JP5036310B2 - 新規な風味、風味改質剤、味覚剤、味覚向上剤、旨味および甘味味覚剤、および/またはそれらの向上剤および使用 - Google Patents
新規な風味、風味改質剤、味覚剤、味覚向上剤、旨味および甘味味覚剤、および/またはそれらの向上剤および使用 Download PDFInfo
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- JP5036310B2 JP5036310B2 JP2006522748A JP2006522748A JP5036310B2 JP 5036310 B2 JP5036310 B2 JP 5036310B2 JP 2006522748 A JP2006522748 A JP 2006522748A JP 2006522748 A JP2006522748 A JP 2006522748A JP 5036310 B2 JP5036310 B2 JP 5036310B2
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- Prior art keywords
- compound
- oxalamide
- methyl
- ethyl
- ppm
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- 235000019640 taste Nutrition 0.000 title claims description 95
- 235000019583 umami taste Nutrition 0.000 title abstract description 178
- 235000019605 sweet taste sensations Nutrition 0.000 title abstract description 12
- 235000019607 umami taste sensations Nutrition 0.000 title abstract description 4
- 239000000796 flavoring agent Substances 0.000 title description 51
- 235000019634 flavors Nutrition 0.000 title description 45
- 239000003623 enhancer Substances 0.000 title description 18
- 239000003607 modifier Substances 0.000 title description 16
- 239000003795 chemical substances by application Substances 0.000 title description 5
- -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 claims description 390
- 239000000203 mixture Substances 0.000 claims description 106
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
- 235000013305 food Nutrition 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000001153 fluoro group Chemical group F* 0.000 claims description 56
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 53
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 52
- 229920002554 vinyl polymer Polymers 0.000 claims description 52
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
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- 235000007315 Satureja hortensis Nutrition 0.000 claims description 22
- 241001465754 Metazoa Species 0.000 claims description 21
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000005936 piperidyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- HETCYFFYGYGQSP-UHFFFAOYSA-N N1-(2,4-Dimethoxybenzyl)-n2-(2-(pyridin-2-yl) ethyl)oxalamide Chemical compound COC1=CC(OC)=CC=C1CNC(=O)C(=O)NCCC1=CC=CC=N1 HETCYFFYGYGQSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- BOVLNTIAPBGJLJ-UHFFFAOYSA-N NC(C(NOC(F)(F)F)=O)=O Chemical class NC(C(NOC(F)(F)F)=O)=O BOVLNTIAPBGJLJ-UHFFFAOYSA-N 0.000 claims 3
- GDMDCNCFVKXNAN-UHFFFAOYSA-N N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(5-methylpyridin-2-yl)ethyl)oxalamide Chemical compound COC1=CC(C)=CC=C1CNC(=O)C(=O)NCCC1=CC=C(C)C=N1 GDMDCNCFVKXNAN-UHFFFAOYSA-N 0.000 claims 1
- DWXUCYSOIKPLJM-UHFFFAOYSA-N N1-(2-Methoxy-4-methylbenzyl)-n2-(2-(pyridin-2-yl) ethyl)oxalamide Chemical compound COC1=CC(C)=CC=C1CNC(=O)C(=O)NCCC1=CC=CC=N1 DWXUCYSOIKPLJM-UHFFFAOYSA-N 0.000 claims 1
- NHANILBHDFUGPP-UHFFFAOYSA-N n'-[(2,3-dimethoxyphenyl)methyl]-n-(2-pyridin-2-ylethyl)oxamide Chemical compound COC1=CC=CC(CNC(=O)C(=O)NCCC=2N=CC=CC=2)=C1OC NHANILBHDFUGPP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 375
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- 101000659767 Homo sapiens Taste receptor type 1 member 1 Proteins 0.000 abstract description 24
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- 101000659765 Homo sapiens Taste receptor type 1 member 2 Proteins 0.000 abstract description 22
- 102100035948 Taste receptor type 1 member 2 Human genes 0.000 abstract description 22
- 108091005708 gustatory receptors Proteins 0.000 abstract description 12
- 230000001939 inductive effect Effects 0.000 abstract description 4
- 239000012634 fragment Substances 0.000 abstract description 3
- 238000000423 cell based assay Methods 0.000 abstract description 2
- 238000003384 imaging method Methods 0.000 abstract description 2
- 238000012188 high-throughput screening assay Methods 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 182
- 210000004027 cell Anatomy 0.000 description 174
- 230000004913 activation Effects 0.000 description 140
- 235000013923 monosodium glutamate Nutrition 0.000 description 74
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
- 239000004223 monosodium glutamate Substances 0.000 description 58
- 235000009508 confectionery Nutrition 0.000 description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 235000011194 food seasoning agent Nutrition 0.000 description 45
- 239000000047 product Substances 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 125000005842 heteroatom Chemical group 0.000 description 41
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- CLJMMQGDJNYDER-UHFFFAOYSA-N heptan-4-amine Chemical compound CCCC(N)CCC CLJMMQGDJNYDER-UHFFFAOYSA-N 0.000 description 39
- 229910052757 nitrogen Inorganic materials 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 33
- 150000003857 carboxamides Chemical class 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 125000002252 acyl group Chemical group 0.000 description 29
- 150000002430 hydrocarbons Chemical group 0.000 description 29
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- 230000001965 increasing effect Effects 0.000 description 27
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- 239000000825 pharmaceutical preparation Substances 0.000 description 26
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 235000003599 food sweetener Nutrition 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 239000003765 sweetening agent Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 125000000547 substituted alkyl group Chemical group 0.000 description 23
- 229910052760 oxygen Inorganic materials 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000002243 precursor Substances 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- 239000001301 oxygen Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 18
- 125000004414 alkyl thio group Chemical group 0.000 description 18
- 125000004122 cyclic group Chemical group 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 17
- 239000011593 sulfur Substances 0.000 description 17
- 241000282412 Homo Species 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 125000003710 aryl alkyl group Chemical group 0.000 description 16
- 235000019264 food flavour enhancer Nutrition 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 15
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004423 acyloxy group Chemical group 0.000 description 15
- 150000001413 amino acids Chemical class 0.000 description 15
- PPFKVYRRIDGJJS-UHFFFAOYSA-N 3-amino-n-heptan-4-yl-4-hydroxybenzamide Chemical compound CCCC(CCC)NC(=O)C1=CC=C(O)C(N)=C1 PPFKVYRRIDGJJS-UHFFFAOYSA-N 0.000 description 14
- 239000004278 EU approved seasoning Substances 0.000 description 14
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 14
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- 235000013409 condiments Nutrition 0.000 description 13
- QVDXUKJJGUSGLS-ZCFIWIBFSA-N methyl (2r)-2-amino-4-methylpentanoate Chemical compound COC(=O)[C@H](N)CC(C)C QVDXUKJJGUSGLS-ZCFIWIBFSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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- 239000012267 brine Substances 0.000 description 12
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 9
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 9
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 8
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- RNTYTQILDXWFLQ-UHFFFAOYSA-N 5-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2OC(C(O)=O)=CC2=C1 RNTYTQILDXWFLQ-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
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- 230000003213 activating effect Effects 0.000 description 8
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
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- QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 description 7
- KYRWRIRWJFXZLS-UHFFFAOYSA-N 2-methylheptan-4-amine Chemical compound CCCC(N)CC(C)C KYRWRIRWJFXZLS-UHFFFAOYSA-N 0.000 description 7
- TXBBASAAFCRUQU-UHFFFAOYSA-N 4-ethoxy-3-methylbenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1C TXBBASAAFCRUQU-UHFFFAOYSA-N 0.000 description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/54—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
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- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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Description
本発明は、食品、飲料、および他の食料品または経口投与される医薬品または組成物のための風味または味覚改質剤(例えば、香味料または調味料)および風味または味覚向上剤(さらに特定すると、薬味(savory)(「旨味」)または甘味改質剤、薬味または甘味剤および薬味または甘味向上剤)に関する。
何世紀にもわたって、食料(食用)品、飲料、および/または経口投与される医薬品組成物には、それらの味を向上させるために、種々の天然および非天然組成物および/または化合物が添加されている。「味覚」の基本形が少数にすぎないことは長く知られているものの、味覚を知覚する生物学的および生化学的な基本は、理解が不十分であり、殆どの味覚改良剤または味覚改質剤は、大部分は、簡単な試行錯誤法により、発見されてきた。
本発明は、多くの局面を有し、それらの全ては、いくつかの様式にて、以下で式(I)で示される特定の天然に存在しないアミド化合物および/またはアミド誘導体化合物に関する:
a)少なくとも1種の食料品もしくは医薬品、またはそれらの前駆物質を提供する工程;および
b)改質食料品または医薬品を形成するために、該食料品または医薬品を、少なくとも薬味調節量または甘味調節量の少なくとも1種の非天然アミド化合物またはそれらの食用に受容可能な塩と混ぜ合わせる工程;
ここで、該アミド化合物は、次式を有する:
ここで、必要に応じて、R2およびR3の一方は、Hであり、そして、ここで、R2およびR3の他方の少なくとも1個は、有機または炭化水素残基を含み、該有機または炭化水素残基は、少なくとも3個の炭素原子、および必要に応じて、1個またはそれ以上のヘテロ原子を含み、該ヘテロ原子は、別個に、酸素、窒素、イオウ、ハロゲンまたはリンから選択される。
本発明は、本発明の種々の実施態様の以下の詳細な説明およびそこに含まれる実施例および化学図面および表および先の記述および以下の記述を参照することにより、さらに容易に理解できる。本発明の化合物、組成物および/または方法を開示し記述する前に、請求の範囲で特に明記しない限り、本発明は、特定の食品または食品調節方法、特定の食用または医薬キャリアまたは処方、または本発明の化合物を食料品または経口投与用医薬品または組成物に処方する特定の様式には限定されず、関連技術の当業者がよく知っているように、このようなことは、もちろん、変えることができることが理解できるはずである。また、本明細書中で使用する専門用語は、特定の実施態様を記述する目的のためのみであり、限定するとは解釈されないことが理解できるはずである。
本明細書中で使用する「医薬品」との用語は、薬効を有するか医薬活性剤を含む摂取可能で非毒性の物質である固形組成物および液状組成物の両方(例えば、咳止めシロップ、咳止めドロップ、アスピリンおよび咀嚼錠剤)を含む。
本発明の化合物は、全て、有機(炭素を含有する)化合物であり、これらは、その中に少なくとも1個の「アミド」基を有し、以下の一般構造を有し、これは、以下、以下で示す式(I)を有するアミド化合物と呼ぶ:
薬味および甘味レセプタ化アゴニスト活性の1つまたは両方を有する式(I)のアミド化合物の多くの好ましい実施態様では、以下の式(II)を有するアミド化合物の好ましい亜属がある:
式(I)のアミド化合物の他の亜属では、このアミド化合物は、式(IV)を有する尿素化合物である:
式(I)のアミド化合物の他の亜属では、このアミド化合物は、式(V)を有するオキサルアミド化合物である:
R20およびR40は、それぞれ別個に、Hまたは炭化水素残基であり、該炭化水素基は、1個またはそれ以上のヘテロ原子を含有し得る;好ましくは、R20およびR40は、HまたはC1〜C3アルキル、またはそれらの必要に応じて置換した基である。さらに好ましくは、R20およびR40は、Hである。さらに、R10およびR30について、0個、1個、2個、3個または4個の任意の置換基が存在し得、該置換基は、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、CO2CH3、SCH3、SEt、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシ基から選択される。
式(I)のアミド化合物の他の亜属では、このアミド化合物は、式(VI)を有するアクリルアミド化合物である:
式(I)のアミド化合物の多く、またはその種々の亜属は、酸性基または塩基性基を含み、したがって、それらが処方されている食用組成物または医薬組成物の酸性または塩基性の特性(「pH」)に依存して、これらは塩として存在し得る。これらの塩は、食用に受容可能である(すなわち、安全として一般に認識されるもの(generally recognized as safe)、またはGRASとして指定される)か、または薬学的に受容可能な塩である(これらの多くは、米国食品医薬品庁(Federal Food and Drug Administrationによって認められている)。
式(I)のアミド化合物およびその種々の亜属または種の化合物は、上記のように、食用または医薬製品のための薬味または甘味の風味剤化合物または風味改質剤であると意図される。本明細書における教示および実施例から明らかであるように、式(I)の化合物の多くは、少なくとも比較的高いアミド化合物濃度で、hT1R1/hT1R3「薬味」レセプタまたはhT1R2/hT1R3甘味レセプタのアゴニストである。したがって、式(I)の化合物の多くは、少なくとも比較的高濃度で、薬味または甘味の風味剤または風味向上剤として、少なくともある程度の有用性を有し得る。
本発明の調味料、風味改質剤、香料、風味向上剤、薬味(「旨味」)風味剤および/または風味向上剤は、薬味または甘味化合物が従来使用されている食用組成物、飲料組成物および医薬組成物への用途を有する。これらの組成物は、ヒトおよび動物の消費のための組成物を包含する。これらは、農業用動物、ペット、および動物園の動物によって消費されるための食品を含む。
1つ以上の菓子類、チョコレート菓子、タブレット、カウントライン(countline)、袋入りセルフライン(selfline)/ソフトライン(softline)、箱入りアソートメント(assortment)、標準的な箱入りアソートメント(assortment)、ねじり包装ミニチュア、季節的なチョコレート、おもちゃ付きチョコレート、アルファジョア(alfajore)、他のチョコレート菓子、ミント、標準的ミント、パワーミント、茹で菓子(boiled sweet)、ペーストリー、ガム、ゼリー、およびチュー(chew)、タフィー、キャラメルおよびヌガー、薬用菓子、ロリポップ、甘草、他の砂糖菓子、ガム、砂糖入りガム、砂糖なしガム、機能的ガム、風船ガム、パン、包装された/工場製パン、非包装/職人製パン、ペーストリー、ケーキ、包装された/工場製ケーキ、非包装/職人製ケーキ、クッキー、チョコレートコートされたビスケット、サンドビスケット、充填ビスケット、薬味ビスケットおよびクラッカー、パン代替物、朝食シリアル、rteシリアル、家族用朝食シリアル、フレーク、ミューズリ、他のrteシリアル、子供用朝食シリアル、ホットシリアル、アイスクリーム、インパルス(impulse)アイスクリーム、単一ポーションの乳性アイスクリーム、単一ポーションの氷菓、マルチパック氷菓、持ち帰りアイスクリーム、持ち帰り乳製品アイスクリーム、アイスクリームデザート、バルクアイスクリーム、持ち帰り氷菓、フローズンヨーグルト、職人製アイスクリーム、乳製品、乳、新鮮/低温殺菌乳、全脂肪新鮮/低温殺菌乳、半脱脂新鮮/低温殺菌乳、長期保存/uht乳、全脂肪長期保存/uht乳、半脱脂長期保存/uht乳、無脂肪長期保存/uht乳、ヤギ乳、濃縮(condensed/evaporated)乳、プレーン濃縮(condensed/evaporated)乳、風味付濃縮乳、機能性濃縮乳および他の濃縮乳、風味付濃縮乳飲料、乳製品のみの風味付乳飲料、フルーツジュース入り調味乳飲料、豆乳、酸乳飲料、発酵乳飲料、コーヒーミルク(coffee whitener)、粉乳、風味付粉乳飲料、クリーム、チーズ、プロセスチーズ、スプレッドプロセスチーズ、非スプレッドプロセスチーズ、非加工チーズ、スプレッド非加工チーズ、非スプレッド非加工チーズ、硬質チーズ、包装された硬質チーズ、非包装硬質チーズ、ヨーグルト、プレーン/ナチュラルヨーグルト、風味付ヨーグルト、フルーツヨーグルト、共生細菌ヨーグルト、飲用ヨーグルト、通常の飲用ヨーグルト、共生細菌飲用ヨーグルト、冷蔵および保存安定デザート、乳製品ベースのデザート、ダイズベースのデザート、冷蔵スナック、フロマージュフレおよびクアルク、プレーンフロマージュフレおよびクアルク、風味付フロマージュフレおよびクアルク、薬味フロマージュフレおよびクアルク、甘味および薬味スナック、フルーツスナック、チップス/クリスプ、押出しスナック、トルティヤ/コーンチップス、ポップコーン、プレッツェル、ナッツ、他の甘味および薬味スナック、スナックバー、グラノーラバー、朝食バー、エネルギーバー、フルーツバー、他のスナックバー、食物代替製品、スリミング用製品、病後用飲料、インスタント食品、缶詰インスタント食品、冷凍インスタント食品、乾燥インスタント食品、冷蔵インスタント食品、ディナーミックス、冷凍ピザ、冷蔵ピザ、スープ、缶詰スープ、脱水スープ、インスタントスープ、冷蔵スープ、uhtスープ、冷凍スープ、パスタ、乾燥パスタ、冷蔵/生パスタ、麺、プレーンな麺、インスタント麺、カップ/ボール入りインスタント麺、袋入りインスタント麺、冷蔵麺、スナック麺、缶詰食品、缶詰肉および肉製品、缶詰野菜、缶詰トマト、缶詰豆、缶詰果物、缶詰インスタント食品、缶詰スープ、缶詰パスタ、他の缶詰食品、冷凍食品、冷凍加工赤肉、冷凍加工鶏肉、冷凍加工魚/魚介類、冷凍加工野菜、冷凍肉置換物、冷凍ポテト、オーブンで焼いたポテトチップス、他のオーブンで焼いたポテト製品、オーブンで焼いていない冷凍ポテト、冷凍ベーカリー製品、冷凍デザート、冷凍インスタント食品、冷凍ピザ、冷凍スープ、冷凍麺、他の冷凍食品、乾燥食品、デザートミックス、乾燥インスタント食品、脱水スープ、インスタントスープ、乾燥パスタ、プレーン麺、インスタント麺、カップ/ボール入りインスタント麺、袋入りインスタント麺、冷蔵食品、冷蔵加工肉、冷蔵魚/魚介類製品、冷蔵加工魚、冷蔵のコートされた魚、冷蔵燻製魚、冷蔵ランチキット、冷蔵インスタント食品、冷蔵ピザ、冷蔵スープ、冷蔵/生パスタ、冷蔵麺、油脂、オリーブオイル、野菜油および種油、調理用油脂、バター、マーガリン、スプレッド油脂、機能性スプレッド油脂、ソース、ドレッシングおよび香辛料、トマトペーストおよびピューレ、ブイヨン/ストックキューブ、ストックキューブ、グレービー顆粒、液体ストックおよびフォンデュ、ハーブおよびスパイス、発酵ソース、ダイズベースのソース、パスタソース、湿性ソース、乾燥ソース/粉末ミックス、ケチャップ、マヨネーズ、通常のマヨネーズ、マスタード、サラダドレッシング、通常のサラダドレッシング、低脂肪サラダドレッシング、ビネグレット、ディップ、酢漬け製品、他のソース、ドレッシングおよび香辛料、ベビーフード、乳調製物、標準的乳調製物、後続(follow−on)乳調製物、幼児用乳調製物、低アレルギー性乳調製物、調製ベビーフード、乾燥ベビーフード、他のベビーフード、スプレッド、ジャムおよびプレザーブ、蜂蜜、チョコレートスプレッド、ナッツベースのスプレッド、および酵母ベースのスプレッド。
a)少なくとも1種の食料品もしくは医薬品、またはそれらの前駆物質を提供する工程;および
b)改質食料品または医薬品を形成するために、該食料品または医薬品を、少なくとも薬味調節量または甘味調節量の少なくとも1種の非天然アミド化合物またはそれらの食用に受容可能な塩と混ぜ合わせる工程;
ここで、該アミド化合物は、次式を有する:
本発明の化合物(すなわち、式(I)のアミド化合物およびそれらの合成前駆物質の種々の構造上の亜属および種(特に、有機カルボン酸および安息香酸、イソシアネート、および種々のアミン、アニリン、アミノ酸など))を調製する際に使用される出発物質は、しばしば、公知化合物であるか、または当業者に周知の種々の業者(例えば、Sigma−Aldrich Corporation of St.Louis Missouri USAおよびその子会社であるFlukaおよびRiedel−de Haenの種々の他の世界中の事務所)および他の周知の業者(例えば、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 Deleware)から市販されている。
CH3CN=アセトニトリル
CHCl3=クロロホルム
DIC=N,N’−ジイソプロピルカルボジイミド
DIPEA=ジイソプロピルエチルアミン
DMAP=4−(ジメチルアミノ)−ピリジン
DMF=N,N−ジメチルホルムアミド
EDCI=1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミド塩酸塩
DCM=ジクロロメタン
ESIMS=エレクトロンスプレー質量分析
Et3N=トリエチルアミン
EtOAc=酢酸エチル
EtOH=エチルアルコール
Fmoc=N−(9−フルオレニルメトキシカルボニル−
HCl=塩酸
H2SO4=硫酸
HOBt=1−ヒドロキシベンゾトリアゾール
MeOH=メチルアルコール
MgSO4=硫酸マグネシウム
NaHCO3=炭酸水素ナトリウム
NaOH=水酸化ナトリウム
Na2SO4=硫酸ナトリウム
Ph=フェニル
r.t.=室温
SPOS=固相有機合成
THF=テトラヒドロフラン
TLC=薄層クロマトグラフィー
アルキル基の略語
Me=メチル
Et=エチル
n−Pr=ノルマルプロピル
i−Pr=イソプロピル
n−Bu=ノルマルブチル
i−Bu=イソブチル
t−Bu=第三級ブチル
s−Bu=第二級ブチル
n−Pen=ノルマルペンチル
i−Pen=イソペンチル
n−Hex=ノルマルヘキシル
i−Hex=イソヘキシル
重合体支持試薬の略語
PS−トリスアミン=トリス−(2−アミノエチル)アミンポリスチレン
PS−クロロアセチル=
PS−NCO=メチルイソシアネートポリスチレン
PS−ベンズアルデヒド=
PS−TsNHNH2=トルエンスルホニルヒドラゾンポリスチレン
以下の例のスキームは、読者への指針のために提供されており、本明細書中で例示された化合物を製造する好ましい方法に相当する。これらの方法は、限定ではなく、これらの化合物を調製するのに他の経路が使用され得ることは明らかである。このような方法には、具体的には、固相ベースの化学反応(組み合わせ化学反応を含めて)が挙げられる。当業者は、文献および本開示で示された方法により、必須および/または請求化合物を調製するのに必要なものを十分に備え付けている。
組み合わせアレイでアミドを合成するのに、以下の手順を使用し、また、使用できる。
Genevacにて、プレートを乾燥する。
細胞ベースの技術およびアッセイ(例えば、WO 02/064631、およびWO 03/001876、ならびに米国特許出願US 2003−0232407 A1に開示されるもの)が、適切な細胞株中で発現されているT1R1/T1R3「薬味」風味レセプタまたはT1R2/T1R3「甘味」風味レセプタについてアゴニスト活性またはアンタゴニスト活性について多岐にわたる分類の化合物を最初にスクリーニングするのに使用された。このような細胞株において、アミド化合物について一旦最初の「ヒット」が得られた場合、同じアッセイそして特定の細胞および/またはレセプタベースのアッセイも、MSGの薬味または公知の甘味料(例えば、スクロース、フルクトース)の甘味を向上させる式(I)の化合物の能力を測定するために分析ツールとして使用され、そして高レベルおよび最適なレベルの所望の生物学的活性を有する化合物の種および属を設計、試験および同定するための、高度に関心のある化合物の予備的なヒト味覚試験と組み合わせてアミド化合物の構造改質体を合成および試験する相互作用プロセスの経験的なデータを提供するために使用された。
新規の薬味剤および向上剤(薬味アゴニストおよび向上剤活性(二重活性)を有する化合物を同定するため、化合物用量反応アッセイおよび増強アッセイを含む一次アッセイおよび二次活性で式(I)の化合物をスクリーニングした。旨味を調節する可能性のある能力についての一次アッセイにおいて、それ自身薬味剤であるかMSGの風味向上剤であるかのいずれかであり得る式(I)のアミド化合物を同定し、その活性のスコアを、最大MSG強度(%)のパーセンテージとして得た。化合物の用量反応において、薬味アゴニストまたは向上剤としての化合物の効力を反映するために、EC50が計算される。
EC50比 対 MSG=EC50(MSG)/EC50(MSG+[化合物])
ここで、「化合物」、は、MSG用量反応を誘起する(増強もしくは強める)ために使用される式(I)の化合物の濃度をいう。
Gal5およびhT1R2/hT1R3(Li,X.,Staszewski,L.,Xu,H.,Durick,K.,Zoller,M.,Adler,E.Proc Natl Acad Sci USA 2002,99,4692−4696、または国際特許公開番号WO03/001876 A2も参照のこと)を安定に発現するHEK293細胞株誘導体(Chandrashekar,J.,Mueller,K.L.,Hoon,M.A.,Adler,E.,Feng,L.,Guo,W.,Zuker,C.S.,Ryba,N.J.,.Cell2000,100,703−711)を使用して、甘味向上特性を有する化合物を同定した。
(N−(ヘプタン−4−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(2−メチルヘプタン−4−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
2−メチルヘプタン−4−オン(4.24g、33.07mmol)のメタノール(60mL)溶液に、酢酸アンモニウム(25.50g、330.71mmol)およびシアノホウ水素化ナトリウム(2.08g、33.07mmol)を加えた。その反応混合物を、室温で、約24時間撹拌した。減圧下にて溶媒を除去し、その残渣を水で希釈し、15%NaOH水溶液で塩基化し、そしてエーテルで抽出した。この抽出物をブラインで洗浄し、無水硫酸マグネシウムで乾燥し、濾過し、そして蒸発させて、3.3gの2−メチルヘプタン−4−アミン(77%)を得た。MS(M+H、130)。
(N−(2−メチルヘキサン−3−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(2,3−ジメチルシクロヘキシル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(5−メチルヘキサン−3−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(2−(ベンゾ[d][1,3]ジオキソール−6−カルボキサミド)−4−メチルペンタン酸(R)−メチル)
(N−(1,2,3,4−テトラヒドロナフタレン−1−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
((R)−N−(1−ヒドロキシ−4−メチルペンタン−2−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
((R)−N−(1−メトキシ−4−メチルペンタン−2−イル)ベンゾ[d][1,3]ジオキソール−5−ベンゾ[d][1,3]ジオキソール−5−カルボン酸)
(R)−2−(1−メトキシ−4−メチルペンタン−2−イル)イソインドリン−1,3−ジオン(実施例9b)(3.87g、14.84mmol)のメタノール(30mL)溶液にヒドラジン水和物(0.866mL、17.81mmol)を加え、その反応混合物を、約3時間にわたって、45℃まで温めた。この混合物を2N HClで酸性化し、そして45℃で、30分間撹拌した。その溶液を室温まで冷却し、濾過し、そして蒸発させた。その残渣を2N NaOHに吸収させ、そしてエーテルで抽出し、MgSO4で乾燥し、濾過し、そして蒸発させて、1.51gの(R)−1−メトキシ−4−メチルペンタン−2−アミンを得た。収率77%。
(R)−2−(1−ヒドロキシ−4−メチルペンタン−2−イル)イソインドリン−1,3−ジオン(実施例9c)(5.88g、23.87mmol)を乾燥THF(25mL)およびヘキサメチル−ホスホラミド(30mL)に溶解し、その溶液を0℃まで冷却した。水素化ナトリウム(鉱油中で60%、1.15g、28.65mmol)を加え、10分後、ヨードメタン(7.43mL、119.35mmol)を滴下し、この溶液を室温までゆっくりと温め、そして一晩撹拌した。その反応混合物を氷/水に注ぎ、EtOACで抽出し、ブラインで洗浄し、MgSO4で乾燥し、濾過し、そして蒸発させた。その残渣をシリカゲル(ヘキサン中で20%EtOAC)で精製して、3.92gの(R)−2−(1−メトキシ−4−メチルペンタン−2−イル)イソインドイン−1,3−ジオン(63%)を得た。
無水フタル酸(10.30g、69.55mmol)およびD−ロイシノール(8.15g、69.55mmol)をTHF(100mL)中で混合し、その反応混合物を、85℃で加熱し、そして18時間還流した。室温まで冷却した後、水を加え、その溶液をEtOACで抽出し、その抽出物を、1N HCl、水、NaHCO3水溶液、水およびブラインで洗浄し、MgSO4で乾燥し、濾過し、そして蒸発させて、8.1gの(R)−2−(1−ヒドロキシ−4−メチルペンタン−2−イル)イソインドリン−1,3−ジオン(47%)を得た。
(2−(ベンゾ[d][1,3]ジオキソール−6−カルボキサミド)−3−メチル安息香酸(R)−メチル)
(2−(ベンゾ[d][1,3]ジオキソール−6−カルボキサミド)−4−メチルペンチル二水素ホスフェート))
(N−(ヘキサン−3−イル)−4−メトキシ−3−メチルベンズアミド)
((R)−N−(1−(ジメチルアミノ)−4−メチル−1−オキソペンタン−2−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
塩化ベンゾ[d][1,3]ジオキソール−5−カルボニルおよびD−ロイシンを使用して、実施例1と類似の様式で、調製した。収率:55%.MS(M+H、280.2)。
(酢酸2−(ベンゾ[d][1,3]ジオキソール−6−カルボキサミド)ペンチル)
((R)−N−(4−メチル−1−オキソ−1−(2−(ピリジン−3−イル)エチルアミノ)ペンタン−2−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキシアミド)
(N−((R)−1−(2−(ヒドロキシメチル)ピロリジン−1−イル)−4−メチル−1−オキソペンタン−2−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(ヘプタン−4−イル)−6−メチルベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(ヘプタン−4−イル)−2−メチルベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(2−(5−(ヘプタン−4−イルカルバモイル)ベンゾ[d][1,3]ジオキソール−2−イル)酢酸エチル)
(N−(ヘプタン−4−イル)−2,2−ジメチルベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
2,2−ジメチルベンゾ[d][1,3]ジオキソール−5−カルボン酸エチル(実施例20b)(461mg、2.08mmol)を、ジオキサン(16mL)および1.0N NaOH水溶液(4.16mL)中にて、室温で、20時間撹拌した。減圧下にて溶媒を除去して、所望生成物(449mg)を得た。(M−H、193)。
3,4−ジヒドロキシ安息香酸エチル(910.9mg、5mmol)を、トルエン中にて、2,2−ジメトキシプロパン(1.23mL、10mmol)および触媒量のp−トルエンスルホン酸と混ぜ合わせた。その混合物を、ディーン−スタークトラップを使用して、20時間にわたって、還流状態まで加熱した。減圧下にて溶媒を除去した後、その粗製物を酢酸エチルに溶解し、そして炭酸水素ナトリウム飽和水溶液、水およびブラインで連続的に洗浄した。有機層を無水硫酸ナトリウムで乾燥した。.シリカゲルクロマトグラフィー(これは、ヘキサン:酢酸エチル、90:10〜75:25の勾配を使用する)で精製すると、白色粉末(539.1mg、49%)が得られた。
(N−(ヘプタン−4−イル)−2−イソプロピルベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(2,2−ジフルオロ−N−(ヘプタン−4−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(2,3−ジヒドロ−ベンゾ[1,4]ジオキシン−6−カルボン酸(1−プロピル−ブチル)−アミド)
(N−(ヘプタン−4−イル)−3,4−ジヒドロ−2H−ベンゾ[1,4]ジオキセピン−7−カルボキサミド)
(ベンゾフラン−2−カルボン酸(1−プロピルブチル)アミド)
(N−(ヘプタン−4−イル)−5−メチルベンゾフラン−2−カルボキサミド)
(4−メチル−2−(5−メチルベンゾフラン−2−カルボキサミド)ペンタン酸(R)−メチル)
(N−(ヘキサン−3−イル)−5−メチルベンゾフラン−2−カルボキサミド)
(N−(ヘキサン−3−イル)−5−メトキシベンゾフラン−2−カルボキサミド)
(3−シクロヘキシル−2−(5−メトキシベンゾフラン−2−カルボキサミド)プロパン酸(R)−メチル)
(5−メトキシ−N−(5−メチルヘキサン−3−イル)ベンゾフラン−2−カルボキサミド)
(4−クロロ−2−(5−メチルベンゾフラン−2−カルボキサミド)ペンタン酸(R)−メチルの調製)
(4−メチル−2−(3−メチルベンゾフラン−2−カルボキサミド)ペンタン酸(R)−メチル)
(N−(ヘプタン−4−イル)ベンゾ[b]チオフェン−2−カルボキサミド)
(N−(ヘプタン−4−イル)−1H−インドール−2−カルボキサミド)
(4−メチル−2−(5−メチル−1H−インドール−2−カルボキサミド)ペンタン酸(R)−メチル)
(N−(ヘプタン−4−イル)−1−メチル−1H−インドール−2−カルボキサミド)
(N−(ヘプタン−4−イル)−1H−ベンゾ[d]イミダゾール−5−カルボキサミド)
(ベンゾオキサゾール−5−カルボン酸(1−プロピルブチル)アミド)
(2−メチル−ベンゾオキサゾール−5−カルボン酸(1−プロピル−ブチル)−アミド)
(2−エチル−ベンゾオキサゾール−5−カルボン酸(1−プロピル−ブチル)−アミド)
(2−メトキシ−ベンゾオキサゾール−5−カルボン酸(1−プロピル−ブチル)−アミド)
(2−エトキシ−ベンゾオキサゾール−5−カルボン酸(1−プロピル−ブチル)−アミド)
(N−(ヘプタン−4−イル)−2−(メチルチオ)ベンゾ[d]オキサゾール−5−カルボキサミド)
(実施例45)
(クロロメチルベンゾオキサゾール−5−カルボン酸(1−プロピル−ブチル)アミド)
(実施例46)
(2−メチル−ベンゾオキサゾール−6−カルボン酸(1−プロピル−ブチル)−アミド)
(2−クロロメチル−ベンゾオキサゾール−6−カルボン酸(1−プロピル−ブチル)−アミド)
(実施例48)
(4−メチル−3−メチルスルファニル−N−(1−プロピルブチル)ベンズアミド)
(実施例49)
(4−メチル−2−(4−メチル−3−(メチルチオ)ベンズアミド)ペンタン酸(R)−メチル)
(4−メチル−2−(4−(メチルチオ)ベンズアミド)ペンタン酸(R)−メチル)
(N−(ヘプタン−4−イル)−3−メチル−4−(メチルチオ)ベンズアミド)
(4−メトキシ−3−メチル−N−(2−メチルヘプタン−4−イル)ベンズアミド)
(4−メトキシ−3−メチル−N−(5−メチルヘキサン−3−イル)ベンズアミド)
(4−メトキシ−N−(1−(4−メトキシフェニル)ブチル)−3−メチルベンズアミド)
((R)−4−メトキシ−3−メチル−N−(3−メチル−1−(3−メチル−1,2,4−オキサジアゾール−5−イル)ブチル)ベンズアミド)
(4−エトキシ−N−(ヘプタン−4−イル)−3−メチルベンズアミド)
(4−エトキシ−N−(1−メトキシペンタン−2−イル)−3−メチルベンズアミド)
(4−ヒドロキシ−3−メチル−N−(1−プロピル−ブチル)−ベンズアミド)
(N−(ヘプタン−4−イル)−4−(2−メトキシエトキシ)−3−メチルベンズアミド)
(2−(3−フルオロ−4−メトキシベンズアミド)−4−メチルペンタン酸(R)−メチル)
(3−クロロ−4−メトキシ−N−(ペンタン−3−イル)ベンズアミド)
(2−(3−クロロ−4−メトキシベンズアミド)−4−メチルペンタン酸(R)−メチル)
((R)−3−クロロ−4−メトキシ−N−(1−フェニルエチル)ベンズアミド)
(4−クロロ−3−メチル−N−(1−プロピル−ブチル)−ベンズアミド)
(3,4−ジメトキシ−N−(1−プロピル−ブチル)−ベンズアミド)
(2−(4−フルオロ−3−メチルベンズアミド)−4−メチルペンタン酸(R)−メチル)
(4−メトキシ−3,5−ジメチル−N−(2−メチルヘプタン−4−イル)ベンズアミド)
(3,4−ジメチル−N−(2−メチルヘキサン−3−イル)ベンズアミド)
(3,4−ジメチル−N−(2−メチルヘプタン−4−イル)ベンズアミド)
(3,4−ジメチル−N−(5−メチルヘキサン−3−イル)ベンズアミド)
((R)−N−(1−メトキシ−4−メチルペンタン−2−イル)−3,4−ジメチルベンズアミド)
((R)−N−(1−(メトキシメトキシ)−4−メチルペンタン−2−イル)−3,4−ジメチルベンズアミド)
(N−(1−メトキシメチル−2−メチル−プロピル)−3,4−ジメチル−ベンズアミド)
(2−(2−メトキシ−4−(メチルチオ)ベンズアミド)−4−メチルペンタン酸(R)−メチル)
(N−(2−メチルヘプタン−4−イル)ベンゾ[d][1,3]ジオキソール−5−カルボキサミド)
(N−(1−エチル−プロピル)−3−[4−(2−ヒドロキシ−エトキシ)−フェニル]−アクリルアミド)
((E)−N−(ヘプタン−4−イル)−3−(チオフェン−2−イル)アクリルアミド)
(4−メチル−2−オクタ−2−エナミドペンタン酸(R,E)−メチル)
(3−(4−メトキシ−フェニル)−N−(3−メチル−1−プロピル−ブチル)−アクリルアミド)
(N−(1−メトキシメチル−3−メチル−ブチル)−3−(4−メトキシ−フェニル)−アクリルアミド)
(N−(1−ベンジル−2−ヒドロキシ−エチル)−3−(4−メトキシ−フェニル)−アクリルアミド)
(3−(4−エトキシ−フェニル)−N−(1−エチル−プロピル)−アクリルアミド)
(4−メチル−2−(3−チオフェン−2−イル−アクリロイルアミノ)−ペンタン酸メチルエステル)
(4−メチル−ペンタ−2−エン酸(1,2,3,4−テトラヒドロ−ナフタレン−1−イル)−アミド)
(3−(2−フルオロ−フェニル)−N−(1−プロピル−ブチル)−アクリルアミド)
(3−(2−メトキシ−フェニル)−N−(1−プロピル−ブチル)−アクリルアミド)
(3−(3,4−ジメトキシ−フェニル)−N−(1−プロピル−ブチル)−アクリルアミド)
(3−(2−メトキシ−フェニル)−N−(2−メチル−シクロヘキシル)−アクリルアミド)
(N−(ヘプタン−4−イル)ベンゾフラン−5−カルボキサミド)
(N−(ヘプタン−4−イル)−5,6−ジメチルピコリンアミド)
(4−(ジエチルアミノ)−N−(ヘプタン−4−イル)ベンズアミド)
(2−(2,6−ジメトキシイソニコチンアミド)−4−メチルペンタン酸(R)−メチル)
(N−(ヘプタン−4−イル)−6−メトキシニコチンアミド)
(5,6−ジメチルピラジン−2−カルボン酸(1−プロピルブチル)アミド)
(2−クロロ−N−(ヘプタン−4−イル)−6−メチルニコチンアミド)
(2−シアノ−N−(ヘプタン−4−イル)−4−メトキシベンズアミド)
(2−(2,3−ジメチルフラン−5−カルボキサミド)−4−メチルペンタン酸(R)−メチル)
(N−(ヘプタン−4−イル)−1,3−ジメチル−1H−ピラゾール−5−カルボキサミド)
(N−(ヘプタン−4−イル)−2−メチルチアゾール−4−カルボキサミド)
(N−(ヘプタン−4−イル)キノリン−6−カルボキサミド)
(N−(ヘプタン−4−イル)キノリン−3−カルボキサミド)
(N−(ヘプタン−4−イル)イソキノリン−1−カルボキサミド)
(4−メトキシ−N−(1−メトキシメチル−3−メチル−ブチル)−3−メチル−ベンズアミド)
(N−(4−(トリフルオロメトキシ)ベンジル)チオフェン−2−カルボキサミド)
(N−(2−(フラン−2−イルメチルチオ)エチル)−4−メトキシ−3−メチルベンズアミド)
(チオフェン−3−カルボン酸4−トリフルオロメトキシ−ベンジルアミド)
(3−メチル−チオフェン−2−カルボン酸2,4−ジメトキシ−ベンジルアミド)
(5−ピリジン−2−イル−チオフェン−2−カルボン酸2,4−ジメトキシ−ベンジルアミド)
(2−メチル−2H−ピラゾール−3−カルボン酸2,4−ジメトキシ−ベンジルアミド)
(4−ヒドロキシ−3−メチル−N−(1−メチル−3−フェニル−プロピル)−ベンズアミド)
(ベンゾ[1,3]ジオキソール−5−カルボン酸[2−(4−エチル−フェニル)−エチル]−アミド)
(4−メトキシ−3−メチル−N−(1−フェニル−ブチル)−ベンズアミド)
(4−メトキシ−3−メチル−N−(1−ピリジン−2−イル−ブチル)−ベンズアミド)
(ベンゾ[1,3]ジオキソール−5−カルボン酸[1−(4−メトキシ−フェニル)−ブチル]−アミド)
(4−エトキシ−N−[1−(4−メトキシ−フェニル)−ブチル]−3−メチル−ベンズアミド)
(4−メトキシ−N−[1−(R)−(4−メトキシ−フェニル)−エチル]−3−メチル−ベンズアミド)
(ベンゾ[1,3]ジオキソール−5−カルボン酸インダン−1−イルアミド)
(4−メトキシ−3−メチル−N−(ペンタン−3−イル)ベンズアミド)
(3−メチル−N−(p−トリルエチル)フラン−2−カルボキサミド)
(N−(2,4−ジメトキシベンジル)−2−(1H−ピロール−1−イル)ベンズアミド)
(オキサルアミドを調製する一般的な手順A)
(N−(2−メトキシ−ベンジル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミドの合成)
(N−(2,4−ジメトキシ−ベンジル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(3−メチル−チオフェン−2−イルメチル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(オキサルアミドを調製する一般的な手順B)
(N−(4−メチル−ベンジル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(2−メチル−4−メトキシベンジル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(2,4−ジメトキシ−ベンジル)−N’−(3−ピリジン−2−イル−プロピル)−オキサルアミド)
(N−(4−メトキシベンジル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(2−(3−メチルピリジン−2−イル)エチル)オキサルアミド)
(N−(2,5−ジメチル−フラン−3−イルメチル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(1,5−ジメチル−1H−ピロール−2−イルメチル)−N’−(2−ピリジン−2−イル−エチル)−オキサルアミド)
(N−(2−メトキシ−4−メチルベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2,4−ジメチルベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
N−(4−エトキシ−2−メトキシベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(4−メトキシ−3−メチルベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2−クロロベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−((2,3−ジヒドロベンゾ[b][1,4]ジオキシン−5−イル)メチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(ベンゾ[d][1,3]ジオキソール−5−イルメチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(4−エチルベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(ベンゾフラン−5−イルメチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−((4−メトキシカルボニルフェニル)メチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−((2−カルバモイルフェニル)メチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(1−(ピリジン−2−イル)プロパン−2−イル)オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(2−(ピリジン−2−イル)プロピル)オキサルアミド)
(N−(2−メトキシベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2,3−ジメトキシベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2−(メチルチオ)ベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2−ヒドロキシベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(ベンゾ[d][1,3]ジオキソール−4−イルメチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(ベンゾ[b]チオフェン−2−イルメチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(ベンゾ[b]チアゾール−2−イルメチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−((5−メチルフラン−2−イル)メチル)−N2−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−((2−メチルフラン−3−イル)メチル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(2−(4−メチルピリジン−2−イル)エチル)オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(2−(5−メチルピリジン−2−イル)エチル)オキサルアミド)
(N−(2,4−ジメトキシベンジル)−N’−(2−(チオフェン−2−イル)エチル)オキサルアミド)
(N1−(2−メトキシ−4−メチルベンジル)−N2−(2−(5−メチルピリジン−2−イル)エチル)オキサルアミド)
(1−(4−クロロフェニル)−3−(ヘプタン−4−イル)尿素)
(1−(2,4−ジメトキシフェニル)−3−(ヘプタン−4−イル)尿素)
(1−(4−エトキシフェニル)−3−(2−(ピリジン−2−イル)エチル)尿素)
(1−(4−イソプロピルフェニル)−3−(2−(ピリジン−2−イル)エチル)尿素)
一般パネリストの選択:味覚試験者の基本的なスクリーニング:パネリストの候補を、5つの基本的な味覚を代表する溶液の強度を順位付けして評価する能力について、試験した。パネリストは、以下の5種の化合物の各々の5つの異なる濃度の強度を順位付けして評定した:スクロース(甘味)、塩化ナトリウム(塩味)、クエン酸(酸味)、カフェイン(苦味)およびグルタミン酸一ナトリウム(薬味)。パネリストは、試験に参加するように選別されるためには、試料の強度を正しく順位付けして評定する必要があり、誤りは、あまり多くなかった。
式(I)の多数のアミド化合物を合成し、そしてHEK293細胞系において発現されるhT1R2/hT1R3甘味レセプタの活性化剤としての有効性について、実験的に試験した。このような甘味化合物についての甘味EC50測定の点からの合成実施例および生物学的有効性を、以下で列挙する。さらに、式(I)の「甘味」アミドの多くはまた、旨味EC50およびEC50比アッセイにおける活性についてスクリーニングし、以下で説明するように、式(I)のアミドが化合物のいくつかは、食料品または医薬品および組成物で使用する薬味および甘味向上剤として同時に役立つ著しい活性および潜在性を有する。
(2,3,5,6−テトラフルオロ−4−メチル−N−(2−メチルシクロヘキシル)ベンズアミド
((S)−2,3,5,6−テトラフルオロ−4−メチル−N−(3−メチルブタン−2−イル)ベンズアミド)
(N−シクロヘプチル−2,3,5,6−テトラフルオロ−4−メチルベンズアミド)
(N−(2,4−ジメチルペンタン−3−イル)−2,3,5,6−テトラフルオロ−4−メチルベンズアミド)
(N−(5,7−ジメチル−1,2,3,4−テトラヒドロナフタレン−1−イル)−3−メチルイソキサゾール−4−カルボキサミド)
(3−クロロ−2−ヒドロキシ−N−(5−メトキシ−1,2,3,4−テトラヒドロナフタレン−1−イル)ベンズアミド)
(2,6−ジメチル−N−(2−メチルシクロヘキシル)ベンズアミド)
(4−メトキシ−2,6−ジメチル−N−(2−メチルシクロヘキシル)ベンズアミド)
((R)−N−(1,2,3,4−テトラヒドロナフタレン−1−イル)フラン−3−カルボキサミド)
((R)−5−メチル−N−(1,2,3,4−テトラヒドロナフタレン−1−イル)イソキサゾール−4−カルボキサミド)
(N−(4−クロロ−2−メチルフェニル)イソインドリン−2−カルボキサミド)
(N−(4−メトキシ−2−メチルフェニル)イソインドリン−2−カルボキサミド)
(N−(3,4−メチレンジオキシフェニル)イソインドリン−2−カルボキサミド)
(3−メチル−イソキサゾール−4−カルボン酸(1,2,3,4−テトラヒドロ−ナフタレン−1−イル)−アミド)
目的:実験化合物の種々の味の強度および味をなくす強度を調べること。実験化合物の所望しない特性および味をなくす特性を引き起こさない最大濃度を決定すること。
目的:実験化合物の試験サンプルの強度が、甘味の場合の参照サンプルの強度とどのように異なるかを決定すること。この型の実験は、統計学的に有意なデータを得るために、より大きなパネル(代表的に、15〜20被験体)を必要とする。
(
エタノールストック溶液を用いたスープ調製物)
本発明の化合物は、200プルーフエタノールを用いて、スープにおける所望の濃度である1000倍に希釈される。化合物は、エタノール中での完全な溶解性を確実にするため超音波処理され得、(安定な場合)加熱され得る。ブイヨンベースのスープは、6gの野菜ブイヨンベースを、ガラス鉢または磁器の鉢中の500mLの温水中に添加することによって、作製される。この水は80℃に加熱される。溶解されたブイヨン中のMSGの濃度は、2.2g/Lであり、添加されたIMPは存在しない。ブイヨンベースが溶解された後、エタノールストック溶液がスープベースに添加される。500 mLのスープに対して、0.1%の最終エタノール濃度について、0.5mLの1000倍エタノールストックが添加される。エタノールがスープの味に干渉する場合、化合物が溶解性であれば、より高濃度のエタノールストック溶液が調製され得る。
(チップ調製物)
本発明の化合物の塩混合物が、塩と混合することによって作製され、チップに対して添加される1.4%(w/w)の塩混合物は、所望の濃度の化合物をもたらす。チップへの化合物の最終1ppmについて、7mgの化合物が、10gの水とともに混合される。化合物は、モーターを用いて粉砕され、塩とともにペースと化され、この化合物および塩は、十分混合される。チップは、ぶれんだーを用いて均一な小片に砕かれる。各々98.6gのチップに対して、1.4gの塩混合物を量り分ける。このチップ片は、マイクロウェーブ中で50秒間または温まるまで最初に加熱される。この片を大きなアルミニウム片上に広げる。この塩混合物をチップ上に均一に広げる。次いで、このチップを、プラスチックバッグ中に配置し、全ての塩がバック中に同じように位置していることを確認する。次いで、この塩混合物およびチップは、攪拌されて、塩がチップ上に均一に広がっていることを確認する。
(クッキー調製物)
本発明の化合物を、200プルーフエタノールを用いて、最終製品における所望の濃度である1000倍に希釈される。化合物は、エタノール中での完全な溶解性を確実にするため超音波処理され得、(安定な場合)加熱され得る。次いで、本発明の化合物を含む溶液は、他の液体成分(すなわち、水、液卵および香料)とともに、十分ブレンドされるまで混合される。この混合物は、乾燥乳化剤(レシチン)とともにブレンドされ、そしてショートニングとともにさらにブレンドされる。ショートニングは、十分混合された乾燥成分(すなわち、粉、砂糖、塩、ココア)とともにブレンドされる。生地は、ベーキングシート状に分割され、所望の温度で出来上がるまで焼かれる。
(ジュース調製物)
本発明の化合物は、200プルーフエタノールを用いて、ジュースにおける所望の濃度である1000倍に希釈される。化合物は、天然および/または人工香料のアルコール成分とさらにブレンドされて、「重要物」を生成する。この香料重要物は、ジュース濃縮物の一部とブレンドされて確実に均一物とする。ジュース組成物の残りを水に希釈し、混合する。甘味料(例えば、HFCS(High fructose Corn Syrup)、アスパルテーム、またはスクラロース)は、その中に混合されて、ブレンドされる。香料/化合物部分を最終工程として添加され、ブレンドされる。
(香辛料の効いたトマトジュースまたはブラッディマリーミックス)
本発明の化合物は、乾燥成分として香辛料ブレンドに添加され、十分ブレンドされる。香辛料ブレンドは、トマトペーストの一部に分散され、ブレンドされ、そしてブレンドされたペーストはさらに残りのペースト中にブレンドされる。次いで、このペーストは、水で希釈される。これは、高温で短時間処理され得る。
Claims (33)
- 次式を有するオキサルアミド化合物またはそれらの食用に受容可能な塩であって:
mおよびnが、別個に、0、1、2または3である;
R20およびR40が、水素である;
R50が、水素またはメチルである;
R60が、C2アルキレンである;
R70およびR80が、別個に、水素、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、CO2CH3、SEt、SCH3、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシから選択される、オキサルアミド化合物。 - 次式を有する、オキサルアミド化合物であって:
mおよびnは、別個に、0、1、2または3である;
R50は、水素またはメチルである;
pは、2である;そして
R70およびR80は、別個に、水素、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、COOCH3、SCH3、SEt、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシからなる群から選択されるか、またはR70の2個は、一緒になって、メチレンジオキシ環を形成する、
オキサルアミド化合物。 - 次式を有する、オキサルアミド化合物であって:
R50は、水素またはメチルである;
nは、0、1、2または3である;
各R80は、別個に、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、CO2CH3、SEt、SCH3、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシからなる群から選択される、
オキサルアミド化合物。 - 次式を有する、請求項1に記載のオキサルアミド化合物であって:
R70およびR80は、別個に、水素、アルキル、アルコキシル、アルコキシ−アルキル、OH、SR9、ハロゲン、CN、NO2、CO2R9、COR9、CONR9R10、NR9R10、NR9COR10、SOR9、SO2R9、SO2NR9R10、NR9SO2R10、アルケニル、シクロアルキル、シクロアルケニル、アリール、ヘテロアリールおよび複素環からなる群から選択される;
R9およびR10は、別個に、H、C1〜C6アルキル、C3〜C6シクロアルキルおよびC1〜C6アルケニルから選択される、
オキサルアミド化合物。 - R70およびR80が、別個に、水素、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、O2CCH3、SH、SCH3、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシからなる群から選択される、請求項6に記載のオキサルアミド化合物。
- 次式を有する、請求項1に記載のオキサルアミド化合物またはその食用に受容可能な塩であって:
mおよびnは、別個に、0、1、2または3である;
各R70およびR80は、別個に、ヒドロキシ、フルオロ、クロロ、NH2、NHCH3、N(CH3)2、COOCH3、SCH3、SEt、メチル、エチル、イソプロピル、ビニル、トリフルオロメチル、メトキシ、エトキシ、イソプロポキシおよびトリフルオロメトキシからなる群から選択されるか、またはR70の2個は、一緒になって、メチレンジオキシ環を形成する、
オキサルアミド化合物またはその食用に受容可能な塩。 - Bが、ピリジル環である、請求項9に記載のオキサルアミド化合物。
- Aが、フェニル環である、請求項10に記載のオキサルアミド化合物。
- Bが、ピリジル環である、請求項12に記載のオキサルアミド化合物。
- Bが、ピリジル環である、請求項15に記載のオキサルアミド化合物。
- 以下:
N1−(2−メトキシ−4−メチルベンジル)−N2−(2−(5−メチルピリジン−2−イル)エチル)オキサルアミド、
N1−(2−メトキシ−4−メチルベンジル)−N2−(2−(ピリジン−2−イル)エチル)オキサルアミド、
N1−(2,4−ジメトキシベンジル)−N2−(2−(5−メチルピリジン−2−イル)エチル)オキサルアミド、
N1−(2,4−ジメチルベンジル)−N2−(2−(ピリジン−2−イル)エチル)オキサルアミド、
N1−(2,4−ジメトキシベンジル)−N2−(2−(ピリジン−2−イル)エチル)オキサルアミド、
N−(2,3−ジメトキシベンジル)−N’−(2−(ピリジン−2−イル)エチル)オキサルアミド;
からなる群より選択される、請求項9に記載のオキサルアミド化合物。 - 少なくとも薬味調節量の少なくとも1種の請求項1に記載のオキサルアミド化合物またはそれらの食用に受容可能な塩を含有し、該オキサルアミド化合物が、約0.01ppm〜約30ppmの濃度で存在している、摂取可能な組成物。
- ヒトまたは動物が消費するための組成物である、請求項19に記載の摂取可能な組成物。
- 食物、飲料、または口腔衛生製品である、請求項19に記載の摂取可能な組成物。
- 経口投与用の医薬組成物である、請求項19に記載の摂取可能な組成物。
- 前記オキサルアミド化合物が、約0.05ppm〜約15ppmの濃度で存在している、請求項19に記載の摂取可能な組成物。
- 前記オキサルアミド化合物が、約0.1ppm〜約5ppmの濃度で存在している、請求項19に記載の摂取可能な組成物。
- 前記オキサルアミド化合物が、約0.1ppm〜約3ppmの濃度で存在している、請求項19に記載の摂取可能な組成物。
- 摂取可能な組成物の味を調節する方法であって、該方法は、
味が改質された摂取可能な組成物を形成するために、該摂取可能な組成物と、少なくとも薬味調節量の請求項1に記載のオキサルアミド化合物またはそれらの食用に受容可能な塩とを混ぜ合わせる工程、
を包含し、該オキサルアミド化合物が、前記改質された摂取可能な組成物中にて、約0.01ppm〜約30ppmの濃度で存在している、方法。 - 前記改質された摂取可能な組成物が、動物が消費する食物である、請求項26に記載の方法。
- 前記改質された摂取可能な組成物が、ヒトが消費する食物である、請求項26に記載の方法。
- 前記改質された摂取可能な組成物が、経口投与用の医薬組成物である、請求項26に記載の方法。
- 前記改質された摂取可能な組成物が、口腔衛生製品である、請求項26に記載の方法。
- 前記オキサルアミド化合物が、前記改質された摂取可能な組成物中にて、約0.05ppm〜約15ppmの濃度で存在している、請求項26に記載の方法。
- 前記オキサルアミド化合物が、前記改質された摂取可能な組成物中にて、約0.1ppm〜約5ppmの濃度で存在している、請求項26に記載の方法。
- 前記オキサルアミド化合物が、前記改質された摂取可能な組成物中にて、約0.1ppm〜約3ppmの濃度で存在している、請求項26に記載の方法。
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