KR20130055601A - 쓴맛을 감소시키거나 제거하기 위한 화합물, 조성물 및 방법 - Google Patents
쓴맛을 감소시키거나 제거하기 위한 화합물, 조성물 및 방법 Download PDFInfo
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- KR20130055601A KR20130055601A KR1020127029635A KR20127029635A KR20130055601A KR 20130055601 A KR20130055601 A KR 20130055601A KR 1020127029635 A KR1020127029635 A KR 1020127029635A KR 20127029635 A KR20127029635 A KR 20127029635A KR 20130055601 A KR20130055601 A KR 20130055601A
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- South Korea
- Prior art keywords
- formula
- alkyl
- compound
- edible
- bitter taste
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 491
- 239000000203 mixture Substances 0.000 title claims abstract description 385
- 235000019658 bitter taste Nutrition 0.000 title claims abstract description 299
- 238000000034 method Methods 0.000 title claims abstract description 190
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 95
- 235000013305 food Nutrition 0.000 claims abstract description 84
- 239000011780 sodium chloride Substances 0.000 claims abstract description 48
- 235000021023 sodium intake Nutrition 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 481
- -1 phenyloxy, phosphoryl Chemical group 0.000 claims description 194
- 125000001072 heteroaryl group Chemical group 0.000 claims description 191
- 125000000623 heterocyclic group Chemical group 0.000 claims description 182
- 235000002639 sodium chloride Nutrition 0.000 claims description 171
- 125000003545 alkoxy group Chemical group 0.000 claims description 159
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 123
- 125000005843 halogen group Chemical group 0.000 claims description 116
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 103
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 84
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 79
- 125000000304 alkynyl group Chemical group 0.000 claims description 76
- 235000000346 sugar Nutrition 0.000 claims description 73
- 125000005842 heteroatom Chemical group 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 65
- 229910052760 oxygen Inorganic materials 0.000 claims description 65
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 63
- 125000004423 acyloxy group Chemical group 0.000 claims description 63
- 229910052717 sulfur Inorganic materials 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 125000002252 acyl group Chemical group 0.000 claims description 54
- 125000001188 haloalkyl group Chemical group 0.000 claims description 53
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 51
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 51
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 51
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 51
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 50
- 235000011088 sodium lactate Nutrition 0.000 claims description 50
- 239000001540 sodium lactate Substances 0.000 claims description 50
- 229940005581 sodium lactate Drugs 0.000 claims description 50
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 49
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 48
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 46
- 125000003282 alkyl amino group Chemical group 0.000 claims description 45
- 125000004414 alkyl thio group Chemical group 0.000 claims description 45
- 229910019142 PO4 Inorganic materials 0.000 claims description 42
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 42
- 239000004202 carbamide Substances 0.000 claims description 42
- 239000010452 phosphate Substances 0.000 claims description 42
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 42
- 125000004442 acylamino group Chemical group 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 41
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 40
- 235000011085 potassium lactate Nutrition 0.000 claims description 40
- 239000001521 potassium lactate Substances 0.000 claims description 40
- 229960001304 potassium lactate Drugs 0.000 claims description 40
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 39
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 38
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 38
- 125000003368 amide group Chemical group 0.000 claims description 36
- 239000011734 sodium Substances 0.000 claims description 36
- 239000001103 potassium chloride Substances 0.000 claims description 35
- 229910052708 sodium Inorganic materials 0.000 claims description 35
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims description 23
- 239000000619 acesulfame-K Substances 0.000 claims description 23
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 23
- 239000002085 irritant Substances 0.000 claims description 22
- 231100000021 irritant Toxicity 0.000 claims description 22
- 230000002829 reductive effect Effects 0.000 claims description 22
- 239000000796 flavoring agent Substances 0.000 claims description 19
- 235000019634 flavors Nutrition 0.000 claims description 19
- 239000000021 stimulant Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 230000008447 perception Effects 0.000 claims description 14
- 159000000000 sodium salts Chemical class 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 210000000214 mouth Anatomy 0.000 claims description 11
- 150000008163 sugars Chemical class 0.000 claims description 11
- 235000009508 confectionery Nutrition 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 230000004936 stimulating effect Effects 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 235000005911 diet Nutrition 0.000 abstract description 3
- 230000037213 diet Effects 0.000 abstract description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 38
- 150000002431 hydrogen Chemical class 0.000 description 36
- 229940083542 sodium Drugs 0.000 description 32
- 108020003175 receptors Proteins 0.000 description 31
- 102000005962 receptors Human genes 0.000 description 31
- 235000019640 taste Nutrition 0.000 description 29
- 235000011164 potassium chloride Nutrition 0.000 description 28
- 125000005553 heteroaryloxy group Chemical group 0.000 description 26
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 22
- 125000003302 alkenyloxy group Chemical group 0.000 description 22
- 239000011591 potassium Substances 0.000 description 22
- 229960003975 potassium Drugs 0.000 description 22
- 229910052700 potassium Inorganic materials 0.000 description 22
- 235000013351 cheese Nutrition 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 125000005133 alkynyloxy group Chemical group 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- 239000004305 biphenyl Substances 0.000 description 12
- 125000006267 biphenyl group Chemical group 0.000 description 12
- 159000000007 calcium salts Chemical class 0.000 description 12
- 159000000003 magnesium salts Chemical class 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000002837 carbocyclic group Chemical group 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical compound OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 0.000 description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 9
- 235000012149 noodles Nutrition 0.000 description 9
- 239000003755 preservative agent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000003765 sweetening agent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 159000000001 potassium salts Chemical class 0.000 description 7
- 235000015067 sauces Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 125000004475 heteroaralkyl group Chemical group 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 6
- 235000013361 beverage Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052757 nitrogen Chemical group 0.000 description 5
- 235000021092 sugar substitutes Nutrition 0.000 description 5
- 206010013911 Dysgeusia Diseases 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000016213 coffee Nutrition 0.000 description 4
- 235000013353 coffee beverage Nutrition 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 244000144972 livestock Species 0.000 description 4
- 235000013372 meat Nutrition 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 229940127557 pharmaceutical product Drugs 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- HELHAJAZNSDZJO-UHFFFAOYSA-L sodium tartrate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)C(O)C([O-])=O HELHAJAZNSDZJO-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000013405 beer Nutrition 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000008429 bread Nutrition 0.000 description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 108091005708 gustatory receptors Proteins 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229910000160 potassium phosphate Inorganic materials 0.000 description 3
- 235000011009 potassium phosphates Nutrition 0.000 description 3
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- 238000006722 reduction reaction Methods 0.000 description 3
- 235000019643 salty taste Nutrition 0.000 description 3
- 235000013580 sausages Nutrition 0.000 description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 3
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- 235000019583 umami taste Nutrition 0.000 description 3
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
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- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
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- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
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- 239000004278 EU approved seasoning Substances 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 2
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- 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 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- 235000009811 Momordica charantia Nutrition 0.000 description 2
- 244000302512 Momordica charantia Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 240000003889 Piper guineense Species 0.000 description 2
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- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Seasonings (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32434510P | 2010-04-15 | 2010-04-15 | |
| US32435910P | 2010-04-15 | 2010-04-15 | |
| US32436210P | 2010-04-15 | 2010-04-15 | |
| US32434610P | 2010-04-15 | 2010-04-15 | |
| US32435110P | 2010-04-15 | 2010-04-15 | |
| US61/324,359 | 2010-04-15 | ||
| US61/324,346 | 2010-04-15 | ||
| US61/324,345 | 2010-04-15 | ||
| US61/324,351 | 2010-04-15 | ||
| US61/324,362 | 2010-04-15 | ||
| PCT/US2011/032782 WO2011130707A2 (en) | 2010-04-15 | 2011-04-15 | Compounds, compositions, and methods for reducing or eliminating bitter taste |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20130055601A true KR20130055601A (ko) | 2013-05-28 |
Family
ID=44799371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127029635A Withdrawn KR20130055601A (ko) | 2010-04-15 | 2011-04-15 | 쓴맛을 감소시키거나 제거하기 위한 화합물, 조성물 및 방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20130101684A1 (enExample) |
| EP (1) | EP2558067A4 (enExample) |
| JP (2) | JP2013523192A (enExample) |
| KR (1) | KR20130055601A (enExample) |
| CN (2) | CN103025313A (enExample) |
| AU (1) | AU2011239447B2 (enExample) |
| CA (1) | CA2796077A1 (enExample) |
| IL (1) | IL222423A (enExample) |
| MX (1) | MX2012011996A (enExample) |
| PE (1) | PE20130633A1 (enExample) |
| PH (1) | PH12012501970A1 (enExample) |
| RU (1) | RU2597438C2 (enExample) |
| WO (1) | WO2011130707A2 (enExample) |
| ZA (1) | ZA201208488B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180030708A (ko) * | 2015-08-07 | 2018-03-23 | 브이. 만느 피스 | 맛 조절 화합물을 포함하는 조성물, 이의 용도 및 이를 포함하는 식품 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150070348A (ko) | 2012-10-16 | 2015-06-24 | 얀센 파마슈티카 엔.브이. | RoRγt의 헤테로아릴 결합 퀴놀리닐 조절제 |
| PE20151203A1 (es) | 2012-10-16 | 2015-08-31 | Janssen Pharmaceutica Nv | MODULADORES DE QUINOLINILO UNIDOS A FENILO DE ROR-GAMMA-t |
| PE20150778A1 (es) | 2012-10-16 | 2015-05-23 | Janssen Pharmaceutica Nv | Moduladores de quinolinilo unidos a metileno de ror-gamma-t |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US9624225B2 (en) | 2013-10-15 | 2017-04-18 | Janssen Pharmaceutica Nv | Quinolinyl modulators of RORγt |
| US9346782B2 (en) | 2013-10-15 | 2016-05-24 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| CN103588660B (zh) * | 2013-11-18 | 2016-06-01 | 中国医学科学院生物医学工程研究所 | 一种新型的酰基苯胺化合物及用途 |
| RU2623876C2 (ru) * | 2014-11-10 | 2017-06-29 | Александр Владимирович Диковский | Фармацевтическая композиция для лечения гиперлипидемии |
| US20190059429A1 (en) | 2016-04-11 | 2019-02-28 | Nestec S.A. | Salt composition including serine |
| CN110121342A (zh) * | 2016-12-28 | 2019-08-13 | 富士胶片富山化学株式会社 | 医药组合物 |
| CN109942537B (zh) * | 2018-03-03 | 2023-11-17 | 中国人民解放军第二军医大学 | 一类aldh2激动剂、制备方法及其用途 |
| EP3911632A1 (en) | 2019-01-15 | 2021-11-24 | Empirico Inc. | Prodrugs of alox-15 inhibitors and methods of using the same |
| US20200260761A1 (en) * | 2019-02-14 | 2020-08-20 | Stanley Weller | Compositions and Methods for Use in Food Processing and Preservation |
| CN112079777B (zh) * | 2020-08-11 | 2022-05-06 | 中山大学 | 一种多取代4-氟吖啶衍生物及其制备方法 |
| US12036286B2 (en) | 2021-03-18 | 2024-07-16 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL45396A0 (en) * | 1973-08-23 | 1974-11-29 | Beecham Group Ltd | Pharmaceutical compositions containing aryl aralkyl ether and thioether derivatives,certain such novel compounds and their preparation |
| JPH02129171A (ja) * | 1988-11-08 | 1990-05-17 | Nissan Chem Ind Ltd | ピラゾールカルボキサニリド誘導体及び有害生物防除剤 |
| HUT68764A (en) * | 1991-11-27 | 1995-07-28 | Bioresearch Inc | Eatable taste modifiers |
| US5925527A (en) * | 1997-02-04 | 1999-07-20 | Trega Biosciences, Inc. | Tricyclic Tetrahydroquinoline derivatives and tricyclic tetrahydroquinoline combinatorial libraries |
| US6297258B1 (en) | 1998-09-29 | 2001-10-02 | American Cyanamid Company | Substituted 3-cyanoquinolines |
| MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| US20050013835A1 (en) * | 2003-07-15 | 2005-01-20 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| NZ619746A (en) * | 2003-08-06 | 2014-05-30 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| CN101400336B (zh) * | 2003-08-06 | 2013-06-05 | 西诺米克斯公司 | 新型调味剂、味道调节剂、促味剂、味觉增强剂、鲜味剂或甜味剂和/或增强剂及其用途 |
| DE102004041496A1 (de) * | 2004-08-27 | 2006-03-02 | Symrise Gmbh & Co. Kg | Hydroxybenzoesäureamide und deren Verwendung zur Maskierung von bitterem Geschmack |
| TW200638882A (en) * | 2005-02-04 | 2006-11-16 | Senomyx Inc | Molecules comprising linked organic moieties as flavor modifiers for comestible compositions |
| JP4688517B2 (ja) * | 2005-02-15 | 2011-05-25 | 小川香料株式会社 | 高甘味度甘味料の呈味改善剤 |
| AU2006218405A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Acridine and quinoline derivatives as sirtuin modulators |
| JP2008540353A (ja) * | 2005-05-07 | 2008-11-20 | メリアル リミテッド | 殺虫剤用置換フェニルエーテル |
| US20070059421A1 (en) * | 2005-09-13 | 2007-03-15 | Catani Steven J | Methods and compositions to improve the palatability of foods |
| TW200800911A (en) | 2005-10-20 | 2008-01-01 | Biolipox Ab | Pyrazoles useful in the treatment of inflammation |
| WO2007063098A1 (en) * | 2005-11-30 | 2007-06-07 | Purac Biochem Bv | Aqueous potassium lactate solution |
| BRPI0716053A2 (pt) * | 2006-08-22 | 2013-08-06 | Redpoint Bio Corp | compostos heterocÍclicos como promotores de adoÇantes |
| JP5596536B2 (ja) * | 2008-03-24 | 2014-09-24 | 日本水産株式会社 | 塩味増強剤及びそれを含有する飲食品 |
-
2011
- 2011-04-15 WO PCT/US2011/032782 patent/WO2011130707A2/en not_active Ceased
- 2011-04-15 CA CA2796077A patent/CA2796077A1/en not_active Abandoned
- 2011-04-15 US US13/641,209 patent/US20130101684A1/en not_active Abandoned
- 2011-04-15 EP EP11769726.8A patent/EP2558067A4/en not_active Withdrawn
- 2011-04-15 MX MX2012011996A patent/MX2012011996A/es unknown
- 2011-04-15 CN CN2011800245658A patent/CN103025313A/zh active Pending
- 2011-04-15 KR KR1020127029635A patent/KR20130055601A/ko not_active Withdrawn
- 2011-04-15 CN CN201610227410.9A patent/CN105962259A/zh active Pending
- 2011-04-15 PH PH1/2012/501970A patent/PH12012501970A1/en unknown
- 2011-04-15 PE PE2012002026A patent/PE20130633A1/es not_active Application Discontinuation
- 2011-04-15 RU RU2012142730/13A patent/RU2597438C2/ru not_active IP Right Cessation
- 2011-04-15 AU AU2011239447A patent/AU2011239447B2/en not_active Ceased
- 2011-04-15 JP JP2013505204A patent/JP2013523192A/ja not_active Withdrawn
-
2012
- 2012-10-14 IL IL222423A patent/IL222423A/en active IP Right Grant
- 2012-11-12 ZA ZA2012/08488A patent/ZA201208488B/en unknown
-
2016
- 2016-08-05 JP JP2016155087A patent/JP2017038594A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20180030708A (ko) * | 2015-08-07 | 2018-03-23 | 브이. 만느 피스 | 맛 조절 화합물을 포함하는 조성물, 이의 용도 및 이를 포함하는 식품 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105962259A (zh) | 2016-09-28 |
| IL222423A (en) | 2016-11-30 |
| AU2011239447A1 (en) | 2012-11-01 |
| JP2017038594A (ja) | 2017-02-23 |
| CN103025313A (zh) | 2013-04-03 |
| PH12012501970A1 (en) | 2019-06-14 |
| US20130101684A1 (en) | 2013-04-25 |
| EP2558067A2 (en) | 2013-02-20 |
| WO2011130707A9 (en) | 2012-01-05 |
| RU2012142730A (ru) | 2014-05-20 |
| CA2796077A1 (en) | 2011-10-20 |
| PE20130633A1 (es) | 2013-07-01 |
| ZA201208488B (en) | 2017-08-30 |
| WO2011130707A2 (en) | 2011-10-20 |
| AU2011239447B2 (en) | 2016-03-17 |
| JP2013523192A (ja) | 2013-06-17 |
| IL222423A0 (en) | 2012-12-31 |
| EP2558067A4 (en) | 2016-05-25 |
| RU2597438C2 (ru) | 2016-09-10 |
| MX2012011996A (es) | 2013-11-27 |
| WO2011130707A3 (en) | 2012-02-23 |
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| US9872514B2 (en) | Compounds, compositions, and methods for reducing or eliminating bitter taste | |
| EP2768492B1 (en) | Compounds, compositions, and methods for reducing or eliminating bitter taste | |
| AU2015258252B2 (en) | Compounds, Compositions, And Methods For Reducing Or Eliminating Bitter Taste |
Legal Events
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Patent event date: 20121112 Patent event code: PA01051R01D Comment text: International Patent Application |
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Patent event date: 20130626 Comment text: Notification of Change of Applicant Patent event code: PN23011R01D |
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| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |