CN105962259A - 用于减小或消除苦味的化合物、组合物和方法 - Google Patents
用于减小或消除苦味的化合物、组合物和方法 Download PDFInfo
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- CN105962259A CN105962259A CN201610227410.9A CN201610227410A CN105962259A CN 105962259 A CN105962259 A CN 105962259A CN 201610227410 A CN201610227410 A CN 201610227410A CN 105962259 A CN105962259 A CN 105962259A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 563
- 239000000203 mixture Substances 0.000 title claims abstract description 501
- 238000000034 method Methods 0.000 title claims abstract description 198
- 235000019658 bitter taste Nutrition 0.000 title claims abstract description 158
- 235000013305 food Nutrition 0.000 claims abstract description 238
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 118
- 239000011780 sodium chloride Substances 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 399
- -1 C1-10Alkoxyl Chemical group 0.000 claims description 191
- 235000002639 sodium chloride Nutrition 0.000 claims description 173
- 125000003545 alkoxy group Chemical group 0.000 claims description 152
- 125000001072 heteroaryl group Chemical group 0.000 claims description 136
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 134
- 125000000623 heterocyclic group Chemical group 0.000 claims description 122
- 150000003839 salts Chemical class 0.000 claims description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 83
- 235000000346 sugar Nutrition 0.000 claims description 75
- 239000001103 potassium chloride Substances 0.000 claims description 71
- 125000005842 heteroatom Chemical group 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 235000011085 potassium lactate Nutrition 0.000 claims description 64
- 239000001521 potassium lactate Substances 0.000 claims description 64
- 229960001304 potassium lactate Drugs 0.000 claims description 64
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 63
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 63
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- 125000004423 acyloxy group Chemical group 0.000 claims description 60
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 59
- 235000011088 sodium lactate Nutrition 0.000 claims description 56
- 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 55
- 239000001540 sodium lactate Substances 0.000 claims description 55
- 229940005581 sodium lactate Drugs 0.000 claims description 55
- 229910052717 sulfur Inorganic materials 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 125000001188 haloalkyl group Chemical group 0.000 claims description 52
- 125000002252 acyl group Chemical group 0.000 claims description 50
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 235000019640 taste Nutrition 0.000 claims description 42
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 38
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 229910019142 PO4 Inorganic materials 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
- 239000010452 phosphate Substances 0.000 claims description 35
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 34
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 claims description 32
- 235000010358 acesulfame potassium Nutrition 0.000 claims description 32
- 229960004998 acesulfame potassium Drugs 0.000 claims description 32
- 239000000619 acesulfame-K Substances 0.000 claims description 32
- 239000011734 sodium Substances 0.000 claims description 32
- 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 31
- 229910052708 sodium Inorganic materials 0.000 claims description 31
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 21
- 159000000000 sodium salts Chemical class 0.000 claims description 19
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 210000000214 mouth Anatomy 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 235000009508 confectionery Nutrition 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 230000035807 sensation Effects 0.000 claims description 6
- 235000019615 sensations Nutrition 0.000 claims description 6
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 25
- 241001597008 Nomeidae Species 0.000 claims 24
- 229940125904 compound 1 Drugs 0.000 claims 14
- 230000001737 promoting effect Effects 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 5
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 4
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical class 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 2
- 239000005864 Sulphur Substances 0.000 claims 1
- PKZVFOVXYKCBCJ-UHFFFAOYSA-N [2-(1H-indol-4-yloxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1C=CC2=C(C=CC=C12)OC1=NC(=CC(=C1)CN)C(F)(F)F PKZVFOVXYKCBCJ-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-M sodium lactate Chemical class [Na+].CC(O)C([O-])=O NGSFWBMYFKHRBD-UHFFFAOYSA-M 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 235000021023 sodium intake Nutrition 0.000 abstract description 23
- 235000005911 diet Nutrition 0.000 abstract description 10
- 230000000378 dietary effect Effects 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 description 84
- 125000003368 amide group Chemical group 0.000 description 72
- 235000011164 potassium chloride Nutrition 0.000 description 64
- 125000003282 alkyl amino group Chemical group 0.000 description 60
- 125000004452 carbocyclyl group Chemical group 0.000 description 60
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 description 46
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 46
- 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 44
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 44
- 150000002431 hydrogen Chemical group 0.000 description 43
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 125000004414 alkyl thio group Chemical group 0.000 description 40
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 39
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 38
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 38
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 36
- 125000001841 imino group Chemical group [H]N=* 0.000 description 36
- 239000011591 potassium Substances 0.000 description 36
- 235000007686 potassium Nutrition 0.000 description 36
- 229960003975 potassium Drugs 0.000 description 36
- 229910052700 potassium Inorganic materials 0.000 description 36
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 30
- 108091005708 gustatory receptors Proteins 0.000 description 29
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 28
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 28
- 235000015424 sodium Nutrition 0.000 description 28
- 125000003302 alkenyloxy group Chemical group 0.000 description 26
- 125000005133 alkynyloxy group Chemical group 0.000 description 26
- 239000004480 active ingredient Substances 0.000 description 24
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 24
- 125000005553 heteroaryloxy group Chemical group 0.000 description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 24
- 235000013351 cheese Nutrition 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 20
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 20
- 229910052749 magnesium Inorganic materials 0.000 description 20
- 239000011777 magnesium Substances 0.000 description 20
- 125000003396 thiol group Chemical group [H]S* 0.000 description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 230000008447 perception Effects 0.000 description 18
- 239000003755 preservative agent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 16
- 159000000007 calcium salts Chemical class 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000000796 flavoring agent Substances 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 125000005587 carbonate group Chemical group 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
- 239000003607 modifier Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 235000015067 sauces Nutrition 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical compound OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 0.000 description 10
- 239000003765 sweetening agent Substances 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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 235000012149 noodles Nutrition 0.000 description 9
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 235000013361 beverage Nutrition 0.000 description 8
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 235000016709 nutrition Nutrition 0.000 description 8
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 8
- 159000000001 potassium salts Chemical class 0.000 description 8
- 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 description 8
- 238000012360 testing method Methods 0.000 description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 235000013355 food flavoring agent Nutrition 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 239000008122 artificial sweetener Substances 0.000 description 6
- 235000021311 artificial sweeteners Nutrition 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000037213 diet Effects 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 230000002335 preservative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 6
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 235000015071 dressings Nutrition 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- QELSKZZBTMNZEB-UHFFFAOYSA-N p-hydroxybenzoic acid propyl ester Natural products CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 5
- 239000006072 paste Substances 0.000 description 5
- 235000013599 spices Nutrition 0.000 description 5
- 235000021092 sugar substitutes Nutrition 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- 206010013911 Dysgeusia Diseases 0.000 description 4
- 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 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
- 150000004651 carbonic acid esters Chemical class 0.000 description 4
- 235000016213 coffee Nutrition 0.000 description 4
- 235000013353 coffee beverage Nutrition 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 244000144972 livestock Species 0.000 description 4
- 230000000873 masking effect Effects 0.000 description 4
- 235000013372 meat Nutrition 0.000 description 4
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical group [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 229960002816 potassium chloride Drugs 0.000 description 4
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 229910000160 potassium phosphate Inorganic materials 0.000 description 4
- 235000011009 potassium phosphates Nutrition 0.000 description 4
- 235000013324 preserved food Nutrition 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 230000011664 signaling Effects 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- 229910000162 sodium phosphate Inorganic materials 0.000 description 4
- 235000011008 sodium phosphates Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 235000019605 sweet taste sensations Nutrition 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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- GTSHREYGKSITGK-UHFFFAOYSA-N sodium ferrocyanide Chemical compound [Na+].[Na+].[Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] GTSHREYGKSITGK-UHFFFAOYSA-N 0.000 description 1
- 239000000264 sodium ferrocyanide Substances 0.000 description 1
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- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
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- QYNMSPKSYXPZHG-UHFFFAOYSA-M sodium;4-ethoxycarbonylphenolate Chemical compound [Na+].CCOC(=O)C1=CC=C([O-])C=C1 QYNMSPKSYXPZHG-UHFFFAOYSA-M 0.000 description 1
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- IXMINYBUNCWGER-UHFFFAOYSA-M sodium;4-propoxycarbonylphenolate Chemical compound [Na+].CCCOC(=O)C1=CC=C([O-])C=C1 IXMINYBUNCWGER-UHFFFAOYSA-M 0.000 description 1
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- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 230000036327 taste response Effects 0.000 description 1
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- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
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- 230000026683 transduction Effects 0.000 description 1
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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
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- MLIKYFGFHUYZAL-UHFFFAOYSA-K trisodium;hydron;phosphonato phosphate Chemical compound [Na+].[Na+].[Na+].OP([O-])(=O)OP([O-])([O-])=O MLIKYFGFHUYZAL-UHFFFAOYSA-K 0.000 description 1
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- 229940045136 urea Drugs 0.000 description 1
- 235000014348 vinaigrettes Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A61K31/03—Halogenated hydrocarbons carbocyclic aromatic
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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 OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/86—Addition of bitterness inhibitors
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
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- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
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- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- 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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| 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 |
| CN112079777A (zh) * | 2020-08-11 | 2020-12-15 | 中山大学 | 一种多取代4-氟吖啶衍生物及其制备方法 |
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| SG11201502935VA (en) | 2012-10-16 | 2015-09-29 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of ror-gamma-t |
| JP6250686B2 (ja) | 2012-10-16 | 2017-12-20 | ヤンセン ファーマシューティカ エヌ.ベー. | Rorγtのヘテロアリール結合させたキノリニルモジュレータ |
| RS56283B1 (sr) | 2012-10-16 | 2017-12-29 | Janssen Pharmaceutica Nv | Metilen vezani hinolinil modulatori ror-gama-t |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| CA2926339A1 (en) | 2013-10-15 | 2015-04-23 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of roryt |
| BR112016008258A2 (pt) | 2013-10-15 | 2017-10-10 | Janssen Pharmaceutica Nv | moduladores de ror?t de quinolinila |
| 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 |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| 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 |
| CA2992522A1 (en) * | 2015-08-07 | 2017-02-16 | V. Mane Fils | Composition comprising taste modulation compounds, their use and foodstuff comprising them |
| WO2017178466A1 (en) | 2016-04-11 | 2017-10-19 | Nestec S.A. | Salt composition including serine |
| 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 |
| US11116778B2 (en) | 2019-01-15 | 2021-09-14 | 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 |
| US12036286B2 (en) | 2021-03-18 | 2024-07-16 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
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| 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 |
| EP0661932A4 (en) * | 1991-11-27 | 1996-06-05 | Bioresearch Inc | SPECIFIC EDIBLE FLAVORING AGENTS. |
| 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 |
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| US20050013835A1 (en) * | 2003-07-15 | 2005-01-20 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
| CA2535036C (en) * | 2003-08-06 | 2015-11-24 | Senomyx, Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| DE102004041496A1 (de) * | 2004-08-27 | 2006-03-02 | Symrise Gmbh & Co. Kg | Hydroxybenzoesäureamide und deren Verwendung zur Maskierung von bitterem Geschmack |
| AR052477A1 (es) * | 2005-02-04 | 2007-03-21 | Senomyx Inc | Moleculas que comprenden restos organicos conectados como modificadores del sabor para composiciones comestibles |
| 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 |
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| BRPI0614676A2 (pt) * | 2005-05-07 | 2011-04-12 | Merial Ltd | éteres fenìlicos substituìdos pesticidas |
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| 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 |
| WO2008024364A2 (en) * | 2006-08-22 | 2008-02-28 | Redpoint Bio Corporation | Heterocyclic compounds as sweetener enhancers |
| EP2263477A4 (en) * | 2008-03-24 | 2011-06-15 | Nippon Suisan Kaisha Ltd | REINFORCING AGENT FOR SALTY TASTE AND FOOD OR BEVERAGE THEREFOR |
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| CN101400336A (zh) * | 2003-08-06 | 2009-04-01 | 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 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN112079777A (zh) * | 2020-08-11 | 2020-12-15 | 中山大学 | 一种多取代4-氟吖啶衍生物及其制备方法 |
| 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 |
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| ZA201208488B (en) | 2017-08-30 |
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| PH12012501970A1 (en) | 2019-06-14 |
| MX2012011996A (es) | 2013-11-27 |
| RU2597438C2 (ru) | 2016-09-10 |
| CA2796077A1 (en) | 2011-10-20 |
| CN103025313A (zh) | 2013-04-03 |
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