FI77852C - Foerfarande foer framstaellning av nya, saosom hjaertmediciner anvaendbara substituerade amid- och (maettad heterocykel)karbonylkarbostyrilderivat. - Google Patents

Info

Publication number

FI77852C

FI77852C FI820338A FI820338A FI77852C FI 77852 C FI77852 C FI 77852C FI 820338 A FI820338 A FI 820338A FI 820338 A FI820338 A FI 820338A FI 77852 C FI77852 C FI 77852C

Authority

FI

Finland

Prior art keywords

group

lower alkyl

compound

alkyl group

piperazinylcarbonyl

Prior art date

1981-02-17

Links

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• 238000000034 method Methods 0.000 title claims description 75
• 238000002360 preparation method Methods 0.000 title claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 title claims description 9
• 229940079593 drug Drugs 0.000 title claims description 5
• 239000003814 drug Substances 0.000 title claims description 5
• 230000000747 cardiac effect Effects 0.000 title claims description 4
• 150000001408 amides Chemical class 0.000 title claims description 3
• KJAPRUUWBMNSHL-UHFFFAOYSA-N 3-(oxomethylidene)quinolin-2-one Chemical class C1=CC=CC2=NC(=O)C(=C=O)C=C21 KJAPRUUWBMNSHL-UHFFFAOYSA-N 0.000 title claims 2
• -1 morpholino, 1-piperazinyl Chemical group 0.000 claims description 653
• 150000001875 compounds Chemical class 0.000 claims description 186
• 125000000217 alkyl group Chemical group 0.000 claims description 136
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
• 125000001424 substituent group Chemical group 0.000 claims description 74
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 63
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000005843 halogen group Chemical group 0.000 claims description 51
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 23
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 19
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
• 125000003277 amino group Chemical group 0.000 claims description 14
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
• 125000004193 piperazinyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000006197 2-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])([H])C([H])([H])* 0.000 claims description 6
• UQYCHNFDTXIQMM-UHFFFAOYSA-N 6-(4-benzylpiperazine-1-carbonyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N(CC1)CCN1CC1=CC=CC=C1 UQYCHNFDTXIQMM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 208000035397 Ring chromosome 7 syndrome Diseases 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 4
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• JXGUHKJKWBEVEP-UHFFFAOYSA-N 6-[4-(2-methylpropyl)piperazine-1-carbonyl]-1h-quinolin-2-one Chemical compound C1CN(CC(C)C)CCN1C(=O)C1=CC=C(NC(=O)C=C2)C2=C1 JXGUHKJKWBEVEP-UHFFFAOYSA-N 0.000 claims description 3
• BRTSRAFGNVSHJV-UHFFFAOYSA-N 6-[4-(2-methylpropyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(CC(C)C)CCN1C(=O)C1=CC=C(NC(=O)CC2)C2=C1 BRTSRAFGNVSHJV-UHFFFAOYSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• ZBRWSODNRGCQMV-UHFFFAOYSA-N 6-[4-(2-phenoxyethyl)piperazine-1-carbonyl]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1C(=O)N(CC1)CCN1CCOC1=CC=CC=C1 ZBRWSODNRGCQMV-UHFFFAOYSA-N 0.000 claims 1
• HIMAPQCWSZVHEJ-UHFFFAOYSA-N 6-[4-(2-phenoxyethyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N(CC1)CCN1CCOC1=CC=CC=C1 HIMAPQCWSZVHEJ-UHFFFAOYSA-N 0.000 claims 1
• CDRWBUGLZBPPCL-UHFFFAOYSA-N 6-[4-(3-phenylpropyl)piperazine-1-carbonyl]-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1C(=O)N(CC1)CCN1CCCC1=CC=CC=C1 CDRWBUGLZBPPCL-UHFFFAOYSA-N 0.000 claims 1
• MMPBSPPVURMDBU-UHFFFAOYSA-N 6-[4-[(4-methoxyphenyl)methyl]piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 MMPBSPPVURMDBU-UHFFFAOYSA-N 0.000 claims 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical group C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 239000013078 crystal Substances 0.000 description 188
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 173
• 238000002844 melting Methods 0.000 description 158
• 230000008018 melting Effects 0.000 description 158
• 238000006243 chemical reaction Methods 0.000 description 135
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 121
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 106
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
• 239000002904 solvent Substances 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
• 239000000243 solution Substances 0.000 description 60
• 239000000203 mixture Substances 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• 239000011541 reaction mixture Substances 0.000 description 50
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 125000004432 carbon atom Chemical group C* 0.000 description 43
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 39
• 235000019441 ethanol Nutrition 0.000 description 37
• 150000001412 amines Chemical class 0.000 description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
• 238000004821 distillation Methods 0.000 description 29
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000007858 starting material Substances 0.000 description 27
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• 238000001914 filtration Methods 0.000 description 26
• 235000002639 sodium chloride Nutrition 0.000 description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 22
• 238000003756 stirring Methods 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 239000011780 sodium chloride Substances 0.000 description 20
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
• 150000007514 bases Chemical class 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 17
• 238000006722 reduction reaction Methods 0.000 description 17
• 238000001953 recrystallisation Methods 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 229940086542 triethylamine Drugs 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
• 239000003826 tablet Substances 0.000 description 11
• TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 10
• UKRYUVLBWGYQBY-UHFFFAOYSA-N 6-(piperazine-1-carbonyl)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1C(=O)N1CCNCC1 UKRYUVLBWGYQBY-UHFFFAOYSA-N 0.000 description 10
• 229920002472 Starch Polymers 0.000 description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
• 239000007924 injection Substances 0.000 description 10
• 238000002347 injection Methods 0.000 description 10
• 235000011007 phosphoric acid Nutrition 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• 239000008107 starch Substances 0.000 description 10
• 235000019698 starch Nutrition 0.000 description 10
• 241000282472 Canis lupus familiaris Species 0.000 description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 9
• 150000008064 anhydrides Chemical class 0.000 description 9
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
• 239000008280 blood Substances 0.000 description 9
• 210000004369 blood Anatomy 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 230000000144 pharmacologic effect Effects 0.000 description 9
• DUFYYKGNRAMGNG-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-carboxylic acid Chemical compound N1C(=O)CCC2=CC(C(=O)O)=CC=C21 DUFYYKGNRAMGNG-UHFFFAOYSA-N 0.000 description 8
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 150000002780 morpholines Chemical class 0.000 description 8
• 239000012452 mother liquor Substances 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 238000012360 testing method Methods 0.000 description 7
• QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 6
• IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 6
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 239000002841 Lewis acid Substances 0.000 description 6
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 230000001746 atrial effect Effects 0.000 description 6
• 239000002026 chloroform extract Substances 0.000 description 6
• UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 150000007517 lewis acids Chemical class 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
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000002798 polar solvent Substances 0.000 description 6
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 230000035484 reaction time Effects 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 239000008096 xylene Substances 0.000 description 6
• ZUGRYLJRHKHZLR-UHFFFAOYSA-N 1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=CC2=C1 ZUGRYLJRHKHZLR-UHFFFAOYSA-N 0.000 description 5
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 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 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 210000004351 coronary vessel Anatomy 0.000 description 5
• IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
• 238000002474 experimental method Methods 0.000 description 5
• 239000008103 glucose Substances 0.000 description 5
• 230000002140 halogenating effect Effects 0.000 description 5
• DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 5
• GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
• 230000004118 muscle contraction Effects 0.000 description 5
• 238000006396 nitration reaction Methods 0.000 description 5
• WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 5
• 229960001412 pentobarbital Drugs 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 238000010898 silica gel chromatography Methods 0.000 description 5
• 239000000126 substance Substances 0.000 description 5
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
• ZJNIZXCCXHUGPO-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-carboxylic acid;pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1.N1C(=O)CCC2=CC(C(=O)O)=CC=C21 ZJNIZXCCXHUGPO-UHFFFAOYSA-N 0.000 description 4
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
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• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
• 125000003944 tolyl group Chemical group 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
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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• 239000011592 zinc chloride Substances 0.000 description 1
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