UA77300C2 - 5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes - Google Patents

5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes Download PDF

Info

Publication number: UA77300C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; thio; alkoxy; glucopyranoside
Prior art date: 2002-08-09

Application number

UA20041210074A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Taisho Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-09

Filing date

2003-08-08

Publication date

2006-11-15

2003-08-08 Application filed by Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd

2006-11-15 Publication of UA77300C2 publication Critical patent/UA77300C2/uk

Links

206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 31
239000008194 pharmaceutical composition Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 39
239000003814 drug Substances 0.000 claims abstract description 23
229940079593 drug Drugs 0.000 claims abstract description 11
230000000694 effects Effects 0.000 claims abstract description 9
201000010099 disease Diseases 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
239000004480 active ingredient Substances 0.000 claims abstract description 6
230000003449 preventive effect Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 108
125000005843 halogen group Chemical group 0.000 claims description 97
-1 Siv alkyl C 6 oxy Chemical group 0.000 claims description 85
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
125000003545 alkoxy group Chemical group 0.000 claims description 67
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
238000002360 preparation method Methods 0.000 claims description 51
125000001424 substituent group Chemical group 0.000 claims description 44
125000002252 acyl group Chemical group 0.000 claims description 37
125000003277 amino group Chemical group 0.000 claims description 35
239000003112 inhibitor Substances 0.000 claims description 32
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
239000000556 agonist Substances 0.000 claims description 25
125000003710 aryl alkyl group Chemical group 0.000 claims description 25
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 claims description 21
125000004423 acyloxy group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 17
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 13
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 12
125000004442 acylamino group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 12
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
125000004104 aryloxy group Chemical group 0.000 claims description 12
239000008103 glucose Substances 0.000 claims description 12
125000001589 carboacyl group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
229940124597 therapeutic agent Drugs 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
229940125396 insulin Drugs 0.000 claims description 10
102000004877 Insulin Human genes 0.000 claims description 9
108090001061 Insulin Proteins 0.000 claims description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
108010078791 Carrier Proteins Proteins 0.000 claims description 8
125000000542 sulfonic acid group Chemical group 0.000 claims description 8
229940123208 Biguanide Drugs 0.000 claims description 7
239000003316 glycosidase inhibitor Substances 0.000 claims description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
230000001419 dependent effect Effects 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 claims description 5
102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 claims description 5
230000001539 anorectic effect Effects 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
206010061428 decreased appetite Diseases 0.000 claims description 5
229940125753 fibrate Drugs 0.000 claims description 5
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
230000003228 microsomal effect Effects 0.000 claims description 5
239000004059 squalene synthase inhibitor Substances 0.000 claims description 5
229940122355 Insulin sensitizer Drugs 0.000 claims description 4
102100030817 Liver carboxylesterase 1 Human genes 0.000 claims description 4
101710181187 Liver carboxylesterase 1 Proteins 0.000 claims description 4
230000003914 insulin secretion Effects 0.000 claims description 4
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 3
229940122069 Glycosidase inhibitor Drugs 0.000 claims description 3
241000269435 Rana <genus> Species 0.000 claims description 3
239000002404 acyltransferase inhibitor Substances 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
229940123324 Acyltransferase inhibitor Drugs 0.000 claims description 2
108020003175 receptors Proteins 0.000 claims description 2
206010021118 Hypotonia Diseases 0.000 claims 1
102000007330 LDL Lipoproteins Human genes 0.000 claims 1
108010007622 LDL Lipoproteins Proteins 0.000 claims 1
235000013744 Passiflora ligularis Nutrition 0.000 claims 1
240000004520 Passiflora ligularis Species 0.000 claims 1
101000870345 Vasconcellea cundinamarcensis Cysteine proteinase 1 Proteins 0.000 claims 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 8
208000002249 Diabetes Complications Diseases 0.000 abstract description 3
150000004677 hydrates Chemical class 0.000 abstract description 2
206010012655 Diabetic complications Diseases 0.000 abstract 1
108091006269 SLC5A2 Proteins 0.000 abstract 1
102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 112
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
239000000203 mixture Substances 0.000 description 82
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 73
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
239000011541 reaction mixture Substances 0.000 description 40
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
239000000741 silica gel Substances 0.000 description 37
229910002027 silica gel Inorganic materials 0.000 description 37
238000004440 column chromatography Methods 0.000 description 36
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 36
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 27
239000000843 powder Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 26
238000003756 stirring Methods 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
229920006395 saturated elastomer Polymers 0.000 description 22
239000007864 aqueous solution Substances 0.000 description 21
230000002829 reductive effect Effects 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000000126 substance Substances 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
229910052740 iodine Inorganic materials 0.000 description 19
238000000034 method Methods 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
238000001704 evaporation Methods 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
230000008020 evaporation Effects 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
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 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
235000000346 sugar Nutrition 0.000 description 6
229910052720 vanadium Inorganic materials 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 5
239000012043 crude product Substances 0.000 description 5
210000003734 kidney Anatomy 0.000 description 5
229910052754 neon Inorganic materials 0.000 description 5
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 5
230000035939 shock Effects 0.000 description 5
238000012360 testing method Methods 0.000 description 5
HWRPGXGZOLYUAL-UHFFFAOYSA-N 2,4-dibromo-6-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(Br)=CC(Br)=C1O HWRPGXGZOLYUAL-UHFFFAOYSA-N 0.000 description 4
PELPQGBUZNQVLR-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC=CC=C1O PELPQGBUZNQVLR-UHFFFAOYSA-N 0.000 description 4
108020004414 DNA Proteins 0.000 description 4
241000282326 Felis catus Species 0.000 description 4
208000031226 Hyperlipidaemia Diseases 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
102000000853 LDL receptors Human genes 0.000 description 4
108010001831 LDL receptors Proteins 0.000 description 4
241000159610 Roya <green alga> Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
241001415849 Strigiformes Species 0.000 description 4
229940100389 Sulfonylurea Drugs 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000007900 aqueous suspension Substances 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
150000004283 biguanides Chemical class 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 4
230000014509 gene expression Effects 0.000 description 4
235000001968 nicotinic acid Nutrition 0.000 description 4
239000011664 nicotinic acid Chemical class 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
IOUVKUPGCMBWBT-QNDFHXLGSA-N phlorizin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-QNDFHXLGSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 3
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
FDNKGQUUGXHVRK-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]benzene-1,3-diol Chemical compound C1=CC(CC)=CC=C1CC1=C(O)C=CC=C1O FDNKGQUUGXHVRK-UHFFFAOYSA-N 0.000 description 3
RUBWVFQHJKJFBG-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]methyl]phenol Chemical compound OC1=CC=CC=C1CC1=CC=C(C(F)(F)F)C=C1 RUBWVFQHJKJFBG-UHFFFAOYSA-N 0.000 description 3
RHCWAJVRIADCQS-UHFFFAOYSA-N 2-bromo-4-fluoro-1-phenylmethoxybenzene Chemical compound BrC1=CC(F)=CC=C1OCC1=CC=CC=C1 RHCWAJVRIADCQS-UHFFFAOYSA-N 0.000 description 3
WAUKRFIHZQQYHT-UHFFFAOYSA-N 4-bromo-2-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(Br)=CC=C1O WAUKRFIHZQQYHT-UHFFFAOYSA-N 0.000 description 3
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 3
239000005541 ACE inhibitor Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
241000566113 Branta sandvicensis Species 0.000 description 3
229940127007 Compound 39 Drugs 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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 3
244000068988 Glycine max Species 0.000 description 3
235000010469 Glycine max Nutrition 0.000 description 3
101000976075 Homo sapiens Insulin Proteins 0.000 description 3
101000578774 Homo sapiens MAP kinase-activated protein kinase 5 Proteins 0.000 description 3
101001090074 Homo sapiens Small nuclear protein PRAC1 Proteins 0.000 description 3
206010022489 Insulin Resistance Diseases 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
102100028396 MAP kinase-activated protein kinase 5 Human genes 0.000 description 3
238000006751 Mitsunobu reaction Methods 0.000 description 3
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102100034766 Small nuclear protein PRAC1 Human genes 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241001377938 Yara Species 0.000 description 3
OSZSMFQZURNRHS-RQICVUQASA-N [(2r,3s,4s,5r)-3,4,5-triacetyloxy-6-hydroxythian-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1SC(O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O OSZSMFQZURNRHS-RQICVUQASA-N 0.000 description 3
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
206010000496 acne Diseases 0.000 description 3
230000009471 action Effects 0.000 description 3
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
229940126086 compound 21 Drugs 0.000 description 3
229940126208 compound 22 Drugs 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
WQZGKKKJIJFFOK-UKLRSMCWSA-N dextrose-2-13c Chemical compound OC[C@H]1OC(O)[13C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-UKLRSMCWSA-N 0.000 description 3
230000029142 excretion Effects 0.000 description 3
239000003102 growth factor Substances 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
201000001421 hyperglycemia Diseases 0.000 description 3
230000002218 hypoglycaemic effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
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 3
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
NRLHCNIDBARPJR-UHFFFAOYSA-N methyl 3-[(4-ethylphenyl)methyl]-4-hydroxybenzoate Chemical compound C1=CC(CC)=CC=C1CC1=CC(C(=O)OC)=CC=C1O NRLHCNIDBARPJR-UHFFFAOYSA-N 0.000 description 3
210000005036 nerve Anatomy 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
125000003226 pyrazolyl group Chemical group 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
125000000168 pyrrolyl group Chemical group 0.000 description 3
229940044551 receptor antagonist Drugs 0.000 description 3
239000002464 receptor antagonist Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-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
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
229930182837 (R)-adrenaline Natural products 0.000 description 2
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 2
DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 2
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
LLLBDLDNTMMZHL-UHFFFAOYSA-N 1-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2OC=CC2=C1 LLLBDLDNTMMZHL-UHFFFAOYSA-N 0.000 description 2
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 2
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 2
VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 2
RYTREZWANNTZBG-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]-1,3-dimethoxybenzene Chemical compound C1=CC(CC)=CC=C1CC1=C(OC)C=CC=C1OC RYTREZWANNTZBG-UHFFFAOYSA-N 0.000 description 2
URGXXKKQQMCQID-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]-4-fluorophenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(F)=CC=C1O URGXXKKQQMCQID-UHFFFAOYSA-N 0.000 description 2
ZCADTUYPVZVCIK-UHFFFAOYSA-N 2-[(4-ethylphenyl)methyl]-4-methylphenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(C)=CC=C1O ZCADTUYPVZVCIK-UHFFFAOYSA-N 0.000 description 2
XMPYZRODFDIJPK-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]phenol Chemical compound OC1=CC=CC=C1CC1=CC=C(F)C=C1 XMPYZRODFDIJPK-UHFFFAOYSA-N 0.000 description 2
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N 4-Ethylbenzaldehyde Chemical compound CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
OTEPHOIGKOUKNC-UHFFFAOYSA-N 4-chloro-2-[(4-ethylphenyl)methyl]phenol Chemical compound C1=CC(CC)=CC=C1CC1=CC(Cl)=CC=C1O OTEPHOIGKOUKNC-UHFFFAOYSA-N 0.000 description 2
VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 2
UPSFNXFLBMJUQW-UHFFFAOYSA-N 5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound CN1C(O)C(=O)NC1=O UPSFNXFLBMJUQW-UHFFFAOYSA-N 0.000 description 2
XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 2
208000002874 Acne Vulgaris Diseases 0.000 description 2
101100049050 Arabidopsis thaliana PVA41 gene Proteins 0.000 description 2
240000005220 Bischofia javanica Species 0.000 description 2
235000010893 Bischofia javanica Nutrition 0.000 description 2
101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 2
108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 2
102000014914 Carrier Proteins Human genes 0.000 description 2
241000283153 Cetacea Species 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
101000616562 Danio rerio Sonic hedgehog protein A Proteins 0.000 description 2
101710088194 Dehydrogenase Proteins 0.000 description 2
102000004860 Dipeptidases Human genes 0.000 description 2
108090001081 Dipeptidases Proteins 0.000 description 2
229940118365 Endothelin receptor antagonist Drugs 0.000 description 2
241000283074 Equus asinus Species 0.000 description 2
101800000224 Glucagon-like peptide 1 Proteins 0.000 description 2
102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 2
108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 2
102000005237 Isophane Insulin Human genes 0.000 description 2
108010081368 Isophane Insulin Proteins 0.000 description 2
229940127470 Lipase Inhibitors Drugs 0.000 description 2
101000831624 Locusta migratoria Locustatachykinin-1 Proteins 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
101001098066 Naja melanoleuca Basic phospholipase A2 1 Proteins 0.000 description 2
240000000220 Panda oleosa Species 0.000 description 2
235000016496 Panda oleosa Nutrition 0.000 description 2
229940122344 Peptidase inhibitor Drugs 0.000 description 2
241001387976 Pera Species 0.000 description 2
102000003992 Peroxidases Human genes 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
102100040918 Pro-glucagon Human genes 0.000 description 2
235000011449 Rosa Nutrition 0.000 description 2
241000220317 Rosa Species 0.000 description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
108091006299 SLC2A2 Proteins 0.000 description 2
241000270295 Serpentes Species 0.000 description 2
229940127505 Sodium Channel Antagonists Drugs 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000009337 Spinacia oleracea Nutrition 0.000 description 2
244000300264 Spinacia oleracea Species 0.000 description 2
229940127535 Thyroid Hormone Receptor Agonists Drugs 0.000 description 2
102000040945 Transcription factor Human genes 0.000 description 2
108091023040 Transcription factor Proteins 0.000 description 2
102100040411 Tripeptidyl-peptidase 2 Human genes 0.000 description 2
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
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 2
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000012190 activator Substances 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
238000005882 aldol condensation reaction Methods 0.000 description 2
239000003288 aldose reductase inhibitor Substances 0.000 description 2
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
239000002220 antihypertensive agent Substances 0.000 description 2
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229910052790 beryllium Inorganic materials 0.000 description 2
239000003613 bile acid Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
229960004203 carnitine Drugs 0.000 description 2
230000001906 cholesterol absorption Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940125810 compound 20 Drugs 0.000 description 2
229940125833 compound 23 Drugs 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
SVABQOITNJTVNJ-UHFFFAOYSA-N diphenyl-2-pyridylphosphine Chemical compound C1=CC=CC=C1P(C=1N=CC=CC=1)C1=CC=CC=C1 SVABQOITNJTVNJ-UHFFFAOYSA-N 0.000 description 2
239000002857 endothelin converting enzyme inhibitor Substances 0.000 description 2
239000002308 endothelin receptor antagonist Substances 0.000 description 2
229960005139 epinephrine Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000004744 fabric Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
229940006445 isophane insulin Drugs 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
244000145841 kine Species 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000010534 mechanism of action Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
ADSJCWKOKYOJSZ-UHFFFAOYSA-N methyl 3-formyl-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(C=O)=C1 ADSJCWKOKYOJSZ-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
108010066090 neutral insulin Proteins 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
210000002445 nipple Anatomy 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
108040007629 peroxidase activity proteins Proteins 0.000 description 2
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229940121649 protein inhibitor Drugs 0.000 description 2
239000012268 protein inhibitor Substances 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 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
125000003107 substituted aryl group Chemical group 0.000 description 2
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
108010039189 tripeptidyl-peptidase 2 Proteins 0.000 description 2
BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
229940116269 uric acid Drugs 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
238000005406 washing Methods 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 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
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
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 1
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
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 1
YSLBFFIVJGJBSA-UHFFFAOYSA-N (4-ethylphenyl)methanol Chemical compound CCC1=CC=C(CO)C=C1 YSLBFFIVJGJBSA-UHFFFAOYSA-N 0.000 description 1
BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
OPDFUQJBZZJZRG-WPJYNPJPSA-N (4r,4as,7r,7ar,12bs)-7-[2-[2-[2-[[(4r,4as,7r,7ar,12bs)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl]amino]ethoxy]ethoxy]ethylamino]-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-me Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CC[C@H]5NCCOCCOCCN[C@H]2[C@@H]3OC=4C(O)=CC=C5C[C@@H]6[C@]([C@@]3(CCN6CC3CC3)C5=4)(O)CC2)O)CC1)O)CC1CC1 OPDFUQJBZZJZRG-WPJYNPJPSA-N 0.000 description 1
STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
PHIQHXFUZVPYII-ZCFIWIBFSA-O (R)-carnitinium Chemical compound C[N+](C)(C)C[C@H](O)CC(O)=O PHIQHXFUZVPYII-ZCFIWIBFSA-O 0.000 description 1
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YYPPFEKHXPADAV-UHFFFAOYSA-N 1-(bromomethyl)-4-ethylbenzene Chemical compound CCC1=CC=C(CBr)C=C1 YYPPFEKHXPADAV-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
CSBKCUSGULKNRS-UHFFFAOYSA-N 1-[4-[(2-hydroxyphenyl)methyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1CC1=CC=CC=C1O CSBKCUSGULKNRS-UHFFFAOYSA-N 0.000 description 1
QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
CDDDRVNOHLVEED-UHFFFAOYSA-N 1-cyclohexyl-3-[1-[[1-(cyclohexylcarbamoylamino)cyclohexyl]diazenyl]cyclohexyl]urea Chemical compound C1CCCCC1(N=NC1(CCCCC1)NC(=O)NC1CCCCC1)NC(=O)NC1CCCCC1 CDDDRVNOHLVEED-UHFFFAOYSA-N 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[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
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-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
VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 description 1
BMPXABNSIVCIID-UHFFFAOYSA-N 2-[(4-ethoxyphenyl)methyl]phenol Chemical compound C1=CC(OCC)=CC=C1CC1=CC=CC=C1O BMPXABNSIVCIID-UHFFFAOYSA-N 0.000 description 1
ALZWVPLMSWPDQR-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]phenol Chemical compound C1=CC(OC)=CC=C1CC1=CC=CC=C1O ALZWVPLMSWPDQR-UHFFFAOYSA-N 0.000 description 1
CMLUGNQVANVZHY-POURPWNDSA-N 2-[1-[2-[(3r,5s)-1-(3-acetyloxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)COC(C)=O)C(=O)[C@@H](CC(=O)N3CCC(CC(O)=O)CC3)O2)=C1OC CMLUGNQVANVZHY-POURPWNDSA-N 0.000 description 1
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-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
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
CCTREOMTIFSZAU-OGFXRTJISA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;5-[(3r)-dithiolan-3-yl]pentanoic acid Chemical compound OCC(N)(CO)CO.OC(=O)CCCC[C@@H]1CCSS1 CCTREOMTIFSZAU-OGFXRTJISA-N 0.000 description 1
NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
MEYRABVEYCFHHB-UHFFFAOYSA-N 2-bromo-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Br MEYRABVEYCFHHB-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ZPPUMAMZIMPJGP-UHFFFAOYSA-N 2-methyl-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)C)=N1 ZPPUMAMZIMPJGP-UHFFFAOYSA-N 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
PBEJTRAJWCNHRS-UHFFFAOYSA-N 2-phenylmethoxybenzaldehyde Chemical compound O=CC1=CC=CC=C1OCC1=CC=CC=C1 PBEJTRAJWCNHRS-UHFFFAOYSA-N 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
235000009434 Actinidia chinensis Nutrition 0.000 description 1
244000298697 Actinidia deliciosa Species 0.000 description 1
235000009436 Actinidia deliciosa Nutrition 0.000 description 1
102000003808 Adiponectin Receptors Human genes 0.000 description 1
108090000179 Adiponectin Receptors Proteins 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
229940127438 Amylin Agonists Drugs 0.000 description 1
235000007119 Ananas comosus Nutrition 0.000 description 1
244000099147 Ananas comosus Species 0.000 description 1
241000554155 Andes Species 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
241000272517 Anseriformes Species 0.000 description 1
208000031104 Arterial Occlusive disease Diseases 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
244000218454 Bambusa tulda Species 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
206010061695 Biliary tract infection Diseases 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
239000002083 C09CA01 - Losartan Substances 0.000 description 1
PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
101100287724 Caenorhabditis elegans shk-1 gene Proteins 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
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 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
229920001268 Cholestyramine Polymers 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
101100102516 Clonostachys rogersoniana vern gene Proteins 0.000 description 1
235000003913 Coccoloba uvifera Nutrition 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
229920002905 Colesevelam Polymers 0.000 description 1
229920000230 Colestilan Polymers 0.000 description 1
206010010071 Coma Diseases 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
244000241257 Cucumis melo Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
235000017788 Cydonia oblonga Nutrition 0.000 description 1
101710200331 Cytochrome b-245 chaperone 1 Proteins 0.000 description 1
102100037186 Cytochrome b-245 chaperone 1 Human genes 0.000 description 1
101710119396 Cytochrome b-245 chaperone 1 homolog Proteins 0.000 description 1
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 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
101150092565 DOHH gene Proteins 0.000 description 1
241001491631 Dasya Species 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
208000007342 Diabetic Nephropathies Diseases 0.000 description 1
208000032131 Diabetic Neuropathies Diseases 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
101100460157 Drosophila melanogaster nenya gene Proteins 0.000 description 1
241000698776 Duma Species 0.000 description 1
102000018386 EGF Family of Proteins Human genes 0.000 description 1
108010066486 EGF Family of Proteins Proteins 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241001505295 Eros Species 0.000 description 1
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
244000187656 Eucalyptus cornuta Species 0.000 description 1
LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 description 1
IBHSRCBKJMEBQB-VMPREFPWSA-N Fetidine Chemical compound CN1CCC2=CC(OC)=C(O)C3=C2[C@@H]1CC1=C3C=C(OC)C(OC2=C(OC)C(OC)=CC=C2C[C@@H]2N(C)CCC=3C=C(C(=CC=32)OC)OC)=C1 IBHSRCBKJMEBQB-VMPREFPWSA-N 0.000 description 1
IBHSRCBKJMEBQB-UHFFFAOYSA-N Fetidine Natural products CN1CCC2=CC(OC)=C(O)C3=C2C1CC1=C3C=C(OC)C(OC2=C(OC)C(OC)=CC=C2CC2N(C)CCC=3C=C(C(=CC=32)OC)OC)=C1 IBHSRCBKJMEBQB-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
206010017711 Gangrene Diseases 0.000 description 1
241001547860 Gaya Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229940122904 Glucagon receptor antagonist Drugs 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
229940121931 Gluconeogenesis inhibitor Drugs 0.000 description 1
102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
102000005744 Glycoside Hydrolases Human genes 0.000 description 1
108010031186 Glycoside Hydrolases Proteins 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
244000301682 Heliotropium curassavicum Species 0.000 description 1
235000015854 Heliotropium curassavicum Nutrition 0.000 description 1
101000589632 Homo sapiens N-acetylaspartate synthetase Proteins 0.000 description 1
101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
244000025221 Humulus lupulus Species 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
206010060378 Hyperinsulinaemia Diseases 0.000 description 1
201000001431 Hyperuricemia Diseases 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
108010001127 Insulin Receptor Proteins 0.000 description 1
102100036721 Insulin receptor Human genes 0.000 description 1
229940122199 Insulin secretagogue Drugs 0.000 description 1
241000731961 Juncaceae Species 0.000 description 1
206010023379 Ketoacidosis Diseases 0.000 description 1
208000007976 Ketosis Diseases 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241001142635 Lema Species 0.000 description 1
102000016267 Leptin Human genes 0.000 description 1
108010092277 Leptin Proteins 0.000 description 1
LKYWLLWWYBVUPP-XOCLESOZSA-L Liotrix Chemical compound [Na+].[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1.IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 LKYWLLWWYBVUPP-XOCLESOZSA-L 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
229930195725 Mannitol Natural products 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
108010008364 Melanocortins Proteins 0.000 description 1
240000000233 Melia azedarach Species 0.000 description 1
IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
101100440233 Mus musculus Cmpk2 gene Proteins 0.000 description 1
101100149256 Mus musculus Sema6b gene Proteins 0.000 description 1
240000005561 Musa balbisiana Species 0.000 description 1
235000018290 Musa x paradisiaca Nutrition 0.000 description 1
241000321422 Mycteroperca jordani Species 0.000 description 1
LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
102100032380 N-acetylaspartate synthetase Human genes 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
241000270282 Nerodia Species 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
241000604301 Ninia Species 0.000 description 1
RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 1
241000468053 Obodhiang virus Species 0.000 description 1
241000283965 Ochotona princeps Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
208000025174 PANDAS Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000021155 Paediatric autoimmune neuropsychiatric disorders associated with streptococcal infection Diseases 0.000 description 1
244000170916 Paeonia officinalis Species 0.000 description 1
235000006484 Paeonia officinalis Nutrition 0.000 description 1
241001659863 Panna Species 0.000 description 1
241000282322 Panthera Species 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
238000007205 Parnes methylation reaction Methods 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
241001442654 Percnon planissimum Species 0.000 description 1
IOUVKUPGCMBWBT-DARKYYSBSA-N Phloridzin Natural products O[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-DARKYYSBSA-N 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
241001377010 Pila Species 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
240000005546 Piper methysticum Species 0.000 description 1
235000016787 Piper methysticum Nutrition 0.000 description 1
102100029365 Piwi-like protein 2 Human genes 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
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229940123924 Protein kinase C inhibitor Drugs 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
240000008976 Pterocarpus marsupium Species 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
101100209990 Rattus norvegicus Slc18a2 gene Proteins 0.000 description 1
206010057190 Respiratory tract infections Diseases 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
241001671603 Ruellia tweediana Species 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
241000168254 Siro Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
206010062255 Soft tissue infection Diseases 0.000 description 1
229920002125 Sokalan® Chemical class 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
241000657469 Spermacoce capitata Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
208000006011 Stroke Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229920000439 Sulodexide Polymers 0.000 description 1
238000006069 Suzuki reaction reaction Methods 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
241000120020 Tela Species 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
101001123837 Thermoactinomyces vulgaris Neopullulanase 1 Proteins 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical class [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
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 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 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
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
208000020329 Zika virus infectious disease Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
FLRQOWAOMJMSTP-JJTRIOAGSA-N [(2s)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethyl] (6z,9z,12z)-octadeca-6,9,12-trienoate Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O FLRQOWAOMJMSTP-JJTRIOAGSA-N 0.000 description 1
GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-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
FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
TVXPDKWTPXJAMA-UHFFFAOYSA-N [4-[(4-ethylphenyl)methyl]-3-hydroxyphenyl]methyl acetate Chemical compound C1=CC(CC)=CC=C1CC1=CC=C(COC(C)=O)C=C1O TVXPDKWTPXJAMA-UHFFFAOYSA-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
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229960002632 acarbose Drugs 0.000 description 1
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 description 1
GDJHWWHNELEJMP-UHFFFAOYSA-N acetic acid;methylhydrazine Chemical compound CNN.CC(O)=O GDJHWWHNELEJMP-UHFFFAOYSA-N 0.000 description 1
229960004308 acetylcysteine Drugs 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
239000000048 adrenergic agonist Substances 0.000 description 1
229940126157 adrenergic receptor agonist Drugs 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229940025084 amphetamine Drugs 0.000 description 1
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940127218 antiplatelet drug Drugs 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
208000021328 arterial occlusion Diseases 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
150000001543 aryl boronic acids Chemical class 0.000 description 1
229950005963 ascorbyl gamolenate Drugs 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
210000000467 autonomic pathway Anatomy 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
239000002585 base Substances 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
229950009252 beclobrate Drugs 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
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 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
102000030904 bile acid binding Human genes 0.000 description 1
108091022863 bile acid binding Proteins 0.000 description 1
229950002409 bimoclomol Drugs 0.000 description 1
239000011230 binding agent Substances 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
229950004495 binifibrate Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 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
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229960004349 candesartan cilexetil Drugs 0.000 description 1
239000002775 capsule Substances 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
230000023852 carbohydrate metabolic process Effects 0.000 description 1
235000021256 carbohydrate metabolism Nutrition 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
229960005110 cerivastatin Drugs 0.000 description 1
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960001761 chlorpropamide Drugs 0.000 description 1
208000003167 cholangitis Diseases 0.000 description 1
150000001840 cholesterol esters Chemical class 0.000 description 1
HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
229960005025 cilazapril Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000005515 coenzyme Substances 0.000 description 1
229960000674 colesevelam hydrochloride Drugs 0.000 description 1
229960004095 colestilan Drugs 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
229940125844 compound 46 Drugs 0.000 description 1
229940125900 compound 59 Drugs 0.000 description 1
229940126179 compound 72 Drugs 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
150000001944 cysteine derivatives Chemical class 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
208000033679 diabetic kidney disease Diseases 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
235000001159 dosh Nutrition 0.000 description 1
244000245171 dosh Species 0.000 description 1
230000035622 drinking Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229960000309 enalapril maleate Drugs 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
239000003623 enhancer Substances 0.000 description 1
BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 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
229960002179 ephedrine Drugs 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
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
229950006213 etomoxir Drugs 0.000 description 1
230000005713 exacerbation Effects 0.000 description 1
210000003414 extremity Anatomy 0.000 description 1
229960000815 ezetimibe Drugs 0.000 description 1
OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
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
229910052731 fluorine Inorganic materials 0.000 description 1
229960003765 fluvastatin Drugs 0.000 description 1
229960004038 fluvoxamine Drugs 0.000 description 1
CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229960000346 gliclazide Drugs 0.000 description 1
229960001381 glipizide Drugs 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
239000003850 glucocorticoid receptor antagonist Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
150000002303 glucose derivatives Chemical class 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229940049906 glutamate Drugs 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
239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 description 1
230000013595 glycosylation Effects 0.000 description 1
238000006206 glycosylation reaction Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
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 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940069330 human zinc insulin Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Chemical class SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000003451 hyperinsulinaemic effect Effects 0.000 description 1
201000008980 hyperinsulinism Diseases 0.000 description 1
208000006575 hypertriglyceridemia Diseases 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002608 insulinlike Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-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
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)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
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
239000008274 jelly Substances 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
208000006443 lactic acidosis Diseases 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940039781 leptin Drugs 0.000 description 1
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
230000037356 lipid metabolism Effects 0.000 description 1
208000000680 lipomatosis Diseases 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
239000003509 long acting drug Substances 0.000 description 1
229960000519 losartan potassium Drugs 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
210000003141 lower extremity Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960000299 mazindol Drugs 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000002865 melanocortin 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
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
AZVARJHZBXHUSO-DZQVEHCYSA-N methyl (1R,4R,12S)-4-methyl-3,7-dioxo-10-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),8-diene-4-carboxylate Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)N[C@@](C5=O)(C)C(=O)OC)=CC2=C1 AZVARJHZBXHUSO-DZQVEHCYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-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
206010062198 microangiopathy Diseases 0.000 description 1
210000000110 microvilli Anatomy 0.000 description 1
229960001110 miglitol Drugs 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229960003365 mitiglinide Drugs 0.000 description 1
WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
201000001119 neuropathy Diseases 0.000 description 1
230000007823 neuropathy Effects 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
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
229960001243 orlistat Drugs 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
208000033808 peripheral neuropathy Diseases 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
229960003243 phenformin Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
IOUVKUPGCMBWBT-UHFFFAOYSA-N phloridzosid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-UHFFFAOYSA-N 0.000 description 1
235000019139 phlorizin Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical class [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005095 pioglitazone Drugs 0.000 description 1
229960002797 pitavastatin Drugs 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
235000013550 pizza Nutrition 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920000058 polyacrylate Chemical class 0.000 description 1
229950010884 ponalrestat Drugs 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000003881 protein kinase C inhibitor Substances 0.000 description 1
239000003801 protein tyrosine phosphatase 1B inhibitor Substances 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
MXRGZXBFSKSZPH-UHFFFAOYSA-N protheobromine Chemical compound O=C1N(CC(O)C)C(=O)N(C)C2=C1N(C)C=N2 MXRGZXBFSKSZPH-UHFFFAOYSA-N 0.000 description 1
210000000512 proximal kidney tubule Anatomy 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229960002354 repaglinide Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
239000011435 rock Substances 0.000 description 1
229960004586 rosiglitazone Drugs 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000000952 serotonin receptor agonist Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000003421 short acting drug Substances 0.000 description 1
229960004425 sibutramine Drugs 0.000 description 1
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
206010040872 skin infection Diseases 0.000 description 1
239000002893 slag Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000000779 smoke Substances 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000008247 solid mixture Substances 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
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229960003491 sulodexide Drugs 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
229940081330 tena Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
229960005155 tirilazad 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
229960003069 tolrestat 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
229960004394 topiramate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone 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
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
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
229940045145 uridine Drugs 0.000 description 1
208000019206 urinary tract infection Diseases 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
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229960001729 voglibose Drugs 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Diabetes (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Cardiology (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Neurology (AREA)
Urology & Nephrology (AREA)
Biomedical Technology (AREA)
Endocrinology (AREA)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Communicable Diseases (AREA)
Child & Adolescent Psychology (AREA)
Oncology (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Dermatology (AREA)

UA20041210074A 2002-08-09 2003-08-08 5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes UA77300C2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2002233015		2002-08-09
JP2003097839		2003-04-01
PCT/JP2003/010159 WO2004014930A1 (ja)	2002-08-09	2003-08-08	選択的なアリール５−チオ−β−Ｄ−アルドヘキソピラノシドの製造法

Publications (1)

Publication Number	Publication Date
UA77300C2 true UA77300C2 (en)	2006-11-15

Family

ID=31719867

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20041210074A UA77300C2 (en)	2002-08-09	2003-08-08	5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes

Country Status (19)

Country	Link
US (2)	US7250522B2 (zh)
EP (2)	EP1528066A4 (zh)
JP (2)	JPWO2004014930A1 (zh)
KR (2)	KR20050056194A (zh)
CN (2)	CN1312165C (zh)
AU (2)	AU2003254904A1 (zh)
BR (1)	BR0310006A (zh)
CA (2)	CA2493491A1 (zh)
HK (2)	HK1077582A1 (zh)
HR (1)	HRP20040814A2 (zh)
MX (2)	MXPA05000725A (zh)
NO (2)	NO20043733L (zh)
NZ (1)	NZ535229A (zh)
PL (2)	PL372865A1 (zh)
RU (1)	RU2322449C2 (zh)
TW (2)	TWI274055B (zh)
UA (1)	UA77300C2 (zh)
WO (2)	WO2004014930A1 (zh)
ZA (1)	ZA200407187B (zh)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1020944C (zh)	1990-01-30	1993-05-26	阿图尔-费希尔股份公司费希尔厂	紧固件
AU2003301900A1 (en) *	2002-11-13	2004-06-03	Fumie Sato	Antipruritic drug
EP1609799A4 (en) *	2003-04-01	2008-10-29	Taisho Pharmaceutical Co Ltd	HETEROARYL-5-THIO-BETA-D-GLUCOPYRANOSIDE DERIVATIVES AND AGENTS AGAINST DIABETES THEREOF
JP4130466B2 (ja)	2003-08-01	2008-08-06	田辺三菱製薬株式会社	新規化合物
US8785403B2 (en)	2003-08-01	2014-07-22	Mitsubishi Tanabe Pharma Corporation	Glucopyranoside compound
TW200606129A (en) *	2004-07-26	2006-02-16	Chugai Pharmaceutical Co Ltd	Novel cyclohexane derivative, its prodrug, its salt and diabetic therapeutic agent containing the same
CN101010276B (zh) *	2004-07-26	2011-01-12	中外制药株式会社	环己烷衍生物、其前体药物及其盐、以及含有它的糖尿病治疗药
TW200637839A (en)	2005-01-07	2006-11-01	Taisho Pharmaceutical Co Ltd	1-thio-d-glucitol derivatives
TW200637869A (en)	2005-01-28	2006-11-01	Chugai Pharmaceutical Co Ltd	The spiroketal derivatives and the use as therapeutical agent for diabetes of the same
MY147375A (en)	2005-01-31	2012-11-30	Mitsubishi Tanabe Pharma Corp	Indole derivatives
JP5073948B2 (ja) *	2005-01-31	2012-11-14	田辺三菱製薬株式会社	医薬組成物
JP2009167104A (ja) *	2006-05-02	2009-07-30	Taisho Pharmaceutical Co Ltd	フェニル５−チオグリコシド化合物
EP1854806A1 (en) *	2006-05-02	2007-11-14	MPG Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.	Thioglycosides as pharmaceutically active agents
PE20080251A1 (es)	2006-05-04	2008-04-25	Boehringer Ingelheim Int	Usos de inhibidores de dpp iv
US7803778B2 (en) *	2006-05-23	2010-09-28	Theracos, Inc.	Glucose transport inhibitors and methods of use
NZ573843A (en) *	2006-06-29	2011-02-25	Taisho Pharmaceutical Co Ltd	C-phenyl 1-thioglucitol compound
TWI418556B (zh)	2006-07-27	2013-12-11	Mitsubishi Tanabe Pharma Corp	吲哚衍生物
FR2906247B1 (fr) *	2006-09-27	2008-12-26	Fournier S A Sa Lab	Nouveaux derives de 5-thioxylopyranose
TWI499414B (zh)	2006-09-29	2015-09-11	Lexicon Pharmaceuticals Inc	鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ２）的抑制物與其應用方法
MX2009003927A (es)	2006-10-13	2009-04-23	Chugai Pharmaceutical Co Ltd	Derivado espirocetal de tioglucosa y uso del mismo como un agente terapeutico para la diabetes.
UY30730A1 (es)	2006-12-04	2008-07-03	Mitsubishi Tanabe Pharma Corp	Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno
JP5298025B2 (ja)	2006-12-04	2013-09-25	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	抗糖尿病薬としてのチエニル含有グリコピラノシル誘導体
WO2008072726A1 (ja)	2006-12-14	2008-06-19	Taisho Pharmaceutical Co., Ltd.	１－フェニル１－チオ－ｄ－グルシト－ル誘導体
US7795228B2 (en) *	2006-12-28	2010-09-14	Theracos, Inc.	Spiroheterocyclic glycosides and methods of use
US7846945B2 (en) *	2007-03-08	2010-12-07	Lexicon Pharmaceuticals, Inc.	Piperdine-based inhibitors of sodium glucose co-transporter 2 and methods of their use
US20070172525A1 (en) *	2007-03-15	2007-07-26	Ramesh Sesha	Anti-diabetic combinations
US20080064701A1 (en) *	2007-04-24	2008-03-13	Ramesh Sesha	Anti-diabetic combinations
CN104803957A (zh) *	2007-04-02	2015-07-29	泰拉科斯有限公司	苄基化糖苷衍生物及其用法
DK2183263T3 (da)	2007-07-26	2012-01-30	Lexicon Pharmaceuticals Inc	Fremgangsmåder og forbindelser anvendelige til fremstilling af natriumglucose-cotransportør-2-inhibitorer
EP3318562A3 (en) *	2007-08-23	2018-09-12	Theracos Sub, LLC	Benzylbenzene derivatives and methods of use
NO2200606T3 (zh)	2007-09-10	2018-03-24
UA101004C2 (en)	2007-12-13	2013-02-25	Теракос, Инк.	Derivatives of benzylphenylcyclohexane and use thereof
CL2008003653A1 (es)	2008-01-17	2010-03-05	Mitsubishi Tanabe Pharma Corp	Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica.
US8551524B2 (en) *	2008-03-14	2013-10-08	Iycus, Llc	Anti-diabetic combinations
EP2312944B1 (en)	2008-07-15	2018-09-05	Theracos, Inc.	Deuterated benzylbenzene derivatives and methods of use
CA2734295C (en)	2008-08-22	2016-12-20	Theracos, Inc.	Processes for the preparation of sglt2 inhibitors
WO2010023594A1 (en) *	2008-08-28	2010-03-04	Pfizer Inc.	Dioxa-bicyclo[3.2.1.]octane-2,3,4-triol derivatives
US9056850B2 (en)	2008-10-17	2015-06-16	Janssen Pharmaceutica N.V.	Process for the preparation of compounds useful as inhibitors of SGLT
US20110009347A1 (en) *	2009-07-08	2011-01-13	Yin Liang	Combination therapy for the treatment of diabetes
CA2767258C (en)	2009-07-10	2016-09-13	Janssen Pharmaceutica Nv	Crystallisation process for 1-(.beta.-d-glucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl] benzene
BR112012008939B1 (pt) *	2009-10-14	2021-06-22	Janssen Pharmaceutica Nv	Processo para a preparação de compostos úteis como inibidores de sglt2
DK2496583T3 (en)	2009-11-02	2015-02-02	Pfizer	Dioxa-bicyclo [3.2.1] octane-2,3,4-triol DERIVATIVES
MX339570B (es)	2010-05-11	2016-05-31	Janssen Pharmaceutica Nv	Formulaciones farmaceuticas que comprenden derivados de 1-(beta-d-glucopiranosil)-2-tienil-metilbenceno como inhibidores de transportadores de glucosa dependientes de sodio.
WO2011153712A1 (en)	2010-06-12	2011-12-15	Theracos, Inc.	Crystalline form of benzylbenzene sglt2 inhibitor
DK2697218T3 (en)	2011-04-13	2016-07-25	Janssen Pharmaceutica Nv	PROCESS FOR THE PREPARATION OF COMPOUNDS useful as inhibitors of SGLT2
US9035044B2 (en)	2011-05-09	2015-05-19	Janssen Pharmaceutica Nv	L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
KR20170082650A (ko)	2012-03-28	2017-07-14	후지필름 가부시키가이샤	1-(2-디옥시-2-플루오로-4-티오-β-D-아라비노푸라노실)시토신의 염
US9193751B2 (en)	2012-04-10	2015-11-24	Theracos, Inc.	Process for the preparation of benzylbenzene SGLT2 inhibitors
TWI603966B (zh)	2012-08-13	2017-11-01	富士軟片股份有限公司	１－（２－去氧－２－氟－４－硫－β－Ｄ－阿拉伯呋喃糖基）胞嘧啶之合成中間體、及硫核苷之合成中間體以及彼等之製造法
CA2905993C (en)	2013-03-14	2022-12-06	Tolero Pharmaceuticals, Inc.	Substituted 4-amino-pyrimidinyl-2-amino-phenyl derivatives and pharmaceutical compositions thereof for use as jak2 and alk2 inhibitors
ES2702174T3 (es)	2013-04-05	2019-02-27	Boehringer Ingelheim Int	Usos terapéuticos de empagliflozina
US11813275B2 (en)	2013-04-05	2023-11-14	Boehringer Ingelheim International Gmbh	Pharmaceutical composition, methods for treating and uses thereof
US20140303097A1 (en)	2013-04-05	2014-10-09	Boehringer Ingelheim International Gmbh	Pharmaceutical composition, methods for treating and uses thereof
MX381599B (es)	2013-04-18	2025-03-12	Boehringer Ingelheim Int Gmbh	Empagliflozina para usarse en el tratamiento de micro y macroalbuminuria
WO2015051484A1 (en)	2013-10-12	2015-04-16	Theracos, Inc.	Preparation of hydroxy-benzylbenzene derivatives
CN106061959B (zh)	2014-02-18	2018-11-09	富士胶片株式会社	四氢噻吩骨架型糖化合物的制造方法及四氢噻吩骨架型糖化合物
JP6204223B2 (ja) *	2014-02-19	2017-09-27	富士フイルム株式会社	チオピラノース化合物等の製造方法
TWI678373B (zh)	2014-10-31	2019-12-01	日商富士軟片股份有限公司	硫代核苷衍生物或其鹽及醫藥組合物
US20170071970A1 (en)	2015-09-15	2017-03-16	Janssen Pharmaceutica Nv	Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders
TWI787201B (zh)	2016-08-31	2022-12-21	日商富士軟片股份有限公司	抗腫瘤劑、抗腫瘤效果增強劑及抗腫瘤用套組
TW201932119A (zh)	2018-01-29	2019-08-16	日商富士軟片股份有限公司	膽道癌用抗腫瘤劑和膽道癌的處理方法
MX2021000977A (es)	2018-07-26	2021-04-12	Sumitomo Pharma Oncology Inc	Metodos para tratar enfermedades asociadas con expresion anormal de receptor de activina a tipo 1 (acvr1) e inhibidores de acvr1 para uso en los mismos.

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0850948B1 (en) *	1996-12-26	2002-04-24	Tanabe Seiyaku Co., Ltd.	Propiophenone derivatives and process for preparing the same
JP3055135B2 (ja)	1996-12-26	2000-06-26	田辺製薬株式会社	プロピオフェノン誘導体及びその製法
AU782330B2 (en) *	1999-08-31	2005-07-21	Kissei Pharmaceutical Co. Ltd.	Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
FR2801055B1 (fr) *	1999-11-17	2002-02-08	Fournier Ind & Sante	Derives de beta-d-5-thioxylose, procede de preparation et utilisation en therapeutique
NZ521369A (en)	2000-03-17	2004-07-30	Kissei Pharmaceutical	Glucopyranosyloxybenzylbenzene derivatives, medicinal compositions containing the same and intermediates for the preparation of the derivatives
US6683056B2 (en) *	2000-03-30	2004-01-27	Bristol-Myers Squibb Company	O-aryl glucoside SGLT2 inhibitors and method
US6555519B2 (en)	2000-03-30	2003-04-29	Bristol-Myers Squibb Company	O-glucosylated benzamide SGLT2 inhibitors and method
JP2003534176A (ja)	2000-05-20	2003-11-18	テサ・アクチエンゲゼルシヤフト	接着テープの被覆材料の支持片としての高密度の紙支持材の使用
AU9025701A (en) *	2000-09-29	2002-04-15	Kissei Pharmaceutical	Glucopyranosyloxybenzylbenzene derivatives and medicinal compositions containingthe same
AU2002210990A1 (en)	2000-11-02	2002-05-15	Ajinomoto Co. Inc.	Novel pyrazole derivatives and diabetes remedies containing the same
JP4035052B2 (ja)	2000-12-28	2008-01-16	キッセイ薬品工業株式会社	グルコピラノシルオキシピラゾール誘導体及びその医薬用途
KR100882179B1 (ko)	2001-06-20	2009-02-06	깃세이 야쿠힌 고교 가부시키가이샤	함질소 복소환 유도체, 그것을 함유하는 의약 조성물, 그의약 용도 및 그 제조 중간체
EP1609799A4 (en) *	2003-04-01	2008-10-29	Taisho Pharmaceutical Co Ltd	HETEROARYL-5-THIO-BETA-D-GLUCOPYRANOSIDE DERIVATIVES AND AGENTS AGAINST DIABETES THEREOF
US7439232B2 (en)	2003-04-01	2008-10-21	Taisho Pharmaceutical Co., Ltd.	Heteroaryl 5-thio-β-D-glucopyranoside derivatives and therapeutic agents for diabetes containing the same

2003
- 2003-08-08 CN CNB038056402A patent/CN1312165C/zh not_active Expired - Fee Related
- 2003-08-08 MX MXPA05000725A patent/MXPA05000725A/es active IP Right Grant
- 2003-08-08 TW TW092121886A patent/TWI274055B/zh not_active IP Right Cessation
- 2003-08-08 NZ NZ535229A patent/NZ535229A/en unknown
- 2003-08-08 BR BR0310006-5A patent/BR0310006A/pt not_active IP Right Cessation
- 2003-08-08 AU AU2003254904A patent/AU2003254904A1/en not_active Abandoned
- 2003-08-08 PL PL03372865A patent/PL372865A1/xx not_active Application Discontinuation
- 2003-08-08 CA CA002493491A patent/CA2493491A1/en not_active Abandoned
- 2003-08-08 EP EP03784623A patent/EP1528066A4/en not_active Withdrawn
- 2003-08-08 WO PCT/JP2003/010159 patent/WO2004014930A1/ja active Application Filing
- 2003-08-08 RU RU2004135914/04A patent/RU2322449C2/ru not_active IP Right Cessation
- 2003-08-08 KR KR1020057002280A patent/KR20050056194A/ko not_active Ceased
- 2003-08-08 US US10/521,809 patent/US7250522B2/en not_active Expired - Fee Related
- 2003-08-08 MX MXPA04009265A patent/MXPA04009265A/es active IP Right Grant
- 2003-08-08 CA CA002478889A patent/CA2478889A1/en not_active Abandoned
- 2003-08-08 TW TW092121895A patent/TW200409778A/zh unknown
- 2003-08-08 UA UA20041210074A patent/UA77300C2/uk unknown
- 2003-08-08 AU AU2003254903A patent/AU2003254903B9/en not_active Ceased
- 2003-08-08 PL PL03375298A patent/PL375298A1/xx not_active Application Discontinuation
- 2003-08-08 EP EP03784622A patent/EP1541578A1/en not_active Withdrawn
- 2003-08-08 JP JP2004527382A patent/JPWO2004014930A1/ja not_active Ceased
- 2003-08-08 JP JP2004527383A patent/JP3813160B2/ja not_active Expired - Fee Related
- 2003-08-08 CN CNB038191423A patent/CN100341885C/zh not_active Expired - Fee Related
- 2003-08-08 KR KR1020047014192A patent/KR100588457B1/ko not_active IP Right Cessation
- 2003-08-08 WO PCT/JP2003/010160 patent/WO2004014931A1/ja active IP Right Grant
- 2003-08-08 US US10/518,788 patent/US7414072B2/en not_active Expired - Fee Related
2004
- 2004-09-07 NO NO20043733A patent/NO20043733L/no not_active Application Discontinuation
- 2004-09-08 HR HR20040814A patent/HRP20040814A2/hr not_active Application Discontinuation
- 2004-09-08 ZA ZA200407187A patent/ZA200407187B/en unknown
2005
- 2005-02-07 NO NO20050650A patent/NO20050650L/no not_active Application Discontinuation
- 2005-10-27 HK HK05109578A patent/HK1077582A1/xx not_active IP Right Cessation
- 2005-12-17 HK HK05111661A patent/HK1079532A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP1541578A1 (en)	2005-06-15
KR100588457B1 (ko)	2006-06-12
AU2003254903A1 (en)	2004-02-25
JPWO2004014930A1 (ja)	2005-12-02
CN1312165C (zh)	2007-04-25
PL375298A1 (en)	2005-11-28
TW200409778A (en)	2004-06-16
EP1528066A1 (en)	2005-05-04
CN1639180A (zh)	2005-07-13
TWI274055B (en)	2007-02-21
NO20043733L (no)	2004-10-20
PL372865A1 (en)	2005-08-08
AU2003254903B9 (en)	2008-08-21
EP1528066A4 (en)	2007-05-02
WO2004014930A1 (ja)	2004-02-19
KR20050056194A (ko)	2005-06-14
HK1079532A1 (en)	2006-04-07
US7414072B2 (en)	2008-08-19
MXPA04009265A (es)	2005-01-25
CA2478889A1 (en)	2004-02-19
MXPA05000725A (es)	2005-04-08
RU2322449C2 (ru)	2008-04-20
CN100341885C (zh)	2007-10-10
CA2493491A1 (en)	2004-02-19
RU2004135914A (ru)	2005-05-10
KR20050018642A (ko)	2005-02-23
JPWO2004014931A1 (ja)	2005-12-02
HK1077582A1 (en)	2006-02-17
WO2004014931A1 (ja)	2004-02-19
CN1675233A (zh)	2005-09-28
AU2003254903B2 (en)	2008-07-31
US20050256317A1 (en)	2005-11-17
NO20050650L (no)	2005-03-04
JP3813160B2 (ja)	2006-08-23
AU2003254904A1 (en)	2004-02-25
TW200406396A (en)	2004-05-01
BR0310006A (pt)	2005-02-15
US7250522B2 (en)	2007-07-31
US20050209309A1 (en)	2005-09-22
NZ535229A (en)	2006-05-26
HRP20040814A2 (en)	2005-06-30
ZA200407187B (en)	2006-02-22

Publication	Publication Date	Title
UA77300C2 (en)	2006-11-15	5-thio-?-d-glucopyranoside derivatives and pharmaceutical composition for treating diabetes
AU2006204258B9 (en)	2011-08-04	1-thio-D-glucitol derivatives
CN106349201B (zh)	2018-09-18	光学纯的苄基-4-氯苯基的c-糖苷衍生物
EP3517112B1 (en)	2021-04-07	Heteroaryl compounds useful as inhibitors of sumo activating enzyme
JP5194588B2 (ja)	2013-05-08	１−チオ−ｄ−グルシトール誘導体を有効成分として含有する糖尿病の予防又は治療剤
CN101495494A (zh)	2009-07-29	稠环螺缩酮衍生物、及其作为糖尿病治疗药的使用
CN110402249A (zh)	2019-11-01	外核苷酸酶抑制剂及其使用方法
CN105492429A (zh)	2016-04-13	Sumo活化酶的杂芳基抑制剂
US20100069460A1 (en)	2010-03-18	1-phenyl 1-thio-d-glucitol derivative
UA76798C2 (uk)	2006-09-15	Заміщені 1,4-бензодіазепіни та їх використання для лікування раку, фармацевтична композиція (варіанти) на їх основі та спосіб лікування захворювань (варіанти)
WO2007129668A1 (ja)	2007-11-15	ピラゾリル５－チオグルコシド化合物
AU2011313191A1 (en)	2013-05-02	Cyclic amide derivative
WO2004089967A1 (ja)	2004-10-21	ヘテロアリール５－チオ－β－Ｄ－グルコピラノシド誘導体及びそれを含有する糖尿病治療薬
US7439232B2 (en)	2008-10-21	Heteroaryl 5-thio-β-D-glucopyranoside derivatives and therapeutic agents for diabetes containing the same
CN101384603A (zh)	2009-03-11	新的、无环取代的呋喃嘧啶衍生物及其应用
JP2006117651A (ja)	2006-05-11	Ｓｇｌｔ２の活性阻害剤
CN101400680B (zh)	2012-04-25	螺吲哚满酮衍生物
CN101010276B (zh)	2011-01-12	环己烷衍生物、其前体药物及其盐、以及含有它的糖尿病治疗药
JP2005247834A (ja)	2005-09-15	ナトリウム依存性グルコース供輸送体２の活性阻害剤
CN111386279A (zh)	2020-07-07	用于治疗高钾血症的甘草次酸衍生物
TW201400495A (zh)	2014-01-01	具有螺環之ｃ－醣苷衍生物
MX2007008489A (es)	2007-09-14	Derivado de espirocetal y uso del mismo como medicina para la diabetes.