TWI585093B - 供治療代謝症候群或發炎性疾病的吡喃苯并吡喃基苯酚衍生物及醫藥組成物 - Google Patents
供治療代謝症候群或發炎性疾病的吡喃苯并吡喃基苯酚衍生物及醫藥組成物 Download PDFInfo
- Publication number
- TWI585093B TWI585093B TW103145316A TW103145316A TWI585093B TW I585093 B TWI585093 B TW I585093B TW 103145316 A TW103145316 A TW 103145316A TW 103145316 A TW103145316 A TW 103145316A TW I585093 B TWI585093 B TW I585093B
- Authority
- TW
- Taiwan
- Prior art keywords
- dimethyl
- compound
- benzyloxy
- hydroxy
- group
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 27
- 208000001145 Metabolic Syndrome Diseases 0.000 title claims description 24
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 title claims description 24
- 208000027866 inflammatory disease Diseases 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- -1 n - butyl Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 25
- 208000008589 Obesity Diseases 0.000 claims description 19
- 235000020824 obesity Nutrition 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 206010012601 diabetes mellitus Diseases 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 208000004930 Fatty Liver Diseases 0.000 claims description 7
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 208000010706 fatty liver disease Diseases 0.000 claims description 7
- 231100000240 steatosis hepatitis Toxicity 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 238000002360 preparation method Methods 0.000 description 98
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 86
- 238000005160 1H NMR spectroscopy Methods 0.000 description 68
- 239000000243 solution Substances 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 56
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- 229940044613 1-propanol Drugs 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 30
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 19
- 229940126142 compound 16 Drugs 0.000 description 19
- 239000012141 concentrate Substances 0.000 description 19
- 238000001000 micrograph Methods 0.000 description 18
- 101001087394 Homo sapiens Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 description 17
- 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- FILYUZSCSMFMBQ-UHFFFAOYSA-N CC1=C(C(=C(C=C1)OC(=O)C)C)OCC2=CC=CC=C2 Chemical compound CC1=C(C(=C(C=C1)OC(=O)C)C)OCC2=CC=CC=C2 FILYUZSCSMFMBQ-UHFFFAOYSA-N 0.000 description 15
- 201000010099 disease Diseases 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 14
- 229940125758 compound 15 Drugs 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 210000005228 liver tissue Anatomy 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 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 11
- 241000202807 Glycyrrhiza Species 0.000 description 11
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 11
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 11
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 11
- 235000008504 concentrate Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 229940010454 licorice Drugs 0.000 description 11
- LYKDOWJROLHYOT-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1O LYKDOWJROLHYOT-UHFFFAOYSA-N 0.000 description 10
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 229940125898 compound 5 Drugs 0.000 description 10
- 239000002552 dosage form Substances 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000004378 Glycyrrhizin Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 9
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 9
- 229960004949 glycyrrhizic acid Drugs 0.000 description 9
- 235000019410 glycyrrhizin Nutrition 0.000 description 9
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 206010022489 Insulin Resistance Diseases 0.000 description 7
- 125000005605 benzo group Chemical group 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 6
- IKJXIGCXRAYEMN-UHFFFAOYSA-N 5-butyl-2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)phenol Chemical compound OC1=C(C=CC(=C1)CCCC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 IKJXIGCXRAYEMN-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 6
- 108090001061 Insulin Proteins 0.000 description 6
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 229940126543 compound 14 Drugs 0.000 description 6
- 238000013229 diet-induced obese mouse Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 5
- 210000001789 adipocyte Anatomy 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 230000003579 anti-obesity Effects 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 235000010980 cellulose Nutrition 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 5
- 229960004106 citric acid Drugs 0.000 description 5
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 5
- 239000008108 microcrystalline cellulose Substances 0.000 description 5
- 229940016286 microcrystalline cellulose Drugs 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- QVZIIZWVTYTWLS-UHFFFAOYSA-N (3,4-dimethyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)C)C)OCC1=CC=CC=C1 QVZIIZWVTYTWLS-UHFFFAOYSA-N 0.000 description 4
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- 229920000858 Cyclodextrin Polymers 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- 238000002965 ELISA Methods 0.000 description 4
- 102000017011 Glycated Hemoglobin A Human genes 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 229940126086 compound 21 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000002158 endotoxin Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 102000016267 Leptin Human genes 0.000 description 3
- 108010092277 Leptin Proteins 0.000 description 3
- 229920000881 Modified starch Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007640 basal medium Substances 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125833 compound 23 Drugs 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 229960001483 eosin Drugs 0.000 description 3
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 3
- 229910017053 inorganic salt Inorganic materials 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229960001375 lactose Drugs 0.000 description 3
- 229940039781 leptin Drugs 0.000 description 3
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 3
- 210000002540 macrophage Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 210000001087 myotubule Anatomy 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- YQAHRCQLWRPRDC-UHFFFAOYSA-N (3,4,5-trimethyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C(=C1)C)C)C)OCC1=CC=CC=C1 YQAHRCQLWRPRDC-UHFFFAOYSA-N 0.000 description 2
- XFTIGMJBLDZZFH-UHFFFAOYSA-N (4-ethyl-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)CC)C)OCC1=CC=CC=C1 XFTIGMJBLDZZFH-UHFFFAOYSA-N 0.000 description 2
- LOOMFZLIHFCMIX-UHFFFAOYSA-N (4-methoxy-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OC)C)OCC1=CC=CC=C1 LOOMFZLIHFCMIX-UHFFFAOYSA-N 0.000 description 2
- CLKKXBAHOASWCP-UHFFFAOYSA-N 1-(4-methyl-2-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1OCC1=CC=CC=C1 CLKKXBAHOASWCP-UHFFFAOYSA-N 0.000 description 2
- CROQUSOQGASVNW-UHFFFAOYSA-N 2-(8,8-diethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-methoxyphenol Chemical compound OC1=C(C=CC(=C1)OC)C1CC=2C(=C3CCC(OC3=CC=2)(CC)CC)OC1 CROQUSOQGASVNW-UHFFFAOYSA-N 0.000 description 2
- XZGZJDJZYPSQJJ-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-ethylphenol Chemical compound OC1=C(C=CC(=C1)CC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 XZGZJDJZYPSQJJ-UHFFFAOYSA-N 0.000 description 2
- YRTQOUWVTAUXOF-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-methylphenol Chemical compound OC1=C(C=CC(=C1)C)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 YRTQOUWVTAUXOF-UHFFFAOYSA-N 0.000 description 2
- GFPXYXJEWKDANV-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-propylphenol Chemical compound OC1=C(C=CC(=C1)CCC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 GFPXYXJEWKDANV-UHFFFAOYSA-N 0.000 description 2
- AUCYLOFJAOZPBM-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2h-pyrano[2,3-h]chromen-3-yl)-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1C1CC(C=CC2=C3CCC(C)(C)O2)=C3OC1 AUCYLOFJAOZPBM-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 2
- RRCYKDUAXZXASF-UHFFFAOYSA-N 5-butoxy-2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)phenol Chemical compound OC1=C(C=CC(=C1)OCCCC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 RRCYKDUAXZXASF-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 108010014663 Glycated Hemoglobin A Proteins 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 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 description 2
- 102000003746 Insulin Receptor Human genes 0.000 description 2
- 108010001127 Insulin Receptor Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 229960004543 anhydrous citric acid Drugs 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940125810 compound 20 Drugs 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- 108091005995 glycated hemoglobin Proteins 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 210000000274 microglia Anatomy 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 239000008203 oral pharmaceutical composition Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 229940069328 povidone Drugs 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 229960004586 rosiglitazone Drugs 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QUTFFEUUGHUPQC-ILWYWAAHSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](C=O)NC1=CC=C([N+]([O-])=O)C2=NON=C12 QUTFFEUUGHUPQC-ILWYWAAHSA-N 0.000 description 1
- XLBKEKADIMRVCK-UHFFFAOYSA-N (3-methyl-2-phenylmethoxy-4-propan-2-yloxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OC(C)C)C)OCC1=CC=CC=C1 XLBKEKADIMRVCK-UHFFFAOYSA-N 0.000 description 1
- UEINEVUCLXTBLV-UHFFFAOYSA-N (3-methyl-2-phenylmethoxy-4-propan-2-ylphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)C(C)C)C)OCC1=CC=CC=C1 UEINEVUCLXTBLV-UHFFFAOYSA-N 0.000 description 1
- WSOCKDRBPGKIPL-UHFFFAOYSA-N (3-methyl-2-phenylmethoxy-4-propoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OCCC)C)OCC1=CC=CC=C1 WSOCKDRBPGKIPL-UHFFFAOYSA-N 0.000 description 1
- SXMFFPFDLHIPCE-UHFFFAOYSA-N (3-methyl-2-phenylmethoxy-4-propylphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)CCC)C)OCC1=CC=CC=C1 SXMFFPFDLHIPCE-UHFFFAOYSA-N 0.000 description 1
- HYOMXRUTMIROMN-UHFFFAOYSA-N (3-methyl-4-pentoxy-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OCCCCC)C)OCC1=CC=CC=C1 HYOMXRUTMIROMN-UHFFFAOYSA-N 0.000 description 1
- ADGNKWZUPYTLEK-UHFFFAOYSA-N (3-methyl-4-pentyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)CCCCC)C)OCC1=CC=CC=C1 ADGNKWZUPYTLEK-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- ZAMPAIMZGDGPDG-UHFFFAOYSA-N (4-butoxy-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OCCCC)C)OCC1=CC=CC=C1 ZAMPAIMZGDGPDG-UHFFFAOYSA-N 0.000 description 1
- GNAMJIMOZCTREW-UHFFFAOYSA-N (4-butyl-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)CCCC)C)OCC1=CC=CC=C1 GNAMJIMOZCTREW-UHFFFAOYSA-N 0.000 description 1
- WNSUYJNZSFSRMM-UHFFFAOYSA-N (4-chloro-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)Cl)C)OCC1=CC=CC=C1 WNSUYJNZSFSRMM-UHFFFAOYSA-N 0.000 description 1
- DEIGWKYSWZAMMU-UHFFFAOYSA-N (4-ethoxy-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OCC)C)OCC1=CC=CC=C1 DEIGWKYSWZAMMU-UHFFFAOYSA-N 0.000 description 1
- QYZXVJHQQDQHMS-UHFFFAOYSA-N (4-fluoro-3-methyl-2-phenylmethoxyphenyl) acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)F)C)OCC1=CC=CC=C1 QYZXVJHQQDQHMS-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- HBMDBMVEHVKMNG-UHFFFAOYSA-N 1-(2-hydroxy-4-propoxyphenyl)ethanone Chemical compound CCCOC1=CC=C(C(C)=O)C(O)=C1 HBMDBMVEHVKMNG-UHFFFAOYSA-N 0.000 description 1
- KMYKXFGANGCZQO-UHFFFAOYSA-N 1-(4-butoxy-2-hydroxyphenyl)ethanone Chemical compound CCCCOC1=CC=C(C(C)=O)C(O)=C1 KMYKXFGANGCZQO-UHFFFAOYSA-N 0.000 description 1
- VBLALYJSGGGWHU-UHFFFAOYSA-N 1-(4-ethoxy-2-hydroxyphenyl)ethanone Chemical compound CCOC1=CC=C(C(C)=O)C(O)=C1 VBLALYJSGGGWHU-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- JADFOLPTRGGJBD-UHFFFAOYSA-N 2-(2-hydroxy-3-methylphenyl)acetic acid Chemical compound CC1=CC=CC(CC(O)=O)=C1O JADFOLPTRGGJBD-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JTTCQNULMUUYGW-UHFFFAOYSA-N 2-(3,4-dimethyl-2-phenylmethoxyphenyl)acetic acid Chemical compound Cc1ccc(CC(O)=O)c(OCc2ccccc2)c1C JTTCQNULMUUYGW-UHFFFAOYSA-N 0.000 description 1
- IUXJXQLTUMGHHL-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-ethoxyphenol Chemical compound OC1=C(C=CC(=C1)OCC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 IUXJXQLTUMGHHL-UHFFFAOYSA-N 0.000 description 1
- JHRDYYSLVXGORW-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-fluorophenol Chemical compound OC1=C(C=CC(=C1)F)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 JHRDYYSLVXGORW-UHFFFAOYSA-N 0.000 description 1
- YRAYVWBUDKTGQK-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-5-propoxyphenol Chemical compound OC1=C(C=CC(=C1)OCCC)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 YRAYVWBUDKTGQK-UHFFFAOYSA-N 0.000 description 1
- KVZVLKOCCCLONS-UHFFFAOYSA-N 2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)phenol Chemical compound OC1=C(C=CC=C1)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 KVZVLKOCCCLONS-UHFFFAOYSA-N 0.000 description 1
- DJPNFFJPIXWYAZ-UHFFFAOYSA-N 2h-chromene-2-carbaldehyde Chemical compound C1=CC=C2C=CC(C=O)OC2=C1 DJPNFFJPIXWYAZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JNOCIPGZKPIIBW-UHFFFAOYSA-N 5-chloro-2-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)phenol Chemical compound OC1=C(C=CC(=C1)Cl)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 JNOCIPGZKPIIBW-UHFFFAOYSA-N 0.000 description 1
- VLHVXYPFWRHKHE-UHFFFAOYSA-N 5-hydroxy-2,2-dimethylchromene-6-carbaldehyde Chemical compound C1=C(C=O)C(O)=C2C=CC(C)(C)OC2=C1 VLHVXYPFWRHKHE-UHFFFAOYSA-N 0.000 description 1
- KOSUVAORRVJURO-UHFFFAOYSA-N 6-(8,8-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-3-yl)-2,3-dimethylphenol Chemical compound OC1=C(C=CC(=C1C)C)C1CC=2C(=C3CCC(OC3=CC=2)(C)C)OC1 KOSUVAORRVJURO-UHFFFAOYSA-N 0.000 description 1
- MPEPZCKINWONIB-UHFFFAOYSA-N 6-[2-(4,5-dimethyl-2-phenylmethoxyphenyl)-3-hydroxypropyl]-2,2-dimethylchromen-5-ol Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C(=C1)C)C)C(CO)CC=1C=CC2=C(C=CC(O2)(C)C)C=1O MPEPZCKINWONIB-UHFFFAOYSA-N 0.000 description 1
- NWFCREZJKNPXPQ-UHFFFAOYSA-N 6-[2-(4-butoxy-2-phenylmethoxyphenyl)-3-hydroxypropyl]-2,2-dimethylchromen-5-ol Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCCCC)C(CO)CC=1C=CC2=C(C=CC(O2)(C)C)C=1O NWFCREZJKNPXPQ-UHFFFAOYSA-N 0.000 description 1
- LRROABKXLUTLLO-UHFFFAOYSA-N 6-[3-hydroxy-2-(2-phenylmethoxy-4-propylphenyl)propyl]-2,2-dimethylchromen-5-ol Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CCC)C(CO)CC=1C=CC2=C(C=CC(O2)(C)C)C=1O LRROABKXLUTLLO-UHFFFAOYSA-N 0.000 description 1
- SAPBROBQAGZRNR-UHFFFAOYSA-N 6-[3-hydroxy-2-(4-methyl-2-phenylmethoxyphenyl)propyl]-2,2-dimethylchromen-5-ol Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)C)C(CO)CC=1C=CC2=C(C=CC(O2)(C)C)C=1O SAPBROBQAGZRNR-UHFFFAOYSA-N 0.000 description 1
- 208000004611 Abdominal Obesity Diseases 0.000 description 1
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- JFKFRXSZICSKKL-UHFFFAOYSA-N C(C)C(=CC=O)CC.CC(=CC=O)CC Chemical compound C(C)C(=CC=O)CC.CC(=CC=O)CC JFKFRXSZICSKKL-UHFFFAOYSA-N 0.000 description 1
- VHUXJJIXKIFCTI-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=C(C(=C1)C)C)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C(=C1)C)C)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 VHUXJJIXKIFCTI-UHFFFAOYSA-N 0.000 description 1
- XNPKCTRQKFDQAV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)C)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)C)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 XNPKCTRQKFDQAV-UHFFFAOYSA-N 0.000 description 1
- XVANJDBVXUQUTL-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 XVANJDBVXUQUTL-UHFFFAOYSA-N 0.000 description 1
- RATYOZHHZDYJLN-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 RATYOZHHZDYJLN-UHFFFAOYSA-N 0.000 description 1
- QEAHVVFPKBLBSL-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 QEAHVVFPKBLBSL-UHFFFAOYSA-N 0.000 description 1
- CPSYSWTWNGEONQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 CPSYSWTWNGEONQ-UHFFFAOYSA-N 0.000 description 1
- UDEQCDNJAPCMKC-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OC)C1CC=2C(=C3C=CC(OC3=CC=2)(CC)CC)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OC)C1CC=2C(=C3C=CC(OC3=CC=2)(CC)CC)OC1 UDEQCDNJAPCMKC-UHFFFAOYSA-N 0.000 description 1
- XKAQRWPLOILDOV-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 XKAQRWPLOILDOV-UHFFFAOYSA-N 0.000 description 1
- JYCCTDHXUGRCCQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 JYCCTDHXUGRCCQ-UHFFFAOYSA-N 0.000 description 1
- AWZXVDKRWWGQAT-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OCCCC)C1CC=2C(=C3C=CC(OC3=CC=2)(C)C)OC1 AWZXVDKRWWGQAT-UHFFFAOYSA-N 0.000 description 1
- 238000011740 C57BL/6 mouse Methods 0.000 description 1
- JFRMCFZUGRYFIJ-UHFFFAOYSA-N CC(CC(C)OC(=O)C)OCC1=CC=CC=C1 Chemical compound CC(CC(C)OC(=O)C)OCC1=CC=CC=C1 JFRMCFZUGRYFIJ-UHFFFAOYSA-N 0.000 description 1
- WYQDXANGMPFORE-UHFFFAOYSA-N CC1(C=CC2=C(O1)C=CC(=C2)SC)C Chemical group CC1(C=CC2=C(O1)C=CC(=C2)SC)C WYQDXANGMPFORE-UHFFFAOYSA-N 0.000 description 1
- JXJQGCGTTQETLN-UHFFFAOYSA-N CC1(C=CC2=C(O1)C=CC(=C2O)C=C(C3=C(C=C(C=C3)OC)OCC4=CC=CC=C4)C(=O)O)C Chemical compound CC1(C=CC2=C(O1)C=CC(=C2O)C=C(C3=C(C=C(C=C3)OC)OCC4=CC=CC=C4)C(=O)O)C JXJQGCGTTQETLN-UHFFFAOYSA-N 0.000 description 1
- CSHMWIVCVJQLCD-UHFFFAOYSA-N CC1(C=CC2=C(O1)C=CC(=C2O)C=C(C3=CC=CC=C3OCOC)C(=O)O)C Chemical compound CC1(C=CC2=C(O1)C=CC(=C2O)C=C(C3=CC=CC=C3OCOC)C(=O)O)C CSHMWIVCVJQLCD-UHFFFAOYSA-N 0.000 description 1
- BTQTVLSMFXOBNZ-UHFFFAOYSA-N CC1(C=CC2=C(O1)C=CC(=C2O)CCC(C3=C(C=C(C=C3)OC)OCC4=CC=CC=C4)O)C Chemical compound CC1(C=CC2=C(O1)C=CC(=C2O)CCC(C3=C(C=C(C=C3)OC)OCC4=CC=CC=C4)O)C BTQTVLSMFXOBNZ-UHFFFAOYSA-N 0.000 description 1
- VOFZBGFGLUCTMB-UHFFFAOYSA-N CC1=C(C(=CC=C1)CC(=O)O)OCOC Chemical compound CC1=C(C(=CC=C1)CC(=O)O)OCOC VOFZBGFGLUCTMB-UHFFFAOYSA-N 0.000 description 1
- OVKSMXDMLWSJNO-UHFFFAOYSA-N CC1=CC(=C(C(=C1C)C)OCC2=CC=CC=C2)CC(=O)O Chemical compound CC1=CC(=C(C(=C1C)C)OCC2=CC=CC=C2)CC(=O)O OVKSMXDMLWSJNO-UHFFFAOYSA-N 0.000 description 1
- CBJDARGSKXBYAW-UHFFFAOYSA-N CC1=CC2=C(C=CC2C3C=CC=CC3(C)C)C=C1 Chemical compound CC1=CC2=C(C=CC2C3C=CC=CC3(C)C)C=C1 CBJDARGSKXBYAW-UHFFFAOYSA-N 0.000 description 1
- GWDALRYGXBOZCO-UHFFFAOYSA-N CCC1(C=CC2=C(O1)C=CC(=C2)S)CC Chemical compound CCC1(C=CC2=C(O1)C=CC(=C2)S)CC GWDALRYGXBOZCO-UHFFFAOYSA-N 0.000 description 1
- GZBCJOPPEBZYRR-UHFFFAOYSA-N CCCC1=CC(=C(C=C1)C(=CC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)C(=O)O)OCC4=CC=CC=C4 Chemical compound CCCC1=CC(=C(C=C1)C(=CC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)C(=O)O)OCC4=CC=CC=C4 GZBCJOPPEBZYRR-UHFFFAOYSA-N 0.000 description 1
- LCUIJKSPCPKOGE-UHFFFAOYSA-N CCCCC1=CC(=C(C=C1)C(=CC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)C(=O)O)OCC4=CC=CC=C4 Chemical compound CCCCC1=CC(=C(C=C1)C(=CC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)C(=O)O)OCC4=CC=CC=C4 LCUIJKSPCPKOGE-UHFFFAOYSA-N 0.000 description 1
- FICFVQVPAQNKIZ-UHFFFAOYSA-N CCCOC1=CC(=C(C=C1)C(CCC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)O)OCC4=CC=CC=C4 Chemical compound CCCOC1=CC(=C(C=C1)C(CCC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)O)OCC4=CC=CC=C4 FICFVQVPAQNKIZ-UHFFFAOYSA-N 0.000 description 1
- MUTUMFAQHMSLRS-UHFFFAOYSA-N CCOC1=CC(=C(C=C1)C(CCC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)O)OCC4=CC=CC=C4 Chemical compound CCOC1=CC(=C(C=C1)C(CCC2=C(C3=C(C=C2)OC(C=C3)(C)C)O)O)OCC4=CC=CC=C4 MUTUMFAQHMSLRS-UHFFFAOYSA-N 0.000 description 1
- PIPIHCSGDCUPGG-UHFFFAOYSA-N COC1=CC(=C(C=C1)CC(=S)N2CCOCC2)OCC3=CC=CC=C3 Chemical compound COC1=CC(=C(C=C1)CC(=S)N2CCOCC2)OCC3=CC=CC=C3 PIPIHCSGDCUPGG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010065941 Central obesity Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010015548 Euthanasia Diseases 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 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 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 240000008917 Glycyrrhiza uralensis Species 0.000 description 1
- 235000000554 Glycyrrhiza uralensis Nutrition 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- AQLLBJAXUCIJSR-UHFFFAOYSA-N OC(=O)C[Na] Chemical compound OC(=O)C[Na] AQLLBJAXUCIJSR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000001744 Sodium fumarate Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000013200 Stress disease Diseases 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DCJUGYUPUYOAGU-UHFFFAOYSA-N [4-(2-methoxyethyl)-3-methyl-2-phenylmethoxyphenyl] acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)CCOC)C)OCC1=CC=CC=C1 DCJUGYUPUYOAGU-UHFFFAOYSA-N 0.000 description 1
- MMUZQUBVNKEXEG-UHFFFAOYSA-N [4-(methoxymethoxy)-3-methyl-2-phenylmethoxyphenyl] acetate Chemical compound C(C)(=O)OC1=C(C(=C(C=C1)OCOC)C)OCC1=CC=CC=C1 MMUZQUBVNKEXEG-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 235000010358 acesulfame potassium Nutrition 0.000 description 1
- 229960004998 acesulfame potassium Drugs 0.000 description 1
- 239000000619 acesulfame-K Substances 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- LEWCAQWVBYTPMP-UHFFFAOYSA-K aluminum;magnesium;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Mg+2].[Al+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O LEWCAQWVBYTPMP-UHFFFAOYSA-K 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- DRVWBEJJZZTIGJ-UHFFFAOYSA-N cerium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Ce+3].[Ce+3] DRVWBEJJZZTIGJ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229940099898 chlorophyllin Drugs 0.000 description 1
- 235000019805 chlorophyllin Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 229920001531 copovidone Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000030609 dephosphorylation Effects 0.000 description 1
- 238000006209 dephosphorylation reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 235000005686 eating Nutrition 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 230000003073 embolic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 235000013410 fast food Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PMPYOYXFIHXBJI-ZDUSSCGKSA-N glabridin Natural products C1([C@H]2CC=3C=CC4=C(C=3OC2)CCC(O4)(C)C)=CC=C(O)C=C1O PMPYOYXFIHXBJI-ZDUSSCGKSA-N 0.000 description 1
- LBQIJVLKGVZRIW-ZDUSSCGKSA-N glabridin Chemical compound C1([C@H]2CC3=CC=C4OC(C=CC4=C3OC2)(C)C)=CC=C(O)C=C1O LBQIJVLKGVZRIW-ZDUSSCGKSA-N 0.000 description 1
- 229940093767 glabridin Drugs 0.000 description 1
- LBQIJVLKGVZRIW-UHFFFAOYSA-N glabridine Natural products C1OC2=C3C=CC(C)(C)OC3=CC=C2CC1C1=CC=C(O)C=C1O LBQIJVLKGVZRIW-UHFFFAOYSA-N 0.000 description 1
- 230000004190 glucose uptake Effects 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229940049654 glyceryl behenate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ODBKBWIBOLYMLQ-UHFFFAOYSA-N methyl 2-(4,5-dimethyl-2-phenylmethoxyphenyl)-3-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-enoate Chemical compound COC(C(=CC=1C=CC2=C(C=CC(O2)(C)C)C=1O)C1=C(C=C(C(=C1)C)C)OCC1=CC=CC=C1)=O ODBKBWIBOLYMLQ-UHFFFAOYSA-N 0.000 description 1
- AKJDZLVHKXJIFD-UHFFFAOYSA-N methyl 2-(4-ethoxy-2-phenylmethoxyphenyl)-3-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-enoate Chemical compound COC(C(=CC=1C=CC2=C(C=CC(O2)(C)C)C=1O)C1=C(C=C(C=C1)OCC)OCC1=CC=CC=C1)=O AKJDZLVHKXJIFD-UHFFFAOYSA-N 0.000 description 1
- MLDBWTCBRWPCOB-UHFFFAOYSA-N methyl 2-(4-ethyl-2-phenylmethoxyphenyl)-3-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-enoate Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC(=C1)CC)C(C(=O)OC)=CC=1C=CC2=C(C=CC(O2)(C)C)C=1O MLDBWTCBRWPCOB-UHFFFAOYSA-N 0.000 description 1
- PJZVYCWIQPSWOK-UHFFFAOYSA-N methyl 2-(4-methoxy-2-phenylmethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C=C1OCC1=CC=CC=C1 PJZVYCWIQPSWOK-UHFFFAOYSA-N 0.000 description 1
- XWORCJHFKSMOSM-UHFFFAOYSA-N methyl 2-[2-(methoxymethoxy)phenyl]acetate Chemical compound COCOC1=CC=CC=C1CC(=O)OC XWORCJHFKSMOSM-UHFFFAOYSA-N 0.000 description 1
- RDLDSQZKXPXCAY-UHFFFAOYSA-N methyl 3-(5-hydroxy-2,2-dimethylchromen-6-yl)-2-(2-phenylmethoxy-4-propoxyphenyl)prop-2-enoate Chemical compound COC(C(=CC=1C=CC2=C(C=CC(O2)(C)C)C=1O)C1=C(C=C(C=C1)OCCC)OCC1=CC=CC=C1)=O RDLDSQZKXPXCAY-UHFFFAOYSA-N 0.000 description 1
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
- 229960002237 metoprolol Drugs 0.000 description 1
- 230000002025 microglial effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000000651 myofibroblast Anatomy 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000031990 negative regulation of inflammatory response Effects 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 239000003801 protein tyrosine phosphatase 1B inhibitor Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 125000004862 thiobutyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20130162909 | 2013-12-24 | ||
| KR1020140181951A KR102344479B1 (ko) | 2013-12-24 | 2014-12-17 | 피라노크로메닐페놀 유도체, 및 대사증후군 또는 염증 질환 치료용 약학 조성물 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201607949A TW201607949A (zh) | 2016-03-01 |
| TWI585093B true TWI585093B (zh) | 2017-06-01 |
Family
ID=53788040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103145316A TWI585093B (zh) | 2013-12-24 | 2014-12-24 | 供治療代謝症候群或發炎性疾病的吡喃苯并吡喃基苯酚衍生物及醫藥組成物 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9783551B2 (enExample) |
| EP (1) | EP3098224B1 (enExample) |
| JP (2) | JP6620096B2 (enExample) |
| KR (1) | KR102344479B1 (enExample) |
| CN (1) | CN105849111B (enExample) |
| AU (1) | AU2014370697B2 (enExample) |
| BR (1) | BR112016011281B1 (enExample) |
| CA (1) | CA2929001C (enExample) |
| CY (1) | CY1121554T1 (enExample) |
| DK (1) | DK3098224T3 (enExample) |
| ES (1) | ES2718878T3 (enExample) |
| HR (1) | HRP20190573T1 (enExample) |
| HU (1) | HUE043902T2 (enExample) |
| IL (1) | IL245908B (enExample) |
| MX (1) | MX374944B (enExample) |
| NZ (1) | NZ720328A (enExample) |
| PL (1) | PL3098224T3 (enExample) |
| PT (1) | PT3098224T (enExample) |
| SG (1) | SG11201604371PA (enExample) |
| TW (1) | TWI585093B (enExample) |
| WO (1) | WO2015099392A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102344479B1 (ko) * | 2013-12-24 | 2021-12-29 | 주식회사 글라세움 | 피라노크로메닐페놀 유도체, 및 대사증후군 또는 염증 질환 치료용 약학 조성물 |
| TWI731998B (zh) | 2016-06-29 | 2021-07-01 | 南韓商格雷森伍股份有限公司 | 光學活性吡喃並苯並吡喃基苯酚衍生物及包含其的醫藥組成物 |
| TWI641610B (zh) * | 2016-10-04 | 2018-11-21 | 南韓商格雷森伍股份有限公司 | 用於合成3-苯基-2,3,4,8,9,10-六氫吡喃並[2,3-f]色烯衍生物及其光學異構物的方法 |
| TWI804600B (zh) * | 2018-04-03 | 2023-06-11 | 南韓商格雷森伍股份有限公司 | 3-苯基-2,8-二氫吡喃[2,3-ƒ]苯并哌喃衍生物的合成方法 |
| WO2019194583A1 (ko) * | 2018-04-03 | 2019-10-10 | 주식회사 글라세움 | 3-페닐-2,8-디히드로피라노[2,3-f]크로멘 유도체 및 이를 포함하는 약학적 조성물 |
| KR20200105198A (ko) * | 2019-02-28 | 2020-09-07 | 주식회사 글라세움 | 신경계 질환의 예방 또는 치료용 약학적 조성물 |
| KR102692932B1 (ko) | 2019-07-30 | 2024-08-07 | 주식회사 글라세움 | 2-((6-(히드록시메틸)크로멘-5-일)옥시)-1-페닐에타논 유도체의 합성 방법 |
| US20250367163A1 (en) | 2021-06-08 | 2025-12-04 | Glaceum, Inc. | Pharmaceutical composition for preventing or treating degenerative eye diseases |
| CN113616548B (zh) * | 2021-09-02 | 2023-04-28 | 河南科技大学 | 一种水溶性光甘草定包合物及其制备方法 |
| CN119343351A (zh) | 2022-04-12 | 2025-01-21 | 格拉斯如睦株式会社 | 用于3-苯基-2,3,4,8,9,10-六氢吡喃并[2,3-f]色烯衍生物的合成方法 |
| CN114903879B (zh) * | 2022-06-23 | 2023-10-31 | 东北大学 | 3-烃基苯酚衍生物在制备预防或治疗高脂血症及相关代谢性疾病产品中的用途 |
| KR20240113389A (ko) | 2023-01-12 | 2024-07-22 | 주식회사 글라세움 | 퇴행성 골관절염의 예방 또는 치료용 약학적 조성물 |
| KR20250081177A (ko) | 2023-11-29 | 2025-06-05 | 한국화학연구원 | Hsg4112 r형을 유효성분으로 포함하는 반려동물의 비만 예방, 개선 또는 치료용 조성물 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007058480A1 (en) * | 2005-11-16 | 2007-05-24 | Md Bioalpha Co., Ltd. | Composition having effect on treatment and prevention of diseases syndrome treatment with glabridin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050035142A (ko) * | 2001-10-11 | 2005-04-15 | 카네카 코포레이션 | 페록시좀 증식제 응답성 수용체 리간드제 및 그 제조 방법 |
| KR100565423B1 (ko) * | 2003-10-20 | 2006-03-30 | 빅 바이오 주식회사 | 이소플라반 유도체 또는 이소플라벤 유도체의 제조방법 |
| JP2006008604A (ja) * | 2004-06-25 | 2006-01-12 | Kuraray Co Ltd | イソフラバン誘導体の製造方法 |
| KR102344479B1 (ko) * | 2013-12-24 | 2021-12-29 | 주식회사 글라세움 | 피라노크로메닐페놀 유도체, 및 대사증후군 또는 염증 질환 치료용 약학 조성물 |
-
2014
- 2014-12-17 KR KR1020140181951A patent/KR102344479B1/ko active Active
- 2014-12-23 CA CA2929001A patent/CA2929001C/en active Active
- 2014-12-23 MX MX2016008429A patent/MX374944B/es active IP Right Grant
- 2014-12-23 EP EP14873860.2A patent/EP3098224B1/en active Active
- 2014-12-23 PL PL14873860T patent/PL3098224T3/pl unknown
- 2014-12-23 HR HRP20190573TT patent/HRP20190573T1/hr unknown
- 2014-12-23 AU AU2014370697A patent/AU2014370697B2/en active Active
- 2014-12-23 PT PT14873860T patent/PT3098224T/pt unknown
- 2014-12-23 US US15/037,230 patent/US9783551B2/en active Active
- 2014-12-23 BR BR112016011281-4A patent/BR112016011281B1/pt active IP Right Grant
- 2014-12-23 SG SG11201604371PA patent/SG11201604371PA/en unknown
- 2014-12-23 HU HUE14873860 patent/HUE043902T2/hu unknown
- 2014-12-23 ES ES14873860T patent/ES2718878T3/es active Active
- 2014-12-23 WO PCT/KR2014/012688 patent/WO2015099392A1/ko not_active Ceased
- 2014-12-23 JP JP2016540481A patent/JP6620096B2/ja active Active
- 2014-12-23 NZ NZ720328A patent/NZ720328A/en unknown
- 2014-12-23 CN CN201480070935.5A patent/CN105849111B/zh active Active
- 2014-12-23 DK DK14873860.2T patent/DK3098224T3/da active
- 2014-12-24 TW TW103145316A patent/TWI585093B/zh active
-
2016
- 2016-05-29 IL IL245908A patent/IL245908B/en active IP Right Grant
-
2018
- 2018-03-23 JP JP2018056783A patent/JP2018135343A/ja active Pending
-
2019
- 2019-04-16 CY CY20191100423T patent/CY1121554T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007058480A1 (en) * | 2005-11-16 | 2007-05-24 | Md Bioalpha Co., Ltd. | Composition having effect on treatment and prevention of diseases syndrome treatment with glabridin |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201607949A (zh) | 供治療代謝症候群或發炎性疾病的呲喃苯并吡喃基苯酚衍生物及醫藥組成物 | |
| KR101192272B1 (ko) | 대사 질환의 치료용 화합물 | |
| JP7036871B2 (ja) | 光学活性ピラノクロメニルフェノール誘導体およびそれを含む薬学的組成物 | |
| TW201033182A (en) | Tetrahydrotriazine compounds for treating diseases associated with AMPK activity | |
| JPWO2004096198A1 (ja) | 治療剤 | |
| US20050260290A1 (en) | Botanical anti-inflammatory compositions and methods | |
| US20060004088A1 (en) | Furan derivatives for preventing and curing osteoporosis and pharmaceutical compositions containing the same | |
| US12545643B2 (en) | 3,5-diaminobenzoic acid compound, and Pin1 inhibitor and therapeutic agent for inflammatory diseases using same | |
| CN104080466B (zh) | 阻碍蛋白质酪氨酸磷酸酶1b的二萜呋喃类化合物及其用途 | |
| JP6576445B2 (ja) | ファルネシル類の芳香族化合物及びその応用 | |
| CN116157120B (zh) | 包含苯并呋喃基n-酰腙衍生物的抗炎组合物 | |
| US7498357B2 (en) | Chalcone compounds | |
| JP2007186515A (ja) | 治療剤 | |
| KR100627643B1 (ko) | 제 2 형 당뇨병 치료 또는 예방용 약제학적 조성물 | |
| KR20120023569A (ko) | ＰＰＡＲδ 활성물질의 태자 재프로그래밍 용도 | |
| HK1227863B (en) | Pyranochromenyl phenol derivative, and pharmaceutical composition for treating metabolic syndrome or inflammatory disease | |
| KR20230019801A (ko) | 신규한 피롤로 피리미딘 유도체 화합물, 이의 제조방법, 및 이를 유효성분으로 포함하는 대사성 간질환의 예방 또는 치료용 약학적 조성물 | |
| JP2014070053A (ja) | 代謝促進剤組成物 | |
| JP2007131637A (ja) | 治療剤 | |
| KR20070001326A (ko) | 핵수용체 피피에이알감마의 신규한 리간드 |