DD237509A5 - Verfahren zur herstellung von 2-(1h)-chinolonen - Google Patents
Verfahren zur herstellung von 2-(1h)-chinolonen Download PDFInfo
- Publication number
- DD237509A5 DD237509A5 DD85276727A DD27672785A DD237509A5 DD 237509 A5 DD237509 A5 DD 237509A5 DD 85276727 A DD85276727 A DD 85276727A DD 27672785 A DD27672785 A DD 27672785A DD 237509 A5 DD237509 A5 DD 237509A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- het
- formula
- item
- quinolone
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 83
- 238000002360 preparation method Methods 0.000 claims description 70
- -1 C 1 -C 4 -alkoxy Chemical group 0.000 claims description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 4
- 230000017858 demethylation Effects 0.000 claims description 4
- 238000010520 demethylation reaction Methods 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- POVXOWVFLAAVBH-UHFFFAOYSA-N n-formamidoformamide Chemical compound O=CNNC=O POVXOWVFLAAVBH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 238000000297 Sandmeyer reaction Methods 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 230000000297 inotrophic effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- 238000004458 analytical method Methods 0.000 description 71
- 239000000243 solution Substances 0.000 description 71
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- 239000012458 free base Substances 0.000 description 56
- 239000000203 mixture Substances 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
- 239000007858 starting material Substances 0.000 description 42
- 239000007787 solid Substances 0.000 description 41
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000000377 silicon dioxide Substances 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 230000008020 evaporation Effects 0.000 description 20
- 239000000284 extract Substances 0.000 description 19
- 239000008346 aqueous phase Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 6
- SFMFACMIOWQIPR-ONEGZZNKSA-N (e)-3-ethoxyprop-2-enoyl chloride Chemical compound CCO\C=C\C(Cl)=O SFMFACMIOWQIPR-ONEGZZNKSA-N 0.000 description 5
- NMNXBEXPAHSXOK-UHFFFAOYSA-N 6-(2,4-dimethylimidazol-1-yl)-8-methyl-1h-quinolin-2-one Chemical compound CC1=NC(C)=CN1C1=CC(C)=C(NC(=O)C=C2)C2=C1 NMNXBEXPAHSXOK-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 230000002861 ventricular Effects 0.000 description 5
- IKAVUUPTFNVPJQ-UHFFFAOYSA-N 6-bromo-2-methoxy-8-methylquinoline Chemical compound C1=C(Br)C=C(C)C2=NC(OC)=CC=C21 IKAVUUPTFNVPJQ-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical class 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000013081 microcrystal Substances 0.000 description 4
- 150000007660 quinolones Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- HYTUDPOPONCSCM-UHFFFAOYSA-N 1-(3-methyl-4-nitrophenyl)imidazole Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N2C=NC=C2)=C1 HYTUDPOPONCSCM-UHFFFAOYSA-N 0.000 description 3
- XWMQLIUJOLXRRV-UHFFFAOYSA-N 2,4-dimethyl-1-(3-methyl-4-nitrophenyl)imidazole Chemical compound CC1=NC(C)=CN1C1=CC=C([N+]([O-])=O)C(C)=C1 XWMQLIUJOLXRRV-UHFFFAOYSA-N 0.000 description 3
- BXKJABVRVAEOES-UHFFFAOYSA-N 2-bromo-4-(2,4-dimethylimidazol-1-yl)-6-(trifluoromethyl)aniline Chemical compound CC1=NC(C)=CN1C1=CC(Br)=C(N)C(C(F)(F)F)=C1 BXKJABVRVAEOES-UHFFFAOYSA-N 0.000 description 3
- QTJUDDCTWNFKPC-UHFFFAOYSA-N 2-iodo-6-methyl-4-(tetrazol-1-yl)aniline Chemical compound IC1=C(N)C(C)=CC(N2N=NN=C2)=C1 QTJUDDCTWNFKPC-UHFFFAOYSA-N 0.000 description 3
- WFEZOLYJPCODOA-UHFFFAOYSA-N 4,5-diiodo-2-methyl-1h-imidazole Chemical compound CC1=NC(I)=C(I)N1 WFEZOLYJPCODOA-UHFFFAOYSA-N 0.000 description 3
- JHFOWEGCZWLHNW-UHFFFAOYSA-N 4-fluoro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(F)=CC=C1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 3
- SEDSLMWYUQACGR-UHFFFAOYSA-N 5-iodo-2-methyl-1h-imidazole Chemical compound CC1=NC=C(I)N1 SEDSLMWYUQACGR-UHFFFAOYSA-N 0.000 description 3
- HASZYZXTRHDOAG-UHFFFAOYSA-N 6-(2-iodo-4-methylimidazol-1-yl)-8-methyl-1h-quinolin-2-one Chemical compound IC1=NC(C)=CN1C1=CC(C)=C(NC(=O)C=C2)C2=C1 HASZYZXTRHDOAG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 206010019280 Heart failures Diseases 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VVSXEGRKRVCDJH-UHFFFAOYSA-N n-(2-methoxy-8-methylquinolin-6-yl)acetamide Chemical compound C1=C(NC(C)=O)C=C(C)C2=NC(OC)=CC=C21 VVSXEGRKRVCDJH-UHFFFAOYSA-N 0.000 description 3
- 150000005181 nitrobenzenes Chemical class 0.000 description 3
- 230000009090 positive inotropic effect Effects 0.000 description 3
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 3
- JMMMQHDFFZCZOS-ONEGZZNKSA-N (e)-3-ethoxyprop-2-enamide Chemical class CCO\C=C\C(N)=O JMMMQHDFFZCZOS-ONEGZZNKSA-N 0.000 description 2
- XVCAAXRIKPVUNC-VOTSOKGWSA-N (e)-n-(4-bromo-2-methylphenyl)-3-ethoxyprop-2-enamide Chemical compound CCO\C=C\C(=O)NC1=CC=C(Br)C=C1C XVCAAXRIKPVUNC-VOTSOKGWSA-N 0.000 description 2
- YMZOWODKFWAXBK-UHFFFAOYSA-N 1-(3-methyl-4-nitrophenyl)tetrazole Chemical compound C1=C([N+]([O-])=O)C(C)=CC(N2N=NN=C2)=C1 YMZOWODKFWAXBK-UHFFFAOYSA-N 0.000 description 2
- YNRHXRGSDWKRDA-UHFFFAOYSA-N 1-(3-methylphenyl)tetrazole Chemical compound CC1=CC=CC(N2N=NN=C2)=C1 YNRHXRGSDWKRDA-UHFFFAOYSA-N 0.000 description 2
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- IPJNVVJOWIEEDY-UHFFFAOYSA-N 2-amino-5-(1,2,4-triazol-4-yl)-3-(trifluoromethyl)benzaldehyde Chemical compound C1=C(C(F)(F)F)C(N)=C(C=O)C=C1N1C=NN=C1 IPJNVVJOWIEEDY-UHFFFAOYSA-N 0.000 description 2
- ZFNDVBVBMKVMOY-UHFFFAOYSA-N 2-amino-5-(2,4-dimethylimidazol-1-yl)-3-(trifluoromethyl)benzaldehyde Chemical compound CC1=NC(C)=CN1C1=CC(C=O)=C(N)C(C(F)(F)F)=C1 ZFNDVBVBMKVMOY-UHFFFAOYSA-N 0.000 description 2
- RWVZDLURCQSAJU-UHFFFAOYSA-N 2-bromo-4-(1,2,4-triazol-4-yl)-6-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=C(Br)C=C1N1C=NN=C1 RWVZDLURCQSAJU-UHFFFAOYSA-N 0.000 description 2
- JBIRDQXAMVOHAO-UHFFFAOYSA-N 2-methoxy-8-methylquinolin-6-amine Chemical compound C1=C(N)C=C(C)C2=NC(OC)=CC=C21 JBIRDQXAMVOHAO-UHFFFAOYSA-N 0.000 description 2
- YBPVXEYERZMYNR-UHFFFAOYSA-N 2-methoxy-8-methylquinoline Chemical compound C1=CC=C(C)C2=NC(OC)=CC=C21 YBPVXEYERZMYNR-UHFFFAOYSA-N 0.000 description 2
- KFXBWHFKOWWYJB-UHFFFAOYSA-N 2-methyl-4-(1,2,4-triazol-4-yl)aniline Chemical compound C1=C(N)C(C)=CC(N2C=NN=C2)=C1 KFXBWHFKOWWYJB-UHFFFAOYSA-N 0.000 description 2
- MCRAZEQVLBDZCA-UHFFFAOYSA-N 4-(2,4-dimethylimidazol-1-yl)-2-(trifluoromethyl)aniline Chemical compound CC1=NC(C)=CN1C1=CC=C(N)C(C(F)(F)F)=C1 MCRAZEQVLBDZCA-UHFFFAOYSA-N 0.000 description 2
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- 239000006227 byproduct Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000022900 cardiac muscle contraction Effects 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- KTZJITYQSMSCCR-UHFFFAOYSA-N n-(2-methoxy-8-methylquinolin-6-yl)formamide Chemical compound C1=C(NC=O)C=C(C)C2=NC(OC)=CC=C21 KTZJITYQSMSCCR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848413685A GB8413685D0 (en) | 1984-05-29 | 1984-05-29 | Quinolone inotropic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD237509A5 true DD237509A5 (de) | 1986-07-16 |
Family
ID=10561640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85276727A DD237509A5 (de) | 1984-05-29 | 1985-05-28 | Verfahren zur herstellung von 2-(1h)-chinolonen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6182A (enrdf_load_stackoverflow) |
| DD (1) | DD237509A5 (enrdf_load_stackoverflow) |
| GB (1) | GB8413685D0 (enrdf_load_stackoverflow) |
| SU (1) | SU1433411A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA853992B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4700150A (en) * | 1985-06-14 | 1987-10-13 | Stanford University | External laser frequency stabilizer |
| US5358949A (en) * | 1986-03-05 | 1994-10-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives and salts thereof and anti-arrhythmic agents containing the carbostyril derivatives |
| GT200600207A (es) * | 2005-06-09 | 2007-01-15 | Novartis Ag | Proceso para la síntesis de compuestos orgánicos |
| MY146795A (en) * | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
-
1984
- 1984-05-29 GB GB848413685A patent/GB8413685D0/en active Pending
-
1985
- 1985-05-27 ZA ZA853992A patent/ZA853992B/xx unknown
- 1985-05-28 DD DD85276727A patent/DD237509A5/de not_active IP Right Cessation
- 1985-05-28 SU SU853901004A patent/SU1433411A3/ru active
- 1985-05-29 JP JP60116316A patent/JPS6182A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB8413685D0 (en) | 1984-07-04 |
| JPS6182A (ja) | 1986-01-06 |
| SU1433411A3 (ru) | 1988-10-23 |
| ZA853992B (en) | 1987-01-28 |
| JPH0255431B2 (enrdf_load_stackoverflow) | 1990-11-27 |
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| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |