JP2009513606A - β−３受容体アゴニストとして使うためのベンゾイミダゾール誘導体 - Google Patents

Info

Publication number

JP2009513606A

JP2009513606A JP2008537112A JP2008537112A JP2009513606A JP 2009513606 A JP2009513606 A JP 2009513606A JP 2008537112 A JP2008537112 A JP 2008537112A JP 2008537112 A JP2008537112 A JP 2008537112A JP 2009513606 A JP2009513606 A JP 2009513606A

Authority

JP

Japan

Prior art keywords

phenyl

hydroxy

methyl

butyl

benzimidazole

Prior art date

2005-10-28

Legal status (The legal status 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 status listed.)

Pending

Links

• Espacenet
• Global Dossier
• Discuss

• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 5
• 229940044601 receptor agonist Drugs 0.000 title description 2
• 239000000018 receptor agonist Substances 0.000 title description 2
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 98
• 239000000203 mixture Substances 0.000 claims abstract description 70
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 26
• 239000000651 prodrug Substances 0.000 claims abstract description 13
• 229940002612 prodrug Drugs 0.000 claims abstract description 13
• 239000012453 solvate Substances 0.000 claims abstract description 11
• 238000000034 method Methods 0.000 claims abstract description 10
• 150000004677 hydrates Chemical class 0.000 claims abstract description 9
• 239000000126 substance Substances 0.000 claims abstract description 8
• 238000002360 preparation method Methods 0.000 claims abstract description 6
• -1 hydroxy, methoxy Chemical group 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 239000000460 chlorine Chemical group 0.000 claims description 36
• 239000011737 fluorine Substances 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 239000013543 active substance Substances 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• FEOUBAYQXHYVTQ-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC(C(O)=O)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 FEOUBAYQXHYVTQ-UHFFFAOYSA-N 0.000 claims description 19
• OUDTVESPNOMJHI-UHFFFAOYSA-N ethyl 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OCC)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 OUDTVESPNOMJHI-UHFFFAOYSA-N 0.000 claims description 17
• LMWJQVTYANHCIM-UHFFFAOYSA-N n-[3-[2-[[4-(5-aminobenzimidazol-1-yl)-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC(N)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 LMWJQVTYANHCIM-UHFFFAOYSA-N 0.000 claims description 15
• 125000001246 bromo group Chemical group Br* 0.000 claims description 14
• 239000000556 agonist Substances 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 238000006243 chemical reaction Methods 0.000 claims description 11
• FEOUBAYQXHYVTQ-VWLOTQADSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC=C(C=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 FEOUBAYQXHYVTQ-VWLOTQADSA-N 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
• 208000008589 Obesity Diseases 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 9
• 235000020824 obesity Nutrition 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Chemical group 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 6
• FIHDRABZAAQKJG-UHFFFAOYSA-N n-[3-[2-[[4-(6-aminobenzimidazol-1-yl)-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC=C(N)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 FIHDRABZAAQKJG-UHFFFAOYSA-N 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• IWZSMSOBKJMUIB-VWLOTQADSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-methoxybenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(C)CCN2C=3C=C(C(=CC=3N=C2)C(O)=O)OC)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 IWZSMSOBKJMUIB-VWLOTQADSA-N 0.000 claims description 5
• ISKUURKCGKMQGQ-VWLOTQADSA-N 3-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC(=CC=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ISKUURKCGKMQGQ-VWLOTQADSA-N 0.000 claims description 5
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
• 239000000969 carrier Substances 0.000 claims description 5
• 239000008103 glucose Substances 0.000 claims description 5
• 230000000638 stimulation Effects 0.000 claims description 5
• OIQFJYZHJGRDOB-QHCPKHFHSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-4-chlorobenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC=C(C(Cl)=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 OIQFJYZHJGRDOB-QHCPKHFHSA-N 0.000 claims description 4
• VKMKJTBPKPJAIJ-VWLOTQADSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-chlorobenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC(Cl)=C(C(O)=O)C=C3N=C2)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 VKMKJTBPKPJAIJ-VWLOTQADSA-N 0.000 claims description 4
• KPUYFRHQLDMBNW-VWLOTQADSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-hydroxybenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC(O)=C(C(O)=O)C=C3N=C2)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 KPUYFRHQLDMBNW-VWLOTQADSA-N 0.000 claims description 4
• 230000001800 adrenalinergic effect Effects 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• YSMUFEAIAAOFHE-UHFFFAOYSA-N ethyl 3-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=CN1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 YSMUFEAIAAOFHE-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• SILNNFMWIMZVEQ-JZRMKITLSA-N 1,3-dihydrobenzimidazol-2-one Chemical group C1=CC=C2N[11C](=O)NC2=C1 SILNNFMWIMZVEQ-JZRMKITLSA-N 0.000 claims description 3
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
• XLNVCXIQJAMZSB-QHCPKHFHSA-N 3-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-4-chlorobenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=C(Cl)C(C(O)=O)=CC=C3N=C2)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 XLNVCXIQJAMZSB-QHCPKHFHSA-N 0.000 claims description 3
• YZTYUSDPESXYFY-VWLOTQADSA-N 3-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-chlorobenzimidazole-5-carboxylic acid Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC(=C(Cl)C=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 YZTYUSDPESXYFY-VWLOTQADSA-N 0.000 claims description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
• 101710204865 Tyrosine-protein phosphatase 1 Proteins 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 230000001906 cholesterol absorption Effects 0.000 claims description 3
• 230000002074 deregulated effect Effects 0.000 claims description 3
• 150000002632 lipids Chemical class 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
• OIQFJYZHJGRDOB-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-4-chlorobenzimidazole-5-carboxylic acid Chemical compound C1=NC2=C(Cl)C(C(O)=O)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 OIQFJYZHJGRDOB-UHFFFAOYSA-N 0.000 claims description 2
• VKMKJTBPKPJAIJ-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-chlorobenzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC(C(O)=O)=C(Cl)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 VKMKJTBPKPJAIJ-UHFFFAOYSA-N 0.000 claims description 2
• KPUYFRHQLDMBNW-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-hydroxybenzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC(C(O)=O)=C(O)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 KPUYFRHQLDMBNW-UHFFFAOYSA-N 0.000 claims description 2
• IWZSMSOBKJMUIB-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-methoxybenzimidazole-5-carboxylic acid Chemical compound C1=NC=2C=C(C(O)=O)C(OC)=CC=2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 IWZSMSOBKJMUIB-UHFFFAOYSA-N 0.000 claims description 2
• XLNVCXIQJAMZSB-UHFFFAOYSA-N 3-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-4-chlorobenzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC=C(C(O)=O)C(Cl)=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 XLNVCXIQJAMZSB-UHFFFAOYSA-N 0.000 claims description 2
• YZTYUSDPESXYFY-UHFFFAOYSA-N 3-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-6-chlorobenzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC(Cl)=C(C(O)=O)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 YZTYUSDPESXYFY-UHFFFAOYSA-N 0.000 claims description 2
• ISKUURKCGKMQGQ-UHFFFAOYSA-N 3-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid Chemical compound C1=NC2=CC=C(C(O)=O)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ISKUURKCGKMQGQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 230000003178 anti-diabetic effect Effects 0.000 claims description 2
• 230000006806 disease prevention Effects 0.000 claims description 2
• RNEXJMZCXHSHIZ-VWLOTQADSA-N n-[3-[(1r)-2-[[4-[5-(hydrazinecarbonyl)benzimidazol-1-yl]-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound C=1C([C@@H](O)CNC(C)(CCN2C3=CC=C(C=C3N=C2)C(=O)NN)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 RNEXJMZCXHSHIZ-VWLOTQADSA-N 0.000 claims description 2
• RNEXJMZCXHSHIZ-UHFFFAOYSA-N n-[3-[2-[[4-[5-(hydrazinecarbonyl)benzimidazol-1-yl]-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC(C(=O)NN)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 RNEXJMZCXHSHIZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000006239 protecting group Chemical group 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
• 239000003814 drug Substances 0.000 abstract description 5
• 150000007524 organic acids Chemical class 0.000 abstract description 5
• 235000005985 organic acids Nutrition 0.000 abstract description 5
• 229940079593 drug Drugs 0.000 abstract description 4
• 150000007522 mineralic acids Chemical class 0.000 abstract description 4
• 230000008569 process Effects 0.000 abstract description 3
• 229940125388 beta agonist Drugs 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 167
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 103
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 73
• 239000000741 silica gel Substances 0.000 description 72
• 229910002027 silica gel Inorganic materials 0.000 description 72
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 69
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 44
• 239000012071 phase Substances 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• 229910021529 ammonia Inorganic materials 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• 238000001704 evaporation Methods 0.000 description 29
• 230000008020 evaporation Effects 0.000 description 29
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 25
• 238000003818 flash chromatography Methods 0.000 description 25
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000012074 organic phase Substances 0.000 description 24
• 239000003208 petroleum Substances 0.000 description 22
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 229920006395 saturated elastomer Polymers 0.000 description 21
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 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 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 230000002441 reversible effect Effects 0.000 description 16
• 238000003756 stirring Methods 0.000 description 15
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• WKDNTKXTOZBKQV-UHFFFAOYSA-N n-[3-(2-ethoxy-2-hydroxyacetyl)phenyl]benzenesulfonamide Chemical compound CCOC(O)C(=O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 WKDNTKXTOZBKQV-UHFFFAOYSA-N 0.000 description 13
• 229910052938 sodium sulfate Inorganic materials 0.000 description 13
• 235000011152 sodium sulphate Nutrition 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 239000005457 ice water Substances 0.000 description 10
• 230000014759 maintenance of location Effects 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 239000012279 sodium borohydride Substances 0.000 description 10
• 229910000033 sodium borohydride Inorganic materials 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 235000019341 magnesium sulphate Nutrition 0.000 description 9
• 239000011780 sodium chloride Substances 0.000 description 9
• 239000008346 aqueous phase Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 238000004128 high performance liquid chromatography Methods 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• 229920002261 Corn starch Polymers 0.000 description 7
• 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 7
• 239000002253 acid Substances 0.000 description 7
• 239000008120 corn starch Substances 0.000 description 7
• 229940099112 cornstarch Drugs 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
• 239000008101 lactose Substances 0.000 description 7
• 235000019359 magnesium stearate Nutrition 0.000 description 7
• 230000027939 micturition Effects 0.000 description 7
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• 208000002193 Pain Diseases 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 235000011187 glycerol Nutrition 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 229910052739 hydrogen Inorganic materials 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• WHGHPURRSLRMIX-AWEZNQCLSA-N n-[3-[(2r)-oxiran-2-yl]phenyl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=1)=CC=CC=1[C@@H]1CO1 WHGHPURRSLRMIX-AWEZNQCLSA-N 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 235000019253 formic acid Nutrition 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 235000019698 starch Nutrition 0.000 description 5
• 239000000454 talc Substances 0.000 description 5
• 235000012222 talc Nutrition 0.000 description 5
• 229910052623 talc Inorganic materials 0.000 description 5
• HQZCKDWAFDGVHG-UHFFFAOYSA-N tert-butyl n-(4-amino-2-methylbutan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCN HQZCKDWAFDGVHG-UHFFFAOYSA-N 0.000 description 5
• FLUAPMDEQLPWPO-UHFFFAOYSA-N tert-butyl n-(4-chloro-2-methylbutan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCCl FLUAPMDEQLPWPO-UHFFFAOYSA-N 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 4
• 0 CC(*)(CCO1)NS1(=O)=O Chemical compound CC(*)(CCO1)NS1(=O)=O 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
• 239000007868 Raney catalyst Substances 0.000 description 4
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
• 229910000564 Raney nickel Inorganic materials 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 210000001789 adipocyte Anatomy 0.000 description 4
• 239000012298 atmosphere Substances 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• 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 4
• GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
• BIROFVBTDWNLKU-UHFFFAOYSA-N ethyl 1h-benzimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1N=CN2 BIROFVBTDWNLKU-UHFFFAOYSA-N 0.000 description 4
• 229940093915 gynecological organic acid Drugs 0.000 description 4
• 229910052736 halogen Inorganic materials 0.000 description 4
• 150000002367 halogens Chemical class 0.000 description 4
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 230000004130 lipolysis Effects 0.000 description 4
• FKUGXHFAIZQGCX-AWEZNQCLSA-N n-[3-[(1r)-2-chloro-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound ClC[C@H](O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 FKUGXHFAIZQGCX-AWEZNQCLSA-N 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• IWYSBVQAUQAYCF-UHFFFAOYSA-N 2-methyl-4-(2-methylbenzimidazol-1-yl)butan-2-amine;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2N(CCC(C)(C)N)C(C)=NC2=C1 IWYSBVQAUQAYCF-UHFFFAOYSA-N 0.000 description 3
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
• MJMDRWRZFSZBHZ-UHFFFAOYSA-N 4-[[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]-3-nitrobenzoic acid Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCNC1=CC=C(C(O)=O)C=C1[N+]([O-])=O MJMDRWRZFSZBHZ-UHFFFAOYSA-N 0.000 description 3
• GOTDZEOIBMTRDU-UHFFFAOYSA-N 4-chloro-2-methylbutan-2-amine;hydrochloride Chemical compound Cl.CC(C)(N)CCCl GOTDZEOIBMTRDU-UHFFFAOYSA-N 0.000 description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
• 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 3
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 208000007107 Stomach Ulcer Diseases 0.000 description 3
• 206010046543 Urinary incontinence Diseases 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 235000011114 ammonium hydroxide Nutrition 0.000 description 3
• 239000003708 ampul Substances 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 3
• 239000003610 charcoal Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
• 230000003111 delayed effect Effects 0.000 description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
• OPVXCIOLKYTNOO-UHFFFAOYSA-N ethyl 1-(3-amino-3-methylbutyl)benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(CCC(C)(C)N)C=NC2=C1 OPVXCIOLKYTNOO-UHFFFAOYSA-N 0.000 description 3
• OUDTVESPNOMJHI-MHZLTWQESA-N ethyl 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylate Chemical compound C=1C([C@@H](O)CNC(C)(C)CCN2C3=CC=C(C=C3N=C2)C(=O)OCC)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 OUDTVESPNOMJHI-MHZLTWQESA-N 0.000 description 3
• RPQLHJYFFUTGGR-UHFFFAOYSA-N ethyl 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-4-carboxylate Chemical compound C1=NC=2C(C(=O)OCC)=CC=CC=2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 RPQLHJYFFUTGGR-UHFFFAOYSA-N 0.000 description 3
• IFWZIEYXNRUVDG-UHFFFAOYSA-N ethyl 1-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1N=CN2CCC(C)(C)NC(=O)OC(C)(C)C IFWZIEYXNRUVDG-UHFFFAOYSA-N 0.000 description 3
• QYOUNCZBMWMEMY-UHFFFAOYSA-N ethyl 3-(3-amino-3-methylbutyl)benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CN(CCC(C)(C)N)C2=C1 QYOUNCZBMWMEMY-UHFFFAOYSA-N 0.000 description 3
• JTNLGLPYMCZHKQ-UHFFFAOYSA-N ethyl 4-[(3-methyl-3-nitrobutyl)amino]-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(NCCC(C)(C)[N+]([O-])=O)C([N+]([O-])=O)=C1 JTNLGLPYMCZHKQ-UHFFFAOYSA-N 0.000 description 3
• FNSRECPZSPPFJC-UHFFFAOYSA-N ethyl 4-chloro-3-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CN(CCC(C)(C)NC(=O)OC(C)(C)C)C2=C1Cl FNSRECPZSPPFJC-UHFFFAOYSA-N 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000012362 glacial acetic acid Substances 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 3
• 239000011630 iodine Substances 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• XNISACBUBKTWFS-UHFFFAOYSA-N methyl 1-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]-2-oxo-3h-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(CCC(C)(C)NC(=O)OC(C)(C)C)C(=O)NC2=C1 XNISACBUBKTWFS-UHFFFAOYSA-N 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
• 235000010446 mineral oil Nutrition 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 210000002307 prostate Anatomy 0.000 description 3
• 201000007094 prostatitis Diseases 0.000 description 3
• 102000005962 receptors Human genes 0.000 description 3
• 108020003175 receptors Proteins 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• QTUCVHJOZFLPQT-UHFFFAOYSA-N tert-butyl 4,4-dimethyl-2,2-dioxooxathiazinane-3-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C)(C)CCOS1(=O)=O QTUCVHJOZFLPQT-UHFFFAOYSA-N 0.000 description 3
• NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• QGWIQBHAINZJLD-UQIIZPHYSA-N 1-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C([C@@H](O)CNC(C)(CCN2C3=CC=C(C=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 QGWIQBHAINZJLD-UQIIZPHYSA-N 0.000 description 2
• NYRVXGFFPAFXDM-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-2-oxo-3h-benzimidazole-5-carboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2NC(=O)N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 NYRVXGFFPAFXDM-UHFFFAOYSA-N 0.000 description 2
• ZRCCGURDIIPFRI-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-4-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC2=C(C(O)=O)C=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ZRCCGURDIIPFRI-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• XQUKXPSAZWPCGK-UHFFFAOYSA-N 2-methyl-4-(6-nitrobenzimidazol-1-yl)butan-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2N(CCC(C)(N)C)C=NC2=C1 XQUKXPSAZWPCGK-UHFFFAOYSA-N 0.000 description 2
• PHRHXTTZZWUGNN-UHFFFAOYSA-N 3-amino-3-methylbutan-1-ol Chemical compound CC(C)(N)CCO PHRHXTTZZWUGNN-UHFFFAOYSA-N 0.000 description 2
• CEJYVPIWPXDBNJ-UHFFFAOYSA-N 3-amino-4-[[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]benzoic acid Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCNC1=CC=C(C(O)=O)C=C1N CEJYVPIWPXDBNJ-UHFFFAOYSA-N 0.000 description 2
• NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 2
• RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
• JRTXYNGGGOWIBM-UHFFFAOYSA-N 4-chloro-5-methyl-1h-benzimidazole Chemical compound CC1=CC=C2N=CNC2=C1Cl JRTXYNGGGOWIBM-UHFFFAOYSA-N 0.000 description 2
• BOJWTAQWPVBIPG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 BOJWTAQWPVBIPG-UHFFFAOYSA-N 0.000 description 2
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
• BQHSHBQZSZIJPC-UHFFFAOYSA-N 5-methyl-1h-benzimidazol-4-amine Chemical compound CC1=CC=C2NC=NC2=C1N BQHSHBQZSZIJPC-UHFFFAOYSA-N 0.000 description 2
• BPGUPKNXAJTAIG-UHFFFAOYSA-N 6-chloro-1h-benzimidazole-5-carboxylic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC2=C1NC=N2 BPGUPKNXAJTAIG-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• 206010010904 Convulsion Diseases 0.000 description 2
• 206010063057 Cystitis noninfective Diseases 0.000 description 2
• NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 239000004097 EU approved flavor enhancer Substances 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 208000018522 Gastrointestinal disease Diseases 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 208000010412 Glaucoma Diseases 0.000 description 2
• 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 2
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• 206010061218 Inflammation Diseases 0.000 description 2
• 206010022489 Insulin Resistance Diseases 0.000 description 2
• 206010022714 Intestinal ulcer Diseases 0.000 description 2
• 206010071289 Lower urinary tract symptoms Diseases 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 208000007920 Neurogenic Inflammation Diseases 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• 208000000921 Urge Urinary Incontinence Diseases 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
• 239000000654 additive Substances 0.000 description 2
• 210000000577 adipose tissue Anatomy 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 239000005557 antagonist Substances 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 239000001506 calcium phosphate Substances 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 230000001684 chronic effect Effects 0.000 description 2
• 230000036461 convulsion Effects 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 206010012601 diabetes mellitus Diseases 0.000 description 2
• GNGACRATGGDKBX-UHFFFAOYSA-N dihydroxyacetone phosphate Chemical compound OCC(=O)COP(O)(O)=O GNGACRATGGDKBX-UHFFFAOYSA-N 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• AEHJFFLYRHVZQZ-UHFFFAOYSA-N ethyl 1-(3-amino-3-methylbutyl)benzimidazole-4-carboxylate Chemical compound CCOC(=O)C1=CC=CC2=C1N=CN2CCC(C)(C)N AEHJFFLYRHVZQZ-UHFFFAOYSA-N 0.000 description 2
• CUSPYFFZNKKQRY-UHFFFAOYSA-N ethyl 3-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CN(CCC(C)(C)NC(=O)OC(C)(C)C)C2=C1 CUSPYFFZNKKQRY-UHFFFAOYSA-N 0.000 description 2
• HUOIDCCHUGUZQS-UHFFFAOYSA-N ethyl 3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CNC2=C1 HUOIDCCHUGUZQS-UHFFFAOYSA-N 0.000 description 2
• ZNLNTBOKWYDJDG-UHFFFAOYSA-N ethyl 4-chloro-1-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(CCC(C)(C)NC(=O)OC(C)(C)C)C=NC2=C1Cl ZNLNTBOKWYDJDG-UHFFFAOYSA-N 0.000 description 2
• YONVBKVUSUGBQR-UHFFFAOYSA-N ethyl 4-fluoro-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 YONVBKVUSUGBQR-UHFFFAOYSA-N 0.000 description 2
• WOIKQHUTSWIWFX-UHFFFAOYSA-N ethyl 6-chloro-1-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC2=C1N(CCC(C)(C)NC(=O)OC(C)(C)C)C=N2 WOIKQHUTSWIWFX-UHFFFAOYSA-N 0.000 description 2
• FKLVCHZGCCYGTF-UHFFFAOYSA-N ethyl 6-chloro-3-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC2=C1N=CN2CCC(C)(C)NC(=O)OC(C)(C)C FKLVCHZGCCYGTF-UHFFFAOYSA-N 0.000 description 2
• 239000003925 fat Substances 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 235000019264 food flavour enhancer Nutrition 0.000 description 2
• 201000005917 gastric ulcer Diseases 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• AWUCVROLDVIAJX-UHFFFAOYSA-N glycerol 1-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 125000006038 hexenyl group Chemical group 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000005980 hexynyl group Chemical group 0.000 description 2
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• 239000003978 infusion fluid Substances 0.000 description 2
• 229910052500 inorganic mineral Inorganic materials 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
• 208000002551 irritable bowel syndrome Diseases 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 239000001630 malic acid Substances 0.000 description 2
• 235000011090 malic acid Nutrition 0.000 description 2
• 229960002510 mandelic acid Drugs 0.000 description 2
• IXGDWDWBTARPDZ-UHFFFAOYSA-N methyl 1-(3-amino-3-methylbutyl)-2-oxo-3h-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(CCC(C)(C)N)C(=O)NC2=C1 IXGDWDWBTARPDZ-UHFFFAOYSA-N 0.000 description 2
• MBEJSVHFSUIEHT-UHFFFAOYSA-N methyl 2-methoxy-4-[[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(NCCC(C)(C)NC(=O)OC(C)(C)C)C=C1OC MBEJSVHFSUIEHT-UHFFFAOYSA-N 0.000 description 2
• 235000010755 mineral Nutrition 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• ACNVYECYPGKMHB-UHFFFAOYSA-N n-(3-acetylphenyl)benzenesulfonamide Chemical compound CC(=O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 ACNVYECYPGKMHB-UHFFFAOYSA-N 0.000 description 2
• CNNKSAPYROLGGF-UHFFFAOYSA-N n-[3-(2-chloroacetyl)phenyl]benzenesulfonamide Chemical compound ClCC(=O)C1=CC=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 CNNKSAPYROLGGF-UHFFFAOYSA-N 0.000 description 2
• ABJIQVGLHJEKRV-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[[2-methyl-4-(2-methylbenzimidazol-1-yl)butan-2-yl]amino]ethyl]phenyl]benzenesulfonamide Chemical compound CC1=NC2=CC=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ABJIQVGLHJEKRV-UHFFFAOYSA-N 0.000 description 2
• ITPGDMWTXHTABC-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[[2-methyl-4-(2-oxo-3h-benzimidazol-1-yl)butan-2-yl]amino]ethyl]phenyl]benzenesulfonamide Chemical compound C12=CC=CC=C2NC(=O)N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ITPGDMWTXHTABC-UHFFFAOYSA-N 0.000 description 2
• XKUOENWTWCMXFZ-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[[2-methyl-4-(3-methyl-2-oxobenzimidazol-1-yl)butan-2-yl]amino]ethyl]phenyl]benzenesulfonamide Chemical compound O=C1N(C)C2=CC=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 XKUOENWTWCMXFZ-UHFFFAOYSA-N 0.000 description 2
• NPINCHWLIGPXGN-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[[2-methyl-4-(6-nitrobenzimidazol-1-yl)butan-2-yl]amino]ethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC=C([N+]([O-])=O)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 NPINCHWLIGPXGN-UHFFFAOYSA-N 0.000 description 2
• LLNREPRHUQSDFT-UHFFFAOYSA-N n-[3-[2-[(4-benzo[f]benzimidazol-3-yl-2-methylbutan-2-yl)amino]-1-hydroxyethyl]phenyl]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC2=CC3=CC=CC=C3C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 LLNREPRHUQSDFT-UHFFFAOYSA-N 0.000 description 2
• UKPVSXNTYXKTAT-UHFFFAOYSA-N n-[3-[2-[[4-(5,6-dichlorobenzimidazol-1-yl)-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC2=CC(Cl)=C(Cl)C=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 UKPVSXNTYXKTAT-UHFFFAOYSA-N 0.000 description 2
• ZQAKBPMUENTWQZ-UHFFFAOYSA-N n-[3-[2-[[4-(benzimidazol-1-yl)-2-methylbutan-2-yl]amino]-1-hydroxyethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 ZQAKBPMUENTWQZ-UHFFFAOYSA-N 0.000 description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 230000001272 neurogenic effect Effects 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• 230000000422 nocturnal effect Effects 0.000 description 2
• 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 2
• 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 210000004197 pelvis Anatomy 0.000 description 2
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
• 125000005981 pentynyl group Chemical group 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
• 125000004193 piperazinyl group Chemical group 0.000 description 2
• CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
• 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
• 239000012286 potassium permanganate Substances 0.000 description 2
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
• 230000004936 stimulating effect Effects 0.000 description 2
• 238000000967 suction filtration Methods 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 238000009492 tablet coating Methods 0.000 description 2
• 239000002700 tablet coating Substances 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
• QHSUFODBDZQCHO-UHFFFAOYSA-N tert-butyl n-(4-hydroxy-2-methylbutan-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)CCO QHSUFODBDZQCHO-UHFFFAOYSA-N 0.000 description 2
• DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
• 150000003536 tetrazoles Chemical class 0.000 description 2
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 210000001635 urinary tract Anatomy 0.000 description 2
• 229940075966 (+)- menthol Drugs 0.000 description 1
• NOOLISFMXDJSKH-AEJSXWLSSA-N (+)-menthol Chemical compound CC(C)[C@H]1CC[C@H](C)C[C@@H]1O NOOLISFMXDJSKH-AEJSXWLSSA-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
• PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 1
• 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 1
• AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 description 1
• AOLYSFNVCBHZHQ-UHFFFAOYSA-N 1-(3-amino-3-methylbutyl)-3-methylbenzimidazol-2-one;hydrochloride Chemical compound Cl.C1=CC=C2N(CCC(C)(C)N)C(=O)N(C)C2=C1 AOLYSFNVCBHZHQ-UHFFFAOYSA-N 0.000 description 1
• SYXOUOUEHIJMBD-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-2-oxo-3h-benzimidazole-5-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=C(C(O)=O)C=C2NC(=O)N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 SYXOUOUEHIJMBD-UHFFFAOYSA-N 0.000 description 1
• KSUIRFNOFGXMPB-UHFFFAOYSA-N 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-4-carboxylic acid Chemical compound C1=NC2=C(C(O)=O)C=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 KSUIRFNOFGXMPB-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• VVQNAFBGAWCMLU-UHFFFAOYSA-N 1h-benzimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1N=CN2 VVQNAFBGAWCMLU-UHFFFAOYSA-N 0.000 description 1
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
• LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
• SHCWQWRTKPNTEM-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1Cl SHCWQWRTKPNTEM-UHFFFAOYSA-N 0.000 description 1
• KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• YNOPZLWHBMWCPX-UHFFFAOYSA-N 2-chloro-4,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=C([N+]([O-])=O)C=C1Cl YNOPZLWHBMWCPX-UHFFFAOYSA-N 0.000 description 1
• LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
• LPZRMKGBALTKKP-UHFFFAOYSA-N 2-methylbutan-2-amine;hydrochloride Chemical compound Cl.CCC(C)(C)N LPZRMKGBALTKKP-UHFFFAOYSA-N 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
• IJTHFYBXOLRGMT-UHFFFAOYSA-N 3-(3-amino-3-methylbutyl)-1h-benzimidazol-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=C2NC(=O)N(CCC(C)(N)C)C2=C1 IJTHFYBXOLRGMT-UHFFFAOYSA-N 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
• WHNKEIBOLPYDKN-UQIIZPHYSA-N 3-[3-[[(2r)-2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]benzimidazole-5-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C([C@@H](O)CNC(C)(CCN2C3=CC(=CC=C3N=C2)C(O)=O)C)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 WHNKEIBOLPYDKN-UQIIZPHYSA-N 0.000 description 1
• AZHLFJXPHWMNRL-UHFFFAOYSA-N 3-[acetyl-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]-2-methoxy-4-methyl-5-nitrobenzoic acid Chemical compound COC1=C(C(O)=O)C=C([N+]([O-])=O)C(C)=C1N(CCC(C)(C)NC(=O)OC(C)(C)C)C(C)=O AZHLFJXPHWMNRL-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
• 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
• HRCXLZDCJRRAKK-UHFFFAOYSA-M 3-methyl-3-nitrobutan-1-amine;chloride Chemical compound [Cl-].[O-][N+](=O)C(C)(C)CCN HRCXLZDCJRRAKK-UHFFFAOYSA-M 0.000 description 1
• ZOFXBKXTQRELNV-UHFFFAOYSA-N 4-(5,6-dichlorobenzimidazol-1-yl)-2-methylbutan-2-amine;dihydrochloride Chemical compound Cl.Cl.ClC1=C(Cl)C=C2N(CCC(C)(N)C)C=NC2=C1 ZOFXBKXTQRELNV-UHFFFAOYSA-N 0.000 description 1
• XKYDVJAJOJGUMX-UHFFFAOYSA-N 4-benzo[f]benzimidazol-3-yl-2-methylbutan-2-amine Chemical compound C1=CC=C2C=C3N(CCC(C)(N)C)C=NC3=CC2=C1 XKYDVJAJOJGUMX-UHFFFAOYSA-N 0.000 description 1
• ZEVSEZPXSDDVOX-UHFFFAOYSA-N 5-methyl-4-nitro-1h-benzimidazole Chemical compound CC1=CC=C2NC=NC2=C1[N+]([O-])=O ZEVSEZPXSDDVOX-UHFFFAOYSA-N 0.000 description 1
• 239000005541 ACE inhibitor Substances 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
• 102000009027 Albumins Human genes 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 240000002470 Amphicarpaea bracteata Species 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• BMFMQGXDDJALKQ-BYPYZUCNSA-N Argininic acid Chemical compound NC(N)=NCCC[C@H](O)C(O)=O BMFMQGXDDJALKQ-BYPYZUCNSA-N 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
• 206010005052 Bladder irritation Diseases 0.000 description 1
• 206010048994 Bladder spasm Diseases 0.000 description 1
• UQBBDXRVKYWTIX-UHFFFAOYSA-N CC(C)(CC[n]1c(cccc2)c2nc1C)N Chemical compound CC(C)(CC[n]1c(cccc2)c2nc1C)N UQBBDXRVKYWTIX-UHFFFAOYSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 239000005973 Carvone Substances 0.000 description 1
• 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
• 229920001268 Cholestyramine Polymers 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 102000029816 Collagenase Human genes 0.000 description 1
• 108060005980 Collagenase Proteins 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• 101710088194 Dehydrogenase Proteins 0.000 description 1
• 206010012735 Diarrhoea Diseases 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-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
• 208000008279 Dumping Syndrome Diseases 0.000 description 1
• 208000005171 Dysmenorrhea Diseases 0.000 description 1
• 206010013935 Dysmenorrhoea Diseases 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 208000004232 Enteritis Diseases 0.000 description 1
• 208000008967 Enuresis Diseases 0.000 description 1
• 208000010228 Erectile Dysfunction Diseases 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
• 108010011459 Exenatide Proteins 0.000 description 1
• 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
• 108091007911 GSKs Proteins 0.000 description 1
• 208000007882 Gastritis Diseases 0.000 description 1
• 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
• VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
• 108010063919 Glucagon Receptors Proteins 0.000 description 1
• 102100040890 Glucagon receptor Human genes 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
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 102000057621 Glycerol kinases Human genes 0.000 description 1
• 108700016170 Glycerol kinases Proteins 0.000 description 1
• 102000007390 Glycogen Phosphorylase Human genes 0.000 description 1
• 108010046163 Glycogen Phosphorylase Proteins 0.000 description 1
• 102000004103 Glycogen Synthase Kinases Human genes 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 102100030488 HEAT repeat-containing protein 6 Human genes 0.000 description 1
• 101000990566 Homo sapiens HEAT repeat-containing protein 6 Proteins 0.000 description 1
• 101000801684 Homo sapiens Phospholipid-transporting ATPase ABCA1 Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• 208000035150 Hypercholesterolemia Diseases 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 1
• 108010041872 Islet Amyloid Polypeptide Proteins 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
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 206010027566 Micturition urgency Diseases 0.000 description 1
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
• 208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 1
• 206010029279 Neurogenic bladder Diseases 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 206010030216 Oesophagitis Diseases 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 102000004316 Oxidoreductases Human genes 0.000 description 1
• 108090000854 Oxidoreductases Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 102000000536 PPAR gamma Human genes 0.000 description 1
• 108010016731 PPAR gamma Proteins 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 208000032395 Post gastric surgery syndrome Diseases 0.000 description 1
• 102100040918 Pro-glucagon Human genes 0.000 description 1
• 206010036774 Proctitis Diseases 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
• AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
• 206010036775 Rectal inflammations Diseases 0.000 description 1
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 206010066218 Stress Urinary Incontinence Diseases 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• 229940123464 Thiazolidinedione Drugs 0.000 description 1
• JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-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
• 208000025865 Ulcer Diseases 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 206010046555 Urinary retention Diseases 0.000 description 1
• 206010062225 Urinary tract pain 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
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-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
• 238000009825 accumulation Methods 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 230000003266 anti-allergic effect Effects 0.000 description 1
• 229940127003 anti-diabetic drug Drugs 0.000 description 1
• 230000002921 anti-spasmodic effect Effects 0.000 description 1
• 239000003472 antidiabetic agent Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 239000007900 aqueous suspension Substances 0.000 description 1
• 208000037849 arterial hypertension Diseases 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229960005370 atorvastatin Drugs 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• 239000002876 beta blocker Substances 0.000 description 1
• 229940097320 beta blocking agent Drugs 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 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
• 239000003613 bile acid Substances 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
• 229940124630 bronchodilator Drugs 0.000 description 1
• 230000001813 broncholytic effect Effects 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 235000019577 caloric intake Nutrition 0.000 description 1
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 210000004027 cell Anatomy 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• PSEHHVRCDVOTID-VMAIWCPRSA-N chloro-bis[(1r,3r,4s,5r)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane Chemical compound C([C@H]([C@@H]1C)B(Cl)[C@H]2[C@H](C)[C@]3(C[C@@](C2)(C3(C)C)[H])[H])[C@@]2([H])C(C)(C)[C@]1([H])C2 PSEHHVRCDVOTID-VMAIWCPRSA-N 0.000 description 1
• 208000003167 cholangitis Diseases 0.000 description 1
• 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 description 1
• 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 1
• 239000000812 cholinergic antagonist Substances 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 201000003139 chronic cystitis Diseases 0.000 description 1
• 208000022371 chronic pain syndrome Diseases 0.000 description 1
• 208000013507 chronic prostatitis Diseases 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 229960002424 collagenase Drugs 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 239000007859 condensation product Substances 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 229940109275 cyclamate Drugs 0.000 description 1
• 125000000392 cycloalkenyl 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
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000013872 defecation Effects 0.000 description 1
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 239000002934 diuretic Substances 0.000 description 1
• 229940030606 diuretics Drugs 0.000 description 1
• 230000002183 duodenal effect Effects 0.000 description 1
• 208000000718 duodenal ulcer Diseases 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 206010013990 dysuria Diseases 0.000 description 1
• 230000004406 elevated intraocular pressure Effects 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 208000006881 esophagitis Diseases 0.000 description 1
• 150000002148 esters Chemical class 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
• VQKSWHONZGQDFH-UHFFFAOYSA-N ethyl 1-(3-amino-3-methylbutyl)-6-chlorobenzimidazole-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC2=C1N(CCC(C)(C)N)C=N2 VQKSWHONZGQDFH-UHFFFAOYSA-N 0.000 description 1
• KRCMDIBHYOFTEN-UHFFFAOYSA-N ethyl 1-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(CCC(C)(C)NC(=O)OC(C)(C)C)C=NC2=C1 KRCMDIBHYOFTEN-UHFFFAOYSA-N 0.000 description 1
• KLWYPRNPRNPORS-UHFFFAOYSA-N ethyl 1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=CN1 KLWYPRNPRNPORS-UHFFFAOYSA-N 0.000 description 1
• YWENVCNNUWCJPT-UHFFFAOYSA-N ethyl 3-(3-amino-3-methylbutyl)-6-chloro-1,2-dihydrobenzimidazole-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC2=C1NCN2CCC(C)(C)N YWENVCNNUWCJPT-UHFFFAOYSA-N 0.000 description 1
• BFEJCZKSFRXXDG-UHFFFAOYSA-N ethyl 3-fluoro-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(F)=C1 BFEJCZKSFRXXDG-UHFFFAOYSA-N 0.000 description 1
• BJBMOADWZYXDAT-UHFFFAOYSA-N ethyl 4-chloro-1h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CNC2=C1Cl BJBMOADWZYXDAT-UHFFFAOYSA-N 0.000 description 1
• MHLIQBWFTKYKBA-UHFFFAOYSA-N ethyl 4-chloro-1h-benzimidazole-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=C2N=CNC2=C1Cl MHLIQBWFTKYKBA-UHFFFAOYSA-N 0.000 description 1
• WMWJFIRNCHTARP-UHFFFAOYSA-N ethyl 6-chloro-1h-benzimidazole-5-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC2=C1NC=N2 WMWJFIRNCHTARP-UHFFFAOYSA-N 0.000 description 1
• KIPZLLVCZMXZJY-UHFFFAOYSA-N ethyl 6-chloro-1h-benzimidazole-5-carboxylate;hydrochloride Chemical compound Cl.C1=C(Cl)C(C(=O)OCC)=CC2=C1NC=N2 KIPZLLVCZMXZJY-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 229960001519 exenatide 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
• 229960000815 ezetimibe Drugs 0.000 description 1
• 150000002191 fatty alcohols Chemical class 0.000 description 1
• 229960002297 fenofibrate Drugs 0.000 description 1
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
• 229940125753 fibrate Drugs 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 230000004927 fusion Effects 0.000 description 1
• 208000020694 gallbladder disease Diseases 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 229960004580 glibenclamide Drugs 0.000 description 1
• WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
• 229960004346 glimepiride Drugs 0.000 description 1
• 230000009229 glucose formation Effects 0.000 description 1
• 230000004153 glucose metabolism Effects 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
• 229960005150 glycerol Drugs 0.000 description 1
• 125000004404 heteroalkyl group Chemical group 0.000 description 1
• 125000005241 heteroarylamino group Chemical group 0.000 description 1
• 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 201000001421 hyperglycemia Diseases 0.000 description 1
• 208000006575 hypertriglyceridemia Diseases 0.000 description 1
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 201000001881 impotence Diseases 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 238000007918 intramuscular administration Methods 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
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 229960001375 lactose Drugs 0.000 description 1
• 229960004873 levomenthol Drugs 0.000 description 1
• 229920005610 lignin Polymers 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000011866 long-term treatment Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
• 229960003105 metformin Drugs 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• WIKHOCFWIQWHJZ-UHFFFAOYSA-N methyl 1-(3-amino-3-methylbutyl)-6-methoxybenzimidazole-5-carboxylate Chemical compound C1=C(OC)C(C(=O)OC)=CC2=C1N(CCC(C)(C)N)C=N2 WIKHOCFWIQWHJZ-UHFFFAOYSA-N 0.000 description 1
• CBSUDERXXIXDGT-UHFFFAOYSA-N methyl 1-[3-[[2-[3-(benzenesulfonamido)phenyl]-2-hydroxyethyl]amino]-3-methylbutyl]-2-oxo-3h-benzimidazole-5-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 CBSUDERXXIXDGT-UHFFFAOYSA-N 0.000 description 1
• AQHKDQYJYUONSS-UHFFFAOYSA-N methyl 2,3-dihydro-1H-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC2=C(NCN2)C=C1 AQHKDQYJYUONSS-UHFFFAOYSA-N 0.000 description 1
• WJHHIVYNOVTVGY-UHFFFAOYSA-N methyl 3h-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N=CNC2=C1 WJHHIVYNOVTVGY-UHFFFAOYSA-N 0.000 description 1
• JLDYRWNJJZMUEX-UHFFFAOYSA-N methyl 4-[acetyl-[3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butyl]amino]-2-methoxy-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(N(CCC(C)(C)NC(=O)OC(C)(C)C)C(C)=O)C=C1OC JLDYRWNJJZMUEX-UHFFFAOYSA-N 0.000 description 1
• AGSSDWHUSPSVFS-UHFFFAOYSA-N methyl 4-acetamido-2-methoxy-5-nitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=C(NC(C)=O)C=C1OC AGSSDWHUSPSVFS-UHFFFAOYSA-N 0.000 description 1
• VHAPGCZLNVXOGW-UHFFFAOYSA-N methyl 6-methoxy-3H-benzimidazole-5-carboxylate Chemical compound C1(OC)=C(C(=O)OC)C=C2N=CNC2=C1 VHAPGCZLNVXOGW-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 230000003387 muscular Effects 0.000 description 1
• DBDUKXZPNKUGAA-UHFFFAOYSA-N n-(2-acetylphenyl)benzenesulfonamide Chemical compound CC(=O)C1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 DBDUKXZPNKUGAA-UHFFFAOYSA-N 0.000 description 1
• DBVIVPAJYOERCJ-UHFFFAOYSA-N n-[3-[1-hydroxy-2-[[2-methyl-4-(5-nitrobenzimidazol-1-yl)butan-2-yl]amino]ethyl]phenyl]benzenesulfonamide Chemical compound C1=NC2=CC([N+]([O-])=O)=CC=C2N1CCC(C)(C)NCC(O)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=CC=C1 DBVIVPAJYOERCJ-UHFFFAOYSA-N 0.000 description 1
• 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
• 125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 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
• 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
• 230000004770 neurodegeneration Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 208000005346 nocturnal enuresis Diseases 0.000 description 1
• JKNKNWJNCOJPLI-UHFFFAOYSA-N o-phthalaldehydic acid Chemical compound C1=CC=C2C(O)OC(=O)C2=C1 JKNKNWJNCOJPLI-UHFFFAOYSA-N 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 238000012856 packing Methods 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 210000003899 penis Anatomy 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229930029653 phosphoenolpyruvate Natural products 0.000 description 1
• DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 1
• 230000037081 physical activity Effects 0.000 description 1
• 229960005095 pioglitazone Drugs 0.000 description 1
• 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
• 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920002689 polyvinyl acetate Polymers 0.000 description 1
• 239000011118 polyvinyl acetate Substances 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 208000017497 prostate disease Diseases 0.000 description 1
• 201000004240 prostatic hypertrophy Diseases 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
• 239000001008 quinone-imine dye Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229960002354 repaglinide Drugs 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229960004586 rosiglitazone Drugs 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 238000007127 saponification reaction Methods 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 229940113147 shellac 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
• 229960004425 sibutramine Drugs 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 229960002855 simvastatin Drugs 0.000 description 1
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
• 210000002460 smooth muscle Anatomy 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 235000015424 sodium Nutrition 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
• 229910001948 sodium oxide Inorganic materials 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
• UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• 150000001467 thiazolidinediones Chemical class 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• 235000010215 titanium dioxide Nutrition 0.000 description 1
• 229960005371 tolbutamide Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
• 230000036269 ulceration Effects 0.000 description 1
• 206010046494 urge incontinence Diseases 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 235000012141 vanillin Nutrition 0.000 description 1
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
• FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229960001729 voglibose Drugs 0.000 description 1
• 239000002699 waste material Substances 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1