PT590428E - Azaquinoxalina processo para a sua preparacao e sua utilizacao - Google Patents
Azaquinoxalina processo para a sua preparacao e sua utilizacao Download PDFInfo
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- PT590428E PT590428E PT93114934T PT93114934T PT590428E PT 590428 E PT590428 E PT 590428E PT 93114934 T PT93114934 T PT 93114934T PT 93114934 T PT93114934 T PT 93114934T PT 590428 E PT590428 E PT 590428E
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- compound
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- hydrogen
- oxygen
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- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 3
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 229950005228 bromoform Drugs 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 238000005987 sulfurization reaction Methods 0.000 claims description 2
- 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 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 241000700605 Viruses Species 0.000 abstract description 3
- 229910052720 vanadium Inorganic materials 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- -1 4-picolyl group Chemical group 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
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- 239000002253 acid Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
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- 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 4
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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- GJRCWSBXBPZIRG-VIFPVBQESA-N (3s)-6-chloro-3-methyl-4-(pyridin-2-ylmethyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound N1([C@H](C(NC2=CC=C(Cl)N=C21)=O)C)CC1=CC=CC=N1 GJRCWSBXBPZIRG-VIFPVBQESA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
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- 230000000840 anti-viral effect Effects 0.000 description 3
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- 210000004698 lymphocyte Anatomy 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- SHCWQWRTKPNTEM-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1Cl SHCWQWRTKPNTEM-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 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
- 239000002841 Lewis acid Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
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- RUDOEPZHGRAHLZ-UHFFFAOYSA-N propan-2-yl 3-(methylsulfanylmethyl)-2-oxo-1,3-dihydropyrido[2,3-b]pyrazine-4-carboxylate Chemical compound C1=CC=C2NC(=O)C(CSC)N(C(=O)OC(C)C)C2=N1 RUDOEPZHGRAHLZ-UHFFFAOYSA-N 0.000 description 2
- OUFHXMSGJIYFPW-UHFFFAOYSA-N pyrazino[2,3-c]pyridazine Chemical class N1=NC=CC2=NC=CN=C21 OUFHXMSGJIYFPW-UHFFFAOYSA-N 0.000 description 2
- 150000003252 quinoxalines Chemical class 0.000 description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
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- CRVCEKLNTIQYBI-BYPYZUCNSA-N (3s)-6-chloro-3-methyl-3,4-dihydro-1h-pyrido[2,3-b]pyrazin-2-one Chemical compound ClC1=CC=C2NC(=O)[C@H](C)NC2=N1 CRVCEKLNTIQYBI-BYPYZUCNSA-N 0.000 description 1
- UDQNRZUJYYIAAU-VIFPVBQESA-N (3s)-6-chloro-3-methyl-4-(3-methylbut-2-enyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound ClC1=CC=C2NC(=O)[C@H](C)N(CC=C(C)C)C2=N1 UDQNRZUJYYIAAU-VIFPVBQESA-N 0.000 description 1
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- LSPSHYKFLQLERB-UHFFFAOYSA-N prop-1-en-2-yl 3-methyl-2-oxo-1,3-dihydropyrido[3,4-b]pyrazine-4-carboxylate Chemical compound N1=CC=C2NC(=O)C(C)N(C(=O)OC(C)=C)C2=C1 LSPSHYKFLQLERB-UHFFFAOYSA-N 0.000 description 1
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- HMWPVNOXKHFNCK-UHFFFAOYSA-N propan-2-yl 6-chloro-3-(methylsulfanylmethyl)-2-oxo-1,3-dihydropyrido[2,3-b]pyrazine-4-carboxylate Chemical compound ClC1=CC=C2NC(=O)C(CSC)N(C(=O)OC(C)C)C2=N1 HMWPVNOXKHFNCK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical class N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- TYLGVQVJCVFREB-UHFFFAOYSA-N pyrido[3,4-b]pyrazine Chemical class C1=NC=CC2=NC=CN=C21 TYLGVQVJCVFREB-UHFFFAOYSA-N 0.000 description 1
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- 150000003606 tin compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- BDIWFCKBPZPBQT-UHFFFAOYSA-N tributyl(tributylstannylsulfanyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)S[Sn](CCCC)(CCCC)CCCC BDIWFCKBPZPBQT-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Radar Systems Or Details Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4232392 | 1992-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT590428E true PT590428E (pt) | 2000-04-28 |
Family
ID=6468974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT93114934T PT590428E (pt) | 1992-09-26 | 1993-09-16 | Azaquinoxalina processo para a sua preparacao e sua utilizacao |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5424311A (enExample) |
| EP (1) | EP0590428B1 (enExample) |
| JP (1) | JPH06211855A (enExample) |
| KR (1) | KR940007035A (enExample) |
| AT (1) | ATE187724T1 (enExample) |
| AU (1) | AU664643B2 (enExample) |
| CA (1) | CA2106882C (enExample) |
| CZ (1) | CZ9302005A3 (enExample) |
| DE (1) | DE59309902D1 (enExample) |
| DK (1) | DK0590428T3 (enExample) |
| ES (1) | ES2141744T3 (enExample) |
| GR (1) | GR3032520T3 (enExample) |
| HU (1) | HUT65302A (enExample) |
| IL (1) | IL107081A (enExample) |
| MX (1) | MX9305894A (enExample) |
| NZ (1) | NZ248762A (enExample) |
| PH (1) | PH30348A (enExample) |
| PT (1) | PT590428E (enExample) |
| TW (1) | TW274550B (enExample) |
| ZA (1) | ZA937081B (enExample) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995018616A2 (en) * | 1994-01-03 | 1995-07-13 | Acea Pharm Inc | 8-aza, 6-aza and 6,8-diaza-1,4-dihydroquinoxaline-2,3-diones and the use thereof as antagonists for the glycine/nmda receptor |
| US5801183A (en) * | 1995-01-27 | 1998-09-01 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Aza and aza (N-oxy) analogs of glycine/NMDA receptor antagonists |
| US5646130A (en) * | 1995-06-30 | 1997-07-08 | Ocean University Of Oingdao | Low molecular weight sulfated polysaccharides and uses thereof |
| ZA973884B (en) * | 1996-05-23 | 1998-11-06 | Du Pont Merck Pharma | Tetrahydropteridines and pyridylpiperazines for treatment of neurological disorders |
| CA2313789A1 (en) | 1998-07-16 | 2000-01-27 | Aaron Tabor | Soy formulations and their use for promoting health |
| US6930101B1 (en) | 1999-05-17 | 2005-08-16 | The Regents Of The University Of California | Thiazolopyrimidines useful as TNFα inhibitors |
| US7101883B2 (en) | 2002-03-18 | 2006-09-05 | Bristol-Myers Squibb Company | Uracil derivatives as inhibitors of TNF-α converting enzyme (TACE) and matrix metalloproteinases |
| US6861422B2 (en) * | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
| DE10323345A1 (de) * | 2003-05-23 | 2004-12-16 | Zentaris Gmbh | Neue Pyridopyrazine und deren Verwendung als Kinase-Inhibitoren |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077955A (en) * | 1977-02-17 | 1978-03-07 | E. R. Squibb & Sons, Inc. | Amino derivatives of 1,2,3,4-tetrahydro-2-oxopyrido[2,2-b]-pyrazine carboxylic acids and esters |
| PH15791A (en) * | 1978-10-20 | 1983-03-25 | Lilly Co Eli | Pharmaceutical composition containing 3,4-dihydro-3-oxoquinoxalines |
| IE58312B1 (en) * | 1984-05-18 | 1993-09-08 | Union Pharma Scient Appl | Heterocyclic derivatives, processes for their preparation and drugs in which they are present, which are useful especially as aldose reductase inhibitors |
| JPH0276860A (ja) * | 1987-10-05 | 1990-03-16 | Toyo Jozo Co Ltd | ６−置換アルコキシ−２−オキソ−１，２−ジヒドロキノキサリン誘導体 |
| DK160876C (da) * | 1987-12-08 | 1991-10-14 | Novo Nordisk As | Imidazoquinoxalinforbindelser, fremgangsmaade til deres fremstilling, anvendelse af forbindelserne og farmaceutiske praeparater, hvori forbindelserne indgaar |
| EP0509398B1 (de) * | 1991-04-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Chinoxaline, Verfahren zu ihrer Herstellung und ihre Verwendung |
-
1993
- 1993-09-09 TW TW082107380A patent/TW274550B/zh active
- 1993-09-16 DK DK93114934T patent/DK0590428T3/da active
- 1993-09-16 DE DE59309902T patent/DE59309902D1/de not_active Expired - Fee Related
- 1993-09-16 EP EP93114934A patent/EP0590428B1/de not_active Expired - Lifetime
- 1993-09-16 ES ES93114934T patent/ES2141744T3/es not_active Expired - Lifetime
- 1993-09-16 AT AT93114934T patent/ATE187724T1/de not_active IP Right Cessation
- 1993-09-16 PT PT93114934T patent/PT590428E/pt unknown
- 1993-09-23 AU AU47553/93A patent/AU664643B2/en not_active Ceased
- 1993-09-23 IL IL10708193A patent/IL107081A/en not_active IP Right Cessation
- 1993-09-23 US US08/125,163 patent/US5424311A/en not_active Expired - Lifetime
- 1993-09-24 CZ CZ932005A patent/CZ9302005A3/cs unknown
- 1993-09-24 CA CA002106882A patent/CA2106882C/en not_active Expired - Fee Related
- 1993-09-24 HU HU9302696A patent/HUT65302A/hu unknown
- 1993-09-24 NZ NZ248762A patent/NZ248762A/en unknown
- 1993-09-24 JP JP5237679A patent/JPH06211855A/ja active Pending
- 1993-09-24 ZA ZA937081A patent/ZA937081B/xx unknown
- 1993-09-24 PH PH46948A patent/PH30348A/en unknown
- 1993-09-24 MX MX9305894A patent/MX9305894A/es not_active IP Right Cessation
- 1993-09-25 KR KR1019930019733A patent/KR940007035A/ko not_active Withdrawn
-
2000
- 2000-01-31 GR GR20000400216T patent/GR3032520T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA937081B (en) | 1994-04-18 |
| IL107081A (en) | 1999-07-14 |
| EP0590428B1 (de) | 1999-12-15 |
| HU9302696D0 (en) | 1993-12-28 |
| MX9305894A (es) | 1994-03-31 |
| JPH06211855A (ja) | 1994-08-02 |
| IL107081A0 (en) | 1993-12-28 |
| TW274550B (enExample) | 1996-04-21 |
| US5424311A (en) | 1995-06-13 |
| HUT65302A (en) | 1994-05-02 |
| KR940007035A (ko) | 1994-04-26 |
| CZ9302005A3 (en) | 1994-04-13 |
| EP0590428A1 (de) | 1994-04-06 |
| CA2106882C (en) | 2007-04-17 |
| GR3032520T3 (en) | 2000-05-31 |
| PH30348A (en) | 1997-04-02 |
| DE59309902D1 (de) | 2000-01-20 |
| AU4755393A (en) | 1994-03-31 |
| AU664643B2 (en) | 1995-11-23 |
| ATE187724T1 (de) | 2000-01-15 |
| ES2141744T3 (es) | 2000-04-01 |
| NZ248762A (en) | 1996-01-26 |
| CA2106882A1 (en) | 1994-03-27 |
| DK0590428T3 (da) | 2000-05-22 |
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