JP5137207B2 - グルコキナーゼ活性化因子 - Google Patents

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Publication number

JP5137207B2

JP5137207B2 JP2008538915A JP2008538915A JP5137207B2 JP 5137207 B2 JP5137207 B2 JP 5137207B2 JP 2008538915 A JP2008538915 A JP 2008538915A JP 2008538915 A JP2008538915 A JP 2008538915A JP 5137207 B2 JP5137207 B2 JP 5137207B2

Authority

JP

Japan

Prior art keywords

alkyl

saturated

mmol

partially unsaturated

pyridin

Prior art date

2005-11-01

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.)

Expired - Fee Related

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• 229940124828 glucokinase activator Drugs 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 349
• 102000030595 Glucokinase Human genes 0.000 claims abstract description 55
• 108010021582 Glucokinase Proteins 0.000 claims abstract description 55
• 238000011282 treatment Methods 0.000 claims abstract description 49
• 230000000694 effects Effects 0.000 claims abstract description 23
• 230000003213 activating effect Effects 0.000 claims abstract description 9
• -1 CN Inorganic materials 0.000 claims description 235
• 229920006395 saturated elastomer Polymers 0.000 claims description 113
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 125000003342 alkenyl group Chemical group 0.000 claims description 68
• 125000000304 alkynyl group Chemical group 0.000 claims description 68
• 229910052801 chlorine Inorganic materials 0.000 claims description 64
• 229910052794 bromium Inorganic materials 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 53
• 229910052740 iodine Inorganic materials 0.000 claims description 50
• 229910052731 fluorine Inorganic materials 0.000 claims description 44
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 32
• 239000002585 base Substances 0.000 claims description 30
• 239000002904 solvent Substances 0.000 claims description 30
• 125000004429 atom Chemical group 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 239000012453 solvate Substances 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 239000003153 chemical reaction reagent Substances 0.000 claims description 23
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 19
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
• 229910052720 vanadium Inorganic materials 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 239000003054 catalyst Substances 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000002837 carbocyclic group Chemical group 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
• 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000004450 alkenylene group Chemical group 0.000 claims description 8
• 229910052751 metal Inorganic materials 0.000 claims description 8
• 239000002184 metal Substances 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
• 238000010168 coupling process Methods 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 125000004419 alkynylene group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 230000008878 coupling Effects 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims 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 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• 230000014509 gene expression Effects 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
• 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 158
• 206010012601 diabetes mellitus Diseases 0.000 abstract description 31
• 230000001404 mediated effect Effects 0.000 abstract description 10
• 208000037765 diseases and disorders Diseases 0.000 abstract description 5
• 230000002950 deficient Effects 0.000 abstract description 3
• 230000006806 disease prevention Effects 0.000 abstract description 2
• 206010011953 Decreased activity Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 152
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 133
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
• 239000000203 mixture Substances 0.000 description 100
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
• 239000011541 reaction mixture Substances 0.000 description 88
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
• 239000007787 solid Substances 0.000 description 84
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 74
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
• 238000006243 chemical reaction Methods 0.000 description 64
• 239000000460 chlorine Substances 0.000 description 62
• 235000019439 ethyl acetate Nutrition 0.000 description 62
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 55
• 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 54
• 239000008103 glucose Substances 0.000 description 54
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 40
• 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 38
• 230000015572 biosynthetic process Effects 0.000 description 37
• 239000003814 drug Substances 0.000 description 34
• 238000002360 preparation method Methods 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 239000000243 solution Substances 0.000 description 30
• 208000035475 disorder Diseases 0.000 description 29
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
• 239000000843 powder Substances 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 26
• 229910002027 silica gel Inorganic materials 0.000 description 26
• 238000009472 formulation Methods 0.000 description 25
• BVQJWGILQNRURY-UHFFFAOYSA-N n-(5-bromo-3-phenylmethoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)OCC=2C=CC=CC=2)=N1 BVQJWGILQNRURY-UHFFFAOYSA-N 0.000 description 25
• 150000003840 hydrochlorides Chemical class 0.000 description 24
• 229940002612 prodrug Drugs 0.000 description 24
• 239000000651 prodrug Substances 0.000 description 24
• 239000012458 free base Substances 0.000 description 22
• 239000002207 metabolite Substances 0.000 description 22
• 239000012267 brine Substances 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• 125000003118 aryl group Chemical group 0.000 description 20
• 229940079593 drug Drugs 0.000 description 20
• 102000004877 Insulin Human genes 0.000 description 19
• 108090001061 Insulin Proteins 0.000 description 19
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 229940125396 insulin Drugs 0.000 description 19
• 239000000543 intermediate Substances 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 239000008280 blood Substances 0.000 description 17
• 210000004369 blood Anatomy 0.000 description 17
• 125000001424 substituent group Chemical group 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 238000003556 assay Methods 0.000 description 16
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 16
• 241000349731 Afzelia bipindensis Species 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 15
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 15
• 125000000753 cycloalkyl group Chemical group 0.000 description 15
• IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 15
• 150000003254 radicals Chemical class 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• 229930195733 hydrocarbon Natural products 0.000 description 14
• 239000010410 layer Substances 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• 239000004215 Carbon black (E152) Substances 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• 241000124008 Mammalia Species 0.000 description 12
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 12
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
• 239000012954 diazonium Substances 0.000 description 12
• 150000001989 diazonium salts Chemical class 0.000 description 12
• XZZMYVGAZYQETB-UHFFFAOYSA-N methyl 3-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenylmethoxypyridin-3-yl]sulfanylpropanoate Chemical compound C=1C=CC=CC=1COC1=CC(SCCC(=O)OC)=CN=C1NC1=NC(C)=CS1 XZZMYVGAZYQETB-UHFFFAOYSA-N 0.000 description 12
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
• 229940124597 therapeutic agent Drugs 0.000 description 12
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 description 10
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 description 10
• 239000000546 pharmaceutical excipient Substances 0.000 description 10
• 238000000926 separation method Methods 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• XWESVPXIDGLPNX-UHFFFAOYSA-N 1,2,4-oxadiazol-3-amine Chemical compound NC=1N=CON=1 XWESVPXIDGLPNX-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• ADHDUTITAKAASJ-UHFFFAOYSA-N 1,2,4-oxadiazol-5-amine Chemical compound NC1=NC=NO1 ADHDUTITAKAASJ-UHFFFAOYSA-N 0.000 description 8
• HLJLOVWQXPNZSU-UHFFFAOYSA-N 2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-ol Chemical compound CC1=CSC(NC=2C(=CC=CN=2)O)=N1 HLJLOVWQXPNZSU-UHFFFAOYSA-N 0.000 description 8
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
• 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 8
• 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 8
• 208000002705 Glucose Intolerance Diseases 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 8
• 229940045189 glucose-6-phosphate Drugs 0.000 description 8
• 150000004820 halides Chemical class 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 150000003140 primary amides Chemical class 0.000 description 8
• 238000010898 silica gel chromatography Methods 0.000 description 8
• 208000024891 symptom Diseases 0.000 description 8
• 208000011580 syndromic disease Diseases 0.000 description 8
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