GB2034302A - Pharmaceutical composition containing 3,4-dihydro-3-oxo-quinoxalines such as quinoxalines and processes for the production thereof - Google Patents
Pharmaceutical composition containing 3,4-dihydro-3-oxo-quinoxalines such as quinoxalines and processes for the production thereof Download PDFInfo
- Publication number
- GB2034302A GB2034302A GB7935844A GB7935844A GB2034302A GB 2034302 A GB2034302 A GB 2034302A GB 7935844 A GB7935844 A GB 7935844A GB 7935844 A GB7935844 A GB 7935844A GB 2034302 A GB2034302 A GB 2034302A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dihydro
- oxo
- formula
- ethyl
- quinoxaline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 32
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 150000003252 quinoxalines Chemical class 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 23
- -1 2-nitro 4,5-disubstituted aniline Chemical class 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 18
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- DBKKFIIYQGGHJO-UHFFFAOYSA-N diethyl 2-oxopropanedioate Chemical compound CCOC(=O)C(=O)C(=O)OCC DBKKFIIYQGGHJO-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000003443 antiviral agent Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 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
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- TTXGKCVKGXHPRI-UHFFFAOYSA-N 4,5-dibromobenzene-1,2-diamine Chemical compound NC1=CC(Br)=C(Br)C=C1N TTXGKCVKGXHPRI-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 208000036142 Viral infection Diseases 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
- ZAFFWAGKFUGBKJ-UHFFFAOYSA-N ethyl 6,7-dibromo-3-oxo-4h-quinoxaline-2-carboxylate Chemical group BrC1=C(Br)C=C2NC(=O)C(C(=O)OCC)=NC2=C1 ZAFFWAGKFUGBKJ-UHFFFAOYSA-N 0.000 claims description 4
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-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
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- OARGFWQSVACNCO-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CC=NC2=C1 OARGFWQSVACNCO-UHFFFAOYSA-N 0.000 claims 1
- KZACLPVBRBYJTP-UHFFFAOYSA-N 1h-2,1,4-benzoxadiazine Chemical compound C1=CC=C2NOC=NC2=C1 KZACLPVBRBYJTP-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- CQZVBBDKVGDSMQ-UHFFFAOYSA-N methyl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical group ClC1=C(Cl)C=C2NC(=O)C(C(=O)OC)=NC2=C1 CQZVBBDKVGDSMQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 27
- 238000001914 filtration Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 241000700605 Viruses Species 0.000 description 12
- 230000000840 anti-viral effect Effects 0.000 description 11
- 241000712461 unidentified influenza virus Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- 206010046865 Vaccinia virus infection Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 208000007089 vaccinia Diseases 0.000 description 9
- 208000009889 Herpes Simplex Diseases 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007787 solid Substances 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
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000001424 substituent group Chemical group 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 239000000470 constituent Substances 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000011877 solvent mixture 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
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 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 4
- 206010022000 influenza Diseases 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
- 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
- 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000002148 esters Chemical class 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
- 239000000706 filtrate Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002609 medium Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 3
- JNTOKFNBDFMTIV-UHFFFAOYSA-N propyl nitrate Chemical compound CCCO[N+]([O-])=O JNTOKFNBDFMTIV-UHFFFAOYSA-N 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- 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 2
- WRONKXRXQBUZGM-UHFFFAOYSA-N 4-chloro-3-oxoquinoxaline-2-carboxylic acid Chemical compound C1=CC=C2C(=C1)N=C(C(=O)N2Cl)C(=O)O WRONKXRXQBUZGM-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
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 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 2
- 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
- 229920002472 Starch Polymers 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- YLQARHIFEKQCLD-UHFFFAOYSA-N ethyl 6,7-dichloro-3-oxo-2,4-dihydro-1h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)OCC)NC2=C1 YLQARHIFEKQCLD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 description 2
- AVRYOOXUIJCQPV-UHFFFAOYSA-N ethyl 7-methoxy-5-nitro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound COC1=CC([N+]([O-])=O)=C2NC(=O)C(C(=O)OCC)=NC2=C1 AVRYOOXUIJCQPV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000543 intermediate 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000004987 o-phenylenediamines Chemical class 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 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
- 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
- XUPCBLUMRUUBPP-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium-2-carboxylic acid Chemical compound C1=CC=CC2=[N+]([O-])C(C(=O)O)=CN=C21 XUPCBLUMRUUBPP-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
- RQAQBPQMXANMRW-UHFFFAOYSA-N 2-methylpropyl 8-chloro-7-nitro-3-oxo-2h-quinoxaline-2-carboxylate Chemical compound ClC1=C([N+]([O-])=O)C=CC2=NC(=O)C(C(=O)OCC(C)C)N=C21 RQAQBPQMXANMRW-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
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 229910015900 BF3 Inorganic materials 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 241000283086 Equidae Species 0.000 description 1
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- 244000199866 Lactobacillus casei Species 0.000 description 1
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- 241000223992 Plasmodium gallinaceum Species 0.000 description 1
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- 241000282887 Suidae Species 0.000 description 1
- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical class C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 description 1
- LDLHZLBHBQRNGR-UHFFFAOYSA-N [3-(sulfanylmethyl)quinoxalin-2-yl]methanethiol Chemical class C1=CC=C2N=C(CS)C(CS)=NC2=C1 LDLHZLBHBQRNGR-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 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
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- 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
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- 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
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- 239000000463 material Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 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
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- QUJZEAOLNDSFAZ-UHFFFAOYSA-N n,n-difluoro-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1N(F)F QUJZEAOLNDSFAZ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- HHAVHBDPWSUKHZ-UHFFFAOYSA-N propan-2-ol;propan-2-one Chemical compound CC(C)O.CC(C)=O HHAVHBDPWSUKHZ-UHFFFAOYSA-N 0.000 description 1
- ZKCOOIBVXUQCIH-UHFFFAOYSA-N propan-2-yl 6,7-dichloro-3-oxo-4h-quinoxaline-2-carboxylate Chemical compound ClC1=C(Cl)C=C2NC(=O)C(C(=O)OC(C)C)=NC2=C1 ZKCOOIBVXUQCIH-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000005180 public health Effects 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
- GULVDPYLWVXKGC-UHFFFAOYSA-N quinoxalin-2-ylhydrazine Chemical class C1=CC=CC2=NC(NN)=CN=C21 GULVDPYLWVXKGC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Communicable Diseases (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 |
|---|---|
| GB2034302A true GB2034302A (en) | 1980-06-04 |
Family
ID=26739938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7935844A Withdrawn GB2034302A (en) | 1978-10-20 | 1979-10-16 | Pharmaceutical composition containing 3,4-dihydro-3-oxo-quinoxalines such as quinoxalines and processes for the production thereof |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4264600A (enExample) |
| EP (1) | EP0010426A1 (enExample) |
| JP (1) | JPS5569514A (enExample) |
| AU (1) | AU5197779A (enExample) |
| BE (1) | BE879472A (enExample) |
| CA (1) | CA1145337A (enExample) |
| DD (1) | DD146705A5 (enExample) |
| DK (1) | DK444479A (enExample) |
| ES (2) | ES485222A1 (enExample) |
| FI (1) | FI793261A7 (enExample) |
| FR (2) | FR2439188A1 (enExample) |
| GB (1) | GB2034302A (enExample) |
| GR (1) | GR72941B (enExample) |
| IL (1) | IL58478A0 (enExample) |
| IT (1) | IT1193847B (enExample) |
| LU (1) | LU81798A1 (enExample) |
| PH (1) | PH15791A (enExample) |
| PT (1) | PT70340A (enExample) |
| RO (1) | RO78225A (enExample) |
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 |
| US4904775A (en) * | 1988-05-16 | 1990-02-27 | E. R. Squibb & Sons, Inc. | Heteroaroylhydrazide derivatives of monocyclic beta-lactam antibiotics |
| US5037983A (en) * | 1988-05-16 | 1991-08-06 | E. R. Squibb & Sons, Inc. | 6,7-dihydroxyquinoxalines as intermediates to 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 |
| AU9049391A (en) * | 1990-12-20 | 1992-07-22 | 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 (enExample) * | 1992-09-26 | 1996-04-21 | Hoechst Ag | |
| BR9811739A (pt) * | 1997-09-01 | 2000-09-19 | Kyorin Seiyaku Kk | Derivados de ácido quinoxalinacarbóxilico assimetricamente dissubstituìdo em 6,7, seus sais de adição, e processos para a preparação de ambos |
| US8742156B2 (en) | 2010-08-14 | 2014-06-03 | British Columbia Cancer Agency Branch | Anti-viral carbamimidothioic acid esters |
| MX2015008010A (es) * | 2012-12-20 | 2016-04-26 | qing-bin Lu | Compuestos radiosensabilizadores para usarse en combinacion con radiacion. |
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 CA CA000337952A patent/CA1145337A/en not_active Expired
- 1979-10-18 PT PT197970340A patent/PT70340A/pt unknown
- 1979-10-18 BE BE1/9573A patent/BE879472A/fr unknown
- 1979-10-18 LU LU81798A patent/LU81798A1/fr unknown
- 1979-10-18 FR FR7925930A patent/FR2439188A1/fr not_active Withdrawn
- 1979-10-19 ES ES79485222A patent/ES485222A1/es not_active Expired
- 1979-10-19 IT IT26662/79A patent/IT1193847B/it active
- 1979-10-19 JP JP13583279A patent/JPS5569514A/ja active Pending
- 1979-10-19 FI FI793261A patent/FI793261A7/fi not_active Application Discontinuation
- 1979-10-19 ES ES79485221A patent/ES485221A1/es not_active Expired
- 1979-10-19 RO RO7999003A patent/RO78225A/ro unknown
- 1979-10-19 DD DD79216342A patent/DD146705A5/de unknown
- 1979-10-19 AU AU51977/79A patent/AU5197779A/en not_active Abandoned
- 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 |
|---|---|
| PH15791A (en) | 1983-03-25 |
| RO78225A (ro) | 1982-02-01 |
| IL58478A0 (en) | 1980-01-31 |
| ES485222A1 (es) | 1980-09-01 |
| EP0010426A1 (en) | 1980-04-30 |
| ES485221A1 (es) | 1980-07-01 |
| FR2439188A1 (fr) | 1980-05-16 |
| DK444479A (da) | 1980-04-21 |
| IT7926662A0 (it) | 1979-10-19 |
| IT1193847B (it) | 1988-08-24 |
| GR72941B (enExample) | 1984-01-16 |
| DD146705A5 (de) | 1981-02-25 |
| AU5197779A (en) | 1980-05-01 |
| LU81798A1 (fr) | 1980-04-21 |
| BE879472A (fr) | 1980-04-18 |
| JPS5569514A (en) | 1980-05-26 |
| PT70340A (en) | 1979-10-01 |
| CA1145337A (en) | 1983-04-26 |
| US4264600A (en) | 1981-04-28 |
| FI793261A7 (fi) | 1981-01-01 |
| FR2448899A1 (fr) | 1980-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |