CH651827A5 - Carbostyrilderivate, verfahren zu ihrer herstellung und kardiotonische zusammensetzungen, welche diese enthalten. - Google Patents

Info

Publication number

CH651827A5

CH651827A5 CH996/82A CH99682A CH651827A5 CH 651827 A5 CH651827 A5 CH 651827A5 CH 996/82 A CH996/82 A CH 996/82A CH 99682 A CH99682 A CH 99682A CH 651827 A5 CH651827 A5 CH 651827A5

Authority

CH

Switzerland

Prior art keywords

group

lower alkyl

alkyl group

carbostyril

phenyl

Prior art date

1981-02-17

Links

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• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 112
• 239000000203 mixture Substances 0.000 title claims description 54
• 238000000034 method Methods 0.000 title claims description 53
• 230000003177 cardiotonic effect Effects 0.000 title claims description 7
• 238000004519 manufacturing process Methods 0.000 title description 6
• -1 1-piperidyl group Chemical group 0.000 claims description 681
• 150000001875 compounds Chemical class 0.000 claims description 176
• 125000000217 alkyl group Chemical group 0.000 claims description 149
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 110
• 125000001424 substituent group Chemical group 0.000 claims description 107
• 125000005843 halogen group Chemical group 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 61
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 27
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 23
• 238000002360 preparation method Methods 0.000 claims description 22
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
• 125000004193 piperazinyl group Chemical group 0.000 claims description 16
• 125000003277 amino group Chemical group 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
• 125000002252 acyl group Chemical group 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 8
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 5
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 238000006467 substitution reaction Methods 0.000 claims description 5
• 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 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 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 description 3
• CLHIDJDMMMVCFX-UHFFFAOYSA-N 6-[4-[(4-chlorophenyl)-phenylmethyl]piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 CLHIDJDMMMVCFX-UHFFFAOYSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 239000012876 carrier material Substances 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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
• MXCARJQEMVOHAU-UHFFFAOYSA-N 6-[4-(3-oxo-3-phenylpropyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CCN1CCC(=O)C1=CC=CC=C1 MXCARJQEMVOHAU-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
• 241000790917 Dioxys <bee> Species 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• 125000004430 oxygen atom Chemical group O* 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• 239000013078 crystal Substances 0.000 description 189
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 130
• 238000006243 chemical reaction Methods 0.000 description 129
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 118
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 101
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 88
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 80
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
• 239000000243 solution Substances 0.000 description 66
• 239000002904 solvent Substances 0.000 description 65
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• 238000000354 decomposition reaction Methods 0.000 description 61
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 235000019441 ethanol Nutrition 0.000 description 47
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• 125000004432 carbon atom Chemical group C* 0.000 description 45
• 239000011541 reaction mixture Substances 0.000 description 44
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 37
• 150000001412 amines Chemical class 0.000 description 34
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• 239000007858 starting material Substances 0.000 description 28
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
• 239000002253 acid Substances 0.000 description 26
• 235000002639 sodium chloride Nutrition 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
• 239000010410 layer Substances 0.000 description 18
• 238000006722 reduction reaction Methods 0.000 description 18
• 239000011780 sodium chloride Substances 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
• 150000007514 bases Chemical class 0.000 description 16
• 238000001914 filtration Methods 0.000 description 16
• 230000009467 reduction Effects 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 239000000725 suspension Substances 0.000 description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
• 238000001953 recrystallisation Methods 0.000 description 12
• 239000003826 tablet Substances 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 241000282472 Canis lupus familiaris Species 0.000 description 11
• 230000000144 pharmacologic effect Effects 0.000 description 11
• 230000008859 change Effects 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• 150000008065 acid anhydrides 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
• 239000012044 organic layer Substances 0.000 description 9
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
• 230000017531 blood circulation Effects 0.000 description 8
• 239000012452 mother liquor Substances 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 7
• 150000008282 halocarbons Chemical class 0.000 description 7
• 230000002140 halogenating effect Effects 0.000 description 7
• 238000001990 intravenous administration Methods 0.000 description 7
• 239000008101 lactose Substances 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 239000011734 sodium Substances 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
• TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 6
• 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 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 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 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
• QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 229920002472 Starch Polymers 0.000 description 6
• 210000004351 coronary vessel Anatomy 0.000 description 6
• 150000002170 ethers Chemical class 0.000 description 6
• 239000012442 inert solvent Substances 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
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 238000010898 silica gel chromatography Methods 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 235000019698 starch Nutrition 0.000 description 6
• 239000008107 starch Substances 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 239000008096 xylene Substances 0.000 description 6
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
• IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 5
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 5
• 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 5
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
• DRMRWGJNMPRBIO-UHFFFAOYSA-N 6-(piperazine-1-carbonyl)-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C=1C=C2NC(=O)C=CC2=CC=1C(=O)N1CCNCC1 DRMRWGJNMPRBIO-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
• 239000002841 Lewis acid Substances 0.000 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
• 238000003436 Schotten-Baumann reaction Methods 0.000 description 5
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
• 210000001367 artery Anatomy 0.000 description 5
• 238000010531 catalytic reduction reaction Methods 0.000 description 5
• 239000003638 chemical reducing agent Substances 0.000 description 5
• 239000002026 chloroform extract Substances 0.000 description 5
• 238000006356 dehydrogenation reaction Methods 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 150000007517 lewis acids Chemical class 0.000 description 5
• 210000003205 muscle Anatomy 0.000 description 5
• 238000006396 nitration reaction Methods 0.000 description 5
• 229960001412 pentobarbital Drugs 0.000 description 5
• 239000002798 polar solvent Substances 0.000 description 5
• 229910000027 potassium carbonate Inorganic materials 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
• ZUGRYLJRHKHZLR-UHFFFAOYSA-N 1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=CC2=C1 ZUGRYLJRHKHZLR-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
• DVAXCYOGICFKQM-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)CCC2=C1 DVAXCYOGICFKQM-UHFFFAOYSA-N 0.000 description 4
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• GCHAVGULYPPIHQ-UHFFFAOYSA-N 6-[4-(3,4-dimethoxybenzoyl)piperazine-1-carbonyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1CCN(C(=O)C=2C=C3CCC(=O)NC3=CC=2)CC1 GCHAVGULYPPIHQ-UHFFFAOYSA-N 0.000 description 4
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