TWI305724B - Diarylcycloalkyl derivatives, process for their preparation and their use as pharmaceutical - Google Patents

Info

Publication number

TWI305724B

TWI305724B TW091119612A TW91119612A TWI305724B TW I305724 B TWI305724 B TW I305724B TW 091119612 A TW091119612 A TW 091119612A TW 91119612 A TW91119612 A TW 91119612A TW I305724 B TWI305724 B TW I305724B

Authority

TW

Taiwan

Prior art keywords

alkyl

compound

patent application

treatment

scope

Prior art date

2001-08-31

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 38
• 238000002360 preparation method Methods 0.000 title claims abstract description 25
• 230000008569 process Effects 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 145
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 19
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
• 230000037356 lipid metabolism Effects 0.000 claims abstract description 4
• 208000035475 disorder Diseases 0.000 claims abstract 2
• 239000000203 mixture Substances 0.000 claims description 49
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 30
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
• 230000002079 cooperative effect Effects 0.000 claims description 15
• 230000003902 lesion Effects 0.000 claims description 13
• 206010012601 diabetes mellitus Diseases 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 235000020824 obesity Nutrition 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
• 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 claims description 5
• 239000008103 glucose Substances 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 230000001105 regulatory effect Effects 0.000 claims description 4
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims 2
• 208000024827 Alzheimer disease Diseases 0.000 claims 1
• 208000001132 Osteoporosis Diseases 0.000 claims 1
• 230000002159 abnormal effect Effects 0.000 claims 1
• 230000007812 deficiency Effects 0.000 claims 1
• 230000004217 heart function Effects 0.000 claims 1
• 230000002107 myocardial effect Effects 0.000 claims 1
• 229940127557 pharmaceutical product Drugs 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
• -1 for example Chemical class 0.000 description 61
• 239000000047 product Substances 0.000 description 41
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
• 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 32
• 210000004027 cell Anatomy 0.000 description 28
• 235000019439 ethyl acetate Nutrition 0.000 description 25
• 239000000556 agonist Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• 239000000243 solution Substances 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 102000023984 PPAR alpha Human genes 0.000 description 17
• 102000004877 Insulin Human genes 0.000 description 16
• 108090001061 Insulin Proteins 0.000 description 16
• 108010028924 PPAR alpha Proteins 0.000 description 16
• 229940125396 insulin Drugs 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 238000007639 printing Methods 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 239000008280 blood Substances 0.000 description 12
• 210000004369 blood Anatomy 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 11
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 101150014691 PPARA gene Proteins 0.000 description 10
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
• 102000005962 receptors Human genes 0.000 description 9
• 108020003175 receptors Proteins 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• 238000004809 thin layer chromatography Methods 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• 206010022489 Insulin Resistance Diseases 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• 229940079593 drug Drugs 0.000 description 8
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 239000012190 activator Substances 0.000 description 7
• 210000001789 adipocyte Anatomy 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 230000015572 biosynthetic process Effects 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 238000005516 engineering process Methods 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 229940095102 methyl benzoate Drugs 0.000 description 7
• 239000012312 sodium hydride Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
• 239000005711 Benzoic acid Substances 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 230000004069 differentiation Effects 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• 210000004185 liver Anatomy 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 6
• 229960003105 metformin Drugs 0.000 description 6
• 206010036790 Productive cough Diseases 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 238000001994 activation Methods 0.000 description 5
• 235000010233 benzoic acid Nutrition 0.000 description 5
• XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 208000029078 coronary artery disease Diseases 0.000 description 5
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 239000003446 ligand Substances 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 238000011160 research Methods 0.000 description 5
• 210000003802 sputum Anatomy 0.000 description 5
• 208000024794 sputum Diseases 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• 208000032928 Dyslipidaemia Diseases 0.000 description 4
• 102000004190 Enzymes Human genes 0.000 description 4
• 108090000790 Enzymes Proteins 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• 206010060378 Hyperinsulinaemia Diseases 0.000 description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 description 4
• 208000017170 Lipid metabolism disease Diseases 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• 108010015181 PPAR delta Proteins 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 239000013543 active substance Substances 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• 238000004113 cell culture Methods 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 229940125851 compound 27 Drugs 0.000 description 4
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• 150000004665 fatty acids Chemical class 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 230000003451 hyperinsulinaemic effect Effects 0.000 description 4
• 201000008980 hyperinsulinism Diseases 0.000 description 4
• 230000002218 hypoglycaemic effect Effects 0.000 description 4
• 150000002632 lipids Chemical class 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 230000004936 stimulating effect Effects 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
• 240000008886 Ceratonia siliqua Species 0.000 description 3
• 235000013912 Ceratonia siliqua Nutrition 0.000 description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
• 108010010803 Gelatin Proteins 0.000 description 3
• FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 3
• 206010020772 Hypertension Diseases 0.000 description 3
• 102000016267 Leptin Human genes 0.000 description 3
• 108010092277 Leptin Proteins 0.000 description 3
• 229940086609 Lipase inhibitor Drugs 0.000 description 3
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• 229940100389 Sulfonylurea Drugs 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
• 229940125708 antidiabetic agent Drugs 0.000 description 3
• 239000003472 antidiabetic agent Substances 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 229940125782 compound 2 Drugs 0.000 description 3
• RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 3
• JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 229910052731 fluorine Inorganic materials 0.000 description 3
• 229920000159 gelatin Polymers 0.000 description 3
• 239000008273 gelatin Substances 0.000 description 3
• 235000019322 gelatine Nutrition 0.000 description 3
• 235000011852 gelatine desserts Nutrition 0.000 description 3
• 230000014509 gene expression Effects 0.000 description 3
• 230000036541 health Effects 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 230000001965 increasing effect Effects 0.000 description 3
• 230000028709 inflammatory response Effects 0.000 description 3
• 229960004844 lovastatin Drugs 0.000 description 3
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 3
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 3
• 208000030159 metabolic disease Diseases 0.000 description 3
• 230000002503 metabolic effect Effects 0.000 description 3
• 230000004060 metabolic process Effects 0.000 description 3
• ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 210000002824 peroxisome Anatomy 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 229960002354 repaglinide Drugs 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 210000001519 tissue Anatomy 0.000 description 3
• 229960001641 troglitazone Drugs 0.000 description 3
• GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 3
• GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 3
• DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 2
• XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 2
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
• BKZHSJNLPPAJKB-UHFFFAOYSA-N 1-(2-methyl-1,3-benzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea;hydrochloride Chemical compound Cl.C1=CN=C2C(NC(=O)NC3=CC=C4N=C(OC4=C3)C)=CC=NC2=C1 BKZHSJNLPPAJKB-UHFFFAOYSA-N 0.000 description 2
• OIDBUADVUVKDSH-UHFFFAOYSA-N 2-[(3-hydroxycyclohexyl)oxymethyl]-6-methylbenzoic acid Chemical compound CC1=CC=CC(COC2CC(O)CCC2)=C1C(O)=O OIDBUADVUVKDSH-UHFFFAOYSA-N 0.000 description 2
• SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 206010003210 Arteriosclerosis Diseases 0.000 description 2
• 229940123208 Biguanide Drugs 0.000 description 2
• 108010037462 Cyclooxygenase 2 Proteins 0.000 description 2
• 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 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 102000019432 Galanin Human genes 0.000 description 2
• 101800002068 Galanin Proteins 0.000 description 2
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 208000035150 Hypercholesterolemia Diseases 0.000 description 2
• 208000013016 Hypoglycemia Diseases 0.000 description 2
• 102000007330 LDL Lipoproteins Human genes 0.000 description 2
• 108010007622 LDL Lipoproteins Proteins 0.000 description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• 102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
• 108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
• 239000005662 Paraffin oil Substances 0.000 description 2
• 229930182555 Penicillin Natural products 0.000 description 2
• 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 2
• 102100038824 Peroxisome proliferator-activated receptor delta Human genes 0.000 description 2
• 101710117029 Peroxisome proliferator-activated receptor delta Proteins 0.000 description 2
• 239000004698 Polyethylene Substances 0.000 description 2
• 102000004257 Potassium Channel Human genes 0.000 description 2
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
• 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• 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 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
• 102100040247 Tumor necrosis factor Human genes 0.000 description 2
• 229960002632 acarbose Drugs 0.000 description 2
• XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 2
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
• 210000000577 adipose tissue Anatomy 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 208000011775 arteriosclerosis disease Diseases 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 230000009286 beneficial effect Effects 0.000 description 2
• 239000003613 bile acid Substances 0.000 description 2
• 230000033228 biological regulation Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 208000026106 cerebrovascular disease Diseases 0.000 description 2
• 230000008859 change Effects 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 2
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 230000018109 developmental process Effects 0.000 description 2
• 229960004597 dexfenfluramine Drugs 0.000 description 2
• 235000013325 dietary fiber Nutrition 0.000 description 2
• 125000005594 diketone group Chemical group 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 208000016097 disease of metabolism Diseases 0.000 description 2
• 238000006073 displacement reaction Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
• 235000019197 fats Nutrition 0.000 description 2
• 229960002297 fenofibrate Drugs 0.000 description 2
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 2
• 239000002657 fibrous material Substances 0.000 description 2
• 210000004051 gastric juice Anatomy 0.000 description 2
• BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
• 229960001381 glipizide Drugs 0.000 description 2
• 230000009229 glucose formation Effects 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 230000002440 hepatic effect Effects 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 229910052739 hydrogen Inorganic materials 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 201000001421 hyperglycemia Diseases 0.000 description 2
• 206010020718 hyperplasia Diseases 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 238000001802 infusion Methods 0.000 description 2
• 239000004615 ingredient Substances 0.000 description 2
• 230000003914 insulin secretion Effects 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 229940039781 leptin Drugs 0.000 description 2
• 239000007937 lozenge Substances 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 229950004994 meglitinide Drugs 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
• UDNSKBMNXZVXKW-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CBr UDNSKBMNXZVXKW-UHFFFAOYSA-N 0.000 description 2
• SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 description 2
• YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 2
• LYAUICDWKQJAGX-UHFFFAOYSA-N n-(7-hydroxy-2,2,4,6-tetramethyl-1,3-dihydroinden-1-yl)-2-[4-(3-methoxyphenyl)piperazin-1-yl]acetamide Chemical compound COC1=CC=CC(N2CCN(CC(=O)NC3C(CC4=C3C(=C(C)C=C4C)O)(C)C)CC2)=C1 LYAUICDWKQJAGX-UHFFFAOYSA-N 0.000 description 2
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
• 229960001243 orlistat Drugs 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 230000001590 oxidative effect Effects 0.000 description 2
• 230000036542 oxidative stress Effects 0.000 description 2
• 229940049954 penicillin Drugs 0.000 description 2
• 239000003614 peroxisome proliferator Substances 0.000 description 2
• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
• 229960005095 pioglitazone Drugs 0.000 description 2
• 108020001213 potassium channel Proteins 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• UQOQENZZLBSFKO-POPPZSFYSA-N prostaglandin J2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O UQOQENZZLBSFKO-POPPZSFYSA-N 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 239000007858 starting material 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
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 229960005371 tolbutamide Drugs 0.000 description 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
• APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
• 208000019553 vascular disease Diseases 0.000 description 2
• DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
• HUSOFJYAGDTKSK-HTQZYQBOSA-N (1r,2r)-cyclooctane-1,2-diol Chemical compound O[C@@H]1CCCCCC[C@H]1O HUSOFJYAGDTKSK-HTQZYQBOSA-N 0.000 description 1
• PFXRPUFYSLHDMF-RQJHMYQMSA-N (1s,3r)-3-(hydroxymethyl)cyclohexan-1-ol Chemical compound OC[C@@H]1CCC[C@H](O)C1 PFXRPUFYSLHDMF-RQJHMYQMSA-N 0.000 description 1
• RLMGYIOTPQVQJR-OLQVQODUSA-N (1s,3r)-cyclohexane-1,3-diol Chemical compound O[C@H]1CCC[C@@H](O)C1 RLMGYIOTPQVQJR-OLQVQODUSA-N 0.000 description 1
• RLMGYIOTPQVQJR-WDSKDSINSA-N (1s,3s)-cyclohexane-1,3-diol Chemical compound O[C@H]1CCC[C@H](O)C1 RLMGYIOTPQVQJR-WDSKDSINSA-N 0.000 description 1
• NOOYIVIUEHDMSF-PKLMIRHRSA-N (2r)-1-phenyl-n-(3-phenylpropyl)propan-2-amine;hydrochloride Chemical compound Cl.C([C@@H](C)NCCCC=1C=CC=CC=1)C1=CC=CC=C1 NOOYIVIUEHDMSF-PKLMIRHRSA-N 0.000 description 1
• ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
• AMNXBQPRODZJQR-DITALETJSA-N (2s)-2-cyclopentyl-2-[3-[(2,4-dimethylpyrido[2,3-b]indol-9-yl)methyl]phenyl]-n-[(1r)-2-hydroxy-1-phenylethyl]acetamide Chemical compound C1([C@@H](C=2C=CC=C(C=2)CN2C3=CC=CC=C3C3=C(C)C=C(N=C32)C)C(=O)N[C@@H](CO)C=2C=CC=CC=2)CCCC1 AMNXBQPRODZJQR-DITALETJSA-N 0.000 description 1
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
• OGTSHGYHILFRHD-UHFFFAOYSA-N (4-fluorophenyl)-phenylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 OGTSHGYHILFRHD-UHFFFAOYSA-N 0.000 description 1
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 1
• OMXRTIUYSHDUTH-UHFFFAOYSA-N 1-(3-ethyl-1-benzofuran-7-yl)piperazine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2C(CC)=COC2=C1N1CCNCC1 OMXRTIUYSHDUTH-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
• BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
• PMGZJNCIQHGNLT-UHFFFAOYSA-N 1-[bis(2,2-dimethylpropanoyloxymethoxy)phosphoryl]-4-(3-phenoxyphenyl)butane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C(S(O)(=O)=O)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PMGZJNCIQHGNLT-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• GUSVHVVOABZHAH-OPZWKQDFSA-N 1aw8p77hkj Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GUSVHVVOABZHAH-OPZWKQDFSA-N 0.000 description 1
• XESDDYSPKWRMMF-UHFFFAOYSA-N 2-(4-fluorophenyl)indazole Chemical compound C1=CC(F)=CC=C1N1N=C2C=CC=CC2=C1 XESDDYSPKWRMMF-UHFFFAOYSA-N 0.000 description 1
• AIJFHFWXQDMLEP-UHFFFAOYSA-N 2-(bromomethyl)-6-methylbenzoic acid Chemical compound CC1=CC=CC(CBr)=C1C(O)=O AIJFHFWXQDMLEP-UHFFFAOYSA-N 0.000 description 1
• VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 description 1
• VWNVTUGLEFEZIT-JPYJTQIMSA-N 2-[2-[(1r,3s)-3-[[2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]ethyl]-6-methylbenzoic acid Chemical compound CC1=CC=CC(CC[C@@H]2C[C@H](CCC2)OCC=2N=C(OC=2)C=2C=CC(F)=CC=2)=C1C(O)=O VWNVTUGLEFEZIT-JPYJTQIMSA-N 0.000 description 1
• VKDNAZGEGFYWAI-UHFFFAOYSA-N 2-[3-[[2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]oxy-6-methylbenzoic acid Chemical compound CC1=CC=CC(OC2CC(CCC2)OCC=2N=C(OC=2)C=2C=CC(F)=CC=2)=C1C(O)=O VKDNAZGEGFYWAI-UHFFFAOYSA-N 0.000 description 1
• QTSLEZQPPBJWKT-FDDCHVKYSA-N 2-[[(1S,3R)-3-[[2-(4-fluorophenyl)-1,3-oxazol-4-yl]methoxy]cyclohexyl]methoxymethyl]-6-methylbenzoic acid Chemical compound CC1=CC=CC(COC[C@@H]2C[C@@H](CCC2)OCC=2N=C(OC=2)C=2C=CC(F)=CC=2)=C1C(O)=O QTSLEZQPPBJWKT-FDDCHVKYSA-N 0.000 description 1
• HXZUUPAHSHVFDZ-UHFFFAOYSA-N 2-methyl-2-sulfanyloxypropane Chemical compound CC(C)(C)OS HXZUUPAHSHVFDZ-UHFFFAOYSA-N 0.000 description 1
• YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 description 1
• VGRZISGVNOKTQU-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1CCC(O)CC1 VGRZISGVNOKTQU-UHFFFAOYSA-N 0.000 description 1
• QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
• GNPUIRFDBYALRI-UHFFFAOYSA-N 4-methyl-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C=CC=C2C GNPUIRFDBYALRI-UHFFFAOYSA-N 0.000 description 1
• AUEUBSJNKBZSKK-UHFFFAOYSA-N 5-benzylsulfonyl-2-[2-(dimethylamino)ethyl-ethylamino]-n,n-diethyl-4-(4-phenylpiperidin-1-yl)benzamide Chemical compound C1=C(N(CC)CCN(C)C)C(C(=O)N(CC)CC)=CC(S(=O)(=O)CC=2C=CC=CC=2)=C1N(CC1)CCC1C1=CC=CC=C1 AUEUBSJNKBZSKK-UHFFFAOYSA-N 0.000 description 1
• MNKYZMHVLUYEBE-UHFFFAOYSA-N 6-methyl-6-sulfanylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC1(S)C=CC=CC1C(O)=O MNKYZMHVLUYEBE-UHFFFAOYSA-N 0.000 description 1
• 102000004146 ATP citrate synthases Human genes 0.000 description 1
• 108090000662 ATP citrate synthases Proteins 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 229940122816 Amylase inhibitor Drugs 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 241001061264 Astragalus Species 0.000 description 1
• PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 description 1
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
• 102000013585 Bombesin Human genes 0.000 description 1
• 108010051479 Bombesin Proteins 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
• 235000002566 Capsicum Nutrition 0.000 description 1
• 208000031229 Cardiomyopathies Diseases 0.000 description 1
• 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• OMPIYDSYGYKWSG-UHFFFAOYSA-N Citronensaeure-alpha-aethylester Natural products CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
• 229920002905 Colesevelam Polymers 0.000 description 1
• 206010010904 Convulsion Diseases 0.000 description 1
• 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 description 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
• 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 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
• 101100326341 Drosophila melanogaster brun gene Proteins 0.000 description 1
• 208000005189 Embolism Diseases 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 206010014561 Emphysema Diseases 0.000 description 1
• VWNVTUGLEFEZIT-WZONZLPQSA-N FC1=CC=C(C=C1)C=1OC=C(N1)CO[C@H]1C[C@H](CCC1)CCC1=C(C(=O)O)C(=CC=C1)C Chemical compound FC1=CC=C(C=C1)C=1OC=C(N1)CO[C@H]1C[C@H](CCC1)CCC1=C(C(=O)O)C(=CC=C1)C VWNVTUGLEFEZIT-WZONZLPQSA-N 0.000 description 1
• 239000001263 FEMA 3042 Substances 0.000 description 1
• 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 description 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
• HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
• 208000002705 Glucose Intolerance Diseases 0.000 description 1
• 229920002527 Glycogen Polymers 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
• 206010019013 Haemorrhagic infarction Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 206010020565 Hyperaemia Diseases 0.000 description 1
• 206010058490 Hyperoxia Diseases 0.000 description 1
• 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 1
• 102000003746 Insulin Receptor Human genes 0.000 description 1
• 108010001127 Insulin Receptor Proteins 0.000 description 1
• 229940122355 Insulin sensitizer Drugs 0.000 description 1
• 229930195714 L-glutamate Natural products 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
• 238000008214 LDL Cholesterol Methods 0.000 description 1
• 108010001831 LDL receptors Proteins 0.000 description 1
• 239000004166 Lanolin Substances 0.000 description 1
• 102000004882 Lipase Human genes 0.000 description 1
• 108090001060 Lipase Proteins 0.000 description 1
• 239000004367 Lipase Substances 0.000 description 1
• 206010024612 Lipoma Diseases 0.000 description 1
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 1
• 102100022119 Lipoprotein lipase Human genes 0.000 description 1
• 102000004895 Lipoproteins Human genes 0.000 description 1
• 108090001030 Lipoproteins Proteins 0.000 description 1
• 102100024640 Low-density lipoprotein receptor Human genes 0.000 description 1
• 108060001084 Luciferase Proteins 0.000 description 1
• 239000005089 Luciferase Substances 0.000 description 1
• 208000004852 Lung Injury Diseases 0.000 description 1
• 229940122014 Lyase inhibitor Drugs 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
• UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 1
• IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• 208000021908 Myocardial disease Diseases 0.000 description 1
• UULIGRNKXHCLQN-UHFFFAOYSA-N N-[[4-[[(4-amino-2-quinazolinyl)amino]methyl]cyclohexyl]methyl]-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(N)=NC(NCC3CCC(CNS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)CC3)=NC2=C1 UULIGRNKXHCLQN-UHFFFAOYSA-N 0.000 description 1
• TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 108091028043 Nucleic acid sequence Proteins 0.000 description 1
• 102000002512 Orexin Human genes 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
• 244000170916 Paeonia officinalis Species 0.000 description 1
• 235000006484 Paeonia officinalis Nutrition 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• 239000006002 Pepper Substances 0.000 description 1
• 108090000279 Peptidyltransferases Proteins 0.000 description 1
• 239000004264 Petrolatum Substances 0.000 description 1
• BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
• 235000016761 Piper aduncum Nutrition 0.000 description 1
• 235000017804 Piper guineense Nutrition 0.000 description 1
• 244000203593 Piper nigrum Species 0.000 description 1
• 235000008184 Piper nigrum Nutrition 0.000 description 1
• 208000005374 Poisoning Diseases 0.000 description 1
• 206010036049 Polycystic ovaries Diseases 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 208000020369 Polymerase proofreading-related adenomatous polyposis Diseases 0.000 description 1
• 208000004880 Polyuria Diseases 0.000 description 1
• 229940127315 Potassium Channel Openers Drugs 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 101710123874 Protein-glutamine gamma-glutamyltransferase Proteins 0.000 description 1
• 208000003251 Pruritus Diseases 0.000 description 1
• 241001026602 Quintana Species 0.000 description 1
• 206010041235 Snoring Diseases 0.000 description 1
• 229940123495 Squalene synthetase inhibitor Drugs 0.000 description 1
• 229930182558 Sterol Natural products 0.000 description 1
• QTENRWWVYAAPBI-YZTFXSNBSA-N Streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.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](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O.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](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O QTENRWWVYAAPBI-YZTFXSNBSA-N 0.000 description 1
• 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 1
• 229940123464 Thiazolidinedione Drugs 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 206010069363 Traumatic lung injury Diseases 0.000 description 1
• DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
• 102000005630 Urocortins Human genes 0.000 description 1
• 108010059705 Urocortins Proteins 0.000 description 1
• 206010047513 Vision blurred Diseases 0.000 description 1
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
• ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
• ZTISUHQLYYPYFA-UHFFFAOYSA-N [5-(hydroxymethyl)-1,3-dioxan-5-yl]methanol Chemical compound OCC1(CO)COCOC1 ZTISUHQLYYPYFA-UHFFFAOYSA-N 0.000 description 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• PUJRSOVINMPNIQ-UHFFFAOYSA-N acetic acid;decanoic acid Chemical compound CC(O)=O.CCCCCCCCCC(O)=O PUJRSOVINMPNIQ-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 229960005305 adenosine Drugs 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 230000011759 adipose tissue development Effects 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 230000001270 agonistic effect Effects 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 150000001413 amino acids Chemical group 0.000 description 1
• 229940025084 amphetamine Drugs 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 239000003392 amylase inhibitor Substances 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 239000003098 androgen Substances 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
• 210000004102 animal cell Anatomy 0.000 description 1
• 229920006318 anionic polymer Polymers 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 239000000883 anti-obesity agent Substances 0.000 description 1
• 239000002220 antihypertensive agent Substances 0.000 description 1
• 229940030600 antihypertensive agent Drugs 0.000 description 1
• 229940125710 antiobesity agent Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 210000001367 artery Anatomy 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 235000006533 astragalus Nutrition 0.000 description 1
• 230000003143 atherosclerotic effect Effects 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 230000001363 autoimmune Effects 0.000 description 1
• 229950010046 avasimibe Drugs 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• 229960000516 bezafibrate Drugs 0.000 description 1
• IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
• 150000004283 biguanides Chemical class 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000031018 biological processes and functions Effects 0.000 description 1
• 229910052797 bismuth Inorganic materials 0.000 description 1
• 150000001622 bismuth compounds Chemical class 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 235000012180 bread and bread product Nutrition 0.000 description 1
• 235000015496 breakfast cereal Nutrition 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• 239000006189 buccal tablet Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 230000023852 carbohydrate metabolic process Effects 0.000 description 1
• 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
• 150000001720 carbohydrates Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical class 0.000 description 1
• 230000003683 cardiac damage Effects 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
• 229960005110 cerivastatin Drugs 0.000 description 1
• SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
• 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
• 229950009226 ciglitazone Drugs 0.000 description 1
• 229960001214 clofibrate Drugs 0.000 description 1
• KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 229960001152 colesevelam Drugs 0.000 description 1
• 239000013066 combination product Substances 0.000 description 1
• 229940127555 combination product Drugs 0.000 description 1
• 238000002648 combination therapy Methods 0.000 description 1
• 239000002299 complementary DNA Substances 0.000 description 1
• 229940125810 compound 20 Drugs 0.000 description 1
• 229940127204 compound 29 Drugs 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 239000002769 corticotropin releasing factor antagonist Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• BDNXUVOJBGHQFD-UHFFFAOYSA-N cyclooctane-1,5-diol Chemical compound OC1CCCC(O)CCC1 BDNXUVOJBGHQFD-UHFFFAOYSA-N 0.000 description 1
• 230000009089 cytolysis Effects 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 230000034994 death Effects 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• SSECFBLOLMBDRJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCCCCCCCCCOC(=O)C(C)=C SSECFBLOLMBDRJ-UHFFFAOYSA-N 0.000 description 1
• CUSUFTNOPPMGBK-UHFFFAOYSA-N decyl benzoate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1 CUSUFTNOPPMGBK-UHFFFAOYSA-N 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 208000002925 dental caries Diseases 0.000 description 1
• 229960000632 dexamfetamine Drugs 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 229930004069 diterpene Natural products 0.000 description 1
• 150000004141 diterpene derivatives Chemical class 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 239000003937 drug carrier Substances 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 230000000081 effect on glucose Effects 0.000 description 1
• 210000002257 embryonic structure Anatomy 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 230000002124 endocrine Effects 0.000 description 1
• 230000037149 energy metabolism Effects 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• KWXBNUYCDMPLEQ-UHFFFAOYSA-N ethyl 2-hydroxy-6-methylbenzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1O KWXBNUYCDMPLEQ-UHFFFAOYSA-N 0.000 description 1
• SOUAXOGPALPTTC-UHFFFAOYSA-N ethyl 2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1C SOUAXOGPALPTTC-UHFFFAOYSA-N 0.000 description 1
• QPXBRDDJQMWNNU-UHFFFAOYSA-N ethyl 5-(bromomethyl)-2-methylbenzoate Chemical compound CCOC(=O)C1=CC(CBr)=CC=C1C QPXBRDDJQMWNNU-UHFFFAOYSA-N 0.000 description 1
• 229940057975 ethyl citrate Drugs 0.000 description 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
• 229960000815 ezetimibe Drugs 0.000 description 1
• 229960001582 fenfluramine Drugs 0.000 description 1
• 239000012894 fetal calf serum Substances 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000004222 fluoren-1-yl group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C([H])([H])C1=C(*)C([H])=C([H])C([H])=C21 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229960003765 fluvastatin Drugs 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 235000012041 food component Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 239000005417 food ingredient Substances 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000012631 food intake Nutrition 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 229930182830 galactose Natural products 0.000 description 1
• 230000030136 gastric emptying Effects 0.000 description 1
• 229960003627 gemfibrozil Drugs 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• 229960000346 gliclazide Drugs 0.000 description 1
• 229960004346 glimepiride Drugs 0.000 description 1
• WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
• ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 230000014101 glucose homeostasis Effects 0.000 description 1
• 230000004190 glucose uptake Effects 0.000 description 1
• 229930182478 glucoside Natural products 0.000 description 1
• 150000008131 glucosides Chemical class 0.000 description 1
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
• 229940096919 glycogen Drugs 0.000 description 1
• 239000003316 glycosidase inhibitor Substances 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 210000002503 granulosa cell Anatomy 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 210000002216 heart Anatomy 0.000 description 1
• 239000008241 heterogeneous mixture Substances 0.000 description 1
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
• 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
• 230000000222 hyperoxic effect Effects 0.000 description 1
• 230000002390 hyperplastic effect Effects 0.000 description 1
• 229950005809 implitapide Drugs 0.000 description 1
• 230000001976 improved effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 239000000411 inducer Substances 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 230000000977 initiatory effect Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 201000002313 intestinal cancer Diseases 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 150000002497 iodine compounds Chemical class 0.000 description 1
• 230000007803 itching Effects 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229940039717 lanolin Drugs 0.000 description 1
• 235000019388 lanolin Nutrition 0.000 description 1
• 229940060975 lantus Drugs 0.000 description 1
• 150000002611 lead compounds Chemical class 0.000 description 1
• 235000019421 lipase Nutrition 0.000 description 1
• 206010024627 liposarcoma Diseases 0.000 description 1
• 150000004668 long chain fatty acids Chemical class 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 231100000515 lung injury Toxicity 0.000 description 1
• 239000002697 lyase inhibitor Substances 0.000 description 1
• 239000006166 lysate Substances 0.000 description 1
• 210000002540 macrophage Anatomy 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 230000014759 maintenance of location Effects 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 229960000299 mazindol Drugs 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 150000004667 medium chain fatty acids Chemical class 0.000 description 1
• 230000003821 menstrual periods Effects 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• WIONSNLWNWJORQ-UHFFFAOYSA-N methyl 2-[(3-hydroxycyclohexyl)oxymethyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1COC1CC(O)CCC1 WIONSNLWNWJORQ-UHFFFAOYSA-N 0.000 description 1
• WIONSNLWNWJORQ-KGLIPLIRSA-N methyl 2-[[(1s,3r)-3-hydroxycyclohexyl]oxymethyl]-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CO[C@@H]1C[C@H](O)CCC1 WIONSNLWNWJORQ-KGLIPLIRSA-N 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 230000027939 micturition Effects 0.000 description 1
• 229960001110 miglitol Drugs 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000007932 molded tablet Substances 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229960002748 norepinephrine Drugs 0.000 description 1
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• 108060005714 orexin Proteins 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 230000008816 organ damage Effects 0.000 description 1
• 201000008968 osteosarcoma Diseases 0.000 description 1
• 230000016087 ovulation Effects 0.000 description 1
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• OOYLEFZKWGZRRS-UHFFFAOYSA-N pent-2-ene-1,4-diol Chemical compound CC(O)C=CCO OOYLEFZKWGZRRS-UHFFFAOYSA-N 0.000 description 1
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 229940066842 petrolatum Drugs 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 238000001050 pharmacotherapy Methods 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
• 229960003562 phentermine Drugs 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 230000007505 plaque formation Effects 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 231100000572 poisoning Toxicity 0.000 description 1
• 230000000607 poisoning effect Effects 0.000 description 1
• 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920002689 polyvinyl acetate Polymers 0.000 description 1
• 239000011118 polyvinyl acetate Substances 0.000 description 1
• 230000008092 positive effect Effects 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
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 201000009104 prediabetes syndrome Diseases 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 239000006041 probiotic Substances 0.000 description 1
• 230000000529 probiotic effect Effects 0.000 description 1
• 235000018291 probiotics Nutrition 0.000 description 1
• 239000000186 progesterone Substances 0.000 description 1
• 229960003387 progesterone Drugs 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• 150000003180 prostaglandins Chemical class 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 229940076376 protein agonist Drugs 0.000 description 1
• 230000006340 racemization Effects 0.000 description 1
• 230000006950 reactive oxygen species formation Effects 0.000 description 1
• 210000003370 receptor cell Anatomy 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000001850 reproductive effect Effects 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• 229960000672 rosuvastatin Drugs 0.000 description 1
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000000952 serotonin receptor agonist Substances 0.000 description 1
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• 230000035939 shock Effects 0.000 description 1
• 229960004425 sibutramine Drugs 0.000 description 1
• UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 210000002027 skeletal muscle Anatomy 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 239000002689 soil Substances 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000004059 squalene synthase inhibitor Substances 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 150000003432 sterols Chemical class 0.000 description 1
• 235000003702 sterols Nutrition 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000011550 stock solution Substances 0.000 description 1
• 239000004575 stone Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 239000007940 sugar coated tablet Substances 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 210000004233 talus Anatomy 0.000 description 1
• LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 150000003505 terpenes Chemical class 0.000 description 1
• 235000007586 terpenes Nutrition 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
• 230000035922 thirst Effects 0.000 description 1
• 229950004437 tiqueside Drugs 0.000 description 1
• 208000037816 tissue injury Diseases 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
• 229960000401 tranexamic acid Drugs 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 235000013769 triethyl citrate Nutrition 0.000 description 1
• 102000003390 tumor necrosis factor Human genes 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• 239000000777 urocortin Substances 0.000 description 1
• 239000013598 vector Substances 0.000 description 1
• 239000000052 vinegar Substances 0.000 description 1
• 235000021419 vinegar Nutrition 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1
• 238000012982 x-ray structure analysis Methods 0.000 description 1