DD146705A5 - Verfahren zur herstellung von 3,4-dihydro-3-oxo-2-chinoxalinen - Google Patents
Verfahren zur herstellung von 3,4-dihydro-3-oxo-2-chinoxalinen Download PDFInfo
- Publication number
- DD146705A5 DD146705A5 DD79216342A DD21634279A DD146705A5 DD 146705 A5 DD146705 A5 DD 146705A5 DD 79216342 A DD79216342 A DD 79216342A DD 21634279 A DD21634279 A DD 21634279A DD 146705 A5 DD146705 A5 DD 146705A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dihydro
- oxo
- ethyl
- quinoxalinecarboxylate
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 19
- 238000010992 reflux Methods 0.000 claims abstract description 19
- DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- TTXGKCVKGXHPRI-UHFFFAOYSA-N 4,5-dibromobenzene-1,2-diamine Chemical compound NC1=CC(Br)=C(Br)C=C1N TTXGKCVKGXHPRI-UHFFFAOYSA-N 0.000 claims abstract description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000004716 alpha keto acids Chemical class 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- -1 2-nitro-4,5-disubstituted-aniline Chemical class 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- OARGFWQSVACNCO-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CC=NC2=C1 OARGFWQSVACNCO-UHFFFAOYSA-N 0.000 claims description 4
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 238000000137 annealing Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 4
- VHHFLIVSBISZQJ-UHFFFAOYSA-N ethyl 7-bromo-6-chloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound BrC1=C(Cl)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 VHHFLIVSBISZQJ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000009385 viral infection Effects 0.000 abstract description 4
- 208000036142 Viral infection Diseases 0.000 abstract description 3
- 230000003285 pharmacodynamic effect Effects 0.000 abstract description 3
- 210000002700 urine Anatomy 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 28
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- 239000000155 melt Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 241000700605 Viruses Species 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 15
- 241000712461 unidentified influenza virus Species 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000338 in vitro Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 206010046865 Vaccinia virus infection Diseases 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 208000007089 vaccinia Diseases 0.000 description 9
- 208000009889 Herpes Simplex Diseases 0.000 description 8
- 230000000840 anti-viral effect Effects 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003252 quinoxalines Chemical class 0.000 description 6
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 5
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- LWFDMVFVKWWYFN-UHFFFAOYSA-N 6,7-Dichloro-3-hydroxy-2-quinoxalinecarboxylicacid Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)O)=NC2=C1 LWFDMVFVKWWYFN-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- KAQQACPCRNDISO-UHFFFAOYSA-N 1,2-diiodo-4,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(I)=C(I)C=C1[N+]([O-])=O KAQQACPCRNDISO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- ZAFFWAGKFUGBKJ-UHFFFAOYSA-N ethyl 6,7-dibromo-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound BrC1=C(Br)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 ZAFFWAGKFUGBKJ-UHFFFAOYSA-N 0.000 description 3
- HVUUAJYWVAZYAU-UHFFFAOYSA-N ethyl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 HVUUAJYWVAZYAU-UHFFFAOYSA-N 0.000 description 3
- OQIPQIAPBBVFDP-UHFFFAOYSA-N ethyl 6,7-difluoro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound FC1=C(F)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 OQIPQIAPBBVFDP-UHFFFAOYSA-N 0.000 description 3
- IXFXXIBNAIXCDU-UHFFFAOYSA-N ethyl 6,7-diiodo-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound IC1=C(I)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 IXFXXIBNAIXCDU-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- PSXXZHPJADTUNB-UHFFFAOYSA-N n-(3,4-difluorophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(F)C(F)=C1 PSXXZHPJADTUNB-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- JNTOKFNBDFMTIV-UHFFFAOYSA-N propyl nitrate Chemical compound CCCO[N+]([O-])=O JNTOKFNBDFMTIV-UHFFFAOYSA-N 0.000 description 3
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
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- 230000001629 suppression Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- YRLPRCXPRAACMC-UHFFFAOYSA-N 2-chloroethyl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)OCCCl)=NC2=C1 YRLPRCXPRAACMC-UHFFFAOYSA-N 0.000 description 2
- QIDSVLUIWDDFKL-UHFFFAOYSA-N 4,5-dibromo-2-nitroaniline Chemical compound NC1=CC(Br)=C(Br)C=C1[N+]([O-])=O QIDSVLUIWDDFKL-UHFFFAOYSA-N 0.000 description 2
- IWFHBRFJOHTIPU-UHFFFAOYSA-N 4,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Cl)C=C1N IWFHBRFJOHTIPU-UHFFFAOYSA-N 0.000 description 2
- WDMCABATCGQAKK-UHFFFAOYSA-N 4,5-difluoro-2-nitroaniline Chemical compound NC1=CC(F)=C(F)C=C1[N+]([O-])=O WDMCABATCGQAKK-UHFFFAOYSA-N 0.000 description 2
- JVJAIGJOWFTCRI-UHFFFAOYSA-N 4,5-diiodo-2-nitroaniline Chemical compound NC1=CC(I)=C(I)C=C1[N+]([O-])=O JVJAIGJOWFTCRI-UHFFFAOYSA-N 0.000 description 2
- DIBFUNSINNCILZ-UHFFFAOYSA-N 4,5-diiodobenzene-1,2-diamine Chemical compound NC1=CC(I)=C(I)C=C1N DIBFUNSINNCILZ-UHFFFAOYSA-N 0.000 description 2
- UHBIZFLONPIQDF-UHFFFAOYSA-N 6,7-difluoro-3-oxo-4h-quinoxaline-2-carboxylic acid Chemical compound FC1=C(F)C=C2NC(=O)C(C(=O)O)=NC2=C1 UHBIZFLONPIQDF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
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- 238000010171 animal model Methods 0.000 description 2
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- 238000003556 assay Methods 0.000 description 2
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- 150000004985 diamines Chemical class 0.000 description 2
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- KXNVUWFDMMEIHY-UHFFFAOYSA-N ethyl 5-chloro-7-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound [O-][N+](=O)C1=CC(Cl)=C2NC(=O)C(C(=O)OCC)=NC2=C1 KXNVUWFDMMEIHY-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- OJFQFPPFAFOXAQ-UHFFFAOYSA-N n-(4,5-difluoro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(F)=C(F)C=C1[N+]([O-])=O OJFQFPPFAFOXAQ-UHFFFAOYSA-N 0.000 description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 description 2
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- GULVDPYLWVXKGC-UHFFFAOYSA-N quinoxalin-2-ylhydrazine Chemical class C1=CC=CC2=NC(NN)=CN=C21 GULVDPYLWVXKGC-UHFFFAOYSA-N 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- JZJFIUXMPBVEFS-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carbaldehyde Chemical class C1=CC=C2N([O-])C(C=O)=C[N+](=O)C2=C1 JZJFIUXMPBVEFS-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DWHVZCLBMTZRQM-UHFFFAOYSA-N 2H-pyrazolo[4,3-b]quinoxalin-3-amine Chemical compound C1=CC=CC2=NC3=C(N)NN=C3N=C21 DWHVZCLBMTZRQM-UHFFFAOYSA-N 0.000 description 1
- QFTJOYLPELHHCO-UHFFFAOYSA-N 3,4-dibromoaniline Chemical compound NC1=CC=C(Br)C(Br)=C1 QFTJOYLPELHHCO-UHFFFAOYSA-N 0.000 description 1
- AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 1
- BRMHMIRMKUHQDT-UHFFFAOYSA-N 3,6-diaminoquinoxaline-2-carboxamide Chemical class C1=C(N)C=C2N=C(N)C(C(=O)N)=NC2=C1 BRMHMIRMKUHQDT-UHFFFAOYSA-N 0.000 description 1
- JCSMNJWYXWGBIM-UHFFFAOYSA-N 3-(6,7-dichloro-3-oxo-4h-quinoxalin-2-yl)propanoic acid Chemical compound ClC1=C(Cl)C=C2NC(=O)C(CCC(=O)O)=NC2=C1 JCSMNJWYXWGBIM-UHFFFAOYSA-N 0.000 description 1
- VSKRLWVUULXUMF-UHFFFAOYSA-N 3-chloro-5-nitrobenzene-1,2-diamine Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1N VSKRLWVUULXUMF-UHFFFAOYSA-N 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 1
- PPWRHKISAQTCCG-UHFFFAOYSA-N 4,5-difluorobenzene-1,2-diamine Chemical compound NC1=CC(F)=C(F)C=C1N PPWRHKISAQTCCG-UHFFFAOYSA-N 0.000 description 1
- XXIFMWKGKJWFOH-UHFFFAOYSA-N 4-bromo-5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=C(Br)C=C1[N+]([O-])=O XXIFMWKGKJWFOH-UHFFFAOYSA-N 0.000 description 1
- VBJCMWQIEHOUAT-UHFFFAOYSA-N 4-bromo-5-chlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=C(Br)C=C1N VBJCMWQIEHOUAT-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- IBMSTSUDOQBTDM-UHFFFAOYSA-N 5-methoxy-3-nitrobenzene-1,2-diamine Chemical compound COC1=CC(N)=C(N)C([N+]([O-])=O)=C1 IBMSTSUDOQBTDM-UHFFFAOYSA-N 0.000 description 1
- QMOACLKFFAVPAA-UHFFFAOYSA-N 7-bromo-6-fluoro-3-oxo-2h-quinoxaline-2-carboxylic acid Chemical compound C1=C(Br)C(F)=CC2=NC(=O)C(C(=O)O)N=C21 QMOACLKFFAVPAA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- KYIKFBSRJQMITG-UHFFFAOYSA-N BrNC1=C(C=CC(=C1)Cl)[N+](=O)[O-] Chemical compound BrNC1=C(C=CC(=C1)Cl)[N+](=O)[O-] KYIKFBSRJQMITG-UHFFFAOYSA-N 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000282552 Chlorocebus aethiops Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241001446459 Heia Species 0.000 description 1
- 244000199866 Lactobacillus casei Species 0.000 description 1
- 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 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 241000223992 Plasmodium gallinaceum Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 206010037151 Psittacosis Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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- 239000003610 charcoal Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ALAROWBVGLJQTP-UHFFFAOYSA-N cyclobutane;methyl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1CCC1.ClC1=C(Cl)C=C2NC(=O)C(C(=O)OC)=NC2=C1 ALAROWBVGLJQTP-UHFFFAOYSA-N 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- HYJMCMPIILIFMD-UHFFFAOYSA-N ethyl 3-(4-bromo-5-chloro-2-nitroanilino)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=CC(Cl)=C(Br)C=C1[N+]([O-])=O HYJMCMPIILIFMD-UHFFFAOYSA-N 0.000 description 1
- MYCWFMHDJPZNGS-UHFFFAOYSA-N ethyl 6-bromo-7-chloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Br)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 MYCWFMHDJPZNGS-UHFFFAOYSA-N 0.000 description 1
- JYBPDBMAMOHPLX-UHFFFAOYSA-N ethyl 6-methoxy-8-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1=C(OC)C=C2NC(=O)C(C(=O)OCC)=NC2=C1[N+]([O-])=O JYBPDBMAMOHPLX-UHFFFAOYSA-N 0.000 description 1
- IFUNTGLNNSIUBQ-UHFFFAOYSA-N ethyl 6-methyl-8-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1=C(C)C=C2NC(=O)C(C(=O)OCC)=NC2=C1[N+]([O-])=O IFUNTGLNNSIUBQ-UHFFFAOYSA-N 0.000 description 1
- MXRQCKOJQVLMPR-UHFFFAOYSA-N ethyl 7-bromo-6-chloro-1-oxido-3-oxo-2h-quinoxalin-1-ium-2-carboxylate Chemical compound C1=C(Cl)C(Br)=CC2=[N+]([O-])C(C(=O)OCC)C(=O)N=C21 MXRQCKOJQVLMPR-UHFFFAOYSA-N 0.000 description 1
- RGAAOKDXIMNYAQ-UHFFFAOYSA-N ethyl 7-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)C(C(=O)OCC)=NC2=C1 RGAAOKDXIMNYAQ-UHFFFAOYSA-N 0.000 description 1
- YJKXCNAGVGPFEI-UHFFFAOYSA-N ethyl 8-chloro-6-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(C(=O)OCC)=NC2=C1Cl YJKXCNAGVGPFEI-UHFFFAOYSA-N 0.000 description 1
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- 208000001581 lymphogranuloma venereum Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CQZVBBDKVGDSMQ-UHFFFAOYSA-N methyl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)OC)=NC2=C1 CQZVBBDKVGDSMQ-UHFFFAOYSA-N 0.000 description 1
- CMFVIPREKMZKDK-UHFFFAOYSA-N methyl 7-methoxy-8-nitro-3-oxo-2h-quinoxaline-2-carboxylate Chemical compound [O-][N+](=O)C1=C(OC)C=CC2=NC(=O)C(C(=O)OC)N=C21 CMFVIPREKMZKDK-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 201000000901 ornithosis Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- VTVIFHGLLNFVOT-UHFFFAOYSA-N propyl 6-chloro-7-iodo-3-oxo-2h-quinoxaline-2-carboxylate Chemical compound C1=C(I)C(Cl)=CC2=NC(=O)C(C(=O)OCCC)N=C21 VTVIFHGLLNFVOT-UHFFFAOYSA-N 0.000 description 1
- JMRDCKFSPLHHHN-UHFFFAOYSA-N propyl 7-chloro-6-iodo-3-oxo-2h-quinoxaline-2-carboxylate Chemical compound C1=C(Cl)C(I)=CC2=NC(=O)C(C(=O)OCCC)N=C21 JMRDCKFSPLHHHN-UHFFFAOYSA-N 0.000 description 1
- 208000009305 pseudorabies Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical compound [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95315778A | 1978-10-20 | 1978-10-20 | |
| US6044579A | 1979-07-25 | 1979-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD146705A5 true DD146705A5 (de) | 1981-02-25 |
Family
ID=26739938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216342A DD146705A5 (de) | 1978-10-20 | 1979-10-19 | Verfahren zur herstellung von 3,4-dihydro-3-oxo-2-chinoxalinen |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4264600A (pt) |
| EP (1) | EP0010426A1 (pt) |
| JP (1) | JPS5569514A (pt) |
| AU (1) | AU5197779A (pt) |
| BE (1) | BE879472A (pt) |
| CA (1) | CA1145337A (pt) |
| DD (1) | DD146705A5 (pt) |
| DK (1) | DK444479A (pt) |
| ES (2) | ES485221A1 (pt) |
| FI (1) | FI793261A (pt) |
| FR (2) | FR2439188A1 (pt) |
| GB (1) | GB2034302A (pt) |
| GR (1) | GR72941B (pt) |
| IL (1) | IL58478A0 (pt) |
| IT (1) | IT1193847B (pt) |
| LU (1) | LU81798A1 (pt) |
| PH (1) | PH15791A (pt) |
| PT (1) | PT70340A (pt) |
| RO (1) | RO78225A (pt) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252954A (en) * | 1979-10-25 | 1981-02-24 | Eli Lilly And Company | Salts of dihalo-3,4-dihydro-3-oxo-2-quinoxaline carboxylic acids and hindered amines |
| US4355030A (en) * | 1980-11-14 | 1982-10-19 | Eli Lilly And Company | Antiviral combinations |
| JPH0678319B2 (ja) * | 1986-03-11 | 1994-10-05 | 東ソー株式会社 | キノキサリノン誘導体 |
| US5037983A (en) * | 1988-05-16 | 1991-08-06 | E. R. Squibb & Sons, Inc. | 6,7-dihydroxyquinoxalines as intermediates to beta-lactam antibiotics |
| US4904775A (en) * | 1988-05-16 | 1990-02-27 | E. R. Squibb & Sons, Inc. | Heteroaroylhydrazide derivatives of monocyclic beta-lactam antibiotics |
| CA2024282A1 (en) * | 1989-09-21 | 1991-03-22 | Peter H. Ermann | Heterocyclic hydrazide derivatives of monocyclic beta-lactam antibiotics |
| US5169955A (en) * | 1990-03-01 | 1992-12-08 | Nippon Kayaku Kabushiki Kaisha | Process for producing 2-hydroxyquinoxaline derivatives |
| ZA918014B (en) * | 1990-11-05 | 1992-07-29 | Squibb & Sons Inc | Heteroaroyl derivatives of monocyclic beta-lactam antibiotics |
| WO1992011245A1 (en) * | 1990-12-20 | 1992-07-09 | Warner-Lambert Company | 2-acylamido derivatives of 3,4-dihydro-3-oxo-quinoxaline having pharmaceutical activity |
| US5250691A (en) * | 1991-09-09 | 1993-10-05 | E. R. Squibb & Sons, Inc. | Heteroaryl derivatives of monocyclic beta-lactam antibiotics |
| TW274550B (pt) * | 1992-09-26 | 1996-04-21 | Hoechst Ag | |
| AU744540B2 (en) * | 1997-09-01 | 2002-02-28 | Kyorin Pharmaceutical Co. Ltd. | 6,7-asymmetrically disubstituted quinoxalinecarboxylic acid derivatives, addition salts thereof, and processes for the preparation of both |
| US8742156B2 (en) | 2010-08-14 | 2014-06-03 | British Columbia Cancer Agency Branch | Anti-viral carbamimidothioic acid esters |
| CA2895526C (en) * | 2012-12-20 | 2021-08-24 | Qing-bin LU | Radiosensitizer compounds for use in combination with radiation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1038505A (en) * | 1963-06-04 | 1966-08-10 | Daiichi Seiyaku Co | Antileprosy ointment |
| DE1804328A1 (de) * | 1967-10-23 | 1969-05-22 | Donau Pharmazie Gmbh | 3-substituierte Chinoxalinone und Verfahren zur Herstellung von 3-substituierten Chinoxalin-2-Onen |
| GB1215815A (en) | 1967-12-20 | 1970-12-16 | Research Corp | Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides |
| GB1408675A (en) | 1973-03-16 | 1975-10-01 | Allen & Hanburys Ltd | Amides derived from quinoxaline |
| US3654275A (en) * | 1969-10-15 | 1972-04-04 | Pfizer & Co C | Quinoxalinecarboxamide antiinflammatory agents |
| GB1308370A (en) | 1969-12-09 | 1973-02-21 | Research Corp | 1-hydroxy-3-oxo-benzimidazoles quinoxaline-di-n-oxides and benzimidazole-mono-and di-n-oxides |
| US3962440A (en) * | 1973-12-26 | 1976-06-08 | Eli Lilly And Company | Quinoxaline compounds as hypnotic agents |
-
1979
- 1979-10-15 GR GR60267A patent/GR72941B/el unknown
- 1979-10-15 PH PH23167A patent/PH15791A/en unknown
- 1979-10-16 GB GB7935844A patent/GB2034302A/en not_active Withdrawn
- 1979-10-16 EP EP79302229A patent/EP0010426A1/en not_active Withdrawn
- 1979-10-17 IL IL58478A patent/IL58478A0/xx unknown
- 1979-10-18 BE BE1/9573A patent/BE879472A/fr unknown
- 1979-10-18 CA CA000337952A patent/CA1145337A/en not_active Expired
- 1979-10-18 FR FR7925930A patent/FR2439188A1/fr not_active Withdrawn
- 1979-10-18 LU LU81798A patent/LU81798A1/fr unknown
- 1979-10-18 PT PT197970340A patent/PT70340A/pt unknown
- 1979-10-19 ES ES79485221A patent/ES485221A1/es not_active Expired
- 1979-10-19 FI FI793261A patent/FI793261A/fi not_active Application Discontinuation
- 1979-10-19 RO RO7999003A patent/RO78225A/ro unknown
- 1979-10-19 ES ES79485222A patent/ES485222A1/es not_active Expired
- 1979-10-19 AU AU51977/79A patent/AU5197779A/en not_active Abandoned
- 1979-10-19 IT IT26662/79A patent/IT1193847B/it active
- 1979-10-19 DD DD79216342A patent/DD146705A5/de unknown
- 1979-10-19 JP JP13583279A patent/JPS5569514A/ja active Pending
- 1979-10-22 DK DK444479A patent/DK444479A/da unknown
- 1979-10-25 US US06/088,274 patent/US4264600A/en not_active Expired - Lifetime
-
1980
- 1980-04-25 FR FR8009368A patent/FR2448899A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT7926662A0 (it) | 1979-10-19 |
| FI793261A (fi) | 1980-04-21 |
| JPS5569514A (en) | 1980-05-26 |
| ES485221A1 (es) | 1980-07-01 |
| PH15791A (en) | 1983-03-25 |
| GR72941B (pt) | 1984-01-16 |
| US4264600A (en) | 1981-04-28 |
| FR2439188A1 (fr) | 1980-05-16 |
| CA1145337A (en) | 1983-04-26 |
| PT70340A (en) | 1979-10-01 |
| RO78225A (ro) | 1982-02-01 |
| BE879472A (fr) | 1980-04-18 |
| GB2034302A (en) | 1980-06-04 |
| ES485222A1 (es) | 1980-09-01 |
| FR2448899A1 (fr) | 1980-09-12 |
| IL58478A0 (en) | 1980-01-31 |
| DK444479A (da) | 1980-04-21 |
| IT1193847B (it) | 1988-08-24 |
| EP0010426A1 (en) | 1980-04-30 |
| LU81798A1 (fr) | 1980-04-21 |
| AU5197779A (en) | 1980-05-01 |
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