JP2019077714A - 甘味香味修飾因子 - Google Patents
甘味香味修飾因子 Download PDFInfo
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- JP2019077714A JP2019077714A JP2019009560A JP2019009560A JP2019077714A JP 2019077714 A JP2019077714 A JP 2019077714A JP 2019009560 A JP2019009560 A JP 2019009560A JP 2019009560 A JP2019009560 A JP 2019009560A JP 2019077714 A JP2019077714 A JP 2019077714A
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- Prior art keywords
- compound
- substituted
- solvate
- salt
- heteroaryl
- Prior art date
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- WEMQMWWWCBYPOV-UHFFFAOYSA-N s-indacene Chemical compound C=1C2=CC=CC2=CC2=CC=CC2=1 WEMQMWWWCBYPOV-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 235000019600 saltiness Nutrition 0.000 description 1
- 235000014612 sandwich biscuits Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 208000013220 shortness of breath Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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- 238000007614 solvation Methods 0.000 description 1
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- OJCLHERKFHHUTB-VIFPVBQESA-N tert-butyl (3s)-3-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H](CO)C1 OJCLHERKFHHUTB-VIFPVBQESA-N 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000012776 toaster pastry Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000020334 white tea Nutrition 0.000 description 1
- 235000009764 yeast-based spreads Nutrition 0.000 description 1
- 235000008924 yoghurt drink Nutrition 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- 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
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/60—Sweeteners
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- 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
- A23L27/30—Artificial sweetening agents
-
- 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
- A23L27/88—Taste or flavour enhancing agents
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
-
- 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
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
-
- 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
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
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- C07—ORGANIC CHEMISTRY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- General Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- Medicinal Preparation (AREA)
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Abstract
Description
本出願は、2013年3月13日に出願の米国仮出願第61/779,502号および2012年8月6日に出願の米国仮出願第61/679,912号に対する優先権の利益を請求し、それぞれの内容は、全ての目的についてこれらの全体が参照により本明細書に援用される。
本発明は、化学感覚もしくは化学感覚関連感覚または反応と関連する受容体およびこれらのリガンドを修飾するために適した化合物に関する。
Aは、任意に置換された4〜8員のアザ環であり;
Xは、共有結合または-NR1-であり;
R1は、水素またはC1〜C6アルキルであり;および
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
「アルキル」は、それ自体によって、またはもう一つの置換基の一部として、親アルカン、アルケンまたはアルキンの単一の炭素原子からの1つの水素原子の除去に由来する飽和もしくは不飽和、分枝、直鎖または環状の一価炭化水素基をいう。用語「アルキル」は、下で本明細書において定義したとおりの「シクロアルキル」を含む。典型的なアルキル基は、以下を含むが、限定されない:メチル;エタニル、エテニル、エチニルなどのエチル;プロパン-1-イル、プロパン-2-イル、シクロプロパン-1-イル、プロパ-1-エン-1-イル、プロパ-1‐エン2-イル、プロパ-2‐エン1-イル(アリル)、シクロプロパ‐1‐エン‐1‐イルなどのプロピル;シクロプロパ-2‐エン1-イル、プロパ-1-イン-1-イル、プロパ-2-イン-1-イル、その他;ブタン-1-イル、ブタン-2-イル、2-メチル-プロパン-1-イル、2-メチル-プロパン-2-イル、シクロブタン-1-イル、ブタ-1‐エン1-イル、ブタ-1‐エン2-イル、2-メチル-プロパ‐1‐エン‐1‐イル、ブタ-2‐エン1-イル、ブタ-2‐エン2-イル、ブタ-1,3-ジエン-1-イル、ブタ-1,3-ジエン-2-イル、シクロブタ-1‐エン1-イル、シクロブタ-1‐エン3-イル、シクロブタ-1,3-ジエン-1-イル、ブタ-1-イン-1-イル、ブタ-1-イン-3-イル、ブタ-3-イン-1-イル、その他などのブチル;および同様のもの。用語「アルキル」は、具体的には、任意の程度またはレベルの飽和を有する基、すなわち単一の炭素-炭素結合だけを有する基、1つまたは複数の二重炭素-炭素結合を有する基、1つまたは複数の三重炭素-炭素結合を有する基および一重、二重、三重炭素-炭素結合の混合物を有する基を含むことが意図される。飽和の具体的レベルが意図される場合、表現「アルカニル」、「アルケニル」および「アルキニル」が使用される。いくつかの態様において、アルキル基は、1〜20炭素原子(C1-C20アルキル)を含む。その他の態様において、アルキル基は、1〜12炭素原子(C1-C12アルキル)を含む。さらに他の態様において、アルキル基は、1〜6炭素原子(C1-C6アルキル)を含む。さらにアルキル基がもう一つの原子に結合するとき、それが「アルキレン」基になることに注意されたい。言い換えれば、用語「アルキレン」は、二価のアルキルをいう。たとえば、-CH2CH3は、エチルであり、その一方で、-CH2CH2-は、エチレンである。すなわち、「アルキレン」は、それ自体によって、またはもう一つの置換基の一部として、親アルカン、アルケンまたはアルキンの単一の炭素原子または2つの異なる炭素原子からの2つの水素原子の除去に由来する飽和または不飽和、分枝、直鎖、または環状の二価の炭化水素基をいう。用語「アルキレン」は、下で本明細書において定義したとおりの「シクロアルキレン」を含む。用語「アルキレン」は、具体的には、任意の程度またはレベルの飽和を有する基、すなわち一重炭素-炭素結合だけを有する基、1つまたは複数の二重炭素-炭素結合を有する基、1つまたは複数の三重炭素-炭素結合を有する基および一重、二重および三重炭素-炭素結合の混合物を有する基を含むことが意図される。飽和の具体的レベルが意図される場合、表現「アルカニレン」、「アルケニレン」および「アルキニレン」が使用される。いくつかの態様において、アルキレン基は、1〜20炭素原子(C1-C20アルキレン)を含む。その他の態様において、アルキレン基は、1〜12炭素原子(C1-C12アルキレン)を含む。さらに他の態様において、アルキレン基は、1〜6炭素原子(C1-C6アルキレン)を含む。
化合物
一つの態様において、本発明は、構造式(I)を有する化合物またはその塩もしくは溶媒和化合物を提供する:
Aは、任意に置換された4、5、6、7または8員アザ環であり;
Xは、共有結合または-NR1-であり;
R1は、水素またはC1〜C6アルキルであり;および
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
mは、1、2、3、4、5または6であり;
nは、0、1、2または3であり;ただし、m+nが1より大きくおよび7未満であることを条件とし;
qは、0、1、2、3、4、5または6である;ただし、qがm+n未満であることを条件とし;
Xは、共有結合または-NR1-であり;
R1は、水素またはC1〜C6アルキルであり;
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルであり;および
独立して、それぞれのR2は、アルキル、ヘテロアルキル、ハロ、ヒドロキシル、アルコキシ、アミノ、アルキルアミノ、シアノ、ニトロ、ハロアルキル、カルボン酸、アミド、エステル、アシル、チオール、アルキルチオおよびスルホンアミドからなる基から選択される。
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
Yは、アルキル、置換アルキル、ヘテロアルキル、置換ヘテロアルキル、カルボシクリル、置換カルボシクリル、ヘテロシクリル、置換ヘテロシクリル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルである。
本化合物は、本発明の1つまたは複数の方法、たとえば化学感覚もしくは化学感覚関連感覚または応答と関連する受容体およびこれらのリガンドの修飾のために使用することができる。本発明によれば、化学感覚受容体および/またはそのリガンドを調節する方法は、化学感覚受容体の活性、構造、機能、発現および/または修飾を調節すること、並びに状態、たとえば化学感覚受容体と関連する生理的または病理学的状態の調節、治療または予防的措置を含む。一般に、化学感覚受容体と関連する生理的または病理学的状態は、化学感覚受容体および/またはそのリガンド、たとえば胃腸障害、代謝性障害、機能胃腸障害、その他と関連する状態、疾患または障害を含む。一つの態様において、方法は、甘味香味を増加または強化することを含む。もう一つの態様において、方法は、内臓などの味蕾以外の体の場所において発現される甘味受容体および/またはそのリガンドを調節することを含む。一般に、本発明の化合物は、個々に、または組み合わせて、たとえば摂取可能な組成物などの組成物において提供することができる。一つの態様において、本化合物は、甘味料組成物における1つまたは複数の甘味料と1つまたは複数の本化合物を組み合わさることにより、より糖様の時間プロフィールおよび/または香味プロフィールを甘味料組成物に与えることができる。もう一つの態様において、本化合物は、1つまたは複数の本化合物とその組成物を接触させることにより、修飾された組成物を形成し、組成物の甘味味覚を増加または強化することができる。もう一つの態様において、本化合物は、味蕾における以外の体において発現される甘味受容体および/またはこれらのリガンドを調節する組成物中にあることができる。
冷蔵加工食品カテゴリーは、冷蔵加工肉、加工魚/シーフード製品、昼食キット、フレッシュカットフルーツ、レディーミール、ピザ、調理されたサラダ、スープ、フレッシュなパスタおよび麺を含むが、限定されない。
本発明の1つの側面において、本化合物は、治療上の目的のために使用することができる。すなわち、本化合物は、治療効果を達成するために化学感覚受容体および/またはそのリガンドを調節するための方法において使用することができる。たとえば、本方法は、味蕾における以外の体において発現される化学感覚受容体および/またはそのリガンドを調節することを含む。
本発明の化合物を調製する際に使用される出発材料、すなわち式(I)の本化合物の合成の前駆体の化合物の種々の構造的なサブクラスおよび種は、たいてい公知の化合物であり、または文献において記述された公知の方法によって合成することができ、またはこれらの種々のその他の世界的なオフィスにて、たとえばSigma- Aldrich Corporation of St. Louis, Missouri USA and their subsidiaries Fluka and Riedel-de Haenなどの当業者に周知の種々の供与源およびFisher Scientific, TCI America of Philadelphia, PA, ChemDiv of San Diego, CA, Chembridge of San Diego, CA, Asinex of Moscow, Russia, SPECS/BIOSPECS of the Netherlands, Maybridge of Cornwall, England, Acros, TimTec of Russia, Comgenex of South San Francisco, CA, and ASDI Biosciences of Newark, DEなどのその他の周知の化学的供給元から市販されている。
および同様のものなどの標準的なテキストにおいて考察される。多様に置換された複素環式、ヘテロアリールおよびアリール環(Ar、hAr1および/またはhAr2の前駆体)を含む出発材料の調製のための多くの一般的な方法は、Methoden der Organischen Chemie (Houben-Weyl) において見いだすことができ、種々の巻および版が、Georg Thieme Verlag, Stuttgartから入手できる。上で詳述した論文の全ての開示は、有機化合物およびこれらの前駆体を合成するための方法に関するこれらの教示について、これらの全体が参照により本明細書に援用される。
0℃にてジクロロメタン(100mL)中のクロロスルホニルイソシアネート(65.2g、461mmol)の溶液に、ジクロロメタン(100mL)中のギ酸酸(17.4mL、461mmol)の溶液を滴状に添加した。混合物を1時間0℃にて撹拌して、室温に暖めて、および18時間撹拌した。次いで、混合物を-78℃まで冷却し、2時間撹拌して、大半の溶媒をデカントした。生じる固体を真空下で乾燥させ、白色固体としてスルファモイルクロリド(48g、90%)を提供した。
熱溶液を除去未溶解の微粉に次いで濾過して、pH 3および溶液までの2MのHClが30分間さらに撹拌した続いて、濾液を室温に冷却して、中性 pHまで0.3MのHClで滴状に処理した。形成された沈殿物を吸引濾過によって収集して、水で洗浄して、真空下で乾燥させ、オフホワイトの粉末(72.44g)として表題化合物を得た。1H NMR (400 MHz, DMSO-d6, 80°C) δ 0.89 (d, 6H, J = 4.0 Hz), 1.37-1.47 (m, 2H), 1.67-1.72 (m, 1H), 1.86-1.91 (m, 1H), 1.94-2.19 (m, 4H), 2.96 (br. s, 2H), 3.55-4.14 (m, 4H), 6.66 (d, 1H, J = 4.0 Hz), 6.75 (d, 1H, J= 8.0 Hz), 7.45 (t, 1H, J = 8.0 Hz), 7.78 (br. s, 1H) 8.00 (br. s, 1H), 10.69 (s, 1H). MS 395 (MH+). Mp 237-238。
溶液をN2バルーン下で0℃にて10分間および次いで室温にて一晩撹拌して、セライトの層を通して濾過して、EtOAcで十分にリンスした。次いで、EtOAc溶液を2N Na2CO3、水および鹹水で連続的に洗浄して、Na2SO4上で乾燥させて、濾過して、濃縮し、オレンジ油として粗生成物を与えた。残渣を0-60%のEtOAc/ヘキサン勾配を使用するシリカゲルクロマトグラフィーによって精製し、続いてEOAc/ヘキサンからの結晶化によって淡黄色固体の表題化合物を得た(27.01g、85.63mmol、2工程にわたって71%)。1H NMR (400 MHz, DMSO-d6) 20°C) δ 0.79-0.92 (3xd, J = 6.4 Hz, 6H), 1.19-1.46 (m, 2H), 1.51-2.01 (m, 4H), 2.03-2.25 (m, 2H), 2.57 (dd, J = 10.4, 12.8 Hz, 0.3H), 2.75-2.88 (m, 0.6H), 2.92-3.10 (m, 1H), 3.65-4.08 (m, 3.6H), 4.27-4.40 (dm, 0.3H), 5.98 & 6.00 (s & s, 2H), 6.18 (pseudo t, J = 8.4 & 9.2 Hz, 1H), 6.32 (pseudo d, J = 8.4 Hz, 1H), 7.11-7.21 (m, 1H). MS 316 (MH+)。
無水THF(300mL)中の(S)-1-(3-(ヒドロキシメチル)ピペリジン-1-イル)-3-メチルブタン-1-オン(実施例5d)(42g、210.75mmol、1.2当量)の溶液を無水THF(600mL)中のNaH(鉱油中に60%、8.43g、273.97mmol、1.63当量)の懸濁液に0℃にて滴状に添加した。混合物を約25℃まで暖められ、および25℃以下の温度を保持しつつ1時間撹拌した。THF(300mL)中の2-アミノ-6-フルオロベンゾニトリル(22.95g、168.6mmol、1当量)の溶液を滴下して添加した。反応を、ゆっくり加熱して還流し、一晩撹拌した。混合物を室温まで冷却して、約400mLの残留材料まで濃縮した。飽和塩化アンモニウム(200mL)を添加した。15分間勢いよく撹拌した後に、EtOAc(800mL)を添加して、撹拌をさらに30分間続けた。その後、有機相を水、鹹水で洗浄して、Na2SO4上で乾燥させた。溶媒を真空下で除去して、残渣をシリカゲルで色層分析した(所望の生成物を提供するためにHex/EtOAc(44.6g、141.40mmol、83.87%)。1H NMR (400 MHz, DMSO-d6, 20°C) δ 0.79-0.92 (3xd, J = 6.4 Hz/each, 6H), 1.19-1.46 (m, 2H), 1.51-2.01 (m, 4H), 2.03-2.25 (m, 2H), 2.57 (dd, J = 10.4, 12.8 Hz, 0.3H), 2.75-2.88 (m, 0.6H), 2.92-3.10 (m, 1H), 3.65-4.08 (m, 3.6H), 4.27-4.40 (dm, 0.3H), 5.98 & 6.00 (s & s, 2H), 6.18 (pseudo t, J = 8.4 & 9.2 Hz, 1H), 6.32 (pseudo d, J = 8.4 Hz, 1H), 7.11-7.21 (m, 1H). MS 316 (MH+)。
溶液をDCMで希釈して、10%のクエン酸、飽和NaHCO3溶液、水、鹹水で連続的に洗浄して、Na2SO4上で乾燥させ、濾過し、および濃縮し、金色の褐色油(43.26g)として粗(S)-2-((1-(3-メチルブタノイル)ピペリジン-3-イル)メトキシ)-6-ニトロベンゾニトリルを得た。MS 346(MH+)。この材料を次の工程において精製することなく使用した。
混合物を15分間撹拌し、および無水THF(25mL)中の塩化イソバレリル(15.90g、131.9mmol、2当量)の溶液を、勢いよく撹拌しつつ、滴状に添加した。0℃にて30分後に、反応を、室温までゆっくり暖めて、および一晩撹拌した。Et2O(500mL)を激しく撹拌しながら反応混合物に添加した。有機層を分離し、および鹹水で洗浄して、Na2SO4上で乾燥させて、濃縮して残渣を与え、これをシリカでのクロマトグラフィーによって精製した(無色油状物(16.27g、82.62mmol、94%)として所望の化合物をえるためにHex/EtOAc 0 - 100。 1H NMR (400 MHz, DMSO-d6, 20°C) δ 0.88 (pseudo d, J = 6.4 Hz, 6H), 1.06-1.75 (m, 5H), 1.88-2.05 (m, 1H), 2.07-2.23 (m, 2H), 2.30 (dd, J = 10.8, 12.8 Hz, 0.5H), 2.64 (ddd, J = 3.2, 10.8, 13.2 Hz, 0.5H), 2.78 (dd, J = 10.4, 13.2 Hz, 0.5H), 2.93 (ddd, J = 2.4, 11.6, 13.6 Hz, 0.5H), 3.14-3.35 (m, 2H), 3.70-3.85 (m, 1H), 4.08-4.18 (dm, 0.5H), 4.31-4.40 (dm, 0.5H), 4.49 (t, J = 5.2 Hz, 0.5H), 4.58 (t, J = 5.2 Hz, 0.5H). MS 200 (MH+)。
無水THF(200mL)中の(S)-エチル1-(3-メチルブタノイル)ピペリジン-3-カルボキシラート(実施例5e、37.4g、154.97mmol)の溶液を0℃まで冷却して、LiCl(17g、401.04mmol)で処理した。5分間撹拌した後に、NaBH4(15g、396.50mmol)を同じ温度にて添加した。反応を-20Cにさらに冷却して下げ、無水エタノール(400mL)を滴状に添加した。反応を冷却上で保持して、室温にゆっくり暖めさせ、および一晩撹拌した。エタノール(100mL)を添加して、反応を飽和水性クエン酸溶液(600mL)で部分的に処理して、さらに30分間撹拌した。揮発性物質を真空下で取り除き、濃い無色の材料を与えた。水(100mL)およびDCM(800mL)を残渣に添加して、混合物を15分間勢いよく撹拌した。相を分離して、水性相おDCM(2×800 ML)でさらに抽出した。合わせた有機抽出物を鹹水で洗浄して、Na2SO4上で乾燥させた。溶媒を真空下で除去して、無色の残渣を与え、シリカゲルでのクロマトグラフィーによって精製た(3溶出剤:Hex/EtOAc 0 - 100)、きれいな生成物(29.65g、148.79mmol、96%)を得た。
1H NMR (400 MHz, DMSO-d6 , 80° C) δ : 1.41 (m, 2H), 1.68 (br s, 1H), 1.87 (br s, 1H), 1.98 (br s, 1H), 2.16 (br s, 2H), 3.65 - 4.00 (br s, 1H), 4.08 (br s, 3H), 6.65 (d, J = 8.0 Hz, 1H), 6.73 (d, J = 8.4 Hz, 1H), 7.43 (t, J = 8.4 Hz, 1H), 7.86 (br s, 2H), 8.12 (d, J = 8.0 Hz, 1H), 9.49 (d, J = 8.0 Hz, 1H,), 9.82 (s, 1H), 10.69 (br s, 1H). MS 417 (MH+)。
。
生じる残渣を、シリカゲル(ヘキサン中の35%のエチルアセテート)でフラッシュクロマトフラフィーし、白色固体(14.2g、82%)として(R)-tert-ブチル-2-(ヒドロキシメチル)ピペリジン-1-カルボキシラートを提供した。MS 116(MH+ boc)。
実施例49b:2-アミノ-6-((1-(3-メチルブタノイル)ピペリジン-3-イル)メトキシ)ベンゾニトリル
本化合物を試験して、甘味味覚を強化する活性が示された。具体的には、本化合物を、T1R2/T1R3受容体の活性化およびT1R2/T1R3受容体の活性化、並びにフルクトースなどの甘味料のための甘味味覚を強化する活性の増強を証明した。ヒト味覚試験について下記の実験1および実験2に記述した化合物Q1、J2、K2、L2、B1およびF3は、実施例を含むこの文書の全体にわたって記述した化合物および表Aに収載された化合物から選択した化合物である。
実験2-1:アイスコーヒーにおける化合物K2のスクロース増強:
全ての試料は、煎じたコーヒー、2%の乳、スクロースおよび水からなるアイスコーヒー配合で作製した。試料は、0.2%の炭酸水素ナトリウムおよび水で作製した0.2%の化合物ストックを使用して調製した。試験試料は、パネリストに一対で示して、彼らには試料のうちどちらがより甘味かについて決定するよう依頼した。
それはない、本明細書に提供された情報のいずれも従来技術であり、または現在請求した発明に関すること、または具体的または暗に参照したいずれの公開も従来技術である。
Claims (43)
- 構造式(Ia)を有する化合物
mは、4であり、nは、0であり;または、mは、3であり、nは、1であり;または、mとnは、ともに2であり;
qは、0、1、または2であり;
Xは、共有結合であり;
それぞれのR2は、独立して、アルキル、ハロ、ヒドロキシル、アルコキシ、および、ハロアルキルからなる群から選択され;および
Yは、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、アラルキル、置換アラルキル、ヘテロアリールアルキルまたは置換ヘテロアリールアルキルであり;
ただし、前記置換は、−Ra、ハロ、=O、−ORb、−SRb、−S−、=S、−NRcRc、=NRb、=N−ORb、−CF3、−CN、−OCN、−SCN、−S(O)2Rb、−S(O)2NRb、−S(O)2O−、−S(O)2ORb、−OS(O)2Rb、−OS(O)2ORb、−C(O)Rb、−C(S)Rb、−C(NRb)Rb、−C(O)O−、−C(O)ORb、−C(S)ORb、−C(O)NRcRc、−C(NRb)NRcRc、−OC(O)−、−OC(O)Rb、−OC(S)Rb、−OC(O)O−、−OC(O)ORb、−OC(S)ORb、−NRbC(O)Rb、−NRbC(S)Rb、−NRbC(O)O−、−NRbC(O)ORb、−NRbC(S)ORb、−NRbC(O)NRcRc、−NRbC(NRb)Rbおよび−NRbC(NRb)NRcRcからなる群から選択され;式中、Raは、アルキル、シクロアルキル、ヘテロアルキル、シクロヘテロアルキル、アリール、アリールアルキル、ヘテロアリールおよびヘテロアリールアルキルからなる群より選択され;それぞれのRbは、独立して水素またはRaであり;およびそれぞれのRcは、独立してRbであり、または代わりに、2つのRcは、これらが結合する窒素原子と共になって4−、5−、6−または7−員のシクロヘテロアルキルを形成してもよく、これらはO、NおよびSからなる群から選択される1〜4の同じまたは異なるさらなるヘテロ原子を任意に含んでもよい。 - Yは、6〜15員のアリール、置換6〜15員のアリール、5〜10員のヘテロアリール、または置換5〜10員のヘテロアリールである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、−(C1〜C3アルキレン)−アリールまたは−(C1〜C3アルキレン)−置換アリールである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、−(C1〜C3アルキレン)−ヘテロアリールまたは−(C1〜C3アルキレン)−置換ヘテロアリールである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、5または6員のヘテロアリール、置換された5もしくは6員のヘテロアリール、−(C1〜C3アルキレン)−(5もしくは6員のヘテロアリール)、または−(C1〜C3アルキレン)−(置換された5もしくは6員のヘテロアリール)である、請求項1の化合物またはその塩もしくは溶媒和化合物。
- ヘテロアリールは、ピロール、ピリジン、ピリミジン、ピリダジンまたはピラジンであり、これらのそれぞれは、任意に置換される、請求項18の化合物またはその塩もしくは溶媒和化合物。
- Yは、フェニルまたは置換フェニルである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、任意に置換された5もしくは6員の単環式ヘテロアリールまたは任意に置換された10〜12員の二環式ヘテロアリールである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、ピロール、ピリジン、ピリミジン、ピリダジン、ピラジン、ピリジンN−オキシド、キノリン、イミダゾピリジンおよびピラゾロピリジンからなる群より選択され、これらのそれぞれは、任意に置換される、請求項21の化合物またはその塩もしくは溶媒和化合物。
- Yは、−CH2−フェニルまたは−C(CH3)2−置換フェニルである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- Yは、−CH2−ヘテロアリールまたは−C(CH3)2−置換ヘテロアリールである、請求項1の化合物またはその塩もしくは溶媒和化合物。
- ヘテロアリールは、ピロール、ピリジン、ピリミジン、ピリダジン、またはピラジンであり、これらのそれぞれは、任意に置換される、請求項24の化合物。
- 請求項1〜26のいずれか一項の化合物;および摂取可能に許容した賦形剤で任意にあるを含む摂取可能な組成物。
- 1つまたは複数の甘味料をさらに含む、請求項27の摂取可能な組成物。
- 甘味料は、スクロース、フルクトース、グルコース、ガラクトース、マンノース、ラクトース、タガトース、マルトース、コーンシロップ(高フルクトースコーンシロップを含む)、D−トリプトファン、グリシン、エリスリトール、イソマルト、ラクチトール、マンニトール、ソルビトール、キシリトール、マルトデキストリン、マルチトール、イソマルト、水素付加したグルコースシロップ(HGS)、水素付加したデンプン水解物(HSH)、ステビオシド、レバウジオシド A、その他の甘味ステビアをベースとしたグリコシド、カレラーム、その他のグアニジンをベースとした甘味料、サッカリン、アセスルファム−K、シクラマート、スクラロース、アリターム、モグロシド、ネオテーム、アスパルテーム、その他のアスパルテーム誘導体およびこれらの組み合わせからなる群より選択される、請求項28の摂取可能な組成物。
- 請求項1〜26のいずれか一項の化合物を含んでいない摂取可能な組成物と比較して、増加した甘味味覚を有する、請求項27の摂取可能な組成物。
- 食品または飲料製品、医薬組成物、栄養製品、栄養補助食品、市販薬または口腔ケア製品である、請求項27の摂取可能な組成物。
- 食品または飲料製品は、ヒトまたは動物消費のためのものである、請求項31の摂取可能な組成物。
- 食品または飲料製品は、スープカテゴリー;乾燥加工食品カテゴリー;飲料カテゴリー;レディーミールカテゴリー;缶詰または保存された食品カテゴリー;冷凍加工 食品カテゴリー;冷蔵加工 食品カテゴリー;スナック食品カテゴリー;焼き菓子カテゴリー;菓子類カテゴリー;乳製品カテゴリー;アイスクリームカテゴリー;食事代替品カテゴリー;パスタおよびめん類カテゴリー;ソース、ドレッシング、調味料カテゴリー;ベビーフードカテゴリー;スプレッドカテゴリー;甘味コーティング、糖衣またはグレーズ;およびこれらの組み合わせからなる群より選択される、請求項27の摂取可能な組成物。
- 組成物の甘味味を増加させる方法であって、その組成物を請求項1〜26のいずれか一項の化合物と接触して改変された組成物を形成することを含む、方法。
- 甘味調節組成物であって、甘味料の第1の量と組み合わせて甘味料を提供するのに有効な量で請求項1〜26のいずれか一項の化合物を含み、甘味料は、化合物を伴わない甘味料の第1の量によって提供される甘味料を超える、甘味調節組成物。
- 請求項35の甘味調節組成物を含む、摂取可能な組成物。
- 食品または飲料製品、医薬組成物、栄養製品、栄養補助食品、市販薬または口腔ケア製品の形態である、請求項23の摂取可能な組成物。
- i)香味修飾成分として、請求項1〜26のいずれか一項の化合物;
ii)一つの担体;および
iii)任意に少なくとも1つのアジュバント
を含む香味料濃縮調合物。 - 少なくとも1つのアジュバントは、1つまたは複数の香味剤を含む、請求項38の香味料濃縮調合物。
- 少なくとも1つのアジュバントは、1つまたは複数の甘味料を含む、請求項38または39の香味料濃縮調合物。
- 少なくとも1つのアジュバントは、乳化剤、安定剤、抗菌保存剤、抗酸化剤、ビタミン、ミネラル、脂肪、デンプン、濃縮タンパク質および単離物、塩、凝固点降下剤、成核剤およびこれらの組み合わせからなる群より選択される1つまたは複数の成分を含む、請求項38〜40のいずれか1つの香味料濃縮調合物。
- 液体、固体、半固体、泡材料、ペースト、ゲル、クリーム、ローションおよびこれらの組み合わせのものからなる群より選択される形態である、請求項38〜41のいずれか1つの香味料濃縮調合物。
- 請求項1〜26のいずれか一項の化合物は、すぐ使用できる組成物における濃度の少なくとも2倍である濃度である、請求項38〜42のいずれか1つの香味料濃縮調合物。
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