RU2369613C2 - Производные пиразола, медицинские композиции, содержащие их, их применение в медицине и промежуточные соединения для их получения - Google Patents

Info

Publication number

RU2369613C2

RU2369613C2 RU2005108055/04A RU2005108055A RU2369613C2 RU 2369613 C2 RU2369613 C2 RU 2369613C2 RU 2005108055/04 A RU2005108055/04 A RU 2005108055/04A RU 2005108055 A RU2005108055 A RU 2005108055A RU 2369613 C2 RU2369613 C2 RU 2369613C2

Authority

RU

Russia

Prior art keywords

group

alkyl

hydroxy

pyrazole

methyl

Prior art date

2002-08-23

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims description 272
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 239000003814 drug Substances 0.000 title abstract description 36
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title abstract description 3
• 239000000203 mixture Substances 0.000 title description 180
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 156
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 41
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 150000002367 halogens Chemical class 0.000 claims abstract description 20
• 201000001421 hyperglycemia Diseases 0.000 claims abstract description 18
• 230000002265 prevention Effects 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 153
• 125000001424 substituent group Chemical group 0.000 claims description 141
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 138
• -1 hydroxy, hydroxy Chemical group 0.000 claims description 127
• 125000003277 amino group Chemical group 0.000 claims description 102
• 238000000034 method Methods 0.000 claims description 80
• 150000003217 pyrazoles Chemical class 0.000 claims description 77
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
• 206010012601 diabetes mellitus Diseases 0.000 claims description 61
• 239000003112 inhibitor Substances 0.000 claims description 57
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 46
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 40
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 31
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 16
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 13
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 13
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 13
• 201000008980 hyperinsulinism Diseases 0.000 claims description 13
• 206010056997 Impaired fasting glucose Diseases 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 101000716688 Homo sapiens Sodium/glucose cotransporter 1 Proteins 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 11
• 102000052194 human SLC5A1 Human genes 0.000 claims description 11
• 230000001771 impaired effect Effects 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 238000011321 prophylaxis Methods 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 10
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
• 230000037356 lipid metabolism Effects 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 208000002249 Diabetes Complications Diseases 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
• 229910052760 oxygen Inorganic materials 0.000 claims 4
• 239000001301 oxygen Substances 0.000 claims 4
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
• 108091006277 SLC5A1 Proteins 0.000 abstract description 13
• 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 abstract description 13
• 230000000694 effects Effects 0.000 abstract description 11
• 239000000126 substance Substances 0.000 abstract description 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 308
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 177
• 239000002904 solvent Substances 0.000 description 158
• 238000005160 1H NMR spectroscopy Methods 0.000 description 139
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
• 239000000243 solution Substances 0.000 description 104
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
• 125000006239 protecting group Chemical group 0.000 description 80
• 238000006243 chemical reaction Methods 0.000 description 79
• 230000002829 reductive effect Effects 0.000 description 74
• 239000011541 reaction mixture Substances 0.000 description 73
• 125000005843 halogen group Chemical group 0.000 description 58
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 55
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 52
• 239000012442 inert solvent Substances 0.000 description 49
• 238000010992 reflux Methods 0.000 description 49
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 47
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 46
• 239000003480 eluent Substances 0.000 description 45
• 230000008569 process Effects 0.000 description 45
• 125000003118 aryl group Chemical group 0.000 description 44
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 34
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
• 125000003545 alkoxy group Chemical group 0.000 description 34
• 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 34
• 239000007858 starting material Substances 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 230000035484 reaction time Effects 0.000 description 33
• 229940079593 drug Drugs 0.000 description 31
• 238000010898 silica gel chromatography Methods 0.000 description 31
• 238000009835 boiling Methods 0.000 description 30
• AFYAXZTVROWEAI-JGALVPIPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-aminopropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AFYAXZTVROWEAI-JGALVPIPSA-N 0.000 description 29
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 28
• 229960001031 glucose Drugs 0.000 description 28
• 239000008103 glucose Substances 0.000 description 28
• 229940002612 prodrug Drugs 0.000 description 28
• 239000000651 prodrug Substances 0.000 description 28
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 28
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 27
• 239000008280 blood Substances 0.000 description 24
• 210000004369 blood Anatomy 0.000 description 24
• 239000000556 agonist Substances 0.000 description 23
• 239000000047 product Substances 0.000 description 23
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
• LEIXQUMIVDQJHX-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-hydroxypropoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCO)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O LEIXQUMIVDQJHX-RAAUJUNPSA-N 0.000 description 22
• 238000006460 hydrolysis reaction Methods 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
• 125000002252 acyl group Chemical group 0.000 description 21
• 239000003795 chemical substances by application Substances 0.000 description 21
• 125000004122 cyclic group Chemical group 0.000 description 21
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
• 230000009102 absorption Effects 0.000 description 19
• 238000010521 absorption reaction Methods 0.000 description 19
• 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 17
• CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 17
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 17
• OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 239000012267 brine Substances 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• LRKKFKACZNRPFW-JGALVPIPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-hydroxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O LRKKFKACZNRPFW-JGALVPIPSA-N 0.000 description 15
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 15
• 229910000024 caesium carbonate Inorganic materials 0.000 description 15
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 15
• 238000002414 normal-phase solid-phase extraction Methods 0.000 description 15
• 125000004043 oxo group Chemical group O=* 0.000 description 15
• 239000012153 distilled water Substances 0.000 description 14
• 230000007062 hydrolysis Effects 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 102000004877 Insulin Human genes 0.000 description 13
• 108090001061 Insulin Proteins 0.000 description 13
• 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 13
• 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 13
• 229940125396 insulin Drugs 0.000 description 13
• UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 13
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound 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 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
• 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 238000001914 filtration Methods 0.000 description 12
• NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 12
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
• KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical class C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 description 11
• 206010020772 Hypertension Diseases 0.000 description 11
• 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 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 229930182830 galactose Natural products 0.000 description 11
• 230000003914 insulin secretion Effects 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 229940083542 sodium Drugs 0.000 description 11
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
• 125000004755 (C2-C7) acylamino group Chemical group 0.000 description 9
• JSQSMUUUWOOZCJ-UHFFFAOYSA-N 2-methyl-2-[(2-nitrophenyl)sulfonylamino]propanamide Chemical compound NC(=O)C(C)(C)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JSQSMUUUWOOZCJ-UHFFFAOYSA-N 0.000 description 9
• 201000001320 Atherosclerosis Diseases 0.000 description 9
• 229940123208 Biguanide Drugs 0.000 description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 9
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• SIBWKOBNKBIQIW-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-aminopropoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O SIBWKOBNKBIQIW-RAAUJUNPSA-N 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• 238000010511 deprotection reaction Methods 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 239000001257 hydrogen Substances 0.000 description 9
• 229910052739 hydrogen Inorganic materials 0.000 description 9
• 210000000813 small intestine Anatomy 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• 235000009518 sodium iodide Nutrition 0.000 description 9
• PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 8
• UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 8
• OULBDBGCIUQACR-UHFFFAOYSA-N 4-[[4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C OULBDBGCIUQACR-UHFFFAOYSA-N 0.000 description 8
• 206010022489 Insulin Resistance Diseases 0.000 description 8
• CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 8
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 8
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 8
• RUMCATXKNGIUSC-JGALVPIPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(2-aminoethoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCN)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O RUMCATXKNGIUSC-JGALVPIPSA-N 0.000 description 8
• YIYYQOQNMXFSMB-JGALVPIPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(2-hydroxyethoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCO)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O YIYYQOQNMXFSMB-JGALVPIPSA-N 0.000 description 8
• UBEVRTCDVBUUEI-WUDHZMGWSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOCC=2C=CC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O UBEVRTCDVBUUEI-WUDHZMGWSA-N 0.000 description 8
• 238000006482 condensation reaction Methods 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 235000017557 sodium bicarbonate Nutrition 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• YKSCNFZDJSTOGT-UHFFFAOYSA-N 2-amino-n-(2-hydroxyethyl)-2-methylpropanamide Chemical compound CC(C)(N)C(=O)NCCO YKSCNFZDJSTOGT-UHFFFAOYSA-N 0.000 description 7
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 7
• 229940122904 Glucagon receptor antagonist Drugs 0.000 description 7
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 7
• 102000003638 Glucose-6-Phosphatase Human genes 0.000 description 7
• 108010086800 Glucose-6-Phosphatase Proteins 0.000 description 7
• 102000003746 Insulin Receptor Human genes 0.000 description 7
• 108010001127 Insulin Receptor Proteins 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• 102100040918 Pro-glucagon Human genes 0.000 description 7
• IQWIJOFMCDRBOO-UHFFFAOYSA-N [4-(3-phenylmethoxypropoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCCOCC1=CC=CC=C1 IQWIJOFMCDRBOO-UHFFFAOYSA-N 0.000 description 7
• 239000002830 appetite depressant Substances 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 230000013595 glycosylation Effects 0.000 description 7
• 238000006206 glycosylation reaction Methods 0.000 description 7
• 239000004026 insulin derivative Substances 0.000 description 7
• 210000004185 liver Anatomy 0.000 description 7
• 239000000021 stimulant Substances 0.000 description 7
• ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 description 6
• PSUXTZLDBVEZTD-UHFFFAOYSA-N 3-bromopropoxymethylbenzene Chemical compound BrCCCOCC1=CC=CC=C1 PSUXTZLDBVEZTD-UHFFFAOYSA-N 0.000 description 6
• UPSFNXFLBMJUQW-UHFFFAOYSA-N 5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound CN1C(O)C(=O)NC1=O UPSFNXFLBMJUQW-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
• 206010007559 Cardiac failure congestive Diseases 0.000 description 6
• 229940121931 Gluconeogenesis inhibitor Drugs 0.000 description 6
• 206010019280 Heart failures Diseases 0.000 description 6
• 206010030113 Oedema Diseases 0.000 description 6
• 229940122907 Phosphatase inhibitor Drugs 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 6
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• 229940077731 carbohydrate nutrients Drugs 0.000 description 6
• 150000001720 carbohydrates Chemical class 0.000 description 6
• 235000014633 carbohydrates Nutrition 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• VRAHURWABUWLHA-JGALVPIPSA-N diazonio-[3-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]propyl]azanide Chemical compound C=1C=C(OCCCN=[N+]=[N-])C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O VRAHURWABUWLHA-JGALVPIPSA-N 0.000 description 6
• 239000002552 dosage form Substances 0.000 description 6
• 239000003623 enhancer Substances 0.000 description 6
• 239000002792 enkephalinase inhibitor Substances 0.000 description 6
• 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 239000003801 protein tyrosine phosphatase 1B inhibitor Substances 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 125000004434 sulfur atom Chemical group 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 229940116269 uric acid Drugs 0.000 description 6
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 5
• WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 5
• KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 5
• SXKBTDJJEQQEGE-UHFFFAOYSA-N 3-(3,5-dibromo-4-hydroxy-benzoyl)-2-ethyl-benzofuran-6-sulfonic acid [4-(thiazol-2-ylsulfamoyl)-phenyl]-amide Chemical compound CCC=1OC2=CC(S(=O)(=O)NC=3C=CC(=CC=3)S(=O)(=O)NC=3SC=CN=3)=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 SXKBTDJJEQQEGE-UHFFFAOYSA-N 0.000 description 5
• 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 description 5
• 108010025020 Nerve Growth Factor Proteins 0.000 description 5
• 229940123924 Protein kinase C inhibitor Drugs 0.000 description 5
• 229940124117 Pyruvate dehydrogenase inhibitor Drugs 0.000 description 5
• 229940123286 Tripeptidyl peptidase II inhibitor Drugs 0.000 description 5
• CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 5
• KHGIMTAOXHDITJ-UINAHMSNSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[2-methyl-4-(3-methylsulfonyloxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOS(C)(=O)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O KHGIMTAOXHDITJ-UINAHMSNSA-N 0.000 description 5
• 239000002168 alkylating agent Substances 0.000 description 5
• 229940100198 alkylating agent Drugs 0.000 description 5
• 239000002333 angiotensin II receptor antagonist Substances 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
• 239000005516 coenzyme A Substances 0.000 description 5
• 229940093530 coenzyme a Drugs 0.000 description 5
• 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 description 5
• 239000002934 diuretic Substances 0.000 description 5
• 125000005640 glucopyranosyl group Chemical group 0.000 description 5
• 125000005905 mesyloxy group Chemical group 0.000 description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
• 108090000765 processed proteins & peptides Proteins 0.000 description 5
• 239000003881 protein kinase C inhibitor Substances 0.000 description 5
• 229940044601 receptor agonist Drugs 0.000 description 5
• 239000000018 receptor agonist Substances 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 5
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
• GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 4
• NMOVJBAGBXIKCG-VKAVYKQESA-N (3z)-n-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidoyl chloride Chemical compound C1CCCCN1CC(O)CO\N=C(/Cl)C1=CC=CN=C1 NMOVJBAGBXIKCG-VKAVYKQESA-N 0.000 description 4
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 description 4
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
• 239000005541 ACE inhibitor Substances 0.000 description 4
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
• 229940118365 Endothelin receptor antagonist Drugs 0.000 description 4
• 229940093498 Fructose bisphosphatase inhibitor Drugs 0.000 description 4
• 201000005569 Gout Diseases 0.000 description 4
• 201000001431 Hyperuricemia Diseases 0.000 description 4
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 4
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• 108010057466 NF-kappa B Proteins 0.000 description 4
• 102000003945 NF-kappa B Human genes 0.000 description 4
• 102000015336 Nerve Growth Factor Human genes 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• 229920000439 Sulodexide Polymers 0.000 description 4
• CYAYKKUWALRRPA-HTOAHKCRSA-N [(2r,3s,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O CYAYKKUWALRRPA-HTOAHKCRSA-N 0.000 description 4
• 125000004423 acyloxy group Chemical group 0.000 description 4
• 239000003288 aldose reductase inhibitor Substances 0.000 description 4
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 4
• 239000002220 antihypertensive agent Substances 0.000 description 4
• 229940127218 antiplatelet drug Drugs 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 4
• 229950002409 bimoclomol Drugs 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 239000007795 chemical reaction product Substances 0.000 description 4
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
• RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 4
• KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 4
• WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 4
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
• 239000002857 endothelin converting enzyme inhibitor Substances 0.000 description 4
• 239000002308 endothelin receptor antagonist Substances 0.000 description 4
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 229940053128 nerve growth factor Drugs 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 229940124530 sulfonamide Drugs 0.000 description 4
• 229960003491 sulodexide Drugs 0.000 description 4
• CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
• DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 4
• 229940045145 uridine Drugs 0.000 description 4
• VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 4
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• 101710175516 14 kDa zinc-binding protein Proteins 0.000 description 3
• ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 3
• QKVCSJBBYNYZNM-UHFFFAOYSA-N 2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)OCC1=CC=CC=C1 QKVCSJBBYNYZNM-UHFFFAOYSA-N 0.000 description 3
• WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
• ZGLOYSNDXJVVCA-UHFFFAOYSA-N 4-[[2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C(=CC(OCCCOCC=3C=CC=CC=3)=CC=2)C)=C1C(C)C ZGLOYSNDXJVVCA-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 3
• 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 3
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 229940127291 Calcium channel antagonist Drugs 0.000 description 3
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 3
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
• 229940122783 Endothelin converting-enzyme inhibitor Drugs 0.000 description 3
• 102400001368 Epidermal growth factor Human genes 0.000 description 3
• 101800003838 Epidermal growth factor Proteins 0.000 description 3
• 229930091371 Fructose Natural products 0.000 description 3
• 239000005715 Fructose Substances 0.000 description 3
• RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 3
• 208000027472 Galactosemias Diseases 0.000 description 3
• 229940123856 Glycogen synthase kinase 3 inhibitor Drugs 0.000 description 3
• 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 3
• 206010054805 Macroangiopathy Diseases 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• 229940089973 Sodium channel antagonist Drugs 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 3
• 108010054082 Sterol O-acyltransferase Proteins 0.000 description 3
• 229940122954 Transcription factor inhibitor Drugs 0.000 description 3
• RUMKNCFMVQDZFO-UINAHMSNSA-N [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[(cyanoamino)-methylsulfanylmethylidene]amino]propoxy]phenyl]methyl]-5-propan-2-yl-1H-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C1=CC(OCCCNC(SC)=NC#N)=CC=C1CC1=C(C(C)C)NN=C1O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1 RUMKNCFMVQDZFO-UINAHMSNSA-N 0.000 description 3
• AVZWEORBGZQCEC-LILOYGOGSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(2-aminoethoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AVZWEORBGZQCEC-LILOYGOGSA-N 0.000 description 3
• SLSOBEJQMAWWFS-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-methylsulfonyloxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOS(C)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O SLSOBEJQMAWWFS-RAAUJUNPSA-N 0.000 description 3
• LURXXWVZBCAKTI-FBFPUXADSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(2-amino-2-oxoethyl)amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNCC(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O LURXXWVZBCAKTI-FBFPUXADSA-N 0.000 description 3
• LEIXQUMIVDQJHX-AUNDWGALSA-N [(2r,3s,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(3-hydroxypropoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCO)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O LEIXQUMIVDQJHX-AUNDWGALSA-N 0.000 description 3
• 229940126317 angiotensin II receptor antagonist Drugs 0.000 description 3
• 230000001142 anti-diarrhea Effects 0.000 description 3
• 229940125714 antidiarrheal agent Drugs 0.000 description 3
• 239000003793 antidiarrheal agent Substances 0.000 description 3
• 229940030600 antihypertensive agent Drugs 0.000 description 3
• BXUMISWXFKCEIA-UHFFFAOYSA-N benzyl (ne)-n-[amino(pyrazol-1-yl)methylidene]carbamate Chemical compound C1=CC=NN1C(N)=NC(=O)OCC1=CC=CC=C1 BXUMISWXFKCEIA-UHFFFAOYSA-N 0.000 description 3
• GUYBTDMZFVUMIU-BTBKUYITSA-N benzyl n-[(5s)-6-amino-5-[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]-6-oxohexyl]carbamate Chemical compound C=1C=C(OCCCN[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C(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 GUYBTDMZFVUMIU-BTBKUYITSA-N 0.000 description 3
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
• 239000003613 bile acid Substances 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• 150000001721 carbon Chemical group 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 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
• KLVRDXBAMSPYKH-RKYZNNDCSA-N corticotropin-releasing hormone (human) Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(N)=O)[C@@H](C)CC)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](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](CO)NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CO)[C@@H](C)CC)C(C)C)C(C)C)C1=CNC=N1 KLVRDXBAMSPYKH-RKYZNNDCSA-N 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• 229940116977 epidermal growth factor Drugs 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• 235000013305 food Nutrition 0.000 description 3
• 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
• 230000003345 hyperglycaemic effect Effects 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 239000008141 laxative Substances 0.000 description 3
• 229940125722 laxative agent Drugs 0.000 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
• QXAPNEGYKYTWGF-UHFFFAOYSA-N methyl 3-[(2-nitrophenyl)sulfonylamino]propanoate Chemical compound COC(=O)CCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O QXAPNEGYKYTWGF-UHFFFAOYSA-N 0.000 description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
• 230000003228 microsomal effect Effects 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 210000002824 peroxisome Anatomy 0.000 description 3
• 230000035755 proliferation Effects 0.000 description 3
• 230000002035 prolonged effect Effects 0.000 description 3
• 229940121649 protein inhibitor Drugs 0.000 description 3
• 239000012268 protein inhibitor Substances 0.000 description 3
• 125000003226 pyrazolyl group Chemical group 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• 239000012279 sodium borohydride Substances 0.000 description 3
• 229910000033 sodium borohydride Inorganic materials 0.000 description 3
• 239000003195 sodium channel blocking agent Substances 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• 238000013268 sustained release Methods 0.000 description 3
• 239000012730 sustained-release form Substances 0.000 description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 238000012546 transfer Methods 0.000 description 3
• 210000002700 urine Anatomy 0.000 description 3
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-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
• BOOOLEGQBVUTKC-NVQSDHBMSA-N (2e,4e)-3-methyl-5-[(1s,2s)-2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\[C@@H]1C[C@]1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 BOOOLEGQBVUTKC-NVQSDHBMSA-N 0.000 description 2
• FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 description 2
• JGLICGWVWBQYCQ-LURJTMIESA-N (2s)-2-[(2-nitrophenyl)sulfonylamino]propanamide Chemical compound NC(=O)[C@H](C)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JGLICGWVWBQYCQ-LURJTMIESA-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
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-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
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 2
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
• HIYMHZLENUINPG-UHFFFAOYSA-N 2,2-dimethyl-3-oxo-3-(4-phenylmethoxycarbonylpiperazin-1-yl)propanoic acid Chemical compound C1CN(C(=O)C(C)(C(O)=O)C)CCN1C(=O)OCC1=CC=CC=C1 HIYMHZLENUINPG-UHFFFAOYSA-N 0.000 description 2
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
• UKHLQJAHGDFIDT-UHFFFAOYSA-N 2-[(2-nitrophenyl)sulfonylamino]acetamide Chemical compound NC(=O)CNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O UKHLQJAHGDFIDT-UHFFFAOYSA-N 0.000 description 2
• ZBGBJZIMCOAJJL-UHFFFAOYSA-N 2-[4-[3-[(2-nitrophenyl)sulfonylamino]propanoyl]piperazin-1-yl]ethyl acetate Chemical compound C1CN(CCOC(=O)C)CCN1C(=O)CCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O ZBGBJZIMCOAJJL-UHFFFAOYSA-N 0.000 description 2
• BHCOXAHSKHZKSC-UHFFFAOYSA-N 2-amino-2-methyl-1-(4-methylpiperazin-1-yl)propan-1-one Chemical compound CN1CCN(C(=O)C(C)(C)N)CC1 BHCOXAHSKHZKSC-UHFFFAOYSA-N 0.000 description 2
• SPPYGZLFIWWRKS-UHFFFAOYSA-N 2-amino-2-methyl-1-morpholin-4-ylpropan-1-one Chemical compound CC(C)(N)C(=O)N1CCOCC1 SPPYGZLFIWWRKS-UHFFFAOYSA-N 0.000 description 2
• XWHCUJQZILEWKU-UHFFFAOYSA-N 2-amino-n-(1-hydroxy-2-methylpropan-2-yl)-2-methylpropanamide Chemical compound CC(C)(N)C(=O)NC(C)(C)CO XWHCUJQZILEWKU-UHFFFAOYSA-N 0.000 description 2
• MUGIGXZITOTTOB-UHFFFAOYSA-N 2-amino-n-(3-hydroxypropyl)-2-methylpropanamide Chemical compound CC(C)(N)C(=O)NCCCO MUGIGXZITOTTOB-UHFFFAOYSA-N 0.000 description 2
• FWOHDAGPWDEWIB-UHFFFAOYSA-N 2-bromoethoxymethylbenzene Chemical compound BrCCOCC1=CC=CC=C1 FWOHDAGPWDEWIB-UHFFFAOYSA-N 0.000 description 2
• WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 2
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 2
• GGJZFUWYCGSBCO-UHFFFAOYSA-N 3-(benzylamino)propanamide Chemical compound NC(=O)CCNCC1=CC=CC=C1 GGJZFUWYCGSBCO-UHFFFAOYSA-N 0.000 description 2
• GEVGRLPYQJTKKS-UHFFFAOYSA-N 3-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC(=O)CCNC(=O)OCC1=CC=CC=C1 GEVGRLPYQJTKKS-UHFFFAOYSA-N 0.000 description 2
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
• AZXMBZCKYJOHBB-UHFFFAOYSA-N 3-amino-n-(2-hydroxyethyl)propanamide Chemical compound NCCC(=O)NCCO AZXMBZCKYJOHBB-UHFFFAOYSA-N 0.000 description 2
• OGJPSKLXUGOZFD-UHFFFAOYSA-N 4-[(4-phenylmethoxyphenyl)methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1C(C)C OGJPSKLXUGOZFD-UHFFFAOYSA-N 0.000 description 2
• WHJJAQSRKKNNKR-UHFFFAOYSA-N 4-[[2-methyl-4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C(=CC(OCCOCC=3C=CC=CC=3)=CC=2)C)=C1C(C)C WHJJAQSRKKNNKR-UHFFFAOYSA-N 0.000 description 2
• HUFUDYLPPPZLHM-UHFFFAOYSA-N 4-[[4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C HUFUDYLPPPZLHM-UHFFFAOYSA-N 0.000 description 2
• RCAGCKFYRWCVQW-UHFFFAOYSA-N 4-[[4-(4-phenylmethoxybutoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C RCAGCKFYRWCVQW-UHFFFAOYSA-N 0.000 description 2
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
• GITSWRINOGOGRB-UHFFFAOYSA-N 90558-39-7 Chemical compound OC(=O)CCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O GITSWRINOGOGRB-UHFFFAOYSA-N 0.000 description 2
• 229940124225 Adrenoreceptor agonist Drugs 0.000 description 2
• 229940118148 Aldose reductase inhibitor Drugs 0.000 description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
• GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 2
• RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 2
• 102100021752 Corticoliberin Human genes 0.000 description 2
• 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 2
• 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
• 101710088194 Dehydrogenase Proteins 0.000 description 2
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
• 229940090955 Dipeptidase inhibitor Drugs 0.000 description 2
• 102000004860 Dipeptidases Human genes 0.000 description 2
• 108090001081 Dipeptidases 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
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
• 102000000853 LDL receptors Human genes 0.000 description 2
• 108010001831 LDL receptors Proteins 0.000 description 2
• 102000016267 Leptin Human genes 0.000 description 2
• 108010092277 Leptin Proteins 0.000 description 2
• 229940086609 Lipase inhibitor Drugs 0.000 description 2
• 229940123635 Lipid peroxidase inhibitor Drugs 0.000 description 2
• 229940122142 Lipoxygenase inhibitor Drugs 0.000 description 2
• 101710151321 Melanostatin Proteins 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
• 238000007126 N-alkylation reaction Methods 0.000 description 2
• 102400000064 Neuropeptide Y Human genes 0.000 description 2
• 238000010934 O-alkylation reaction Methods 0.000 description 2
• 229940122344 Peptidase inhibitor Drugs 0.000 description 2
• 102000003992 Peroxidases Human genes 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 102100040411 Tripeptidyl-peptidase 2 Human genes 0.000 description 2
• ORJLGFDZXUDPEU-FOORKGQUSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[(4-hydroxyphenyl)methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O ORJLGFDZXUDPEU-FOORKGQUSA-N 0.000 description 2
• UGYSXJILJPIUIR-HQTCGSRDSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[(4-phenylmethoxyphenyl)methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O UGYSXJILJPIUIR-HQTCGSRDSA-N 0.000 description 2
• INRYUQGVBYYMMJ-WUDHZMGWSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[2-methyl-4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCOCC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O INRYUQGVBYYMMJ-WUDHZMGWSA-N 0.000 description 2
• OKTCSMLEHJZLQM-VKTDQVFKSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOCC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OKTCSMLEHJZLQM-VKTDQVFKSA-N 0.000 description 2
• KLHKMSKYRDRFNX-LILOYGOGSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(2-hydroxyethoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O KLHKMSKYRDRFNX-LILOYGOGSA-N 0.000 description 2
• HQNUVLJAYKLYSO-BDOIURIFSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCOCC=2C=CC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O HQNUVLJAYKLYSO-BDOIURIFSA-N 0.000 description 2
• UQIALPYHPXDBJA-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(4-aminobutoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O UQIALPYHPXDBJA-RAAUJUNPSA-N 0.000 description 2
• OLXBABBBVLHGTL-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(4-hydroxybutoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OLXBABBBVLHGTL-RAAUJUNPSA-N 0.000 description 2
• DHLKAVDTBFLKJD-VKTDQVFKSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-(4-phenylmethoxybutoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCCOCC=2C=CC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O DHLKAVDTBFLKJD-VKTDQVFKSA-N 0.000 description 2
• YWHSXVOBXACCAR-NTWRQFCJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[2-[(2-amino-2-oxoethyl)amino]ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCNCC(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O YWHSXVOBXACCAR-NTWRQFCJSA-N 0.000 description 2
• NSSRGGVAYOBHAT-FBFPUXADSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[2-[(3-amino-3-oxopropyl)amino]ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCNCCC(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NSSRGGVAYOBHAT-FBFPUXADSA-N 0.000 description 2
• PWEROHFRFOLPLH-UINAHMSNSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(1-amino-2-methyl-1-oxopropan-2-yl)amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(C)(C)C(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O PWEROHFRFOLPLH-UINAHMSNSA-N 0.000 description 2
• OYRUXXBPSWGRAI-NTWRQFCJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(2-amino-2-oxoethyl)amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNCC(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OYRUXXBPSWGRAI-NTWRQFCJSA-N 0.000 description 2
• FIVWFPWXHIULFT-JUEYYMJZSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(3-amino-3-oxopropyl)-benzylamino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN(CCC(N)=O)CC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O FIVWFPWXHIULFT-JUEYYMJZSA-N 0.000 description 2
• CDVLJHRPKJGEDW-WUDHZMGWSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN2CCN(CCO)CC2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O CDVLJHRPKJGEDW-WUDHZMGWSA-N 0.000 description 2
• TWSXUAVOZVEEFF-ZRRGNFRJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[(2s)-1-amino-1-oxopropan-2-yl]amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN[C@@H](C)C(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O TWSXUAVOZVEEFF-ZRRGNFRJSA-N 0.000 description 2
• BSDBCYHGMPHOAL-ICUGJSFKSA-N [(2r,3s,4s,5r,6r)-6-bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC[C@H]1O[C@H](Br)[C@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)[C@H]1OC(=O)C(C)(C)C BSDBCYHGMPHOAL-ICUGJSFKSA-N 0.000 description 2
• OKTCSMLEHJZLQM-UCIYIMANSA-N [(2r,3s,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOCC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OKTCSMLEHJZLQM-UCIYIMANSA-N 0.000 description 2
• FIVWFPWXHIULFT-BYKWTCEVSA-N [(2r,3s,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(3-amino-3-oxopropyl)-benzylamino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN(CCC(N)=O)CC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O FIVWFPWXHIULFT-BYKWTCEVSA-N 0.000 description 2
• KLZUXDPJWSUAGO-UHFFFAOYSA-N [2-methyl-4-(2-phenylmethoxyethoxy)phenyl]methanol Chemical compound C1=C(CO)C(C)=CC(OCCOCC=2C=CC=CC=2)=C1 KLZUXDPJWSUAGO-UHFFFAOYSA-N 0.000 description 2
• JIWMYVFLOMJOTH-UHFFFAOYSA-N [2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methanol Chemical compound C1=C(CO)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 JIWMYVFLOMJOTH-UHFFFAOYSA-N 0.000 description 2
• JANXAAOLQGFURG-UHFFFAOYSA-N [4-(2-phenylmethoxyethoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCOCC1=CC=CC=C1 JANXAAOLQGFURG-UHFFFAOYSA-N 0.000 description 2
• BZROTFMKPQIQDQ-UHFFFAOYSA-N [4-(4-phenylmethoxybutoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCCCOCC1=CC=CC=C1 BZROTFMKPQIQDQ-UHFFFAOYSA-N 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
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 239000002404 acyltransferase inhibitor Substances 0.000 description 2
• 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
• 230000003113 alkalizing effect Effects 0.000 description 2
• WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
• 108010059617 amylinamide Proteins 0.000 description 2
• 230000003276 anti-hypertensive effect Effects 0.000 description 2
• 239000000739 antihistaminic agent Substances 0.000 description 2
• CKEJGNIUSGCOTI-UHFFFAOYSA-N benzyl n-[3-(2-hydroxyethylamino)-3-oxopropyl]carbamate Chemical compound OCCNC(=O)CCNC(=O)OCC1=CC=CC=C1 CKEJGNIUSGCOTI-UHFFFAOYSA-N 0.000 description 2
• VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 150000004283 biguanides Chemical class 0.000 description 2
• 210000000941 bile Anatomy 0.000 description 2
• XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
• 239000000480 calcium channel blocker Substances 0.000 description 2
• 229960004349 candesartan cilexetil Drugs 0.000 description 2
• 150000001718 carbodiimides Chemical class 0.000 description 2
• 235000021258 carbohydrate absorption Nutrition 0.000 description 2
• 229960004203 carnitine Drugs 0.000 description 2
• 239000003638 chemical reducing agent Substances 0.000 description 2
• 229910052801 chlorine Inorganic materials 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
• 150000001840 cholesterol esters Chemical class 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• YGLFEJXKOQXDLM-JGALVPIPSA-N diazonio-[2-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]ethyl]azanide Chemical compound C=1C=C(OCCN=[N+]=[N-])C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O YGLFEJXKOQXDLM-JGALVPIPSA-N 0.000 description 2
• LHIGTYVGENWNMM-LILOYGOGSA-N diazonio-[2-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]ethyl]azanide Chemical compound C=1C=C(OCCN=[N+]=[N-])C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O LHIGTYVGENWNMM-LILOYGOGSA-N 0.000 description 2
• PAQXTMVZGIGENW-RAAUJUNPSA-N diazonio-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]propyl]azanide Chemical compound C=1C=C(OCCCN=[N+]=[N-])C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O PAQXTMVZGIGENW-RAAUJUNPSA-N 0.000 description 2
• RKMKARXCINISGG-RAAUJUNPSA-N diazonio-[4-[4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1h-pyrazol-4-yl]methyl]phenoxy]butyl]azanide Chemical compound C=1C=C(OCCCCN=[N+]=[N-])C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O RKMKARXCINISGG-RAAUJUNPSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 230000001882 diuretic effect Effects 0.000 description 2
• 229940052760 dopamine agonists Drugs 0.000 description 2
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
• 235000005686 eating Nutrition 0.000 description 2
• 238000005265 energy consumption Methods 0.000 description 2
• 230000029142 excretion Effects 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 238000000855 fermentation Methods 0.000 description 2
• 230000004151 fermentation Effects 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 230000004110 gluconeogenesis Effects 0.000 description 2
• 238000005858 glycosidation reaction Methods 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
• 229960002003 hydrochlorothiazide Drugs 0.000 description 2
• PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) 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)=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](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229940039781 leptin Drugs 0.000 description 2
• 102000005861 leptin receptors Human genes 0.000 description 2
• 108010019813 leptin receptors Proteins 0.000 description 2
• 150000002632 lipids Chemical class 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 108020004999 messenger RNA Proteins 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
• 230000000407 monoamine reuptake Effects 0.000 description 2
• 150000004682 monohydrates Chemical class 0.000 description 2
• HCQCQEPTCZVUIK-UHFFFAOYSA-N n-(diphenoxymethylidene)methanesulfonamide Chemical compound C=1C=CC=CC=1OC(=NS(=O)(=O)C)OC1=CC=CC=C1 HCQCQEPTCZVUIK-UHFFFAOYSA-N 0.000 description 2
• WDWZDQRRSLDOLZ-UHFFFAOYSA-N n-[3-(4-benzylpiperazin-1-yl)-3-oxopropyl]-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NCCC(=O)N1CCN(CC=2C=CC=CC=2)CC1 WDWZDQRRSLDOLZ-UHFFFAOYSA-N 0.000 description 2
• RWDHZBYDEFDXGK-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)-3-oxopropyl]-2-nitrobenzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)CCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O RWDHZBYDEFDXGK-UHFFFAOYSA-N 0.000 description 2
• JUPJZPXHCCVKBQ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-nitrobenzenesulfonamide Chemical compound CN(C)CCCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JUPJZPXHCCVKBQ-UHFFFAOYSA-N 0.000 description 2
• KKOVRHHJPWQILS-UHFFFAOYSA-N n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl]-2-nitrobenzenesulfonamide Chemical compound C1CN(CCO)CCN1C(=O)CCNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O KKOVRHHJPWQILS-UHFFFAOYSA-N 0.000 description 2
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 2
• 229960002748 norepinephrine Drugs 0.000 description 2
• SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
• 230000002093 peripheral effect Effects 0.000 description 2
• 108040007629 peroxidase activity proteins Proteins 0.000 description 2
• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 239000000106 platelet aggregation inhibitor Substances 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 230000001681 protective effect Effects 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
• 229940044551 receptor antagonist Drugs 0.000 description 2
• 239000002464 receptor antagonist Substances 0.000 description 2
• 102000005962 receptors Human genes 0.000 description 2
• 108020003175 receptors Proteins 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• 230000001235 sensitizing effect Effects 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
• 239000000952 serotonin receptor agonist Substances 0.000 description 2
• 239000003772 serotonin uptake inhibitor Substances 0.000 description 2
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
• 239000011877 solvent mixture Substances 0.000 description 2
• NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
• 229960002920 sorbitol Drugs 0.000 description 2
• 239000004059 squalene synthase inhibitor Substances 0.000 description 2
• 239000003774 sulfhydryl reagent Substances 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
• 229960004394 topiramate Drugs 0.000 description 2
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
• 108010039189 tripeptidyl-peptidase 2 Proteins 0.000 description 2
• 229940124549 vasodilator Drugs 0.000 description 2
• 239000003071 vasodilator agent Substances 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
• HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 description 1
• IRGRYQMMGLZGMY-UHFFFAOYSA-N (2-methyl-4-phenylmethoxyphenyl)methanol Chemical compound C1=C(CO)C(C)=CC(OCC=2C=CC=CC=2)=C1 IRGRYQMMGLZGMY-UHFFFAOYSA-N 0.000 description 1
• DZLOHEOHWICNIL-QGZVFWFLSA-N (2R)-2-[6-(4-chlorophenoxy)hexyl]-2-oxiranecarboxylic acid ethyl ester Chemical compound C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)OCC)CO1 DZLOHEOHWICNIL-QGZVFWFLSA-N 0.000 description 1
• MLBHFBKZUPLWBD-ZETCQYMHSA-N (2S)-1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound C[C@H](N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-ZETCQYMHSA-N 0.000 description 1
• HNODNXQAYXJFMQ-LQUSFLDPSA-N (2e,4e,6z)-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienoic acid Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(\C(C)=C/C=C/C(/C)=C/C(O)=O)C(OCCC)=C2 HNODNXQAYXJFMQ-LQUSFLDPSA-N 0.000 description 1
• FONCZICQWCUXEB-RUZDIDTESA-N (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C(Br)=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 FONCZICQWCUXEB-RUZDIDTESA-N 0.000 description 1
• QHSRPPJQBFQWSC-OJDZSJEKSA-N (2r)-2-[[(2r)-2-[[(2s)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1-formylindol-3-yl)propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@H](CC=1C2=CC=CC=C2N(C=O)C=1)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)C(=O)N1CCCCCC1 QHSRPPJQBFQWSC-OJDZSJEKSA-N 0.000 description 1
• QEGKXSHUKXMDRW-UWTATZPHSA-N (2r)-2-chlorobutanedioic acid Chemical compound OC(=O)C[C@@H](Cl)C(O)=O QEGKXSHUKXMDRW-UWTATZPHSA-N 0.000 description 1
• XSOXUIXLUNBLJA-RNRVQEDPSA-N (2r)-6-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC[C@@H](OC3=CC=2)C(O)=O)C)=CC=CC(Cl)=C1 XSOXUIXLUNBLJA-RNRVQEDPSA-N 0.000 description 1
• VCIPQQCYKMORDY-KBYFLBCBSA-N (2r,3r,4s,5s,6r)-2-(hydroxymethyl)-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)N[C@@H]1CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCIPQQCYKMORDY-KBYFLBCBSA-N 0.000 description 1
• HKEYVGIJUICATB-HPWZOEIVSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[4-[[4-[2-(3-hydroxypropylamino)ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxane-3,4,5-triol Chemical compound C=1C=C(OCCNCCCO)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 HKEYVGIJUICATB-HPWZOEIVSA-N 0.000 description 1
• OHPKJUDWQFFUGP-TXKDOCKMSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[4-[[4-[3-(3-hydroxypropylamino)propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNCCCO)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 OHPKJUDWQFFUGP-TXKDOCKMSA-N 0.000 description 1
• XWNPCKTWRRGIGN-TXKDOCKMSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[4-[[4-[3-[(1-hydroxy-2-methylpropan-2-yl)amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(C)(C)CO)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 XWNPCKTWRRGIGN-TXKDOCKMSA-N 0.000 description 1
• BIVMABLOCWBMJY-HPWZOEIVSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[4-[[4-[3-[(1-hydroxy-2-methylpropan-2-yl)amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(C)(C)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O BIVMABLOCWBMJY-HPWZOEIVSA-N 0.000 description 1
• ANKLURWGHGVUKR-YKUHLWEKSA-N (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[5-propan-2-yl-4-[[4-[3-(pyridin-3-ylmethylamino)propoxy]phenyl]methyl]-1h-pyrazol-3-yl]oxy]oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNCC=2C=NC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ANKLURWGHGVUKR-YKUHLWEKSA-N 0.000 description 1
• BAVDEDVBIHTHJQ-UVJOBNTFSA-N (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid;hydrate Chemical compound O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 BAVDEDVBIHTHJQ-UVJOBNTFSA-N 0.000 description 1
• VBENHRFIEOLOJJ-SFHVURJKSA-N (2s)-2,5-bis(phenylmethoxycarbonylamino)pentanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)CCNC(=O)OCC1=CC=CC=C1 VBENHRFIEOLOJJ-SFHVURJKSA-N 0.000 description 1
• WIJQKPINNOHJCZ-SBFLOYGISA-N (2s)-2,5-diamino-n-[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]propyl]pentanamide Chemical compound C=1C=C(OCCCNC(=O)[C@@H](N)CCCN)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 WIJQKPINNOHJCZ-SBFLOYGISA-N 0.000 description 1
• HWEMEKZYQCJVEZ-PPHPATTJSA-N (2s)-2-[(7-fluoro-2,3-dihydro-1h-inden-4-yl)oxymethyl]morpholine;hydrochloride Chemical compound Cl.C1=2CCCC=2C(F)=CC=C1OC[C@@H]1CNCCO1 HWEMEKZYQCJVEZ-PPHPATTJSA-N 0.000 description 1
• QBWSEZQWZYLFIE-GWQKUDGSSA-N (2s)-2-[3-[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(OCCCN[C@@H](C)C(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QBWSEZQWZYLFIE-GWQKUDGSSA-N 0.000 description 1
• YPGILAVWVRBSAJ-MOPGFXCFSA-N (2s)-2-[[(2s)-2-benzyl-3-sulfanylpropanoyl]amino]-3-[4-(1,3-thiazol-2-yl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@@H](CS)CC=1C=CC=CC=1)C(C=C1)=CC=C1C1=NC=CS1 YPGILAVWVRBSAJ-MOPGFXCFSA-N 0.000 description 1
• GKYIONYOYVKKQI-MPGHIAIKSA-N (2s)-2-[[(2s,3r)-2-(benzoylsulfanylmethyl)-3-phenylbutanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C(O)=O)[C@@H](C)C=1C=CC=CC=1)SC(=O)C1=CC=CC=C1 GKYIONYOYVKKQI-MPGHIAIKSA-N 0.000 description 1
• LPUDGHQMOAHMMF-JBACZVJFSA-N (2s)-2-[[[(2s)-6-amino-2-(methanesulfonamido)hexanoyl]amino]methyl]-3-[1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl]cyclopentyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C(=O)C1(C[C@@H](CNC(=O)[C@H](CCCCN)NS(=O)(=O)C)C(O)=O)CCCC1 LPUDGHQMOAHMMF-JBACZVJFSA-N 0.000 description 1
• KGSYZDYPOJPQIM-SBFLOYGISA-N (2s)-2-amino-3-(1h-imidazol-5-yl)-n-[3-[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]propyl]propanamide Chemical compound C=1C=C(OCCCNC(=O)[C@@H](N)CC=2N=CNC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KGSYZDYPOJPQIM-SBFLOYGISA-N 0.000 description 1
• YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
• KQSWDIVYZBNQBM-RRUWFPKISA-N (2s)-2-amino-3-hydroxy-n-[3-[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]propyl]propanamide Chemical compound C=1C=C(OCCCNC(=O)[C@@H](N)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KQSWDIVYZBNQBM-RRUWFPKISA-N 0.000 description 1
• XOPCPPGNKPQYRR-GWQKUDGSSA-N (2s)-2-amino-n-[3-[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]propyl]propanamide Chemical compound C=1C=C(OCCCNC(=O)[C@H](C)N)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XOPCPPGNKPQYRR-GWQKUDGSSA-N 0.000 description 1
• QNDFBOXBUCDYNZ-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(NC(=O)OC(C)(C)C)C=C1 QNDFBOXBUCDYNZ-NRFANRHFSA-N 0.000 description 1
• WCOJOHPAKJFUDF-LBPRGKRZSA-N (2s)-3-(1h-imidazol-5-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CN=CN1 WCOJOHPAKJFUDF-LBPRGKRZSA-N 0.000 description 1
• RDGUFKZGMLPVHL-QFIPXVFZSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(propylamino)propanoic acid Chemical compound C1=CC(C[C@H](NCCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 RDGUFKZGMLPVHL-QFIPXVFZSA-N 0.000 description 1
• CRUVAUSVWLATAE-ZDUSSCGKSA-N (2s)-3-dibenzofuran-3-yl-2-(phosphonomethylamino)propanoic acid Chemical compound C1=CC=C2C3=CC=C(C[C@@H](C(=O)O)NCP(O)(O)=O)C=C3OC2=C1 CRUVAUSVWLATAE-ZDUSSCGKSA-N 0.000 description 1
• GNIDSOFZAKMQAO-VIFPVBQESA-N (2s)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 GNIDSOFZAKMQAO-VIFPVBQESA-N 0.000 description 1
• UYGABZGQHFAYLV-SKZWMFFWSA-N (2s)-6-amino-2-[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]hexanamide Chemical compound C=1C=C(OCCCN[C@@H](CCCCN)C(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 UYGABZGQHFAYLV-SKZWMFFWSA-N 0.000 description 1
• OAEWNSKRLBVVBV-QSEAXJEQSA-N (2s,3r,4s)-1-[2-(dibutylamino)-2-oxoethyl]-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylic acid Chemical compound OC(=O)[C@H]1[C@H](CC(C)(C)CCC)N(CC(=O)N(CCCC)CCCC)C[C@@H]1C(C=C1OC)=CC2=C1OCO2 OAEWNSKRLBVVBV-QSEAXJEQSA-N 0.000 description 1
• FMEBZNADEHKESL-KQDNOMNESA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-(2-aminoethoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCN)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 FMEBZNADEHKESL-KQDNOMNESA-N 0.000 description 1
• ZKGPTPBOLGLGJE-UVPIGPOJSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-(2-aminoethoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZKGPTPBOLGLGJE-UVPIGPOJSA-N 0.000 description 1
• FDCAFIAWDJZAHV-SQKWCZRTSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-(3-aminopropoxy)-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCN)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 FDCAFIAWDJZAHV-SQKWCZRTSA-N 0.000 description 1
• HIKMGKJNOLEWMQ-KQDNOMNESA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-(3-aminopropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HIKMGKJNOLEWMQ-KQDNOMNESA-N 0.000 description 1
• NEQGAUIZSPMEJF-SQKWCZRTSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-(4-aminobutoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O NEQGAUIZSPMEJF-SQKWCZRTSA-N 0.000 description 1
• KNHZTGSILCCJRY-WZTWURHFSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[(2r)-2-hydroxy-3-(2-hydroxyethylamino)propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OC[C@H](O)CNCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KNHZTGSILCCJRY-WZTWURHFSA-N 0.000 description 1
• KABILOJCEBJHDD-FNJNVWBGSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[(2r)-3-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]-2-hydroxypropoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OC[C@H](O)CNC(C)(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KABILOJCEBJHDD-FNJNVWBGSA-N 0.000 description 1
• KPIGRUJGIGTAQI-HPWZOEIVSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[2-(1,3-dihydroxypropan-2-ylamino)ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCNC(CO)CO)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 KPIGRUJGIGTAQI-HPWZOEIVSA-N 0.000 description 1
• NETQJEPWDYZBPW-YVTYUBGGSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[2-(2-hydroxyethylamino)ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCNCCO)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 NETQJEPWDYZBPW-YVTYUBGGSA-N 0.000 description 1
• PXDCZGQSGDXIHE-HPWZOEIVSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[2-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]ethoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCNC(C)(CO)CO)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 PXDCZGQSGDXIHE-HPWZOEIVSA-N 0.000 description 1
• DHAUHQHDWYDQLA-TXKDOCKMSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-(1,3-dihydroxypropan-2-ylamino)propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(CO)CO)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 DHAUHQHDWYDQLA-TXKDOCKMSA-N 0.000 description 1
• UADDJIUFNUNXAC-HPWZOEIVSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-(1,3-dihydroxypropan-2-ylamino)propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UADDJIUFNUNXAC-HPWZOEIVSA-N 0.000 description 1
• KICHXCPUQZIAPK-HPWZOEIVSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-(2-hydroxyethylamino)propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNCCO)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 KICHXCPUQZIAPK-HPWZOEIVSA-N 0.000 description 1
• UZJBVKPMUCPKIJ-TXKDOCKMSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-[(1,3-dihydroxy-2-methylpropan-2-yl)amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(C)(CO)CO)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 UZJBVKPMUCPKIJ-TXKDOCKMSA-N 0.000 description 1
• PWELODKEYOUYSS-YKUHLWEKSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-[3-(dimethylamino)propylamino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNCCCN(C)C)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 PWELODKEYOUYSS-YKUHLWEKSA-N 0.000 description 1
• YPKYMLHQXSOJSN-LILOYGOGSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCN2CCN(CCO)CC2)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 YPKYMLHQXSOJSN-LILOYGOGSA-N 0.000 description 1
• LMJLOEGYYKKXPX-TXKDOCKMSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(CO)(CO)CO)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 LMJLOEGYYKKXPX-TXKDOCKMSA-N 0.000 description 1
• JAUMITHFDSLYSH-HPWZOEIVSA-N (2s,3r,4s,5s,6r)-2-[[4-[[4-[3-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C=1C=C(OCCCNC(CO)(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JAUMITHFDSLYSH-HPWZOEIVSA-N 0.000 description 1
• CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 1
• DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
• JICDBMXIQNEXKV-QFIPXVFZSA-N (3r)-3-(4-quinolin-6-ylphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N1=CC=CC2=CC(C3=CC=C(C=C3)[C@@]3(C4CCN(CC4)C3)O)=CC=C21 JICDBMXIQNEXKV-QFIPXVFZSA-N 0.000 description 1
• KTFMPDDJYRFWQE-DDWIOCJRSA-N (3r)-3-propanoyloxy-4-(trimethylazaniumyl)butanoate;hydrochloride Chemical compound [Cl-].CCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C KTFMPDDJYRFWQE-DDWIOCJRSA-N 0.000 description 1
• CKFWDLFFXXVSBJ-DHIUTWEWSA-N (3r,5r)-3-butyl-3-ethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OC)=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 CKFWDLFFXXVSBJ-DHIUTWEWSA-N 0.000 description 1
• HPFIYXJJZZWEPC-MMKWGKFASA-N (3r,5s,6e)-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyltetrazol-5-yl)nona-6,8-dienoic acid Chemical compound CN1N=NN=C1C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 HPFIYXJJZZWEPC-MMKWGKFASA-N 0.000 description 1
• RICKQPKTSOSCOF-HKUYNNGSSA-N (3s)-2-[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1C2=CC=CC=C2C[C@@H](C(O)=O)N1C(=O)[C@@H](N)CC1=CNC2=CC=CC=C12 RICKQPKTSOSCOF-HKUYNNGSSA-N 0.000 description 1
• DLOJBPLQFCFYKX-QQYYTUMTSA-N (3s)-4-[[(2r)-1-[2-[[(2s)-2-[[1h-indol-3-ylmethyl-[2-[[(2s)-2-[3-(4-sulfooxyphenyl)propanoylamino]hexanoyl]amino]acetyl]carbamoyl]amino]hexanoyl]carbamoyl]phenyl]propan-2-yl]amino]-3-(methylamino)-4-oxobutanoic acid Chemical compound N([C@@H](CCCC)C(=O)NCC(=O)N(CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCC)C(=O)NC(=O)C=1C(=CC=CC=1)C[C@@H](C)NC(=O)[C@H](CC(O)=O)NC)C(=O)CCC1=CC=C(OS(O)(=O)=O)C=C1 DLOJBPLQFCFYKX-QQYYTUMTSA-N 0.000 description 1
• VMDKRSNUUUUARH-MQDBWYGVSA-N (3s)-4-[[(2s)-1-[[(2s)-2-[[(2s)-3-(1h-indol-3-yl)-2-[[2-[[(2s)-2-[[2-(4-sulfooxyphenyl)acetyl]amino]hexanoyl]amino]acetyl]amino]propanoyl]amino]hexanoyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(methylamino)-4-oxobutanoic acid Chemical compound N([C@@H](CCCC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCC)C(=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC)C(=O)CC1=CC=C(OS(O)(=O)=O)C=C1 VMDKRSNUUUUARH-MQDBWYGVSA-N 0.000 description 1
• 108010040581 (4-hydroxy-3-(2-(2-propenyl)-4-quinoline)benzoyl)-(3-chloro-4-hydroxyarginyl)-(3-hydroxy-3-methylprolyl)-dehydrovaline Proteins 0.000 description 1
• NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
• VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 description 1
• AIEZUMPHACQOGT-BJESRGMDSA-N (4s,7s,12br)-7-[[(2s)-2-acetylsulfanyl-3-phenylpropanoyl]amino]-6-oxo-2,3,4,7,8,12b-hexahydro-1h-pyrido[2,1-a][2]benzazepine-4-carboxylic acid Chemical compound C([C@H](SC(=O)C)C(=O)N[C@@H]1C(N2[C@@H](CCC[C@@H]2C2=CC=CC=C2C1)C(O)=O)=O)C1=CC=CC=C1 AIEZUMPHACQOGT-BJESRGMDSA-N 0.000 description 1
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
• METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 description 1
• WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 description 1
• YGEPYVAQKIHLFY-FYWRMAATSA-N (e)-3-(3,5-dimethoxy-4-octoxyphenyl)-1-[4-(3,4-dimethylphenyl)piperazin-1-yl]prop-2-en-1-one Chemical compound C1=C(OC)C(OCCCCCCCC)=C(OC)C=C1\C=C\C(=O)N1CCN(C=2C=C(C)C(C)=CC=2)CC1 YGEPYVAQKIHLFY-FYWRMAATSA-N 0.000 description 1
• RZPZLFIUFMNCLY-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(propan-2-ylamino)-3-[4-(2-propan-2-yloxyethoxymethyl)phenoxy]propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 RZPZLFIUFMNCLY-WLHGVMLRSA-N 0.000 description 1
• LONWRQOYFPYMQD-DTQAZKPQSA-N (e)-n-[6-methoxy-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OC)=C1NS(=O)(=O)\C=C\C1=CC=CC=C1 LONWRQOYFPYMQD-DTQAZKPQSA-N 0.000 description 1
• GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
• ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
• JMUQZBBNECHRNF-HPWZOEIVSA-N 1-(1,3-dihydroxy-2-methylpropan-2-yl)-3-[2-[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]ethyl]urea Chemical compound C=1C=C(OCCNC(=O)NC(C)(CO)CO)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 JMUQZBBNECHRNF-HPWZOEIVSA-N 0.000 description 1
• JTZFOOWPSIOPBF-TXKDOCKMSA-N 1-(1,3-dihydroxy-2-methylpropan-2-yl)-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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(C)(CO)CO)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 JTZFOOWPSIOPBF-TXKDOCKMSA-N 0.000 description 1
• KHJQUCGNWMTSQI-HPWZOEIVSA-N 1-(1,3-dihydroxy-2-methylpropan-2-yl)-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(C)(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KHJQUCGNWMTSQI-HPWZOEIVSA-N 0.000 description 1
• XDCJHZQVKUEHCR-HPWZOEIVSA-N 1-(1,3-dihydroxypropan-2-yl)-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O XDCJHZQVKUEHCR-HPWZOEIVSA-N 0.000 description 1
• KUUDGHOSYIMCRB-HPWZOEIVSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-3-[2-[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]ethyl]urea Chemical compound C=1C=C(OCCNC(=O)NC(C)(C)CO)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 KUUDGHOSYIMCRB-HPWZOEIVSA-N 0.000 description 1
• INCJCWKHMAWIFU-TXKDOCKMSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(C)(C)CO)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 INCJCWKHMAWIFU-TXKDOCKMSA-N 0.000 description 1
• KRPBXNHXVPMBTB-HPWZOEIVSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(C)(C)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KRPBXNHXVPMBTB-HPWZOEIVSA-N 0.000 description 1
• VXKLVOZWYQOWEW-UHFFFAOYSA-N 1-(2,6-diethylphenyl)-3-[3-(2-methylphenyl)-6,7-dihydro-5h-cyclopenta[f][1]benzothiol-2-yl]urea Chemical compound CCC1=CC=CC(CC)=C1NC(=O)NC1=C(C=2C(=CC=CC=2)C)C2=CC(CCC3)=C3C=C2S1 VXKLVOZWYQOWEW-UHFFFAOYSA-N 0.000 description 1
• QLXCKZGRQOWTLL-HPWZOEIVSA-N 1-(2-hydroxyethyl)-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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NCCO)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 QLXCKZGRQOWTLL-HPWZOEIVSA-N 0.000 description 1
• OOVJBPBNRYGIHS-YVTYUBGGSA-N 1-(2-hydroxyethyl)-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OOVJBPBNRYGIHS-YVTYUBGGSA-N 0.000 description 1
• UFMIMTLGMYLWMY-YKUHLWEKSA-N 1-(2-morpholin-4-ylethyl)-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NCCN2CCOCC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UFMIMTLGMYLWMY-YKUHLWEKSA-N 0.000 description 1
• FSJFNSPLIBDKDO-MWVAGWFGSA-N 1-(4-benzylpiperazin-1-yl)-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]propan-1-one Chemical compound C=1C=C(OCCCNCCC(=O)N2CCN(CC=3C=CC=CC=3)CC2)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 FSJFNSPLIBDKDO-MWVAGWFGSA-N 0.000 description 1
• HREFSABIJLZMRD-RZDOQYSOSA-N 1-(4-methylpiperazin-1-yl)-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]propan-1-one Chemical compound C=1C=C(OCCCNCCC(=O)N2CCN(C)CC2)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 HREFSABIJLZMRD-RZDOQYSOSA-N 0.000 description 1
• UUOJIACWOAYWEZ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1 UUOJIACWOAYWEZ-UHFFFAOYSA-N 0.000 description 1
• DDZPRFMWEDTZML-HPWZOEIVSA-N 1-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NC(CO)(CO)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DDZPRFMWEDTZML-HPWZOEIVSA-N 0.000 description 1
• GEVQMCFWDDZLMU-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)propyl]-7-(pyrimidin-5-ylmethoxy)-4,5-dihydrobenzo[g]indazole-3-carboxylic acid Chemical compound CCOC1=CC=CC(C(CC)N2C=3C4=CC=C(OCC=5C=NC=NC=5)C=C4CCC=3C(C(O)=O)=N2)=C1 GEVQMCFWDDZLMU-UHFFFAOYSA-N 0.000 description 1
• KFNNPQDSPLWLCX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine;hydron;chloride;hydrate Chemical compound O.Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 KFNNPQDSPLWLCX-UHFFFAOYSA-N 0.000 description 1
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
• VDTWKXAPIQBOMO-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical compound CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 VDTWKXAPIQBOMO-UHFFFAOYSA-N 0.000 description 1
• LICPJVFSBSRFAQ-TXKDOCKMSA-N 1-[2-(dimethylamino)ethyl]-3-[3-[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]propyl]urea Chemical compound C=1C=C(OCCCNC(=O)NCCN(C)C)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LICPJVFSBSRFAQ-TXKDOCKMSA-N 0.000 description 1
• GEXOEDVBNIBSGF-YKUHLWEKSA-N 1-[3-[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]propyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C=1C=C(OCCCNC(=O)NCCN2CCCC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GEXOEDVBNIBSGF-YKUHLWEKSA-N 0.000 description 1
• MFFPZCVEKKMIQY-NTWRQFCJSA-N 1-[4-(2-hydroxyethyl)piperazin-1-yl]-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]propan-1-one Chemical compound C=1C=C(OCCCNCCC(=O)N2CCN(CCO)CC2)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 MFFPZCVEKKMIQY-NTWRQFCJSA-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
• IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
• NHVQKYFNCQUKFI-UHFFFAOYSA-N 1-bromo-2-methyl-4-(3-phenylmethoxypropoxy)benzene Chemical compound C1=C(Br)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 NHVQKYFNCQUKFI-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• YHGXXJPOAVEBFT-YVTYUBGGSA-N 1-cyano-2-methyl-3-[3-[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]propyl]guanidine Chemical compound C1=CC(OCCCNC(NC)=NC#N)=CC=C1CC1=C(C(C)C)NN=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YHGXXJPOAVEBFT-YVTYUBGGSA-N 0.000 description 1
• AAHNMQIKXPNMOV-HPWZOEIVSA-N 1-cyano-3-(2-hydroxyethyl)-2-[3-[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]propyl]guanidine Chemical compound C=1C=C(OCCCNC(NCCO)=NC#N)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AAHNMQIKXPNMOV-HPWZOEIVSA-N 0.000 description 1
• AKJWTZIUYIFCCS-UHFFFAOYSA-N 1-cycloheptyl-1-[[3-[[cycloheptyl-[[4-(dimethylamino)phenyl]carbamoyl]amino]methyl]phenyl]methyl]-3-[4-(dimethylamino)phenyl]urea;dihydrochloride Chemical compound Cl.Cl.C1=CC(N(C)C)=CC=C1NC(=O)N(C1CCCCCC1)CC1=CC=CC(CN(C2CCCCCC2)C(=O)NC=2C=CC(=CC=2)N(C)C)=C1 AKJWTZIUYIFCCS-UHFFFAOYSA-N 0.000 description 1
• SIHFCVXQGXGQQO-UHFFFAOYSA-N 1-cyclohexyl-1-[[4-[[cyclohexyl-[[4-(dimethylamino)phenyl]carbamoyl]amino]methyl]cyclohexyl]methyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)N(C1CCCCC1)CC1CCC(CN(C2CCCCC2)C(=O)NC=2C=CC(=CC=2)N(C)C)CC1 SIHFCVXQGXGQQO-UHFFFAOYSA-N 0.000 description 1
• KFRPWMWQOMPNMA-UHFFFAOYSA-N 1-heptyl-1-[[4-(3-methylbutyl)phenyl]methyl]-3-(2,4,6-trifluorophenyl)urea Chemical compound FC=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCC(C)C)C=C1 KFRPWMWQOMPNMA-UHFFFAOYSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000006411 1-propenylene group Chemical group [H]\C(*)=C(\[H])C([H])([H])[H] 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
• OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 description 1
• ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical class O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
• NJAXEAJPBCDOMU-YKUHLWEKSA-N 2,2-dimethyl-n-[2-[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]ethyl]-3-oxo-3-piperazin-1-ylpropanamide Chemical compound C=1C=C(OCCNC(=O)C(C)(C)C(=O)N2CCNCC2)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 NJAXEAJPBCDOMU-YKUHLWEKSA-N 0.000 description 1
• QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 description 1
• NVYSVDRYESXWBD-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanyl)-1-(3,4-dihydroxyphenyl)ethanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)CSC1=NC2=CC=CC=C2N1 NVYSVDRYESXWBD-UHFFFAOYSA-N 0.000 description 1
• ANTCFCCEYPUFNQ-HPWZOEIVSA-N 2-(2-hydroxyethyl)-1-[2-[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]ethyl]-3-methylsulfonylguanidine Chemical compound C=1C=C(OCCNC(NCCO)=NS(C)(=O)=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 ANTCFCCEYPUFNQ-HPWZOEIVSA-N 0.000 description 1
• FNLNSQHJKVQCBP-UHFFFAOYSA-N 2-(3-sulfanylpropyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CCCS FNLNSQHJKVQCBP-UHFFFAOYSA-N 0.000 description 1
• RIMAGTAWNVQRCT-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(=O)C1=CC=CC=C1C(O)=O RIMAGTAWNVQRCT-UHFFFAOYSA-N 0.000 description 1
• DEMLYXMVPJAVFU-UHFFFAOYSA-N 2-(chloromethyl)oxirane;2-methyl-1h-imidazole Chemical compound ClCC1CO1.CC1=NC=CN1 DEMLYXMVPJAVFU-UHFFFAOYSA-N 0.000 description 1
• YIDWKBOMLCKIII-UHFFFAOYSA-N 2-(oxan-4-yloxy)-4-phenylmethoxybenzaldehyde Chemical compound C1=C(OC2CCOCC2)C(C=O)=CC=C1OCC1=CC=CC=C1 YIDWKBOMLCKIII-UHFFFAOYSA-N 0.000 description 1
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
• XMQODGUTLZXUGZ-RPBOFIJWSA-N 2-[(3s)-3-[[1-[(2r)-2-ethoxycarbonyl-4-phenylbutyl]cyclopentanecarbonyl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic acid Chemical compound C([C@@H](C(=O)OCC)CC1(CCCC1)C(=O)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XMQODGUTLZXUGZ-RPBOFIJWSA-N 0.000 description 1
• FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 description 1
• LKNNLUUYQBHQFC-KQDNOMNESA-N 2-[2-[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]ethyl]guanidine Chemical compound C=1C=C(OCCNC(N)=N)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 LKNNLUUYQBHQFC-KQDNOMNESA-N 0.000 description 1
• JGGAQFHVBHOYLG-WDVFSZROSA-N 2-[2-[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]ethylamino]acetamide Chemical compound C=1C=C(OCCNCC(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 JGGAQFHVBHOYLG-WDVFSZROSA-N 0.000 description 1
• YREIRIKJAMPPHC-UHFFFAOYSA-N 2-[3-[(3-nitrophenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]acetic acid Chemical compound O=C1C(=O)N(CC(=O)O)C(=O)N1CC1=CC=CC([N+]([O-])=O)=C1 YREIRIKJAMPPHC-UHFFFAOYSA-N 0.000 description 1
• DLZGQGBHYCAKQA-UHFFFAOYSA-N 2-[3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid;hydrate Chemical compound O.C12=CC=CC=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 DLZGQGBHYCAKQA-UHFFFAOYSA-N 0.000 description 1
• LKBFFDOJUKLQNY-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-4-oxo-1-phthalazinyl]acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=CC=C(Br)C=C1F LKBFFDOJUKLQNY-UHFFFAOYSA-N 0.000 description 1
• UERVQLLUXBWIAH-MNDUUMEHSA-N 2-[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]propyl-methylsulfonylamino]acetamide Chemical compound C=1C=C(OCCCN(CC(N)=O)S(C)(=O)=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 UERVQLLUXBWIAH-MNDUUMEHSA-N 0.000 description 1
• NASZFCGUPXHRBK-SQKWCZRTSA-N 2-[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]propyl]guanidine Chemical compound C=1C=C(OCCCNC(N)=N)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 NASZFCGUPXHRBK-SQKWCZRTSA-N 0.000 description 1
• ZRJLMOQUHZXEMC-FLYQRFDZSA-N 2-[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]acetamide Chemical compound C=1C=C(OCCCNCC(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 ZRJLMOQUHZXEMC-FLYQRFDZSA-N 0.000 description 1
• ZCMXGGCWYLTBFK-WDVFSZROSA-N 2-[3-[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]acetamide Chemical compound C=1C=C(OCCCNCC(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZCMXGGCWYLTBFK-WDVFSZROSA-N 0.000 description 1
• ZGGNJJJYUVRADP-ACJLOTCBSA-N 2-[4-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]phenoxy]acetic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C1=CC=C(OCC(O)=O)C=C1 ZGGNJJJYUVRADP-ACJLOTCBSA-N 0.000 description 1
• BKONADSQADEJJP-SFTDATJTSA-N 2-[4-[(2s)-2-[[(1s)-1-carboxy-2-phenylethyl]carbamoylamino]-3-oxo-3-(pentylamino)propyl]phenoxy]propanedioic acid Chemical compound C([C@@H](C(=O)NCCCCC)NC(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=C(OC(C(O)=O)C(O)=O)C=C1 BKONADSQADEJJP-SFTDATJTSA-N 0.000 description 1
• KCEFVYIWOQSJCH-LMOVPXPDSA-N 2-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]acetic acid;hydrochloride Chemical compound Cl.C([C@H](O)C=1C=CC=CC=1)NCCOC1=CC=C(CC(O)=O)C=C1 KCEFVYIWOQSJCH-LMOVPXPDSA-N 0.000 description 1
• RVMBDLSFFNKKLG-SFHVURJKSA-N 2-[4-[2-[[(2s)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenoxy]-n-(2-methoxyethyl)acetamide Chemical compound C1=CC(OCC(=O)NCCOC)=CC=C1OCCNC[C@H](O)COC1=CC=CC=C1 RVMBDLSFFNKKLG-SFHVURJKSA-N 0.000 description 1
• MUGOTNWCTZMBLV-UHFFFAOYSA-N 2-[4-oxo-2-(2-propan-2-ylidenehydrazinyl)-1,3-thiazol-5-yl]-n-phenylacetamide Chemical compound S1C(NN=C(C)C)=NC(=O)C1CC(=O)NC1=CC=CC=C1 MUGOTNWCTZMBLV-UHFFFAOYSA-N 0.000 description 1
• MKJQESRCXYYHFR-UHFFFAOYSA-N 2-[7-(2,2-dimethylpropanoylamino)-4,6-dimethyl-1-octyl-2,3-dihydroindol-5-yl]acetic acid;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)(C)C(=O)NC1=C(C)C(CC(O)=O)=C(C)C2=C1N(CCCCCCCC)CC2.CC(C)(C)C(=O)NC1=C(C)C(CC(O)=O)=C(C)C2=C1N(CCCCCCCC)CC2 MKJQESRCXYYHFR-UHFFFAOYSA-N 0.000 description 1
• PLYWAKPAFSZPAL-HKUYNNGSSA-N 2-[[(7s)-7-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]oxy]acetic acid Chemical compound C1([C@H](CN[C@@H]2CC3=CC(OCC(O)=O)=CC=C3CC2)O)=CC=CC(Cl)=C1 PLYWAKPAFSZPAL-HKUYNNGSSA-N 0.000 description 1
• MCHCGWZNXSZKJY-OEAKJJBVSA-N 2-[[2-[2-butyl-4-[(e)-2-carboxy-3-(6-methoxy-1,3-benzodioxol-5-yl)prop-1-enyl]pyrazol-3-yl]-5-methoxyphenoxy]methyl]benzoic acid Chemical compound CCCCN1N=CC(\C=C(/CC=2C(=CC=3OCOC=3C=2)OC)C(O)=O)=C1C1=CC=C(OC)C=C1OCC1=CC=CC=C1C(O)=O MCHCGWZNXSZKJY-OEAKJJBVSA-N 0.000 description 1
• FHEYFIGWYQJVDR-ACJLOTCBSA-N 2-[[3-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C3=CC=CC(OCC(O)=O)=C3NC=2)C)=CC=CC(Cl)=C1 FHEYFIGWYQJVDR-ACJLOTCBSA-N 0.000 description 1
• NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 description 1
• BJBCSGQLZQGGIQ-QGZVFWFLSA-N 2-acetamidoethyl (2r)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetate Chemical compound O([C@@H](C(=O)OCCNC(=O)C)C=1C=CC(Cl)=CC=1)C1=CC=CC(C(F)(F)F)=C1 BJBCSGQLZQGGIQ-QGZVFWFLSA-N 0.000 description 1
• KDYUZDXJHBQWMP-YVTYUBGGSA-N 2-amino-2-methyl-n-[3-[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]propyl]propanamide Chemical compound C=1C=C(OCCCNC(=O)C(C)(C)N)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KDYUZDXJHBQWMP-YVTYUBGGSA-N 0.000 description 1
• TVSGNAGCYLRPBT-WDVFSZROSA-N 2-amino-n-[3-[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]propyl]acetamide Chemical compound C=1C=C(OCCCNC(=O)CN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O TVSGNAGCYLRPBT-WDVFSZROSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• WMUIIGVAWPWQAW-UHFFFAOYSA-N 2-ethoxy-3-[4-(2-phenoxazin-10-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OC2=CC=CC=C21 WMUIIGVAWPWQAW-UHFFFAOYSA-N 0.000 description 1
• AMLKEDBYDOCGEG-UHFFFAOYSA-N 2-hydroxy-4-phenylmethoxybenzaldehyde Chemical compound C1=C(C=O)C(O)=CC(OCC=2C=CC=CC=2)=C1 AMLKEDBYDOCGEG-UHFFFAOYSA-N 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• KBBDYGQBGZQFOA-LILOYGOGSA-N 2-methyl-1-(4-methylpiperazin-1-yl)-2-[3-[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]propan-1-one Chemical compound C=1C=C(OCCCNC(C)(C)C(=O)N2CCN(C)CC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KBBDYGQBGZQFOA-LILOYGOGSA-N 0.000 description 1
• CLRYWOSLYUGYHH-YKUHLWEKSA-N 2-methyl-1-morpholin-4-yl-2-[3-[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]propan-1-one Chemical compound C=1C=C(OCCCNC(C)(C)C(=O)N2CCOCC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CLRYWOSLYUGYHH-YKUHLWEKSA-N 0.000 description 1
• QOITXEJBTPXLSF-YVTYUBGGSA-N 2-methyl-2-[2-[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]ethylcarbamoylamino]propanamide Chemical compound C=1C=C(OCCNC(=O)NC(C)(C)C(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 QOITXEJBTPXLSF-YVTYUBGGSA-N 0.000 description 1
• LEGGNBCJZMVXFQ-HPWZOEIVSA-N 2-methyl-2-[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(OCCCNC(C)(C)C(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 LEGGNBCJZMVXFQ-HPWZOEIVSA-N 0.000 description 1
• CKEKIZKJNMUICY-YVTYUBGGSA-N 2-methyl-2-[3-[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(OCCCNC(C)(C)C(N)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CKEKIZKJNMUICY-YVTYUBGGSA-N 0.000 description 1
• TYEFTVXWOJQNJF-UHFFFAOYSA-N 2-methyl-4-(3-phenylmethoxypropoxy)benzaldehyde Chemical compound C1=C(C=O)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 TYEFTVXWOJQNJF-UHFFFAOYSA-N 0.000 description 1
• HZOABPDJUQEYFK-UHFFFAOYSA-N 2-methyl-n-[4-(1,2,3,4-tetrahydro-1,5-benzodiazepine-5-carbonyl)phenyl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)N2C3=CC=CC=C3NCCC2)C=C1 HZOABPDJUQEYFK-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
• WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
• BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 1
• TVXOXGBTADZYCZ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanyl]pentyl]-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCCCCSC(N1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 TVXOXGBTADZYCZ-UHFFFAOYSA-N 0.000 description 1
• JXZZEXZZKAWDSP-UHFFFAOYSA-N 3-(2-(4-Benzamidopiperid-1-yl)ethyl)indole Chemical compound C1CN(CCC=2C3=CC=CC=C3NC=2)CCC1NC(=O)C1=CC=CC=C1 JXZZEXZZKAWDSP-UHFFFAOYSA-N 0.000 description 1
• VMJQLPNCUPGMNQ-HNNXBMFYSA-N 3-[(2s)-6-hydroxy-2,7,8-trimethyl-3,4-dihydrochromen-2-yl]propanoic acid Chemical compound C1C[C@@](C)(CCC(O)=O)OC2=C(C)C(C)=C(O)C=C21 VMJQLPNCUPGMNQ-HNNXBMFYSA-N 0.000 description 1
• VTECYVNYNQFWBB-FLYQRFDZSA-N 3-[2-[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]ethylamino]propanamide Chemical compound C=1C=C(OCCNCCC(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 VTECYVNYNQFWBB-FLYQRFDZSA-N 0.000 description 1
• MDBARDSTXONTFS-MPCSEPLMSA-N 3-[3-[3-methyl-4-[[5-propan-2-yl-3-[(2s,3r,4s,5r,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-MPCSEPLMSA-N 0.000 description 1
• TXWKDYCDLHHIFA-RHBSMATHSA-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]-1-piperazin-1-ylpropan-1-one Chemical compound C=1C=C(OCCCNCCC(=O)N2CCNCC2)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 TXWKDYCDLHHIFA-RHBSMATHSA-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
• IWALJJXAPFCSCL-FBFPUXADSA-N 3-[benzyl-[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]propyl]amino]propanamide Chemical compound C=1C=C(OCCCN(CCC(N)=O)CC=2C=CC=CC=2)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 IWALJJXAPFCSCL-FBFPUXADSA-N 0.000 description 1
• UVUYEFLGRZTPGJ-FLYQRFDZSA-N 3-amino-n-[3-[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]propyl]propanamide Chemical compound C=1C=C(OCCCNC(=O)CCN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UVUYEFLGRZTPGJ-FLYQRFDZSA-N 0.000 description 1
• OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
• GAGJMOQGABUOBK-UHFFFAOYSA-N 3-aminopropanamide;hydrochloride Chemical compound Cl.NCCC(N)=O GAGJMOQGABUOBK-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• DPLJNTWBXCKJOL-UHFFFAOYSA-N 3-bromo-4,5-diethoxybenzonitrile Chemical compound CCOC1=CC(C#N)=CC(Br)=C1OCC DPLJNTWBXCKJOL-UHFFFAOYSA-N 0.000 description 1
• MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 description 1
• ZGRIPYHIFXGCHR-UHFFFAOYSA-N 3-o-[2-[(4-fluorophenyl)methyl-methylamino]ethyl] 5-o-propan-2-yl 4-(1,3-benzodioxol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C=1C=CC=2OCOC=2C=1C1C(C(=O)OC(C)C)=C(C)NC(C)=C1C(=O)OCCN(C)CC1=CC=C(F)C=C1 ZGRIPYHIFXGCHR-UHFFFAOYSA-N 0.000 description 1
• XTFPDGZNWTZCMF-DHZHZOJOSA-N 3-o-methyl 5-o-[(e)-3-phenylprop-2-enyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC\C=C\C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XTFPDGZNWTZCMF-DHZHZOJOSA-N 0.000 description 1
• LINVVMHRTUSXHL-GGVPDPBRSA-N 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1C2=C2C(=O)C[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 LINVVMHRTUSXHL-GGVPDPBRSA-N 0.000 description 1
• IPVXPDWYJCWDIK-LILOYGOGSA-N 4-(2-hydroxyethyl)-n-[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]propyl]piperazine-1-carboxamide Chemical compound C=1C=C(OCCCNC(=O)N2CCN(CCO)CC2)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 IPVXPDWYJCWDIK-LILOYGOGSA-N 0.000 description 1
• GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• HPTISECXMUCRSR-UHFFFAOYSA-N 4-(3-phenylmethoxypropoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCCCOCC1=CC=CC=C1 HPTISECXMUCRSR-UHFFFAOYSA-N 0.000 description 1
• OEBIVOHKFYSBPE-UHFFFAOYSA-N 4-Benzyloxybenzyl alcohol Chemical compound C1=CC(CO)=CC=C1OCC1=CC=CC=C1 OEBIVOHKFYSBPE-UHFFFAOYSA-N 0.000 description 1
• LUPJXXHWXBKHOO-DYVFJYSZSA-N 4-[(2r)-2-[[(2r)-2-hydroxy-2-phenylethyl]amino]propyl]benzoic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=CC=CC=1)C1=CC=C(C(O)=O)C=C1 LUPJXXHWXBKHOO-DYVFJYSZSA-N 0.000 description 1
• LGSOKZOQANLOEU-UHFFFAOYSA-N 4-[2-(2,4-dioxo-1,3-thiazolidin-5-yl)ethoxy]benzonitrile Chemical compound S1C(=O)NC(=O)C1CCOC1=CC=C(C#N)C=C1 LGSOKZOQANLOEU-UHFFFAOYSA-N 0.000 description 1
• GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 1
• MJRGSRRZKSJHOE-UHFFFAOYSA-N 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC=1ON=C(C)C=1C MJRGSRRZKSJHOE-UHFFFAOYSA-N 0.000 description 1
• NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
• MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
• PCAZCAZVHLGDBA-UHFFFAOYSA-N 5-[[4-(2-indol-1-ylethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCCN1C2=CC=CC=C2C=C1 PCAZCAZVHLGDBA-UHFFFAOYSA-N 0.000 description 1
• IMVDZFOSXJSXFP-UHFFFAOYSA-N 5-chloro-2-propyl-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carbaldehyde Chemical compound CCCC1=NC(Cl)=C(C=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 IMVDZFOSXJSXFP-UHFFFAOYSA-N 0.000 description 1
• RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 1
• LWXHLNHAYCDUGT-UHFFFAOYSA-N 5-phenylmethoxy-1h-pyrazole Chemical class C=1C=CC=CC=1COC=1C=CNN=1 LWXHLNHAYCDUGT-UHFFFAOYSA-N 0.000 description 1
• VBMYXYVAQPTQCN-KQDNOMNESA-N 5-propan-2-yl-4-[[4-[3-(sulfamoylamino)propoxy]phenyl]methyl]-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1h-pyrazole Chemical compound C=1C=C(OCCCNS(N)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VBMYXYVAQPTQCN-KQDNOMNESA-N 0.000 description 1
• SLXTWXQUEZSSTJ-UHFFFAOYSA-N 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1(C=2N=CC(=CC=2)C(O)=O)CC1 SLXTWXQUEZSSTJ-UHFFFAOYSA-N 0.000 description 1
• RBSGUQYXRDKPAE-QFIPXVFZSA-N 6-[4-[2-[[(2s)-3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]-2-methylpropyl]phenoxy]pyridine-3-carboxamide Chemical compound C([C@H](O)COC=1C=2C3=CC=CC=C3NC=2C=CC=1)NC(C)(C)CC(C=C1)=CC=C1OC1=CC=C(C(N)=O)C=N1 RBSGUQYXRDKPAE-QFIPXVFZSA-N 0.000 description 1
• DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 108010023016 A 71378 Proteins 0.000 description 1
• ITZMJCSORYKOSI-AJNGGQMLSA-N APGPR Enterostatin Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1[C@H](C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)CCC1 ITZMJCSORYKOSI-AJNGGQMLSA-N 0.000 description 1
• DTDZLJHKVNTQGZ-GOSISDBHSA-N AZD7545 Chemical compound C1=CC(C(=O)N(C)C)=CC=C1S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 DTDZLJHKVNTQGZ-GOSISDBHSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 241000260897 Acidota Species 0.000 description 1
• DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-UHFFFAOYSA-N 0.000 description 1
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
• 108060003345 Adrenergic Receptor Proteins 0.000 description 1
• 102000017910 Adrenergic receptor Human genes 0.000 description 1
• 241001514645 Agonis Species 0.000 description 1
• 102000006822 Agouti Signaling Protein Human genes 0.000 description 1
• 108010072151 Agouti Signaling Protein Proteins 0.000 description 1
• FHHHOYXPRDYHEZ-COXVUDFISA-N Alacepril Chemical compound CC(=O)SC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 FHHHOYXPRDYHEZ-COXVUDFISA-N 0.000 description 1
• 102000016912 Aldehyde Reductase Human genes 0.000 description 1
• 108010053754 Aldehyde reductase Proteins 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 229940127438 Amylin Agonists Drugs 0.000 description 1
• 241000272517 Anseriformes Species 0.000 description 1
• NCUCGYYHUFIYNU-UHFFFAOYSA-N Aranidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)=O)C1C1=CC=CC=C1[N+]([O-])=O NCUCGYYHUFIYNU-UHFFFAOYSA-N 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• 102100027936 Attractin Human genes 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
• FBMCYYWIBYEOST-GJFSDDNBSA-N BIBO-3304 Chemical compound OC(=O)C(F)(F)F.N([C@H](CCCNC(=N)N)C(=O)NCC=1C=CC(CNC(N)=O)=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 FBMCYYWIBYEOST-GJFSDDNBSA-N 0.000 description 1
• 108010073982 BQ 610 Proteins 0.000 description 1
• XEMPUKIZUCIZEY-YSCHMLPRSA-N Barnidipine hydrochloride Chemical compound Cl.C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=CC([N+]([O-])=O)=C1 XEMPUKIZUCIZEY-YSCHMLPRSA-N 0.000 description 1
• 108010081589 Becaplermin Proteins 0.000 description 1
• BWSSMIJUDVUASQ-UHFFFAOYSA-N Benzylhydrochlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 BWSSMIJUDVUASQ-UHFFFAOYSA-N 0.000 description 1
• 108010051479 Bombesin Proteins 0.000 description 1
• 102000013585 Bombesin Human genes 0.000 description 1
• 235000011960 Brassica ruvo Nutrition 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
• 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
• OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 description 1
• IOIFDQGQRNVROG-UHFFFAOYSA-N CCCCNC(=O)N=C Chemical compound CCCCNC(=O)N=C IOIFDQGQRNVROG-UHFFFAOYSA-N 0.000 description 1
• 108010055448 CJC 1131 Proteins 0.000 description 1
• PHKYGBHARUTZOY-UHFFFAOYSA-N CKD-711 Natural products OC1C(O)C(NC2C(C(O)C(O)C3(CO)OC32)O)C(CO)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O PHKYGBHARUTZOY-UHFFFAOYSA-N 0.000 description 1
• QLTVVOATEHFXLT-UHFFFAOYSA-N Cadralazine Chemical compound CCOC(=O)NNC1=CC=C(N(CC)CC(C)O)N=N1 QLTVVOATEHFXLT-UHFFFAOYSA-N 0.000 description 1
• 102000055006 Calcitonin Human genes 0.000 description 1
• 108060001064 Calcitonin Proteins 0.000 description 1
• 229940122820 Cannabinoid receptor antagonist Drugs 0.000 description 1
• 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 1
• 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 1
• 229940122184 Carnitine palmitoyltransferase inhibitor Drugs 0.000 description 1
• 108010078791 Carrier Proteins Proteins 0.000 description 1
• RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
• 101800001982 Cholecystokinin Proteins 0.000 description 1
• 102100025841 Cholecystokinin Human genes 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 1
• 102100031614 Ciliary neurotrophic factor Human genes 0.000 description 1
• KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 description 1
• BMOVQUBVGICXQN-UHFFFAOYSA-N Clinofibrate Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1C1(C=2C=CC(OC(C)(CC)C(O)=O)=CC=2)CCCCC1 BMOVQUBVGICXQN-UHFFFAOYSA-N 0.000 description 1
• ZNIFSRGNXRYGHF-UHFFFAOYSA-N Clonidine hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1 ZNIFSRGNXRYGHF-UHFFFAOYSA-N 0.000 description 1
• 102100035932 Cocaine- and amphetamine-regulated transcript protein Human genes 0.000 description 1
• 229920000230 Colestilan Polymers 0.000 description 1
• 206010010356 Congenital anomaly Diseases 0.000 description 1
• 206010010774 Constipation Diseases 0.000 description 1
• YVIXXPCJZAUQHJ-YGRLFVJLSA-N Cp-114271 Chemical compound C([C@@H](C)NC[C@H](O)C=1N=C(SC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C=C1 YVIXXPCJZAUQHJ-YGRLFVJLSA-N 0.000 description 1
• 241000484025 Cuniculus Species 0.000 description 1
• FDJCVHVKXFIEPJ-JCNFZFLDSA-N Delapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 FDJCVHVKXFIEPJ-JCNFZFLDSA-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
• 206010012655 Diabetic complications Diseases 0.000 description 1
• 206010012735 Diarrhoea Diseases 0.000 description 1
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 1
• 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 description 1
• 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 description 1
• 229940097420 Diuretic Drugs 0.000 description 1
• 108010061435 Enalapril Proteins 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• LFMYNZPAVPMEGP-PIDGMYBPSA-N Fluvoxamine maleate Chemical compound OC(=O)\C=C/C(O)=O.COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 LFMYNZPAVPMEGP-PIDGMYBPSA-N 0.000 description 1
• 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
• 108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
• 102000005915 GABA Receptors Human genes 0.000 description 1
• 108010005551 GABA Receptors Proteins 0.000 description 1
• QTQMRBZOBKYXCG-MHZLTWQESA-N GW 1929 Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCN(C)C=1N=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 QTQMRBZOBKYXCG-MHZLTWQESA-N 0.000 description 1
• GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 1
• 102400001370 Galanin Human genes 0.000 description 1
• 101800002068 Galanin Proteins 0.000 description 1
• XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 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
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 1
• 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 1
• 102000030595 Glucokinase Human genes 0.000 description 1
• 108010021582 Glucokinase Proteins 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 229920002527 Glycogen Polymers 0.000 description 1
• 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
• 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• DGFYECXYGUIODH-UHFFFAOYSA-N Guanfacine hydrochloride Chemical compound Cl.NC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl DGFYECXYGUIODH-UHFFFAOYSA-N 0.000 description 1
• LJIZUXQINHXGAO-ITWZMISCSA-N HR 780 Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 LJIZUXQINHXGAO-ITWZMISCSA-N 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000697936 Homo sapiens Attractin Proteins 0.000 description 1
• 101000715592 Homo sapiens Cocaine- and amphetamine-regulated transcript protein Proteins 0.000 description 1
• 101000976075 Homo sapiens Insulin Proteins 0.000 description 1
• OMCPLEZZPVJJIS-UHFFFAOYSA-N Hypadil (TN) Chemical compound C1C(O[N+]([O-])=O)COC2=C1C=CC=C2OCC(O)CNC(C)C OMCPLEZZPVJJIS-UHFFFAOYSA-N 0.000 description 1
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
• KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 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
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• 102000007330 LDL Lipoproteins Human genes 0.000 description 1
• 108010007622 LDL Lipoproteins Proteins 0.000 description 1
• 108010018112 LY 315902 Proteins 0.000 description 1
• WTOVRSWDBLIFHU-UHFFFAOYSA-N Lemildipine Chemical compound COC(=O)C1=C(C)NC(COC(N)=O)=C(C(=O)OC(C)C)C1C1=CC=CC(Cl)=C1Cl WTOVRSWDBLIFHU-UHFFFAOYSA-N 0.000 description 1
• WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 description 1
• 229940127470 Lipase Inhibitors Drugs 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 1
• 102100022119 Lipoprotein lipase Human genes 0.000 description 1
• 108010007859 Lisinopril Proteins 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 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
• 102400001132 Melanin-concentrating hormone Human genes 0.000 description 1
• 101800002739 Melanin-concentrating hormone Proteins 0.000 description 1
• 102100023726 Melanocortin receptor 3 Human genes 0.000 description 1
• 101710085774 Melanocortin receptor 3 Proteins 0.000 description 1
• 102100023724 Melanocortin receptor 4 Human genes 0.000 description 1
• 101710085775 Melanocortin receptor 4 Proteins 0.000 description 1
• 101800001751 Melanocyte-stimulating hormone alpha Proteins 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
• JXRAXHBVZQZSIC-JKVLGAQCSA-N Moexipril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 JXRAXHBVZQZSIC-JKVLGAQCSA-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
• WPNJAUFVNXKLIM-UHFFFAOYSA-N Moxonidine Chemical compound COC1=NC(C)=NC(Cl)=C1NC1=NCCN1 WPNJAUFVNXKLIM-UHFFFAOYSA-N 0.000 description 1
• WGZDBVOTUVNQFP-UHFFFAOYSA-N N-(1-phthalazinylamino)carbamic acid ethyl ester Chemical compound C1=CC=C2C(NNC(=O)OCC)=NN=CC2=C1 WGZDBVOTUVNQFP-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 102000007072 Nerve Growth Factors Human genes 0.000 description 1
• 102400001103 Neurotensin Human genes 0.000 description 1
• 101800001814 Neurotensin Proteins 0.000 description 1
• KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-UHFFFAOYSA-N 0.000 description 1
• VRAHPESAMYMDQI-UHFFFAOYSA-N Nicomol Chemical compound C1CCC(COC(=O)C=2C=NC=CC=2)(COC(=O)C=2C=NC=CC=2)C(O)C1(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 VRAHPESAMYMDQI-UHFFFAOYSA-N 0.000 description 1
• FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 102000001490 Opioid Peptides Human genes 0.000 description 1
• 108010093625 Opioid Peptides Proteins 0.000 description 1
• 229940123730 Orexin receptor antagonist Drugs 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 101710176384 Peptide 1 Proteins 0.000 description 1
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
• GHUUBYQTCDQWRA-UHFFFAOYSA-N Pioglitazone hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GHUUBYQTCDQWRA-UHFFFAOYSA-N 0.000 description 1
• 229920000148 Polycarbophil calcium Polymers 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
• 102100027467 Pro-opiomelanocortin Human genes 0.000 description 1
• 102000003923 Protein Kinase C Human genes 0.000 description 1
• 108090000315 Protein Kinase C Proteins 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• 229940123934 Reductase inhibitor Drugs 0.000 description 1
• LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
• QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
• 208000017442 Retinal disease Diseases 0.000 description 1
• 206010038923 Retinopathy Diseases 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
• AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
• 229940127505 Sodium Channel Antagonists Drugs 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 102100029795 Sodium-dependent glucose transporter 1 Human genes 0.000 description 1
• 101710181093 Sodium-dependent glucose transporter 1 Proteins 0.000 description 1
• 102000005157 Somatostatin Human genes 0.000 description 1
• 108010056088 Somatostatin Proteins 0.000 description 1
• 229940127504 Somatostatin Receptor Agonists Drugs 0.000 description 1
• ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-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
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• 229940127535 Thyroid Hormone Receptor Agonists Drugs 0.000 description 1
• 229940121886 Thyroid hormone receptor agonist Drugs 0.000 description 1
• JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
• VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
• GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 1
• FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 1
• 108010059705 Urocortins Proteins 0.000 description 1
• 102000005630 Urocortins Human genes 0.000 description 1
• MVMIPBPFTZGTBS-UHFFFAOYSA-N Vatanidipine hydrochloride Chemical compound Cl.Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=2C=CC(=CC=2)N2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 MVMIPBPFTZGTBS-UHFFFAOYSA-N 0.000 description 1
• 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
• FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
• AIHIHVZYAAMDPM-MRVPVSSYSA-N [(2r)-oxiran-2-yl]methyl 3-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)OC[C@@H]2OC2)=C1 AIHIHVZYAAMDPM-MRVPVSSYSA-N 0.000 description 1
• POWBGDGNUPSGCX-BDOIURIFSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-(2-morpholin-4-ylethylcarbamoylamino)propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(=O)NCCN2CCOCC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O POWBGDGNUPSGCX-BDOIURIFSA-N 0.000 description 1
• PRQNHCGPLRRNME-RAAUJUNPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-(methanesulfonamido)propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNS(C)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O PRQNHCGPLRRNME-RAAUJUNPSA-N 0.000 description 1
• HRTONKQMXXTSSP-PDTCTMLJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(1-amino-2-methyl-1-oxopropan-2-yl)-(2-nitrophenyl)sulfonylamino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN(C(C)(C)C(N)=O)S(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O HRTONKQMXXTSSP-PDTCTMLJSA-N 0.000 description 1
• OGZIBJWTRALJMS-QRRWAWJYSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(1-amino-2-methyl-1-oxopropan-2-yl)amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(C)(C)C(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OGZIBJWTRALJMS-QRRWAWJYSA-N 0.000 description 1
• IKEGEHTWLLTRRS-TWMFCQFCSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(2-amino-2-oxoethyl)-(2-nitrophenyl)sulfonylamino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCN(CC(N)=O)S(=O)(=O)C=2C(=CC=CC=2)[N+]([O-])=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O IKEGEHTWLLTRRS-TWMFCQFCSA-N 0.000 description 1
• WQJYAQWFVBQAKV-NTWRQFCJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(2-aminoacetyl)amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(=O)CN)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O WQJYAQWFVBQAKV-NTWRQFCJSA-N 0.000 description 1
• NVWOBNZIBRSMJK-HQTCGSRDSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(C)(C)C(=O)NCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NVWOBNZIBRSMJK-HQTCGSRDSA-N 0.000 description 1
• AAPKZXVLSDBBEO-PDTCTMLJSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(=O)CNC(=O)OCC=2C=CC=CC=2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AAPKZXVLSDBBEO-PDTCTMLJSA-N 0.000 description 1
• BTXOQTZDMXAOKV-SROOKAQWSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[3-(2-hydroxyethylamino)-3-oxopropyl]amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNCCC(=O)NCCO)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O BTXOQTZDMXAOKV-SROOKAQWSA-N 0.000 description 1
• DQYAJHBRCUWTKK-VKTDQVFKSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[[amino(phenylmethoxycarbonylamino)methylidene]amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNC(N)=NC(=O)OCC=2C=CC=CC=2)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O DQYAJHBRCUWTKK-VKTDQVFKSA-N 0.000 description 1
• VFWLTRZFWAOYGW-BBMHUDGSSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[[(2r)-oxiran-2-yl]methoxy]phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OC[C@@H]2OC2)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O VFWLTRZFWAOYGW-BBMHUDGSSA-N 0.000 description 1
• CGJUVYBHXWEGLF-JGALVPIPSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-[[5-propan-2-yl-4-[[4-[3-(sulfamoylamino)propoxy]phenyl]methyl]-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNS(N)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O CGJUVYBHXWEGLF-JGALVPIPSA-N 0.000 description 1
• KHGIMTAOXHDITJ-ILFQJPBHSA-N [(2r,3s,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[2-methyl-4-(3-methylsulfonyloxypropoxy)phenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCOS(C)(=O)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O KHGIMTAOXHDITJ-ILFQJPBHSA-N 0.000 description 1
• XONKJEAOLQRILJ-OMNLYPNUSA-N [(2r,3s,4s,5r,6s)-3,4,5-triacetyloxy-6-[[4-[[4-[3-[(3-amino-3-oxopropyl)amino]propoxy]-2-methylphenyl]methyl]-5-propan-2-yl-1h-pyrazol-3-yl]oxy]oxan-2-yl]methyl acetate Chemical compound C=1C=C(OCCCNCCC(N)=O)C=C(C)C=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O XONKJEAOLQRILJ-OMNLYPNUSA-N 0.000 description 1
• BXNCIERBDJYIQT-PRDVQWLOSA-N [(2r,3s,4s,5r,6s)-6-[2-[3-(1-benzofuran-5-yl)propanoyl]-3-hydroxy-5-methylphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl methyl carbonate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)OC)O[C@H]1OC1=CC(C)=CC(O)=C1C(=O)CCC1=CC=C(OC=C2)C2=C1 BXNCIERBDJYIQT-PRDVQWLOSA-N 0.000 description 1
• FIAINKIUSZGVGX-DKWTVANSSA-N [(2s)-1-amino-1-oxopropan-2-yl]azanium;chloride Chemical compound Cl.C[C@H](N)C(N)=O FIAINKIUSZGVGX-DKWTVANSSA-N 0.000 description 1
• DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
• RYHWEHPQGOJNFM-UHFFFAOYSA-N [2-(oxan-4-yloxy)-4-phenylmethoxyphenyl]methanol Chemical compound C1=C(OC2CCOCC2)C(CO)=CC=C1OCC1=CC=CC=C1 RYHWEHPQGOJNFM-UHFFFAOYSA-N 0.000 description 1
• FDKIDFYIEWFERB-UHFFFAOYSA-N [2-butyl-5-chloro-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol;potassium Chemical compound [K].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 FDKIDFYIEWFERB-UHFFFAOYSA-N 0.000 description 1
• HIILOVHYWAEGDS-QBHOUYDASA-N [3-naphthalen-1-yl-1-[[(1s)-2-(4-phenylphenyl)-1-(2h-tetrazol-5-yl)ethyl]amino]propyl]phosphonic acid Chemical compound C([C@H](NC(CCC=1C2=CC=CC=C2C=CC=1)P(O)(=O)O)C1=NNN=N1)C(C=C1)=CC=C1C1=CC=CC=C1 HIILOVHYWAEGDS-QBHOUYDASA-N 0.000 description 1
• JNLNXPCQHIQTRM-ACJLOTCBSA-N [4-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]phenoxy]methanesulfonic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C1=CC=C(OCS(O)(=O)=O)C=C1 JNLNXPCQHIQTRM-ACJLOTCBSA-N 0.000 description 1
• WUEHURHTEPWPPO-QZTJIDSGSA-N [4-[(4r,5r)-2-[[[2,6-di(propan-2-yl)phenyl]carbamoylamino]methyl]-4,5-dimethyl-1,3-dioxolan-2-yl]phenyl] dihydrogen phosphate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NCC1(C=2C=CC(OP(O)(O)=O)=CC=2)O[C@H](C)[C@@H](C)O1 WUEHURHTEPWPPO-QZTJIDSGSA-N 0.000 description 1
• KNDHRUPPBXRELB-UHFFFAOYSA-M [4-[3-(4-ethylphenyl)butyl]phenyl]-trimethylazanium;chloride Chemical compound [Cl-].C1=CC(CC)=CC=C1C(C)CCC1=CC=C([N+](C)(C)C)C=C1 KNDHRUPPBXRELB-UHFFFAOYSA-M 0.000 description 1
• DOQPXTMNIUCOSY-UHFFFAOYSA-N [4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl]-[2-(3,4-dimethoxyphenyl)ethyl]-methylazanium;chloride Chemical compound [H+].[Cl-].C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 DOQPXTMNIUCOSY-UHFFFAOYSA-N 0.000 description 1
• GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 1
• 229940022663 acetate Drugs 0.000 description 1
• BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 1
• 229960000571 acetazolamide Drugs 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• 229960001466 acetohexamide Drugs 0.000 description 1
• VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
• 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
• 229960001138 acetylsalicylic acid Drugs 0.000 description 1
• 229960003526 acipimox Drugs 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000012190 activator Substances 0.000 description 1
• 102000030621 adenylate cyclase Human genes 0.000 description 1
• 108060000200 adenylate cyclase Proteins 0.000 description 1
• 210000000577 adipose tissue Anatomy 0.000 description 1
• WSLOHMLGIVSUPR-UHFFFAOYSA-N adn-138 Chemical compound C1COC2=CC(Cl)=CC3=C2N1C(=O)C31CC(=O)NC1=O WSLOHMLGIVSUPR-UHFFFAOYSA-N 0.000 description 1
• 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 description 1
• 229950007884 alacepril Drugs 0.000 description 1
• MKOMESMZHZNBIZ-UHFFFAOYSA-M alagebrium Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=C1 MKOMESMZHZNBIZ-UHFFFAOYSA-M 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 125000004450 alkenylene group Chemical group 0.000 description 1
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 125000002947 alkylene group Chemical group 0.000 description 1
• OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
• 229960003459 allopurinol Drugs 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• 239000002163 alpha 1-adrenoceptor agonist Substances 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
• 229960003556 aminophylline Drugs 0.000 description 1
• ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 1
• 229960004005 amlodipine besylate Drugs 0.000 description 1
• LVEXHFZHOIWIIP-UHFFFAOYSA-N amosulalol Chemical compound COC1=CC=CC=C1OCCNCC(O)C1=CC=C(C)C(S(N)(=O)=O)=C1 LVEXHFZHOIWIIP-UHFFFAOYSA-N 0.000 description 1
• 229950010351 amosulalol Drugs 0.000 description 1
• 229940025084 amphetamine Drugs 0.000 description 1
• 239000003392 amylase inhibitor Substances 0.000 description 1
• 230000006538 anaerobic glycolysis Effects 0.000 description 1
• 229940127282 angiotensin receptor antagonist Drugs 0.000 description 1
• 230000002421 anti-septic effect Effects 0.000 description 1
• 239000003472 antidiabetic agent Substances 0.000 description 1
• 229940125708 antidiabetic agent Drugs 0.000 description 1
• 229940127088 antihypertensive drug Drugs 0.000 description 1
• 229940064004 antiseptic throat preparations Drugs 0.000 description 1
• 235000019789 appetite Nutrition 0.000 description 1
• 230000036528 appetite Effects 0.000 description 1
• 235000021229 appetite regulation Nutrition 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 229950007556 aranidipine Drugs 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229960002274 atenolol Drugs 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 239000012752 auxiliary agent Substances 0.000 description 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
• 150000001540 azides Chemical class 0.000 description 1
• 229950009252 beclobrate Drugs 0.000 description 1
• YWQGBCXVCXMSLJ-UHFFFAOYSA-N beclobrate Chemical compound C1=CC(OC(C)(CC)C(=O)OCC)=CC=C1CC1=CC=C(Cl)C=C1 YWQGBCXVCXMSLJ-UHFFFAOYSA-N 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 229960004916 benidipine Drugs 0.000 description 1
• QZVNQOLPLYWLHQ-ZEQKJWHPSA-N benidipine Chemical compound C1([C@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@H]2CN(CC=3C=CC=CC=3)CCC2)=CC=CC([N+]([O-])=O)=C1 QZVNQOLPLYWLHQ-ZEQKJWHPSA-N 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 1
• 229960002529 benzbromarone Drugs 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
• 229950003745 benzfetamine Drugs 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• YXKTVDFXDRQTKV-HNNXBMFYSA-N benzphetamine Chemical compound C([C@H](C)N(C)CC=1C=CC=CC=1)C1=CC=CC=C1 YXKTVDFXDRQTKV-HNNXBMFYSA-N 0.000 description 1
• IUGQFMIATSVYLK-UHFFFAOYSA-N benzyl 2-(4-hydroxyphenyl)acetate Chemical compound C1=CC(O)=CC=C1CC(=O)OCC1=CC=CC=C1 IUGQFMIATSVYLK-UHFFFAOYSA-N 0.000 description 1
• CBNPLAUVQUQTRU-UHFFFAOYSA-N benzyl 4-(3-ethoxy-2,2-dimethyl-3-oxopropanoyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)C(C)(C)C(=O)OCC)CCN1C(=O)OCC1=CC=CC=C1 CBNPLAUVQUQTRU-UHFFFAOYSA-N 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• PIIYOXFGVHEMGI-UHFFFAOYSA-N benzyl n-(1-amino-2-methyl-1-oxopropan-2-yl)carbamate Chemical compound NC(=O)C(C)(C)NC(=O)OCC1=CC=CC=C1 PIIYOXFGVHEMGI-UHFFFAOYSA-N 0.000 description 1
• KZEBEQIWVUMFSB-LBPRGKRZSA-N benzyl n-[(5s)-5,6-diamino-6-oxohexyl]carbamate Chemical compound NC(=O)[C@@H](N)CCCCNC(=O)OCC1=CC=CC=C1 KZEBEQIWVUMFSB-LBPRGKRZSA-N 0.000 description 1
• LVZVXGHWVOMHEU-UHFFFAOYSA-N benzyl n-[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]carbamate Chemical compound OCCNC(=O)C(C)(C)NC(=O)OCC1=CC=CC=C1 LVZVXGHWVOMHEU-UHFFFAOYSA-N 0.000 description 1
• VSWGMILRXVYWEK-JGALVPIPSA-N benzyl n-[n'-[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]propyl]carbamimidoyl]carbamate Chemical compound C=1C=C(OCCCNC(N)=NC(=O)OCC=2C=CC=CC=2)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 VSWGMILRXVYWEK-JGALVPIPSA-N 0.000 description 1
• CTOUWUYDDUSBQE-UHFFFAOYSA-N benzyl piperazine-1-carboxylate Chemical compound C1CNCCN1C(=O)OCC1=CC=CC=C1 CTOUWUYDDUSBQE-UHFFFAOYSA-N 0.000 description 1
• UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 1
• 229950007003 benzylhydrochlorothiazide Drugs 0.000 description 1
• 229960004156 bepridil hydrochloride Drugs 0.000 description 1
• UEECHQPWQHYEDE-UHFFFAOYSA-N bepridil hydrochloride monohydrate Chemical compound [H+].O.[Cl-].C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UEECHQPWQHYEDE-UHFFFAOYSA-N 0.000 description 1
• 229950005357 bervastatin Drugs 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 229960002938 bexarotene Drugs 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
• KUWBXRGRMQZCSS-HSZRJFAPSA-N bibp-3226 Chemical compound N([C@H](CCCN=C(N)N)C(=O)NCC=1C=CC(O)=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 KUWBXRGRMQZCSS-HSZRJFAPSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 229950004495 binifibrate Drugs 0.000 description 1
• BFYRHDVAEJIBON-UHFFFAOYSA-N binifibrate Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 BFYRHDVAEJIBON-UHFFFAOYSA-N 0.000 description 1
• 230000000975 bioactive effect Effects 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 1
• RSMSFENOAKAUJU-UHFFFAOYSA-L bis[[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy]aluminum;hydrate Chemical compound O.C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)O[Al]OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RSMSFENOAKAUJU-UHFFFAOYSA-L 0.000 description 1
• 229960002781 bisoprolol Drugs 0.000 description 1
• 230000036772 blood pressure Effects 0.000 description 1
• 230000037396 body weight Effects 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
• 229960001035 bopindolol Drugs 0.000 description 1
• 229960003065 bosentan Drugs 0.000 description 1
• SXTRWVVIEPWAKM-UHFFFAOYSA-N bosentan hydrate Chemical compound O.COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SXTRWVVIEPWAKM-UHFFFAOYSA-N 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 229960002802 bromocriptine Drugs 0.000 description 1
• NOJMTMIRQRDZMT-GSPXQYRGSA-N bromocriptine methanesulfonate Chemical compound CS(O)(=O)=O.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 NOJMTMIRQRDZMT-GSPXQYRGSA-N 0.000 description 1
• DQGFCLJXYFXXIJ-LFIBNONCSA-N budralazine Chemical compound C1=CC=C2C(N/N=C(C)/C=C(C)C)=NN=CC2=C1 DQGFCLJXYFXXIJ-LFIBNONCSA-N 0.000 description 1
• 229950001730 budralazine Drugs 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 229960004111 buformin Drugs 0.000 description 1
• XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
• 229960003612 bunazosin hydrochloride Drugs 0.000 description 1
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
• 229960001058 bupropion Drugs 0.000 description 1
• SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960005211 cadralazine Drugs 0.000 description 1
• BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
• 229960004015 calcitonin Drugs 0.000 description 1
• 229940095498 calcium polycarbophil Drugs 0.000 description 1
• QEVLNUAVAONTEW-UZYHXJQGSA-L calcium;(2s)-4-[(3as,7ar)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-2-benzyl-4-oxobutanoate;dihydrate Chemical compound O.O.[Ca+2].C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1.C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)[O-])C1=CC=CC=C1 QEVLNUAVAONTEW-UZYHXJQGSA-L 0.000 description 1
• 229950001261 camiglibose Drugs 0.000 description 1
• 239000003536 cannabinoid receptor antagonist Substances 0.000 description 1
• 210000000692 cap cell Anatomy 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 229960000830 captopril Drugs 0.000 description 1
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
• 229960003362 carbutamide Drugs 0.000 description 1
• 238000010531 catalytic reduction reaction Methods 0.000 description 1
• 230000005779 cell damage Effects 0.000 description 1
• 208000037887 cell injury Diseases 0.000 description 1
• 229940083181 centrally acting adntiadrenergic agent methyldopa 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
• 229960005110 cerivastatin Drugs 0.000 description 1
• 229950005749 ceronapril Drugs 0.000 description 1
• MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 description 1
• 229950002397 cetilistat Drugs 0.000 description 1
• JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 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(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=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 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
• ZWGWSFHAZWNQQE-VPLSKCCHSA-N chembl1836102 Chemical compound Cl.C1=CC=C2C(N)=NC(NC[C@@H]3CC[C@@H](CNS(=O)(=O)C=4C=C5C=CC=CC5=CC=4)CC3)=NC2=C1 ZWGWSFHAZWNQQE-VPLSKCCHSA-N 0.000 description 1
• KFUIXDNQSMKKJQ-ZLFMSJRASA-N chembl439883 Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1N(C(=O)CNC(=O)[C@H]2NC(=O)CC2)CCC1 KFUIXDNQSMKKJQ-ZLFMSJRASA-N 0.000 description 1
• WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
• 229960001761 chlorpropamide Drugs 0.000 description 1
• 229940107137 cholecystokinin Drugs 0.000 description 1
• 230000001906 cholesterol absorption Effects 0.000 description 1
• 239000003354 cholesterol ester transfer protein inhibitor Substances 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
• 229960005025 cilazapril Drugs 0.000 description 1
• JQRZBPFGBRIWSN-YOTVLOEGSA-N cilazapril monohydrate Chemical compound O.C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 JQRZBPFGBRIWSN-YOTVLOEGSA-N 0.000 description 1
• RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
• 229960004588 cilostazol Drugs 0.000 description 1
• 229960002174 ciprofibrate Drugs 0.000 description 1
• KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• PHKYGBHARUTZOY-KTVVNDHVSA-N ckd-711 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@]2(CO)O[C@@H]21)O)CO)[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O PHKYGBHARUTZOY-KTVVNDHVSA-N 0.000 description 1
• 229950003072 clinofibrate Drugs 0.000 description 1
• LRXXRIXDSAEIOR-ZDUSSCGKSA-N clobenzorex Chemical compound C([C@H](C)NCC=1C(=CC=CC=1)Cl)C1=CC=CC=C1 LRXXRIXDSAEIOR-ZDUSSCGKSA-N 0.000 description 1
• 229960002492 clobenzorex 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
• 229960002925 clonidine hydrochloride Drugs 0.000 description 1
• 239000005515 coenzyme Substances 0.000 description 1
• 229960004095 colestilan Drugs 0.000 description 1
• 229950010523 colestolone Drugs 0.000 description 1
• 229960001678 colestyramine Drugs 0.000 description 1
• 229960004092 conivaptan hydrochloride Drugs 0.000 description 1
• BTYHAFSDANBVMJ-UHFFFAOYSA-N conivaptan hydrochloride Chemical compound Cl.C12=CC=CC=C2C=2NC(C)=NC=2CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 BTYHAFSDANBVMJ-UHFFFAOYSA-N 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• DZFSTAUMUPHORN-NRFANRHFSA-N cyclohexyl-[[4-[2-[[(2s)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenoxy]methyl]phosphinic acid Chemical compound C([C@H](O)COC=1C=CC(O)=CC=1)NCCC(C=C1)=CC=C1OCP(O)(=O)C1CCCCC1 DZFSTAUMUPHORN-NRFANRHFSA-N 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229950003040 dalvastatin Drugs 0.000 description 1
• 230000006735 deficit Effects 0.000 description 1
• 229960000632 dexamfetamine Drugs 0.000 description 1
• 238000000502 dialysis Methods 0.000 description 1
• 125000003963 dichloro group Chemical group Cl* 0.000 description 1
• JFCMAIACBGBZRX-UHFFFAOYSA-N dichloromethoxybenzene Chemical compound ClC(Cl)OC1=CC=CC=C1 JFCMAIACBGBZRX-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• UELKSYXXNGHTSE-UHFFFAOYSA-N diethyl 2,2-dimethylpropanedioate Chemical compound CCOC(=O)C(C)(C)C(=O)OCC UELKSYXXNGHTSE-UHFFFAOYSA-N 0.000 description 1
• 229960004890 diethylpropion Drugs 0.000 description 1
• XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 description 1
• 229960001079 dilazep Drugs 0.000 description 1
• VILIWRRWAWKXRW-UHFFFAOYSA-N dilazep dihydrochloride Chemical compound [Cl-].[Cl-].COC1=C(OC)C(OC)=CC(C(=O)OCCC[NH+]2CC[NH+](CCCOC(=O)C=3C=C(OC)C(OC)=C(OC)C=3)CCC2)=C1 VILIWRRWAWKXRW-UHFFFAOYSA-N 0.000 description 1
• 229960005316 diltiazem hydrochloride Drugs 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
• IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
• 229960002768 dipyridamole Drugs 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• FXHKSTYWSZZOBF-NTEVMMBTSA-L disodium;(3s)-4-[2-[1-(4-fluorophenyl)-3-propan-2-ylindol-2-yl]ethynyl-oxidophosphoryl]-3-hydroxybutanoate Chemical compound [Na+].[Na+].C12=CC=CC=C2C(C(C)C)=C(C#CP([O-])(=O)C[C@@H](O)CC([O-])=O)N1C1=CC=C(F)C=C1 FXHKSTYWSZZOBF-NTEVMMBTSA-L 0.000 description 1
• FUZBPOHHSBDTJQ-CFOQQKEYSA-L disodium;5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Na+].[Na+].C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C([O-])=O)C([O-])=O)C)=CC=CC(Cl)=C1 FUZBPOHHSBDTJQ-CFOQQKEYSA-L 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 229940030606 diuretics Drugs 0.000 description 1
• DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
• VJECBOKJABCYMF-UHFFFAOYSA-N doxazosin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 VJECBOKJABCYMF-UHFFFAOYSA-N 0.000 description 1
• 229960000220 doxazosin mesylate Drugs 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 235000006694 eating habits Nutrition 0.000 description 1
• ODUOJXZPIYUATO-LJQANCHMSA-N ecadotril Chemical compound C([C@H](CSC(=O)C)C(=O)NCC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 ODUOJXZPIYUATO-LJQANCHMSA-N 0.000 description 1
• 229950001184 ecadotril Drugs 0.000 description 1
• 229950003102 efonidipine Drugs 0.000 description 1
• 229950010020 elgodipine Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
• 229960000309 enalapril maleate Drugs 0.000 description 1
• 229950002375 englitazone Drugs 0.000 description 1
• 230000006862 enzymatic digestion Effects 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
• 229950010170 epalrestat Drugs 0.000 description 1
• CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-UHFFFAOYSA-N 0.000 description 1
• 229960000573 eprosartan mesylate Drugs 0.000 description 1
• DJSLTDBPKHORNY-XMMWENQYSA-N eprosartan methanesulfonate Chemical compound CS(O)(=O)=O.C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 DJSLTDBPKHORNY-XMMWENQYSA-N 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
• ZADJRRFMOOACHL-WQICJITCSA-N ethyl (e,3s,5r)-7-[4-(4-fluorophenyl)spiro[chromene-2,1'-cyclopentane]-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C12=CC=CC=C2OC2(CCCC2)C(/C=C/[C@H](O)C[C@H](O)CC(=O)OCC)=C1C1=CC=C(F)C=C1 ZADJRRFMOOACHL-WQICJITCSA-N 0.000 description 1
• PWRYMMTWSPKRJD-NSLUPJTDSA-N ethyl 3-[(7r)-7-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]propanoate;hydrochloride Chemical compound Cl.C1([C@@H](O)CN[C@@H]2CCC3=CC=C(C=C3C2)CCC(=O)OCC)=CC=CC(Cl)=C1 PWRYMMTWSPKRJD-NSLUPJTDSA-N 0.000 description 1
• XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
• 229960003501 etofibrate Drugs 0.000 description 1
• XXRVYAFBUDSLJX-UHFFFAOYSA-N etofibrate Chemical compound C=1C=CN=CC=1C(=O)OCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XXRVYAFBUDSLJX-UHFFFAOYSA-N 0.000 description 1
• 229950006213 etomoxir Drugs 0.000 description 1
• 229960001519 exenatide Drugs 0.000 description 1
• 238000009207 exercise therapy 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
• ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 1
• FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
• NGOGFTYYXHNFQH-UHFFFAOYSA-N fasudil Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 NGOGFTYYXHNFQH-UHFFFAOYSA-N 0.000 description 1
• 229960002435 fasudil Drugs 0.000 description 1
• 229960003580 felodipine Drugs 0.000 description 1
• 229960001582 fenfluramine Drugs 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
• 229940125753 fibrate Drugs 0.000 description 1
• WAAPEIZFCHNLKK-PELKAZGASA-N fidarestat Chemical compound C([C@@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-PELKAZGASA-N 0.000 description 1
• 229950007256 fidarestat Drugs 0.000 description 1
• 229960002107 fluvoxamine maleate Drugs 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 229940013688 formic acid Drugs 0.000 description 1
• 238000010575 fractional recrystallization Methods 0.000 description 1
• 229960002737 fructose Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
• AIWAEWBZDJARBJ-PXUUZXDZSA-N fz7co35x2s Chemical compound 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](CCCN=C(N)N)C(=O)N[C@@H](CCCCNC(=O)COCCOCCNC(=O)CCN1C(C=CC1=O)=O)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 AIWAEWBZDJARBJ-PXUUZXDZSA-N 0.000 description 1
• 150000002256 galaktoses Chemical class 0.000 description 1
• 229960000457 gallopamil Drugs 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 229960003627 gemfibrozil Drugs 0.000 description 1
• 229950000806 glenvastatin Drugs 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• 229960001764 glibornuride Drugs 0.000 description 1
• RMTYNAPTNBJHQI-LLDVTBCESA-N glibornuride Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N[C@H]1[C@H](C2(C)C)CC[C@@]2(C)[C@H]1O RMTYNAPTNBJHQI-LLDVTBCESA-N 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
• 229960001381 glipizide Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 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
• MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
• 235000011187 glycerol Nutrition 0.000 description 1
• 229960005150 glycerol Drugs 0.000 description 1
• 229940096919 glycogen Drugs 0.000 description 1
• 229950005514 glycyclamide Drugs 0.000 description 1
• RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 1
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 229960004746 guanfacine hydrochloride Drugs 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• ZUXNZUWOTSUBMN-UHFFFAOYSA-N hydralazine hydrochloride Chemical compound Cl.C1=CC=C2C(NN)=NN=CC2=C1 ZUXNZUWOTSUBMN-UHFFFAOYSA-N 0.000 description 1
• 229960005384 hydralazine hydrochloride Drugs 0.000 description 1
• DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 1
• 229960003313 hydroflumethiazide Drugs 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• TWTMQRXNAZGSCE-UHFFFAOYSA-N hydron;[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate;chloride Chemical compound Cl.C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 TWTMQRXNAZGSCE-UHFFFAOYSA-N 0.000 description 1
• 229960002600 icosapent ethyl Drugs 0.000 description 1
• KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
• 229960003409 imidapril hydrochloride Drugs 0.000 description 1
• 229950007327 imirestat Drugs 0.000 description 1
• NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 1
• 229960004569 indapamide Drugs 0.000 description 1
• 229960002056 indoramin Drugs 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 230000016507 interphase Effects 0.000 description 1
• 230000007154 intracellular accumulation Effects 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 229960002198 irbesartan Drugs 0.000 description 1
• YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 229960002479 isosorbide Drugs 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 229960004427 isradipine Drugs 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 229960004340 lacidipine Drugs 0.000 description 1
• GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-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
• 229950005959 lecimibide Drugs 0.000 description 1
• 229950001530 lemildipine Drugs 0.000 description 1
• 229960002162 lercanidipine hydrochloride Drugs 0.000 description 1
• 229960001518 levocarnitine Drugs 0.000 description 1
• YDTFRJLNMPSCFM-YDALLXLXSA-M levothyroxine sodium anhydrous Chemical compound [Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YDTFRJLNMPSCFM-YDALLXLXSA-M 0.000 description 1
• 229960002394 lisinopril Drugs 0.000 description 1
• 150000002641 lithium Chemical group 0.000 description 1
• PPHTXRNHTVLQED-UHFFFAOYSA-N lixivaptan Chemical compound CC1=CC=C(F)C=C1C(=O)NC(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 PPHTXRNHTVLQED-UHFFFAOYSA-N 0.000 description 1
• 229950011475 lixivaptan Drugs 0.000 description 1
• KSMAGQUYOIHWFS-UHFFFAOYSA-N lofexidine Chemical compound N=1CCNC=1C(C)OC1=C(Cl)C=CC=C1Cl KSMAGQUYOIHWFS-UHFFFAOYSA-N 0.000 description 1
• 229960005209 lofexidine Drugs 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• ZEUXAIYYDDCIRX-UHFFFAOYSA-N losartan carboxylic acid Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 ZEUXAIYYDDCIRX-UHFFFAOYSA-N 0.000 description 1
• 229960004844 lovastatin Drugs 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
• 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
• 239000000314 lubricant Substances 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960003963 manidipine Drugs 0.000 description 1
• ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 229960000299 mazindol Drugs 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 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 1
• 239000000336 melanocortin receptor agonist Substances 0.000 description 1
• 229960004329 metformin hydrochloride Drugs 0.000 description 1
• OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
• 125000005394 methallyl group Chemical group 0.000 description 1
• 229960001252 methamphetamine Drugs 0.000 description 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
• FLOSMHQXBMRNHR-DAXSKMNVSA-N methazolamide Chemical compound CC(=O)\N=C1/SC(S(N)(=O)=O)=NN1C FLOSMHQXBMRNHR-DAXSKMNVSA-N 0.000 description 1
• 229960004083 methazolamide Drugs 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• IVAQJHSXBVHUQT-ZVHZXABRSA-N methyl (e)-3-(3,5-dimethoxyphenyl)-2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]prop-2-enoate Chemical compound C=1C=C(OC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C=CC=1/C(C(=O)OC)=C\C1=CC(OC)=CC(OC)=C1 IVAQJHSXBVHUQT-ZVHZXABRSA-N 0.000 description 1
• ZFLBZHXQAMUEFS-KUHUBIRLSA-N methyl 2-[4-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=CC(Cl)=C1 ZFLBZHXQAMUEFS-KUHUBIRLSA-N 0.000 description 1
• MVQOMOXWRUVMOG-UHFFFAOYSA-N methyl 2-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate;hydrochloride Chemical compound Cl.C1=CC(OCC(=O)OC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 MVQOMOXWRUVMOG-UHFFFAOYSA-N 0.000 description 1
• VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
• WTIWDQPRXAVWAR-CVMXSPHISA-N methyl 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]propanoate Chemical compound CC1=CC(OCCCNCCC(=O)OC)=CC=C1CC1=C(C(C)C)NN=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 WTIWDQPRXAVWAR-CVMXSPHISA-N 0.000 description 1
• OIZISCUUSLPUEN-LMORPYAASA-N methyl 4-[(2s)-2-[[(2s)-2-hydroxy-2-phenylethyl]amino]propyl]benzoate;(e)-4-oxopent-2-enoic acid Chemical compound CC(=O)\C=C\C(O)=O.C1=CC(C(=O)OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=CC=C1 OIZISCUUSLPUEN-LMORPYAASA-N 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 1
• 229960002817 metolazone Drugs 0.000 description 1
• AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
• 229950009116 mevastatin Drugs 0.000 description 1
• BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
• VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
• 229960001070 mexiletine hydrochloride Drugs 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
• 229960003365 mitiglinide Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 229960004185 moexipril hydrochloride Drugs 0.000 description 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 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 229960003938 moxonidine Drugs 0.000 description 1
• 229950000546 mozavaptan Drugs 0.000 description 1
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
• CVABPTLRAQIZJU-UHFFFAOYSA-N n'-[3-(2,6-dichloro-4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-n-(oxan-4-yl)ethane-1,2-diamine Chemical compound ClC1=CC(OC)=CC(Cl)=C1C1=C2N=C(C)C=C(NCCNC3CCOCC3)N2N=C1C CVABPTLRAQIZJU-UHFFFAOYSA-N 0.000 description 1
• HNVAYYXAXQZKAG-GPXXLQEOSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-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(=O)NC(C)(CO)CO)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 HNVAYYXAXQZKAG-GPXXLQEOSA-N 0.000 description 1
• HFWUFKSVSAUVOS-GPXXLQEOSA-N n-(1,3-dihydroxypropan-2-yl)-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(=O)NC(CO)CO)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 HFWUFKSVSAUVOS-GPXXLQEOSA-N 0.000 description 1
• YGRQQAUFPWDIDM-FOORKGQUSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-methyl-2-[3-[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(OCCCNC(C)(C)C(=O)NC(C)(C)CO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YGRQQAUFPWDIDM-FOORKGQUSA-N 0.000 description 1
• IAYNHDZSSDUYHY-UHFFFAOYSA-N n-(2-acetyl-4,6-dimethylphenyl)-3-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxamide Chemical compound CC(=O)C1=CC(C)=CC(C)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)C)C=CS1 IAYNHDZSSDUYHY-UHFFFAOYSA-N 0.000 description 1
• YFJUSGDKCDQMNE-UHFFFAOYSA-N n-(2-acetyl-4,6-dimethylphenyl)-3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxamide Chemical compound CC(=O)C1=CC(C)=CC(C)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 YFJUSGDKCDQMNE-UHFFFAOYSA-N 0.000 description 1
• KOJPCSSMDNWJQX-TXKDOCKMSA-N n-(2-hydroxyethyl)-2-methyl-2-[3-[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(OCCCNC(C)(C)C(=O)NCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KOJPCSSMDNWJQX-TXKDOCKMSA-N 0.000 description 1
• ATTFQYSNELCQBB-DEPSJERBSA-N n-(2-hydroxyethyl)-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(=O)NCCO)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 ATTFQYSNELCQBB-DEPSJERBSA-N 0.000 description 1
• LJGUZUROJOJEMI-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[4-(1,3-oxazol-2-yl)phenyl]benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C=2OC=CN=2)=C1C LJGUZUROJOJEMI-UHFFFAOYSA-N 0.000 description 1
• AKWJGQUORCLXED-FOORKGQUSA-N n-(3-hydroxypropyl)-2-methyl-2-[3-[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(OCCCNC(C)(C)C(=O)NCCCO)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AKWJGQUORCLXED-FOORKGQUSA-N 0.000 description 1
• ZOXDRBUOWRDXAY-GPXXLQEOSA-N n-(3-hydroxypropyl)-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(=O)NCCCO)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 ZOXDRBUOWRDXAY-GPXXLQEOSA-N 0.000 description 1
• AUAQMCUOFLALQY-GPXXLQEOSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-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(=O)NC(CO)(CO)CO)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 AUAQMCUOFLALQY-GPXXLQEOSA-N 0.000 description 1
• CMCWIHQJEQYHPX-UHFFFAOYSA-N n-[2-[(2-aminohydrazinyl)methylideneamino]ethyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCN=CNNN CMCWIHQJEQYHPX-UHFFFAOYSA-N 0.000 description 1
• ZIWFFCXXHIUFDF-KQDNOMNESA-N n-[2-[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]ethyl]methanesulfonamide Chemical compound C=1C=C(OCCNS(C)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O ZIWFFCXXHIUFDF-KQDNOMNESA-N 0.000 description 1
• OQZBNLYNFLOKRM-SQKWCZRTSA-N n-[3-[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]propyl]methanesulfonamide Chemical compound C=1C=C(OCCCNS(C)(=O)=O)C=CC=1CC1=C(C(C)C)NN=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OQZBNLYNFLOKRM-SQKWCZRTSA-N 0.000 description 1
• DSEGFUSAJVUFLK-OFNKIYASSA-N n-[5-[(1r)-2-[[(1r)-2-(3-chlorophenyl)-1-[4-(difluoromethoxy)phenyl]ethyl]amino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CN[C@H](CC=2C=C(Cl)C=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1 DSEGFUSAJVUFLK-OFNKIYASSA-N 0.000 description 1
• FUKHGCVTMAEHRG-NRFANRHFSA-N n-[5-[(1r)-2-[bis[4-(difluoromethoxy)phenyl]methylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNC(C=2C=CC(OC(F)F)=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1 FUKHGCVTMAEHRG-NRFANRHFSA-N 0.000 description 1
• LFWCJABOXHSRGC-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-methylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C2=NNN=N2)OCCO)=C1NS(=O)(=O)C1=CC=C(C)C=N1 LFWCJABOXHSRGC-UHFFFAOYSA-N 0.000 description 1
• GBHZRMWZYDRRRK-UHFFFAOYSA-N n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-3,3-dimethylbutanamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C(=CC(=CC=2)C=2OC=CN=2)CNC(=O)CC(C)(C)C)=C1C GBHZRMWZYDRRRK-UHFFFAOYSA-N 0.000 description 1
• TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 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
• 125000005484 neopentoxy group Chemical group 0.000 description 1
• 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
• PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
• PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 description 1
• 239000003900 neurotrophic factor Substances 0.000 description 1
• 150000002814 niacins Chemical class 0.000 description 1
• AIKVCUNQWYTVTO-UHFFFAOYSA-N nicardipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AIKVCUNQWYTVTO-UHFFFAOYSA-N 0.000 description 1
• 229960002289 nicardipine hydrochloride Drugs 0.000 description 1
• 229960000827 niceritrol Drugs 0.000 description 1
• 229950005171 nicofibrate Drugs 0.000 description 1
• RARQHAFNGNPQCZ-UHFFFAOYSA-N nicofibrate Chemical compound C=1C=CN=CC=1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RARQHAFNGNPQCZ-UHFFFAOYSA-N 0.000 description 1
• 229950001071 nicomol Drugs 0.000 description 1
• 229960002497 nicorandil Drugs 0.000 description 1
• LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
• 229960001597 nifedipine Drugs 0.000 description 1
• 229960005366 nilvadipine Drugs 0.000 description 1
• 229950000754 nipradilol Drugs 0.000 description 1
• 229960000227 nisoldipine Drugs 0.000 description 1
• 229960005425 nitrendipine Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
• 239000003399 opiate peptide Substances 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 229960001243 orlistat Drugs 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
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 1
• 229960001816 oxcarbazepine Drugs 0.000 description 1
• CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 1
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
• HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• FEDSNBHHWZEYTP-ZFQYHYQMSA-N penbutolol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 FEDSNBHHWZEYTP-ZFQYHYQMSA-N 0.000 description 1
• 229960004493 penbutolol sulfate Drugs 0.000 description 1
• QGWDKKHSDXWPET-UHFFFAOYSA-E pentabismuth;oxygen(2-);nonahydroxide;tetranitrate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[O-2].[Bi+3].[Bi+3].[Bi+3].[Bi+3].[Bi+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O QGWDKKHSDXWPET-UHFFFAOYSA-E 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
• 125000001151 peptidyl group Chemical group 0.000 description 1
• 208000033808 peripheral neuropathy Diseases 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 229950008557 phenbutamide Drugs 0.000 description 1
• AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 1
• 229960003243 phenformin Drugs 0.000 description 1
• ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
• 229960003562 phentermine Drugs 0.000 description 1
• 229960000395 phenylpropanolamine Drugs 0.000 description 1
• DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
• 230000035479 physiological effects, processes and functions Effects 0.000 description 1
• 229960002827 pioglitazone hydrochloride Drugs 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
• 229960002797 pitavastatin Drugs 0.000 description 1
• 230000001817 pituitary effect Effects 0.000 description 1
• 108010017843 platelet-derived growth factor A Proteins 0.000 description 1
• 108010000685 platelet-derived growth factor AB Proteins 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 229910003446 platinum oxide Inorganic materials 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229950010884 ponalrestat Drugs 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229960003975 potassium Drugs 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
• 239000001508 potassium citrate Substances 0.000 description 1
• 229960002635 potassium citrate Drugs 0.000 description 1
• QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
• 235000011082 potassium citrates Nutrition 0.000 description 1
• MZWCHWWQSPPZRH-UHFFFAOYSA-M potassium;4-(7-ethyl-1,3-benzodioxol-5-yl)-1,1-dioxo-2-[2-(trifluoromethyl)phenyl]-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound [K+].C=1C=2OCOC=2C(CC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C([O-])=O)N1C1=CC=CC=C1C(F)(F)F MZWCHWWQSPPZRH-UHFFFAOYSA-M 0.000 description 1
• WVULZDFWPQCPPJ-UHFFFAOYSA-N potassium;hydrochloride Chemical compound Cl.[K] WVULZDFWPQCPPJ-UHFFFAOYSA-N 0.000 description 1
• 108010029667 pramlintide Proteins 0.000 description 1
• NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 description 1
• 229960004457 pramlintide acetate Drugs 0.000 description 1
• 229950004891 pranidipine Drugs 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
• WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 1
• 229960002386 prazosin hydrochloride Drugs 0.000 description 1
• 238000000039 preparative column chromatography Methods 0.000 description 1
• DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
• 229960003081 probenecid Drugs 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 108010070701 procolipase Proteins 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 229960004604 propranolol hydrochloride Drugs 0.000 description 1
• AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
• 229940076372 protein antagonist Drugs 0.000 description 1
• 239000013014 purified material Substances 0.000 description 1
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
• 239000011699 pyridoxamine Substances 0.000 description 1
• 235000008151 pyridoxamine Nutrition 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 108700040249 racecadotril Proteins 0.000 description 1
• 229960003401 ramipril Drugs 0.000 description 1
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000030558 renal glucose absorption Effects 0.000 description 1
• 229950010098 rentiapril Drugs 0.000 description 1
• BSHDUMDXSRLRBI-JOYOIKCWSA-N rentiapril Chemical compound SCCC(=O)N1[C@H](C(=O)O)CS[C@@H]1C1=CC=CC=C1O BSHDUMDXSRLRBI-JOYOIKCWSA-N 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 229960003147 reserpine Drugs 0.000 description 1
• BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
• 102000027483 retinoid hormone receptors Human genes 0.000 description 1
• 108091008679 retinoid hormone receptors Proteins 0.000 description 1
• 230000002441 reversible effect 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
• CRPGRUONUFDYBG-UHFFFAOYSA-N risarestat Chemical compound C1=C(OCC)C(OCCCCC)=CC=C1C1C(=O)NC(=O)S1 CRPGRUONUFDYBG-UHFFFAOYSA-N 0.000 description 1
• 229950006433 risarestat Drugs 0.000 description 1
• XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
• HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
• 229950005741 rolipram Drugs 0.000 description 1
• MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
• SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
• 229960003271 rosiglitazone maleate 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
• 229950001780 sampatrilat Drugs 0.000 description 1
• 229950005789 sarpogrelate Drugs 0.000 description 1
• FFYNAVGJSYHHFO-UHFFFAOYSA-N sarpogrelate Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OCC(CN(C)C)OC(=O)CCC(O)=O)=C1 FFYNAVGJSYHHFO-UHFFFAOYSA-N 0.000 description 1
• 108010086511 sauvagine Proteins 0.000 description 1
• IMNTVVOUWFPRSB-JWQCQUIFSA-N sch-48461 Chemical compound C1=CC(OC)=CC=C1[C@H]1N(C=2C=CC(OC)=CC=2)C(=O)[C@@H]1CCCC1=CC=CC=C1 IMNTVVOUWFPRSB-JWQCQUIFSA-N 0.000 description 1
• 125000005920 sec-butoxy group Chemical group 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 229940076279 serotonin Drugs 0.000 description 1
• 229960003660 sertraline hydrochloride Drugs 0.000 description 1
• 229960003466 sibutramine hydrochloride Drugs 0.000 description 1
• LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
• 229910001958 silver carbonate Inorganic materials 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
• IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000011083 sodium citrates Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• NTDIRNUKAZNMSW-IYVGUKHKSA-M sodium;(3s,5r,6e)-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyltetrazol-5-yl)nona-6,8-dienoate Chemical compound [Na+].CN1N=NN=C1C(\C=C\[C@H](O)C[C@H](O)CC([O-])=O)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NTDIRNUKAZNMSW-IYVGUKHKSA-M 0.000 description 1
• FBSZSOXTWRKLKD-UHFFFAOYSA-M sodium;(4-chlorophenyl)sulfonyl-[(4-cyano-5-methyl-2-phenylpyrazol-3-yl)carbamoyl]azanide Chemical compound [Na+].N#CC=1C(C)=NN(C=2C=CC=CC=2)C=1NC(=O)[N-]S(=O)(=O)C1=CC=C(Cl)C=C1 FBSZSOXTWRKLKD-UHFFFAOYSA-M 0.000 description 1
• AMCPCELVARAPHJ-UHFFFAOYSA-M sodium;5-[[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [Na+].CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)[N-]C1=O AMCPCELVARAPHJ-UHFFFAOYSA-M 0.000 description 1
• 239000012453 solvate Substances 0.000 description 1
• 238000000638 solvent extraction Methods 0.000 description 1
• 229960000553 somatostatin Drugs 0.000 description 1
• LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 1
• 229950004311 sorbinil Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
• 229960001052 streptozocin Drugs 0.000 description 1
• 150000008163 sugars Chemical group 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 229950008418 talipexole Drugs 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229960005187 telmisartan Drugs 0.000 description 1
• VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
• 229960001909 terazosin hydrochloride Drugs 0.000 description 1
• 125000005922 tert-pentoxy group Chemical group 0.000 description 1
• 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• 125000005505 thiomorpholino group Chemical group 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 108090000721 thyroid hormone receptors Proteins 0.000 description 1
• 102000004217 thyroid hormone receptors Human genes 0.000 description 1
• 229960002961 ticlopidine hydrochloride Drugs 0.000 description 1
• MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 1
• 229960005221 timolol maleate Drugs 0.000 description 1
• RBKASMJPSJDQKY-RBFSKHHSSA-N tirilazad Chemical compound O=C([C@@H]1[C@@]2(C)CC=C3[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)CN(CC1)CCN1C(N=1)=CC(N2CCCC2)=NC=1N1CCCC1 RBKASMJPSJDQKY-RBFSKHHSSA-N 0.000 description 1
• 229960005155 tirilazad Drugs 0.000 description 1
• 229950001089 todralazine Drugs 0.000 description 1
• 229960002277 tolazamide Drugs 0.000 description 1
• OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
• 229960005371 tolbutamide Drugs 0.000 description 1
• LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
• 229960003069 tolrestat Drugs 0.000 description 1
• 229960002051 trandolapril Drugs 0.000 description 1
• 229960000363 trapidil Drugs 0.000 description 1
• 150000003626 triacylglycerols Chemical class 0.000 description 1
• 229960001288 triamterene Drugs 0.000 description 1
• LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
• 229960004813 trichlormethiazide Drugs 0.000 description 1
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
• 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
• UHLOVGKIEARANS-QZHINBJYSA-N tripamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NN2C[C@@H]3[C@H]4CC[C@H](C4)[C@@H]3C2)=C1 UHLOVGKIEARANS-QZHINBJYSA-N 0.000 description 1
• 229950004678 tripamide Drugs 0.000 description 1
• 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 1
• 229960001641 troglitazone Drugs 0.000 description 1
• 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 1
• 210000005239 tubule Anatomy 0.000 description 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 229960001130 urapidil Drugs 0.000 description 1
• 239000000777 urocortin Substances 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000000304 vasodilatating effect Effects 0.000 description 1
• 229960001722 verapamil Drugs 0.000 description 1
• 229960000881 verapamil hydrochloride Drugs 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229960001729 voglibose Drugs 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
• 229950006343 zenarestat Drugs 0.000 description 1
• 229960002769 zofenopril Drugs 0.000 description 1
• IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
• 229950005346 zopolrestat Drugs 0.000 description 1
• WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 1