DK2484669T3 - Fenolderivat - Google Patents

Info

Publication number

DK2484669T3

DK2484669T3 DK10820564.2T DK10820564T DK2484669T3 DK 2484669 T3 DK2484669 T3 DK 2484669T3 DK 10820564 T DK10820564 T DK 10820564T DK 2484669 T3 DK2484669 T3 DK 2484669T3

Authority

DK

Denmark

Prior art keywords

added

mixture

dihydro

distilled

solvent

Prior art date

2009-09-30

Links

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• 150000001875 compounds Chemical class 0.000 claims description 233
• 239000000126 substance Substances 0.000 claims description 70
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 63
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 50
• 229940116269 uric acid Drugs 0.000 claims description 50
• 201000010099 disease Diseases 0.000 claims description 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
• 201000001431 Hyperuricemia Diseases 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 25
• 210000004369 blood Anatomy 0.000 claims description 20
• 239000008280 blood Substances 0.000 claims description 20
• -1 isopropylsulfanyl group Chemical group 0.000 claims description 19
• 150000002989 phenols Chemical class 0.000 claims description 19
• 230000002265 prevention Effects 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 230000029142 excretion Effects 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• VOFLAIHEELWYGO-UHFFFAOYSA-N (3,5-dichloro-4-hydroxyphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 VOFLAIHEELWYGO-UHFFFAOYSA-N 0.000 claims description 6
• QHUSRJSYQNJEFQ-UHFFFAOYSA-N 3-chloro-5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxybenzonitrile Chemical compound C1=C(C#N)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 QHUSRJSYQNJEFQ-UHFFFAOYSA-N 0.000 claims description 6
• SBCRKZJEEDTVFK-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-methylsulfanylbenzonitrile Chemical compound N#CC1=C(O)C(SC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 SBCRKZJEEDTVFK-UHFFFAOYSA-N 0.000 claims description 6
• JVXASWJRFPUFOH-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-3-ethyl-2-hydroxybenzonitrile Chemical compound N#CC1=C(O)C(CC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 JVXASWJRFPUFOH-UHFFFAOYSA-N 0.000 claims description 6
• HJNFPLCCPXAZSE-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-3-ethylsulfanyl-2-hydroxybenzonitrile Chemical compound N#CC1=C(O)C(SCC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 HJNFPLCCPXAZSE-UHFFFAOYSA-N 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• HJNASESSRLKUIE-UHFFFAOYSA-N 3-cyclopropyl-5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxybenzonitrile Chemical compound OC1=C(C#N)C=C(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)C=C1C1CC1 HJNASESSRLKUIE-UHFFFAOYSA-N 0.000 claims description 5
• MTHRZZFLSQRKKO-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-(trifluoromethyl)benzonitrile Chemical compound C1=C(C(F)(F)F)C(O)=C(C#N)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 MTHRZZFLSQRKKO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 208000017169 kidney disease Diseases 0.000 claims description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 4
• 201000005577 familial hyperlipidemia Diseases 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 208000014882 Carotid artery disease Diseases 0.000 claims description 3
• 206010048554 Endothelial dysfunction Diseases 0.000 claims description 3
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 230000008694 endothelial dysfunction Effects 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 2
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 2
• 208000007536 Thrombosis Diseases 0.000 claims description 2
• 239000008177 pharmaceutical agent Substances 0.000 claims 9
• 206010003246 arthritis Diseases 0.000 claims 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
• 208000000913 Kidney Calculi Diseases 0.000 claims 1
• 206010029148 Nephrolithiasis Diseases 0.000 claims 1
• 239000000654 additive Substances 0.000 claims 1
• 208000019622 heart disease Diseases 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 672
• 239000000203 mixture Substances 0.000 description 369
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 315
• 239000000243 solution Substances 0.000 description 312
• 230000002829 reductive effect Effects 0.000 description 299
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 288
• 239000002904 solvent Substances 0.000 description 288
• 238000003786 synthesis reaction Methods 0.000 description 249
• 230000015572 biosynthetic process Effects 0.000 description 246
• 239000012044 organic layer Substances 0.000 description 185
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 179
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 179
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 147
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 134
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 133
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 121
• 239000013078 crystal Substances 0.000 description 106
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 102
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 100
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
• 238000006243 chemical reaction Methods 0.000 description 93
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 70
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 59
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 238000010898 silica gel chromatography Methods 0.000 description 51
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 38
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 33
• LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 33
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
• WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 description 30
• 239000003814 drug Substances 0.000 description 30
• 229940079593 drug Drugs 0.000 description 29
• 210000002700 urine Anatomy 0.000 description 29
• VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 28
• 239000007787 solid Substances 0.000 description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
• 229910000027 potassium carbonate Inorganic materials 0.000 description 24
• 230000003424 uricosuric effect Effects 0.000 description 24
• 239000003960 organic solvent Substances 0.000 description 22
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 22
• 235000019345 sodium thiosulphate Nutrition 0.000 description 22
• 239000010410 layer Substances 0.000 description 21
• 238000003756 stirring Methods 0.000 description 20
• 201000005569 Gout Diseases 0.000 description 18
• 239000000047 product Substances 0.000 description 17
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 16
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 16
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 16
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
• OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 13
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 238000000034 method Methods 0.000 description 12
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 210000001519 tissue Anatomy 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• 241000700159 Rattus Species 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000004093 cyano group Chemical group *C#N 0.000 description 9
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 229920002678 cellulose Polymers 0.000 description 8
• 239000001913 cellulose Substances 0.000 description 8
• 235000010980 cellulose Nutrition 0.000 description 8
• WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 8
• 125000000524 functional group Chemical group 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
• 229960003511 macrogol Drugs 0.000 description 7
• 238000004519 manufacturing process Methods 0.000 description 7
• WTDNIIPBZKOONK-UHFFFAOYSA-N (3-chloro-4-hydroxy-5-methylsulfanylphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound ClC1=C(O)C(SC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 WTDNIIPBZKOONK-UHFFFAOYSA-N 0.000 description 6
• AJMQHWJRSXQFKQ-UHFFFAOYSA-N 5-(1,1-dioxo-2h-1,3-benzothiazole-3-carbonyl)-2-hydroxy-3-iodobenzonitrile Chemical compound C1=C(C#N)C(O)=C(I)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 AJMQHWJRSXQFKQ-UHFFFAOYSA-N 0.000 description 6
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 6
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 6
• XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 6
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 6
• 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 6
• 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 6
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 6
• 229940061627 chloromethyl methyl ether Drugs 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• DXSRZGRDEIGJIE-UHFFFAOYSA-N methyl 4-hydroxy-3-(trifluoromethoxy)benzoate Chemical compound COC(=O)C1=CC=C(O)C(OC(F)(F)F)=C1 DXSRZGRDEIGJIE-UHFFFAOYSA-N 0.000 description 6
• IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 6
• 150000007523 nucleic acids Chemical group 0.000 description 6
• 102000039446 nucleic acids Human genes 0.000 description 6
• 108020004707 nucleic acids Proteins 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• GGDJFJSYIAKEMJ-UHFFFAOYSA-N (3-chloro-4-hydroxy-5-methoxyphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound ClC1=C(O)C(OC)=CC(C(=O)N2C3=CC=CC=C3S(=O)(=O)C2)=C1 GGDJFJSYIAKEMJ-UHFFFAOYSA-N 0.000 description 5
• RBZCJZFMISVUCZ-UHFFFAOYSA-N (3-chloro-5-fluoro-4-hydroxyphenyl)-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(Cl)C(O)=C(F)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 RBZCJZFMISVUCZ-UHFFFAOYSA-N 0.000 description 5
• YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 5
• GQWMNVOVQZIPJC-UHFFFAOYSA-N 2-(trifluoromethoxy)phenol Chemical compound OC1=CC=CC=C1OC(F)(F)F GQWMNVOVQZIPJC-UHFFFAOYSA-N 0.000 description 5
• PZSZFFGGWLDZEL-UHFFFAOYSA-N 3-formyl-4-methoxy-5-(trifluoromethyl)benzoic acid Chemical compound COC1=C(C=O)C=C(C(O)=O)C=C1C(F)(F)F PZSZFFGGWLDZEL-UHFFFAOYSA-N 0.000 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 5
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
• 229930006000 Sucrose Natural products 0.000 description 5
• RZXBSMVVNURIFG-UHFFFAOYSA-N [3-chloro-4-hydroxy-5-(trifluoromethyl)phenyl]-(1,1-dioxo-2h-1,3-benzothiazol-3-yl)methanone Chemical compound C1=C(C(F)(F)F)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2S(=O)(=O)C1 RZXBSMVVNURIFG-UHFFFAOYSA-N 0.000 description 5
• 230000001133 acceleration Effects 0.000 description 5
• 230000009471 action Effects 0.000 description 5
• WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 5
• 239000001569 carbon dioxide Substances 0.000 description 5
• 229910002092 carbon dioxide Inorganic materials 0.000 description 5
• 229960004132 diethyl ether Drugs 0.000 description 5
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