TW200815367A - 4,5-diphenyl-pyrimidinyl-oxy or -mercapto substituted carboxylic acids, process for their preparation and their use as pharmaceuticals - Google Patents

Info

Publication number

TW200815367A

TW200815367A TW096116360A TW96116360A TW200815367A TW 200815367 A TW200815367 A TW 200815367A TW 096116360 A TW096116360 A TW 096116360A TW 96116360 A TW96116360 A TW 96116360A TW 200815367 A TW200815367 A TW 200815367A

Authority

TW

Taiwan

Prior art keywords

alkyl

agonist

inhibitor

compound

group

Prior art date

2006-05-11

Links

• Espacenet
• Global Dossier
• Discuss

• -1 4,5-diphenyl-pyrimidinyl-oxy Chemical group 0.000 title claims abstract description 23
• 150000001735 carboxylic acids Chemical class 0.000 title claims abstract 4
• 239000003814 drug Substances 0.000 title claims description 12
• 238000000034 method Methods 0.000 title claims description 12
• 238000002360 preparation method Methods 0.000 title claims description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 128
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
• 239000003112 inhibitor Substances 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 239000004480 active ingredient Substances 0.000 claims description 32
• 239000000556 agonist Substances 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 239000000203 mixture Substances 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 239000005557 antagonist Substances 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 108091006300 SLC2A4 Proteins 0.000 claims description 6
• 102000004190 Enzymes Human genes 0.000 claims description 5
• 108090000790 Enzymes Proteins 0.000 claims description 5
• 102000004169 proteins and genes Human genes 0.000 claims description 5
• 108090000623 proteins and genes Proteins 0.000 claims description 5
• 229940044551 receptor antagonist Drugs 0.000 claims description 5
• 239000002464 receptor antagonist Substances 0.000 claims description 5
• 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 claims description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 4
• 239000003613 bile acid Substances 0.000 claims description 4
• 238000000576 coating method Methods 0.000 claims description 4
• 150000002632 lipids Chemical class 0.000 claims description 4
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 3
• 229940123208 Biguanide Drugs 0.000 claims description 3
• 108010051696 Growth Hormone Proteins 0.000 claims description 3
• 102000004882 Lipase Human genes 0.000 claims description 3
• 239000004367 Lipase Substances 0.000 claims description 3
• 108090001060 Lipase Proteins 0.000 claims description 3
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 3
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 3
• 102000004257 Potassium Channel Human genes 0.000 claims description 3
• 206010036790 Productive cough Diseases 0.000 claims description 3
• 239000012190 activator Substances 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 229940025084 amphetamine Drugs 0.000 claims description 3
• 238000009472 formulation Methods 0.000 claims description 3
• 239000000122 growth hormone Substances 0.000 claims description 3
• 229940088597 hormone Drugs 0.000 claims description 3
• 239000005556 hormone Substances 0.000 claims description 3
• 235000019421 lipase Nutrition 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 108020001213 potassium channel Proteins 0.000 claims description 3
• 229940044601 receptor agonist Drugs 0.000 claims description 3
• 239000000018 receptor agonist Substances 0.000 claims description 3
• 210000003802 sputum Anatomy 0.000 claims description 3
• 208000024794 sputum Diseases 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 102100032165 Corticotropin-releasing factor-binding protein Human genes 0.000 claims description 2
• 239000005715 Fructose Substances 0.000 claims description 2
• 101000921095 Homo sapiens Corticotropin-releasing factor-binding protein Proteins 0.000 claims description 2
• 101000843809 Homo sapiens Hydroxycarboxylic acid receptor 2 Proteins 0.000 claims description 2
• 102100030643 Hydroxycarboxylic acid receptor 2 Human genes 0.000 claims description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
• 102000000853 LDL receptors Human genes 0.000 claims description 2
• 108010001831 LDL receptors Proteins 0.000 claims description 2
• 108010013563 Lipoprotein Lipase Proteins 0.000 claims description 2
• 102100022119 Lipoprotein lipase Human genes 0.000 claims description 2
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
• 239000004472 Lysine Substances 0.000 claims description 2
• 108091006296 SLC2A1 Proteins 0.000 claims description 2
• 108091006299 SLC2A2 Proteins 0.000 claims description 2
• 229930182558 Sterol Natural products 0.000 claims description 2
• 238000010521 absorption reaction Methods 0.000 claims description 2
• 125000002619 bicyclic group Chemical group 0.000 claims description 2
• 210000004369 blood Anatomy 0.000 claims description 2
• 239000008280 blood Substances 0.000 claims description 2
• 239000003026 cod liver oil Substances 0.000 claims description 2
• 235000012716 cod liver oil Nutrition 0.000 claims description 2
• 239000000835 fiber Substances 0.000 claims description 2
• 235000011187 glycerol Nutrition 0.000 claims description 2
• 210000002752 melanocyte Anatomy 0.000 claims description 2
• 150000002923 oximes Chemical class 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
• 229940076279 serotonin Drugs 0.000 claims description 2
• 239000000952 serotonin receptor agonist Substances 0.000 claims description 2
• 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 2
• 230000003637 steroidlike Effects 0.000 claims description 2
• 150000003431 steroids Chemical class 0.000 claims description 2
• 150000003432 sterols Chemical class 0.000 claims description 2
• 235000003702 sterols Nutrition 0.000 claims description 2
• 230000004936 stimulating effect Effects 0.000 claims description 2
• 230000005764 inhibitory process Effects 0.000 claims 3
• 101150014691 PPARA gene Proteins 0.000 claims 2
• 102100038803 Somatotropin Human genes 0.000 claims 2
• 229940043355 kinase inhibitor Drugs 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 1
• 108010051479 Bombesin Proteins 0.000 claims 1
• 102000013585 Bombesin Human genes 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• 102000019034 Chemokines Human genes 0.000 claims 1
• 108010012236 Chemokines Proteins 0.000 claims 1
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
• 229920002307 Dextran Polymers 0.000 claims 1
• 108010016626 Dipeptides Proteins 0.000 claims 1
• 108050009340 Endothelin Proteins 0.000 claims 1
• 102000002045 Endothelin Human genes 0.000 claims 1
• 229930091371 Fructose Natural products 0.000 claims 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 claims 1
• 101800002068 Galanin Proteins 0.000 claims 1
• 102000019432 Galanin Human genes 0.000 claims 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims 1
• 229940123502 Hormone receptor antagonist Drugs 0.000 claims 1
• 108050008546 Hyperglycemic hormone Proteins 0.000 claims 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
• 108050007673 Somatotropin Proteins 0.000 claims 1
• 239000006096 absorbing agent Substances 0.000 claims 1
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
• 230000003042 antagnostic effect Effects 0.000 claims 1
• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
• 229940125388 beta agonist Drugs 0.000 claims 1
• BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical group FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 claims 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 claims 1
• 229940125782 compound 2 Drugs 0.000 claims 1
• 238000012217 deletion Methods 0.000 claims 1
• 230000037430 deletion Effects 0.000 claims 1
• 239000000841 delta opiate receptor agonist Substances 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 239000001177 diphosphate Substances 0.000 claims 1
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
• 235000011180 diphosphates Nutrition 0.000 claims 1
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims 1
• 239000002532 enzyme inhibitor Substances 0.000 claims 1
• 229940125532 enzyme inhibitor Drugs 0.000 claims 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
• 239000003862 glucocorticoid Substances 0.000 claims 1
• 229930195712 glutamate Natural products 0.000 claims 1
• 102000011054 glycogenin Human genes 0.000 claims 1
• 108010062764 glycogenin Proteins 0.000 claims 1
• 239000003689 hormone receptor blocking agent Substances 0.000 claims 1
• 108091008039 hormone receptors Proteins 0.000 claims 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
• 239000000411 inducer Substances 0.000 claims 1
• 230000003914 insulin secretion Effects 0.000 claims 1
• 230000002934 lysing effect Effects 0.000 claims 1
• 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 claims 1
• 229960002748 norepinephrine Drugs 0.000 claims 1
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims 1
• 239000007800 oxidant agent Substances 0.000 claims 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
• 239000003909 protein kinase inhibitor Substances 0.000 claims 1
• 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 1
• 210000002700 urine Anatomy 0.000 claims 1
• 229910052740 iodine Inorganic materials 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
• 235000019439 ethyl acetate Nutrition 0.000 description 23
• 239000002253 acid Substances 0.000 description 14
• 239000000460 chlorine Substances 0.000 description 14
• 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
• 239000000243 solution Substances 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 102000004877 Insulin Human genes 0.000 description 6
• 108090001061 Insulin Proteins 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000004305 biphenyl Substances 0.000 description 6
• 229940125396 insulin Drugs 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• BOGNNSACLXIPOA-UHFFFAOYSA-N 2-chloro-4,5-diphenylpyrimidine Chemical compound C=1C=CC=CC=1C1=NC(Cl)=NC=C1C1=CC=CC=C1 BOGNNSACLXIPOA-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 4
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• 101800001672 Peptide YY(3-36) Proteins 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
• 239000003472 antidiabetic agent Substances 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 239000004615 ingredient Substances 0.000 description 4
• YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 235000019198 oils Nutrition 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
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• 239000013543 active substance Substances 0.000 description 3
• 229940125708 antidiabetic agent Drugs 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000011248 coating agent Substances 0.000 description 3
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
• 150000004141 diterpene derivatives Chemical class 0.000 description 3
• 229960004580 glibenclamide Drugs 0.000 description 3
• 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 3
• 239000008187 granular material Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 239000000825 pharmaceutical preparation Substances 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• 229960004034 sitagliptin Drugs 0.000 description 3
• MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 description 3
• 239000011734 sodium Substances 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• 239000000052 vinegar Substances 0.000 description 3
• 235000021419 vinegar Nutrition 0.000 description 3
• KKDOHEVLSPAAHT-ORDUMYNUSA-N (e)-5-[(2r)-2-[(1r,2r,3s,4as,6r,8r,8as)-3,6-dihydroxy-1-[(z)-3-hydroxyprop-2-enoyl]-1,3,6,8-tetramethyl-4-oxo-2,4a,5,7,8,8a-hexahydronaphthalen-2-yl]butoxy]-3-methyl-5-oxopent-2-enoic acid Chemical compound C1[C@](C)(O)C[C@@H](C)[C@@H]2[C@](C(=O)\C=C/O)(C)[C@@H]([C@H](COC(=O)C\C(C)=C\C(O)=O)CC)[C@](C)(O)C(=O)[C@H]21 KKDOHEVLSPAAHT-ORDUMYNUSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• NRDIBBGYMLVMIR-UHFFFAOYSA-N 2-[5-(4,5-diphenylpyrimidin-2-yl)sulfanylpentyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CCCCCSC(N=C1C=2C=CC=CC=2)=NC=C1C1=CC=CC=C1 NRDIBBGYMLVMIR-UHFFFAOYSA-N 0.000 description 2
• UIQOZVSFTPSBEC-UHFFFAOYSA-N 5,6-diphenyl-1h-pyrimidin-2-one Chemical compound C=1C=CC=CC=1C=1NC(=O)N=CC=1C1=CC=CC=C1 UIQOZVSFTPSBEC-UHFFFAOYSA-N 0.000 description 2
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 description 2
• 108010016219 Acetyl-CoA carboxylase Proteins 0.000 description 2
• 102100022089 Acyl-[acyl-carrier-protein] hydrolase Human genes 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• 108010018763 Biotin carboxylase Proteins 0.000 description 2
• 102000004506 Blood Proteins Human genes 0.000 description 2
• 108010017384 Blood Proteins Proteins 0.000 description 2
• 240000008886 Ceratonia siliqua Species 0.000 description 2
• 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 108010039731 Fatty Acid Synthases Proteins 0.000 description 2
• 102100026148 Free fatty acid receptor 1 Human genes 0.000 description 2
• 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 2
• 108010017464 Fructose-Bisphosphatase Proteins 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
• 102400000321 Glucagon Human genes 0.000 description 2
• 108060003199 Glucagon Proteins 0.000 description 2
• 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 2
• 101710185468 Glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 description 2
• 102100033429 Glutamine-fructose-6-phosphate aminotransferase [isomerizing] 1 Human genes 0.000 description 2
• 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 2
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 102000018997 Growth Hormone Human genes 0.000 description 2
• 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 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
• 102400001132 Melanin-concentrating hormone Human genes 0.000 description 2
• 101800002739 Melanin-concentrating hormone Proteins 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108091000080 Phosphotransferase Proteins 0.000 description 2
• 101710176049 Probable glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 description 2
• 102000003923 Protein Kinase C Human genes 0.000 description 2
• 108090000315 Protein Kinase C Proteins 0.000 description 2
• 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 2
• 101710198235 Putative glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 description 2
• REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
• 108091006277 SLC5A1 Proteins 0.000 description 2
• 241000207929 Scutellaria Species 0.000 description 2
• 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 2
• 102000000019 Sterol Esterase Human genes 0.000 description 2
• 108010055297 Sterol Esterase Proteins 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
• 229940100389 Sulfonylurea Drugs 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
• 102000004357 Transferases Human genes 0.000 description 2
• 108090000992 Transferases Proteins 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 108010059705 Urocortins Proteins 0.000 description 2
• 102000005630 Urocortins Human genes 0.000 description 2
• MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• 125000005604 azodicarboxylate group Chemical group 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• 235000010290 biphenyl Nutrition 0.000 description 2
• 125000006267 biphenyl group Chemical group 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 230000008859 change Effects 0.000 description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
• 238000010494 dissociation reaction Methods 0.000 description 2
• 230000005593 dissociations Effects 0.000 description 2
• 229930004069 diterpene Natural products 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 150000002148 esters Chemical group 0.000 description 2
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 210000004051 gastric juice Anatomy 0.000 description 2
• 229960004346 glimepiride Drugs 0.000 description 2
• 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 2
• 229960001381 glipizide Drugs 0.000 description 2
• 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 2
• MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)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(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 2
• 229960004666 glucagon Drugs 0.000 description 2
• 230000002218 hypoglycaemic effect Effects 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 230000003834 intracellular effect Effects 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229940060975 lantus Drugs 0.000 description 2
• ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
• 229960003105 metformin Drugs 0.000 description 2
• 238000000465 moulding Methods 0.000 description 2
• YBWLTKFZAOSWSM-UHFFFAOYSA-N n-[6-methoxy-5-(2-methoxyphenoxy)-2-pyridin-4-ylpyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=CN=CC=2)OC)=C1NS(=O)(=O)C1=CC=C(C)C=N1 YBWLTKFZAOSWSM-UHFFFAOYSA-N 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• 239000008194 pharmaceutical composition 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
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
• 229960005095 pioglitazone Drugs 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
• 230000002265 prevention Effects 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
• 229960002354 repaglinide Drugs 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 229960004586 rosiglitazone Drugs 0.000 description 2
• NWDYUEBPNXOFDA-UHFFFAOYSA-N s-hept-6-enyl ethanethioate Chemical compound CC(=O)SCCCCCC=C NWDYUEBPNXOFDA-UHFFFAOYSA-N 0.000 description 2
• QGJUIPDUBHWZPV-SGTAVMJGSA-N saxagliptin Chemical compound C1C(C2)CC(C3)CC2(O)CC13[C@H](N)C(=O)N1[C@H](C#N)C[C@@H]2C[C@@H]21 QGJUIPDUBHWZPV-SGTAVMJGSA-N 0.000 description 2
• 229960004937 saxagliptin Drugs 0.000 description 2
• 108010033693 saxagliptin Proteins 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 230000002195 synergetic effect Effects 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 229960005371 tolbutamide Drugs 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
• 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 2
• 229960001641 troglitazone Drugs 0.000 description 2
• 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 2
• 239000000777 urocortin Substances 0.000 description 2
• NYQDTMHOWYUXHU-XLIONFOSSA-N (1s,3r)-3-[(4,5-diphenylpyrimidin-2-yl)oxymethyl]cyclohexane-1-carboxylic acid Chemical compound C1[C@@H](C(=O)O)CCC[C@H]1COC(N=C1C=2C=CC=CC=2)=NC=C1C1=CC=CC=C1 NYQDTMHOWYUXHU-XLIONFOSSA-N 0.000 description 1
• VGSSUFQMXBFFTM-UHFFFAOYSA-N (24R)-24-ethyl-5alpha-cholestane-3beta,5,6beta-triol Natural products C1C(O)C2(O)CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 VGSSUFQMXBFFTM-UHFFFAOYSA-N 0.000 description 1
• 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 1
• VRHOBXXCNBZJRX-IBGZPJMESA-N (2s)-2-[[3-[[4-(4-fluorophenoxy)phenyl]methylcarbamoyl]-4-methoxyphenyl]methyl]butanoic acid Chemical compound CC[C@H](C(O)=O)CC1=CC=C(OC)C(C(=O)NCC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)=C1 VRHOBXXCNBZJRX-IBGZPJMESA-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
• KWSPYUOBNIMILB-SANMLTNESA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1SC=CC=1)C(O)=O)C1=CC=CC=C1 KWSPYUOBNIMILB-SANMLTNESA-N 0.000 description 1
• JSYGLDMGERSRPC-FQUUOJAGSA-N (2s,4s)-4-fluoro-1-[2-[[(1r,3s)-3-(1,2,4-triazol-1-ylmethyl)cyclopentyl]amino]acetyl]pyrrolidine-2-carbonitrile Chemical compound C1[C@@H](F)C[C@@H](C#N)N1C(=O)CN[C@H]1C[C@@H](CN2N=CN=C2)CC1 JSYGLDMGERSRPC-FQUUOJAGSA-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
• HLCHESOMJVGDSJ-LOYHVIPDSA-N (3r)-n-[(2r)-3-(4-chlorophenyl)-1-[4-cyclohexyl-4-(1,2,4-triazol-1-ylmethyl)piperidin-1-yl]-1-oxopropan-2-yl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C[C@H](C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)[C@@H]1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-LOYHVIPDSA-N 0.000 description 1
• 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
• GGOFJXABVRZLJH-UHFFFAOYSA-N 1,2,3,4-tetrachloroanthracene Chemical compound C1=CC=CC2=CC3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C=C21 GGOFJXABVRZLJH-UHFFFAOYSA-N 0.000 description 1
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
• RABZYUWMIDILPP-UHFFFAOYSA-N 1,3-bis(sulfanyl)propane-1,2,3-triol Chemical compound SC(C(C(O)S)O)O RABZYUWMIDILPP-UHFFFAOYSA-N 0.000 description 1
• NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
• AKMNUCBQGHFICM-UHFFFAOYSA-N 1-(2-methyl-1,3-benzoxazol-6-yl)-3-(1,5-naphthyridin-4-yl)urea Chemical compound C1=CN=C2C(NC(=O)NC3=CC=C4N=C(OC4=C3)C)=CC=NC2=C1 AKMNUCBQGHFICM-UHFFFAOYSA-N 0.000 description 1
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
• KMAFERRSBFSHME-UHFFFAOYSA-N 1-hydrazinylcyclohexan-1-ol Chemical compound NNC1(O)CCCCC1 KMAFERRSBFSHME-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
• JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
• AYUPOTWFYYVIGE-UHFFFAOYSA-N 2,7-dichloropyrene Chemical compound C1=C(Cl)C=C2C=CC3=CC(Cl)=CC4=CC=C1C2=C43 AYUPOTWFYYVIGE-UHFFFAOYSA-N 0.000 description 1
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
• DDTQLPXXNHLBAB-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetic acid Chemical compound C=1C=C(Cl)C=CC=1C(C(=O)O)OC1=CC=CC(C(F)(F)F)=C1 DDTQLPXXNHLBAB-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
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
• HQSRVYUCBOCBLY-XOOFNSLWSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2s,4r)-2-(4-chlorophenyl)-2-[(4-methyl-1,2,4-triazol-3-yl)sulfanylmethyl]-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@H]3O[C@@](CSC=4N(C=NN=4)C)(OC3)C=3C=CC(Cl)=CC=3)=CC=2)C=C1 HQSRVYUCBOCBLY-XOOFNSLWSA-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
• MDBARDSTXONTFS-MNDUUMEHSA-N 3-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]propylamino]propanamide Chemical compound C=1C=C(OCCCNCCC(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O MDBARDSTXONTFS-MNDUUMEHSA-N 0.000 description 1
• YDPRNGAPPNPYQQ-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CC1=CSC(NS(=O)(=O)C=2C(=C(Cl)C=CC=2)C)=N1 YDPRNGAPPNPYQQ-UHFFFAOYSA-N 0.000 description 1
• VQMIUUBKKPIDBN-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexane-1-carboxylic acid Chemical compound OCC1CCC(C(O)=O)CC1 VQMIUUBKKPIDBN-UHFFFAOYSA-N 0.000 description 1
• 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 1
• VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-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
• 108091005435 5-HT6 receptors Proteins 0.000 description 1
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
• SDMBRCRVFFHJKR-UHFFFAOYSA-N 6-(5-carboxy-5-methylhexoxy)-2,2-dimethylhexanoic acid Chemical compound OC(=O)C(C)(C)CCCCOCCCCC(C)(C)C(O)=O SDMBRCRVFFHJKR-UHFFFAOYSA-N 0.000 description 1
• OCBMECSFDVUYQN-ROUUACIJSA-N 6-[[3-[(2s)-1-methoxypropan-2-yl]oxy-5-[(2s)-1-phenylpropan-2-yl]oxybenzoyl]amino]pyridine-3-carboxylic acid Chemical compound C([C@H](C)OC=1C=C(C=C(C=1)C(=O)NC=1N=CC(=CC=1)C(O)=O)O[C@@H](C)COC)C1=CC=CC=C1 OCBMECSFDVUYQN-ROUUACIJSA-N 0.000 description 1
• GNYDYUQVALBGGZ-UHFFFAOYSA-N 7-bromohept-1-ene Chemical compound BrCCCCCC=C GNYDYUQVALBGGZ-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 108010070305 AOD 9604 Proteins 0.000 description 1
• 102000004146 ATP citrate synthases Human genes 0.000 description 1
• 108090000662 ATP citrate synthases Proteins 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
• 208000019901 Anxiety disease Diseases 0.000 description 1
• 102100033367 Appetite-regulating hormone Human genes 0.000 description 1
• 101710111255 Appetite-regulating hormone Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 241000416162 Astragalus gummifer 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
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 229940123694 Bombesin receptor agonist Drugs 0.000 description 1
• 102100028628 Bombesin receptor subtype-3 Human genes 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• QJAADVQWDPBXCQ-UHFFFAOYSA-N C(C1=CC=C(C(=O)O)C=C1)(=O)O.CC=CCCCC Chemical compound C(C1=CC=C(C(=O)O)C=C1)(=O)O.CC=CCCCC QJAADVQWDPBXCQ-UHFFFAOYSA-N 0.000 description 1
• JNVVAKBPLCEZNT-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC(=NC=C1C1=CC=CC=C1)SCCCCCC1C(C1)C(=O)O Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1C1=CC=CC=C1)SCCCCCC1C(C1)C(=O)O JNVVAKBPLCEZNT-UHFFFAOYSA-N 0.000 description 1
• 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 1
• 101710187010 Cannabinoid receptor 1 Proteins 0.000 description 1
• 208000024172 Cardiovascular disease Diseases 0.000 description 1
• 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 1
• 229920002905 Colesevelam Polymers 0.000 description 1
• 244000241257 Cucumis melo Species 0.000 description 1
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
• 101710088194 Dehydrogenase Proteins 0.000 description 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
• 229940121889 Endothelin A receptor antagonist Drugs 0.000 description 1
• HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)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)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• 108010043222 Exubera Proteins 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 1
• 102100040134 Free fatty acid receptor 4 Human genes 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• 229940121970 Galanin receptor antagonist Drugs 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 101800001586 Ghrelin Proteins 0.000 description 1
• 102400000442 Ghrelin-28 Human genes 0.000 description 1
• 108090000079 Glucocorticoid Receptors Proteins 0.000 description 1
• 102100033417 Glucocorticoid receptor Human genes 0.000 description 1
• 102000030595 Glucokinase Human genes 0.000 description 1
• 108010021582 Glucokinase Proteins 0.000 description 1
• 108091052347 Glucose transporter family Proteins 0.000 description 1
• 102000042092 Glucose transporter family Human genes 0.000 description 1
• 102000004366 Glucosidases Human genes 0.000 description 1
• 108010056771 Glucosidases Proteins 0.000 description 1
• 229920002527 Glycogen Polymers 0.000 description 1
• 102000001895 Gonadotropin Receptors Human genes 0.000 description 1
• 108010040490 Gonadotropin Receptors Proteins 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 229940121914 Histamine H3 receptor agonist Drugs 0.000 description 1
• 101000890672 Homo sapiens Free fatty acid receptor 4 Proteins 0.000 description 1
• 102000002265 Human Growth Hormone Human genes 0.000 description 1
• 108010000521 Human Growth Hormone Proteins 0.000 description 1
• 239000000854 Human Growth Hormone Substances 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 239000003458 I kappa b kinase inhibitor Substances 0.000 description 1
• 108010057186 Insulin Glargine Proteins 0.000 description 1
• 206010022489 Insulin Resistance Diseases 0.000 description 1
• COCFEDIXXNGUNL-RFKWWTKHSA-N Insulin glargine Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(=O)NCC(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 COCFEDIXXNGUNL-RFKWWTKHSA-N 0.000 description 1
• 229940122355 Insulin sensitizer Drugs 0.000 description 1
• 206010022998 Irritability Diseases 0.000 description 1
• 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 1
• 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• 102000007330 LDL Lipoproteins Human genes 0.000 description 1
• 108010007622 LDL Lipoproteins Proteins 0.000 description 1
• 102000016267 Leptin Human genes 0.000 description 1
• 108010092277 Leptin Proteins 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• 102000057248 Lipoprotein(a) Human genes 0.000 description 1
• 108010033266 Lipoprotein(a) Proteins 0.000 description 1
• YSDQQAXHVYUZIW-QCIJIYAXSA-N Liraglutide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCNC(=O)CC[C@H](NC(=O)CCCCCCCCCCCCCCC)C(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)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](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)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=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=C(O)C=C1 YSDQQAXHVYUZIW-QCIJIYAXSA-N 0.000 description 1
• 108010019598 Liraglutide Proteins 0.000 description 1
• 229940122014 Lyase inhibitor Drugs 0.000 description 1
• 208000001145 Metabolic Syndrome Diseases 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
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-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
• 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 1
• 241000699670 Mus sp. Species 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
• OKJHGOPITGTTIM-DEOSSOPVSA-N Naveglitazar Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCCCOC(C=C1)=CC=C1OC1=CC=CC=C1 OKJHGOPITGTTIM-DEOSSOPVSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 208000008589 Obesity Diseases 0.000 description 1
• 102000002512 Orexin Human genes 0.000 description 1
• 101800001388 Oxyntomodulin Proteins 0.000 description 1
• 108010028924 PPAR alpha Proteins 0.000 description 1
• 102000023984 PPAR alpha Human genes 0.000 description 1
• 229940124754 PPAR-alpha/gamma agonist Drugs 0.000 description 1
• 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 description 1
• 108090000472 Phosphoenolpyruvate carboxykinase (ATP) Proteins 0.000 description 1
• 102100034792 Phosphoenolpyruvate carboxykinase [GTP], mitochondrial Human genes 0.000 description 1
• 229940127315 Potassium Channel Openers Drugs 0.000 description 1
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
• ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
• HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• 108091006269 SLC5A2 Proteins 0.000 description 1
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
• LGJMUZUPVCAVPU-JFBKYFIKSA-N Sitostanol Natural products O[C@@H]1C[C@H]2[C@@](C)([C@@H]3[C@@H]([C@H]4[C@@](C)([C@@H]([C@@H](CC[C@H](C(C)C)CC)C)CC4)CC3)CC2)CC1 LGJMUZUPVCAVPU-JFBKYFIKSA-N 0.000 description 1
• 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• 239000005864 Sulphur Substances 0.000 description 1
• 229940123464 Thiazolidinedione Drugs 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
• 229930003779 Vitamin B12 Natural products 0.000 description 1
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000009102 absorption Effects 0.000 description 1
• 229960002632 acarbose Drugs 0.000 description 1
• 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 1
• 230000009471 action Effects 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
• ZSBOMTDTBDDKMP-OAHLLOKOSA-N alogliptin Chemical compound C=1C=CC=C(C#N)C=1CN1C(=O)N(C)C(=O)C=C1N1CCC[C@@H](N)C1 ZSBOMTDTBDDKMP-OAHLLOKOSA-N 0.000 description 1
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
• BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
• 239000003392 amylase inhibitor Substances 0.000 description 1
• 125000000129 anionic group Chemical class 0.000 description 1
• 229920006318 anionic polymer Polymers 0.000 description 1
• 150000001450 anions Chemical class 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 239000000883 anti-obesity agent Substances 0.000 description 1
• 230000002785 anti-thrombosis Effects 0.000 description 1
• 239000003146 anticoagulant agent Substances 0.000 description 1
• 239000003524 antilipemic agent Substances 0.000 description 1
• 239000004599 antimicrobial Substances 0.000 description 1
• 229940125710 antiobesity agent Drugs 0.000 description 1
• 230000036506 anxiety Effects 0.000 description 1
• RCHHVVGSTHAVPF-ZPHPLDECSA-N apidra Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CNC=N1 RCHHVVGSTHAVPF-ZPHPLDECSA-N 0.000 description 1
• 239000002830 appetite depressant Substances 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• GEMDZKRHHVNHLW-UHFFFAOYSA-N argon;carbonic acid Chemical class [Ar].OC(O)=O GEMDZKRHHVNHLW-UHFFFAOYSA-N 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 229950010046 avasimibe Drugs 0.000 description 1
• 229950011524 avosentan Drugs 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-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
• 230000036772 blood pressure Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 108010063504 bombesin receptor subtype 3 Proteins 0.000 description 1
• 235000012180 bread and bread product Nutrition 0.000 description 1
• FFHBJDQSGDNCIV-MFVUMRCOSA-N bremelanotide Chemical compound C([C@@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCNC(=O)C[C@@H](C(N[C@@H](CC=2NC=NC=2)C(=O)N1)=O)NC(=O)[C@@H](NC(C)=O)CCCC)C(O)=O)C1=CC=CC=C1 FFHBJDQSGDNCIV-MFVUMRCOSA-N 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
• 239000004067 bulking agent Substances 0.000 description 1
• CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 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
• FAIMGWSOSCFGRU-IYBDPMFKSA-N chembl182150 Chemical compound N([C@H]1CC[C@H](CC1)NC=1N=C(C2=CC=CC=C2N=1)N(C)C)C(=O)C1=CC=C(F)C(F)=C1 FAIMGWSOSCFGRU-IYBDPMFKSA-N 0.000 description 1
• SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical group C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
• 229960003291 chlorphenamine Drugs 0.000 description 1
• 238000004587 chromatography analysis Methods 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
• 238000003776 cleavage reaction Methods 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
• AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 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
• 230000000875 corresponding effect Effects 0.000 description 1
• ZQWPRMPSCMSAJU-UHFFFAOYSA-N cyclohexanecarboxylic acid methyl ester Natural products COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 1
• UCZUCGRGTXIWLR-UHFFFAOYSA-N cyclohexyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1CCCCC1 UCZUCGRGTXIWLR-UHFFFAOYSA-N 0.000 description 1
• CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229960000632 dexamfetamine Drugs 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
• 229940090949 docosahexaenoic acid Drugs 0.000 description 1
• 239000003937 drug carrier Substances 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
• 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
• JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
• 239000005712 elicitor Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 239000003062 endothelin A receptor antagonist Substances 0.000 description 1
• 230000037149 energy metabolism Effects 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• 229960003399 estrone Drugs 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• DTMGIJFHGGCSLO-FIAQIACWSA-N ethyl (4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoate;ethyl (5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC.CCOC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC DTMGIJFHGGCSLO-FIAQIACWSA-N 0.000 description 1
• GKQSMOUSEVEPEX-UHFFFAOYSA-N ethyl acetate;phthalic acid Chemical compound CCOC(C)=O.OC(=O)C1=CC=CC=C1C(O)=O GKQSMOUSEVEPEX-UHFFFAOYSA-N 0.000 description 1
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 229960001519 exenatide Drugs 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 229940012151 exubera Drugs 0.000 description 1
• 229960000815 ezetimibe Drugs 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
• 235000019197 fats Nutrition 0.000 description 1
• 229960002297 fenofibrate Drugs 0.000 description 1
• 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 1
• 230000035558 fertility Effects 0.000 description 1
• 229940125753 fibrate Drugs 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 230000009969 flowable effect Effects 0.000 description 1
• 239000007850 fluorescent dye 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
• 238000011990 functional testing Methods 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 238000002309 gasification Methods 0.000 description 1
• 230000030136 gastric emptying Effects 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 229950004781 gemcabene Drugs 0.000 description 1
• GNKDKYIHGQKHHM-RJKLHVOGSA-N ghrelin Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CN)COC(=O)CCCCCCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CC=CC=C1 GNKDKYIHGQKHHM-RJKLHVOGSA-N 0.000 description 1
• 230000006377 glucose transport 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
• 229940096919 glycogen Drugs 0.000 description 1
• 230000004116 glycogenolysis Effects 0.000 description 1
• 239000003324 growth hormone secretagogue Substances 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• UFULDTPDHIRNGS-UHFFFAOYSA-N hept-6-en-1-ol Chemical compound OCCCCCC=C UFULDTPDHIRNGS-UHFFFAOYSA-N 0.000 description 1
• ZTIQVACABLDUGK-UHFFFAOYSA-H hexasodium;trioxido(oxo)-$l^{5}-arsane Chemical class [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O ZTIQVACABLDUGK-UHFFFAOYSA-H 0.000 description 1
• 239000003382 histamine H3 receptor agonist Substances 0.000 description 1
• 239000003667 hormone antagonist Substances 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 238000003384 imaging method Methods 0.000 description 1
• 229950005809 implitapide Drugs 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical compound C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 229940045996 isethionic acid Drugs 0.000 description 1
• MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000010410 layer Substances 0.000 description 1
• 229940039781 leptin Drugs 0.000 description 1
• 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 1
• 235000020778 linoleic acid Nutrition 0.000 description 1
• OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
• 230000037356 lipid metabolism Effects 0.000 description 1
• 229960002701 liraglutide Drugs 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 229960003566 lomitapide Drugs 0.000 description 1
• QKVKOFVWUHNEBX-UHFFFAOYSA-N lomitapide mesylate Chemical compound CS(O)(=O)=O.C12=CC=CC=C2C2=CC=CC=C2C1(C(=O)NCC(F)(F)F)CCCCN(CC1)CCC1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QKVKOFVWUHNEBX-UHFFFAOYSA-N 0.000 description 1
• 229960005060 lorcaserin Drugs 0.000 description 1
• XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 description 1
• 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 1
• 229960004844 lovastatin Drugs 0.000 description 1
• 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 1
• 239000002697 lyase inhibitor Substances 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
• 230000036210 malignancy Effects 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 229950004994 meglitinide Drugs 0.000 description 1
• 208000030159 metabolic disease Diseases 0.000 description 1
• JEENWEAPRWGXSG-UHFFFAOYSA-N methyl 2-oxocyclohexane-1-carboxylate Chemical compound COC(=O)C1CCCCC1=O JEENWEAPRWGXSG-UHFFFAOYSA-N 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 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
• 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 1
• 229960000698 nateglinide Drugs 0.000 description 1
• OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
• 229950003494 naveglitazar Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 150000002871 norepinephrines Chemical class 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 235000020824 obesity Nutrition 0.000 description 1
• 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
• 229940012843 omega-3 fatty acid Drugs 0.000 description 1
• 229940125395 oral insulin Drugs 0.000 description 1
• 108060005714 orexin Proteins 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 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 1
• 229960001243 orlistat Drugs 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• VWMZIGBYZQUQOA-QEEMJVPDSA-N pamaqueside 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(=O)[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 VWMZIGBYZQUQOA-QEEMJVPDSA-N 0.000 description 1
• 229950005482 pamaqueside Drugs 0.000 description 1
• 229960005489 paracetamol Drugs 0.000 description 1
• 239000000546 pharmaceutical excipient Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 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
• 229940067157 phenylhydrazine Drugs 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 150000003003 phosphines Chemical class 0.000 description 1
• 229960002965 pravastatin Drugs 0.000 description 1
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 229960003912 probucol Drugs 0.000 description 1
• FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
• NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
• RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
• 235000005875 quercetin Nutrition 0.000 description 1
• 229960001285 quercetin Drugs 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000005215 recombination Methods 0.000 description 1
• 230000006798 recombination Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000030558 renal glucose absorption Effects 0.000 description 1
• JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 1
• 229960003015 rimonabant 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
• 230000007017 scission Effects 0.000 description 1
• 229910052711 selenium Inorganic materials 0.000 description 1
• 239000011669 selenium Substances 0.000 description 1
• 238000000926 separation method Methods 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
• 229960002855 simvastatin Drugs 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
• 210000003491 skin Anatomy 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 150000003388 sodium compounds Chemical class 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• 235000007586 terpenes Nutrition 0.000 description 1
• CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
• 229950004704 tesaglitazar Drugs 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 150000001467 thiazolidinediones Chemical class 0.000 description 1
• 125000003396 thiol group Chemical group [H]S* 0.000 description 1
• 229950004437 tiqueside Drugs 0.000 description 1
• CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
• 229950004514 torcetrapib Drugs 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229930003231 vitamin Natural products 0.000 description 1
• 239000011782 vitamin Substances 0.000 description 1
• 229940088594 vitamin Drugs 0.000 description 1
• 235000013343 vitamin Nutrition 0.000 description 1
• 235000019163 vitamin B12 Nutrition 0.000 description 1
• 239000011715 vitamin B12 Substances 0.000 description 1
• 235000019158 vitamin B6 Nutrition 0.000 description 1
• 239000011726 vitamin B6 Substances 0.000 description 1
• 229940011671 vitamin b6 Drugs 0.000 description 1
• 150000003722 vitamin derivatives Chemical class 0.000 description 1
• 230000004580 weight loss Effects 0.000 description 1