP0495998A1 (fr) * 1990-08-10 1992-07-29 MITSUI TOATSU CHEMICALS, Inc. Derive d'amide d'acide dihydrocafeique et utilisation de ce dernier comme medicament
ATE320196T1 (de) * 2001-12-27 2006-04-15 Symrise Gmbh & Co Kg Verwendung von ferulasäureamiden als aromastoffe
US7057040B2 (en) 2002-02-07 2006-06-06 Council Of Scientific And Industrial Research Substituted aryl alkenoic acid heterocyclic amides
DE10227462A1 (de) 2002-06-20 2004-01-08 Symrise Gmbh & Co. Kg Herstellung von cis-Pellitorin und Verwendung als Aromastoff
GB0221697D0 (en) 2002-09-18 2002-10-30 Unilever Plc Novel compouds and their uses
DE10253331A1 (de) 2002-11-14 2004-06-03 Symrise Gmbh & Co. Kg Verwendung von trans-Pellitori als Aromastoff
JP2006179076A (ja) * 2004-12-21 2006-07-06 Funai Electric Co Ltd ディスク装置
ITMI20050674A1 (it) * 2005-04-15 2006-10-16 Univ Degli Studi Milano Uso di derivati ammidici come agenti modificatori del gusto composizioni aromatizzanti e prodotti che li contengono
US8778987B2 (en) 2007-03-13 2014-07-15 Symrise Ag Use of 4-hydroxychalcone derivatives for masking an unpleasant taste
ES2379304T3 (es) 2007-08-20 2012-04-24 Smith & Nephew, Plc Método para fabricar un material bioactivo para implantes
DE102010002558A1 (de) 2009-11-20 2011-06-01 Symrise Ag Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe
EP2529632B1 (fr) 2011-05-31 2013-08-28 Symrise AG Acide aminé cinnamique comme arômes épicés
EP2737807B1 (fr) * 2012-11-30 2017-04-05 Symrise AG Utilisation de dérivés d'acide cinnamique contenant de l'azote en tant qu'aromates
EP2932858A1 (fr) * 2014-04-16 2015-10-21 Symrise AG Ester d'acide homovallinique, en particulier pour obtenir une impression de chaleur et/ou de netteté

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