CN101798298B - 咪唑衍生物 - Google Patents

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Publication number

CN101798298B

CN101798298B CN2010101215002A CN201010121500A CN101798298B CN 101798298 B CN101798298 B CN 101798298B CN 2010101215002 A CN2010101215002 A CN 2010101215002A CN 201010121500 A CN201010121500 A CN 201010121500A CN 101798298 B CN101798298 B CN 101798298B

Authority

CN

China

Prior art keywords

methyl

phenyl

imidazol

methanol

imidazole

Prior art date

2001-01-29

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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• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
• 150000002460 imidazoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 525
• 238000000034 method Methods 0.000 claims abstract description 215
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
• 201000010099 disease Diseases 0.000 claims abstract description 7
• -1 nitro, benzyloxy, hydroxyl Chemical group 0.000 claims description 219
• 238000006243 chemical reaction Methods 0.000 claims description 116
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 230000004770 neurodegeneration Effects 0.000 claims description 9
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 7
• 230000001684 chronic effect Effects 0.000 claims description 7
• 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 6
• 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 6
• 208000002193 Pain Diseases 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 208000000094 Chronic Pain Diseases 0.000 claims description 3
• 208000005298 acute pain Diseases 0.000 claims description 3
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 230000009385 viral infection Effects 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 7
• 239000000654 additive Substances 0.000 claims 4
• 230000000996 additive effect Effects 0.000 claims 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 241000894006 Bacteria Species 0.000 claims 2
• 206010008190 Cerebrovascular accident Diseases 0.000 claims 2
• 208000006011 Stroke Diseases 0.000 claims 2
• 230000002490 cerebral effect Effects 0.000 claims 2
• 208000035475 disorder Diseases 0.000 claims 2
• 208000024732 dysthymic disease Diseases 0.000 claims 2
• 125000001072 heteroaryl group Chemical group 0.000 claims 2
• 208000014674 injury Diseases 0.000 claims 2
• 230000008733 trauma Effects 0.000 claims 2
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 abstract description 11
• HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 abstract description 5
• 230000001537 neural effect Effects 0.000 abstract description 3
• 230000007996 neuronal plasticity Effects 0.000 abstract description 3
• 230000006870 function Effects 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 726
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 414
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 399
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 364
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 260
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 225
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 221
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 192
• 239000012312 sodium hydride Substances 0.000 description 192
• 229910000104 sodium hydride Inorganic materials 0.000 description 192
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 172
• 238000010626 work up procedure Methods 0.000 description 142
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 134
• 239000012458 free base Substances 0.000 description 127
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 122
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 121
• 239000011541 reaction mixture Substances 0.000 description 111
• 238000004587 chromatography analysis Methods 0.000 description 109
• 239000000126 substance Substances 0.000 description 105
• 239000007787 solid Substances 0.000 description 101
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
• 238000011097 chromatography purification Methods 0.000 description 98
• 239000000203 mixture Substances 0.000 description 89
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 85
• 238000002425 crystallisation Methods 0.000 description 77
• 230000008025 crystallization Effects 0.000 description 77
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
• LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 69
• 230000007062 hydrolysis Effects 0.000 description 69
• 238000006460 hydrolysis reaction Methods 0.000 description 69
• 229910052742 iron Inorganic materials 0.000 description 64
• 238000000354 decomposition reaction Methods 0.000 description 61
• FTKASJMIPSSXBP-UHFFFAOYSA-N ethyl 2-nitroacetate Chemical compound CCOC(=O)C[N+]([O-])=O FTKASJMIPSSXBP-UHFFFAOYSA-N 0.000 description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
• 239000000243 solution Substances 0.000 description 55
• PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 51
• 230000003301 hydrolyzing effect Effects 0.000 description 46
• UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 44
• 239000000377 silicon dioxide Substances 0.000 description 41
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 39
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
• 229910052938 sodium sulfate Inorganic materials 0.000 description 38
• 235000011152 sodium sulphate Nutrition 0.000 description 38
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 36
• 125000000217 alkyl group Chemical group 0.000 description 35
• 239000002178 crystalline material Substances 0.000 description 35
• 239000002904 solvent Substances 0.000 description 35
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 239000012074 organic phase Substances 0.000 description 25
• 239000003921 oil Substances 0.000 description 24
• 235000019198 oils Nutrition 0.000 description 24
• 238000010828 elution Methods 0.000 description 21
• 238000001704 evaporation Methods 0.000 description 21
• 230000008020 evaporation Effects 0.000 description 21
• ROERXQQNEPTAMA-UHFFFAOYSA-N 3-bromo-5-[(2-methylimidazol-1-yl)methyl]pyridine Chemical compound CC1=NC=CN1CC1=CN=CC(Br)=C1 ROERXQQNEPTAMA-UHFFFAOYSA-N 0.000 description 20
• 239000003480 eluent Substances 0.000 description 19
• 238000001914 filtration Methods 0.000 description 18
• 239000000725 suspension Substances 0.000 description 15
• ZYQAQDVNZZIEQW-UHFFFAOYSA-N 4-(chloromethyl)-1-(3,4-dichlorophenyl)imidazole Chemical compound C1=NC(CCl)=CN1C1=CC=C(Cl)C(Cl)=C1 ZYQAQDVNZZIEQW-UHFFFAOYSA-N 0.000 description 14
• 239000012300 argon atmosphere Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
• 239000000284 extract Substances 0.000 description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
• 239000012280 lithium aluminium hydride Substances 0.000 description 11
• 238000012545 processing Methods 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 239000000908 ammonium hydroxide Substances 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000013078 crystal Substances 0.000 description 10
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• 239000012230 colorless oil Substances 0.000 description 9
• 239000006260 foam Substances 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
• NNGIXGSVAKRJMY-UHFFFAOYSA-N [1-(4-chloro-3-methylphenyl)imidazol-4-yl]methanol Chemical compound C1=C(Cl)C(C)=CC(N2C=C(CO)N=C2)=C1 NNGIXGSVAKRJMY-UHFFFAOYSA-N 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
• 238000000605 extraction Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 7
• 239000002480 mineral oil Substances 0.000 description 7
• 235000010446 mineral oil Nutrition 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• FGQVWDFJJBOQJA-UHFFFAOYSA-N [1-[3-fluoro-5-(trifluoromethyl)phenyl]imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC(F)=CC(C(F)(F)F)=C1 FGQVWDFJJBOQJA-UHFFFAOYSA-N 0.000 description 6
• 239000008346 aqueous phase Substances 0.000 description 6
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
• 238000002474 experimental method Methods 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 239000003039 volatile agent Substances 0.000 description 6
• JKIGHOARKAIPJI-UHFFFAOYSA-N (3,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(Cl)=C1 JKIGHOARKAIPJI-UHFFFAOYSA-N 0.000 description 5
• YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• XTULRBGJGPZGJX-UHFFFAOYSA-N [1-(1,3-benzodioxol-5-yl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(OCO2)C2=C1 XTULRBGJGPZGJX-UHFFFAOYSA-N 0.000 description 5
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
• 229910000024 caesium carbonate Inorganic materials 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000012279 sodium borohydride Substances 0.000 description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• VVIWVQXSOPHAHQ-UHFFFAOYSA-N (1-quinolin-2-ylimidazol-4-yl)methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(C=CC=C2)C2=N1 VVIWVQXSOPHAHQ-UHFFFAOYSA-N 0.000 description 4
• JCIJCHSRVPSOML-UHFFFAOYSA-N (4-fluoro-3-methylphenyl)boronic acid Chemical compound CC1=CC(B(O)O)=CC=C1F JCIJCHSRVPSOML-UHFFFAOYSA-N 0.000 description 4
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
• GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 description 4
• FKYKLCCAVXYPJK-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)imidazole-4-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN1C1=CC=C(Cl)C(Cl)=C1 FKYKLCCAVXYPJK-UHFFFAOYSA-N 0.000 description 4
• GWAKORYPOIOXMB-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)imidazol-4-yl]ethanol Chemical compound C1=NC(C(O)C)=CN1C1=CC=C(Cl)C(Cl)=C1 GWAKORYPOIOXMB-UHFFFAOYSA-N 0.000 description 4
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 4
• ZJWJZAJGAHXWAD-UHFFFAOYSA-N 3-(chloromethyl)-5-(3,4-dichlorophenyl)pyridine;hydrochloride Chemical compound Cl.ClCC1=CN=CC(C=2C=C(Cl)C(Cl)=CC=2)=C1 ZJWJZAJGAHXWAD-UHFFFAOYSA-N 0.000 description 4
• LZHCUMPFZKOLLM-UHFFFAOYSA-N 4-(chloromethyl)-1-(3,4-dichlorophenyl)pyrazole Chemical compound C1=C(CCl)C=NN1C1=CC=C(Cl)C(Cl)=C1 LZHCUMPFZKOLLM-UHFFFAOYSA-N 0.000 description 4
• CATIRMBZLCOOBF-UHFFFAOYSA-N 5-bromo-1-methyl-2-[(2-methylimidazol-1-yl)methyl]imidazole Chemical compound CC1=NC=CN1CC1=NC=C(Br)N1C CATIRMBZLCOOBF-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• WZWHBHBLGTVFLN-UHFFFAOYSA-N [1-(2,2-difluoro-1,3-benzodioxol-5-yl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(OC(F)(F)O2)C2=C1 WZWHBHBLGTVFLN-UHFFFAOYSA-N 0.000 description 4
• VCBHUUUCZJFSOJ-UHFFFAOYSA-N [1-(2,3-dihydro-1h-inden-5-yl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(CCC2)C2=C1 VCBHUUUCZJFSOJ-UHFFFAOYSA-N 0.000 description 4
• AQLSINLFHZBATF-UHFFFAOYSA-N [1-(3-bromo-4-fluorophenyl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(F)C(Br)=C1 AQLSINLFHZBATF-UHFFFAOYSA-N 0.000 description 4
• OIPBQGDCBIAWMA-UHFFFAOYSA-N [1-(3-bromo-5-fluorophenyl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC(F)=CC(Br)=C1 OIPBQGDCBIAWMA-UHFFFAOYSA-N 0.000 description 4
• LCZQJUPBICWMNS-UHFFFAOYSA-N [1-(3-chloro-4-fluorophenyl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=C(F)C(Cl)=C1 LCZQJUPBICWMNS-UHFFFAOYSA-N 0.000 description 4
• VPTIUYHHCCKFHA-UHFFFAOYSA-N [1-(3-chloro-4-methoxyphenyl)imidazol-4-yl]methanol Chemical compound C1=C(Cl)C(OC)=CC=C1N1C=C(CO)N=C1 VPTIUYHHCCKFHA-UHFFFAOYSA-N 0.000 description 4
• ZAYPBSPSAPYSGD-UHFFFAOYSA-N [1-(3-chloro-4-methylphenyl)imidazol-4-yl]methanol Chemical compound C1=C(Cl)C(C)=CC=C1N1C=C(CO)N=C1 ZAYPBSPSAPYSGD-UHFFFAOYSA-N 0.000 description 4
• CCOMFUIKIQUCQB-UHFFFAOYSA-N [1-(3-chlorophenyl)imidazol-4-yl]methanol Chemical compound C1=NC(CO)=CN1C1=CC=CC(Cl)=C1 CCOMFUIKIQUCQB-UHFFFAOYSA-N 0.000 description 4
• CNOXSCFGRSZZHM-UHFFFAOYSA-N [1-(3-fluoro-4-methylphenyl)imidazol-4-yl]methanol Chemical compound C1=C(F)C(C)=CC=C1N1C=C(CO)N=C1 CNOXSCFGRSZZHM-UHFFFAOYSA-N 0.000 description 4
• HLVJWYZDGPSROU-UHFFFAOYSA-N [1-(3-methoxy-4-methylphenyl)imidazol-4-yl]methanol Chemical compound C1=C(C)C(OC)=CC(N2C=C(CO)N=C2)=C1 HLVJWYZDGPSROU-UHFFFAOYSA-N 0.000 description 4
• LJQQNFPUTPYHSG-UHFFFAOYSA-N [1-(3-methoxyphenyl)imidazol-4-yl]methanol Chemical compound COC1=CC=CC(N2C=C(CO)N=C2)=C1 LJQQNFPUTPYHSG-UHFFFAOYSA-N 0.000 description 4
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