SI9520108A - New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use - Google Patents

New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use Download PDF

Info

Publication number: SI9520108A
Authority: SI; Slovenia
Prior art keywords: alkyl; group; trifluoromethyl; nitro; phenyl
Prior art date: 1994-09-30

Application number

SI9520108A

Other languages

English (en)

Slovenian (sl)

Inventor

Hans-Joerg Treiber

Wilfried Lubisch

Berthold Behl

Hans Peter Hofmann

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1994-09-30

Filing date

1995-09-19

Publication date

1997-10-31

1995-02-06 Priority claimed from DE19503825A external-priority patent/DE19503825A1/de

1995-09-19 Application filed by Basf Ag filed Critical Basf Ag

1997-10-31 Publication of SI9520108A publication Critical patent/SI9520108A/sl

Links

125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 16
HOFSPGAYXKNFAM-UHFFFAOYSA-N imidazo[4,5-f]quinoxalin-2-one Chemical class C1=CN=C2C3=NC(=O)N=C3C=CC2=N1 HOFSPGAYXKNFAM-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims description 25
-1 nitrodioxy Chemical group 0.000 claims abstract description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 6
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
239000003814 drug Substances 0.000 claims description 9
210000003169 central nervous system Anatomy 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 5
210000004556 brain Anatomy 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
208000007125 Neurotoxicity Syndromes Diseases 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 2
230000036506 anxiety Effects 0.000 claims description 2
230000037396 body weight Effects 0.000 claims description 2
238000007912 intraperitoneal administration Methods 0.000 claims description 2
125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
206010015037 epilepsy Diseases 0.000 claims 1
238000001990 intravenous administration Methods 0.000 claims 1
230000003902 lesion Effects 0.000 claims 1
210000000278 spinal cord Anatomy 0.000 claims 1
230000001629 suppression Effects 0.000 claims 1
230000000472 traumatic effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 50
239000000126 substance Substances 0.000 abstract description 9
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract description 5
229930195712 glutamate Natural products 0.000 abstract description 4
230000004770 neurodegeneration Effects 0.000 abstract description 3
230000003042 antagnostic effect Effects 0.000 abstract description 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
150000003254 radicals Chemical class 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
239000012528 membrane Substances 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 11
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
230000027455 binding Effects 0.000 description 9
239000004471 Glycine Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000005119 centrifugation Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 7
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000012148 binding buffer Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000007853 buffer solution Substances 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
238000011534 incubation Methods 0.000 description 5
239000003446 ligand Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
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 4
JSFLFNPZGIDUBV-UHFFFAOYSA-N 3-(2-amino-3-hydroxy-5-methyl-3h-1,2-oxazol-4-yl)propanoic acid Chemical compound CC1=C(CCC(O)=O)C(O)N(N)O1 JSFLFNPZGIDUBV-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000000872 buffer Substances 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 4
150000005181 nitrobenzenes Chemical class 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
125000000168 pyrrolyl group Chemical group 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229940122459 Glutamate antagonist Drugs 0.000 description 3
102000000079 Kainic Acid Receptors Human genes 0.000 description 3
108010069902 Kainic Acid Receptors Proteins 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000556 agonist Substances 0.000 description 3
239000003194 amino acid receptor blocking agent Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000003257 excitatory amino acid Substances 0.000 description 3
230000002461 excitatory amino acid Effects 0.000 description 3
239000012467 final product Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002460 imidazoles Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000008188 pellet Substances 0.000 description 3
238000000159 protein binding assay Methods 0.000 description 3
UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 2
OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
102000003678 AMPA Receptors Human genes 0.000 description 2
108090000078 AMPA Receptors Proteins 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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HZMKSGSOBKQGJX-UHFFFAOYSA-N Ethyl 2-quinoxalinecarboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CN=C21 HZMKSGSOBKQGJX-UHFFFAOYSA-N 0.000 description 2
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
229920002873 Polyethylenimine Polymers 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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125000003277 amino group Chemical group 0.000 description 2
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239000002585 base Substances 0.000 description 2
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
230000009610 hypersensitivity Effects 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
229910052751 metal Chemical class 0.000 description 2
239000002184 metal Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
239000002674 ointment Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
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150000003233 pyrroles Chemical class 0.000 description 2
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238000006268 reductive amination reaction Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000000611 regression analysis Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000003345 scintillation counting Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003536 tetrazoles Chemical class 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
VLVNHMVSVDVAOA-UHFFFAOYSA-N 1,5-dichloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C=C1Cl VLVNHMVSVDVAOA-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
RKNOKOSHCJDSLE-UHFFFAOYSA-N 1-ethyl-8-imidazol-1-yl-4-oxo-7-(trifluoromethyl)-5h-imidazo[1,2-a]quinoxaline-2-carboxylic acid Chemical compound CCC1=C(C(O)=O)N=C(C(NC2=CC=3C(F)(F)F)=O)N1C2=CC=3N1C=CN=C1 RKNOKOSHCJDSLE-UHFFFAOYSA-N 0.000 description 1
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CHNYVNOFAWYUEG-UHFFFAOYSA-N 1h-pyrrole-3-carbaldehyde Chemical compound O=CC=1C=CNC=1 CHNYVNOFAWYUEG-UHFFFAOYSA-N 0.000 description 1
LYWNQLCSOFZLOR-UHFFFAOYSA-N 2,4-difluoro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=C(F)C=C1F LYWNQLCSOFZLOR-UHFFFAOYSA-N 0.000 description 1
KXZIBRUIJDEWKY-UHFFFAOYSA-N 2,5-dimethoxyfuran Chemical class COC1=CC=C(OC)O1 KXZIBRUIJDEWKY-UHFFFAOYSA-N 0.000 description 1
QMIGEDXMDGEZSR-UHFFFAOYSA-N 2,5-dimethoxyoxolane-3-carbaldehyde Chemical compound COC1CC(C=O)C(OC)O1 QMIGEDXMDGEZSR-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
OBWDPLOCTVOTMA-UHFFFAOYSA-N 2-fluoro-1-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(C(F)(F)F)C=C1F OBWDPLOCTVOTMA-UHFFFAOYSA-N 0.000 description 1
AKHSNASBDCNKAG-UHFFFAOYSA-N 2-fluoro-4-imidazol-1-yl-5-nitroaniline Chemical compound C1=C(F)C(N)=CC([N+]([O-])=O)=C1N1C=NC=C1 AKHSNASBDCNKAG-UHFFFAOYSA-N 0.000 description 1
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PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical class O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
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ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
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SVNCLIKYORSMFB-UHFFFAOYSA-N ethyl 1-methyl-4-oxo-8-(1,2,4-triazol-1-yl)-7-(trifluoromethyl)-5h-imidazo[1,2-a]quinoxaline-2-carboxylate Chemical compound CC1=C(C(=O)OCC)N=C(C(NC2=CC=3C(F)(F)F)=O)N1C2=CC=3N1C=NC=N1 SVNCLIKYORSMFB-UHFFFAOYSA-N 0.000 description 1
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239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
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239000003495 polar organic solvent Substances 0.000 description 1
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229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
RIDYGARTUIQVAD-UHFFFAOYSA-N potassium sulfuric acid nitrate Chemical compound [K+].[O-][N+]([O-])=O.OS(O)(=O)=O RIDYGARTUIQVAD-UHFFFAOYSA-N 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
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BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
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238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SI9520108A 1994-09-30 1995-09-19 New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use SI9520108A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4434941		1994-09-30
DE19503825A DE19503825A1 (de)	1994-09-30	1995-02-06	Neue heterocyclische substituierte Imidazolo-chinoxalinone, ihre Herstellung und Verwendung
PCT/EP1995/003686 WO1996010572A1 (de)	1994-09-30	1995-09-19	Neue heterocyclische substituierte imidazolo-chinoxalinone, ihre herstellung und verwendung

Publications (1)

Publication Number	Publication Date
SI9520108A true SI9520108A (en)	1997-10-31

Family

ID=25940620

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9520108A SI9520108A (en)	1994-09-30	1995-09-19	New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use

Country Status (16)

Country	Link
US (1)	US6121265A (pt)
EP (1)	EP0783506A1 (pt)
JP (1)	JPH10513435A (pt)
CN (1)	CN1046518C (pt)
AU (1)	AU3650695A (pt)
BG (1)	BG101328A (pt)
BR (1)	BR9509055A (pt)
CA (1)	CA2200358A1 (pt)
CZ (1)	CZ94297A3 (pt)
FI (1)	FI971317A7 (pt)
HU (1)	HUT73969A (pt)
IL (1)	IL115444A0 (pt)
NO (1)	NO971424L (pt)
PL (1)	PL319406A1 (pt)
SI (1)	SI9520108A (pt)
WO (1)	WO1996010572A1 (pt)

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* Cited by examiner, † Cited by third party
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DE19611476A1 (de) *	1996-03-22	1997-09-25	Basf Ag	Neue heterocyclische substituierte Imidazolo-chinoxalinone, ihre Herstellung und Verwendung
US6555564B1 (en) *	1999-03-04	2003-04-29	The Board Of Trustees Of The University Of Illinois	Neuropharmacological treatments of sleep-related breathing disorders
US7542773B2 (en) *	2002-03-29	2009-06-02	At&T Intellectual Property I, L.P.	Customized alerts for incoming data messages
CN100386326C (zh) *	2003-10-22	2008-05-07	中国人民解放军军事医学科学院毒物药物研究所	1-羟甲基咪唑并[1，2-a]喹喔啉化合物及其应用
EP1978966A4 (en) *	2006-01-23	2010-11-10	Amira Pharmaceuticals Inc	TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE
EP2666775A1 (en) *	2012-05-21	2013-11-27	Domain Therapeutics	Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors
FR3031105B1 (fr) *	2014-12-31	2018-04-06	Universite De Montpellier	Nouveaux imidazo[1,2-a]quinoxalines et derives pour le traitement des cancers

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FR2448541A1 (fr) *	1979-02-09	1980-09-05	Roussel Uclaf	Nouveaux derives de l'oxoimidazoquinoxaline et leurs sels, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
SE441449B (sv) *	1979-02-09	1985-10-07	Roussel Uclaf	Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat
SE462338B (sv) *	1982-04-28	1990-06-11	Roussel Uclaf	Nya imidazo /1,2-a/ kinoxaliner och deras salter, foerfarande foer framstaellning daerav samt farmaceutiska kompositioner innehaallande densamma
IE66149B1 (en) *	1986-09-16	1995-12-13	Novo Nordisk As	Quinoxaline compounds and their preparation and use
DK716188D0 (da) *	1988-12-22	1988-12-22	Ferrosan As	Quinoxalinforbindelser, deres fremstilling og anvendelse
US5055465A (en) *	1989-05-31	1991-10-08	Berlex Laboratories, Inc.	Imidazoquinoxalinones, their aza analogs and process for their preparation
US5196421A (en) *	1991-06-05	1993-03-23	Eli Lilly And Company	Excitatory amino acid receptor antagonists in methods for the use thereof
US5153196A (en) *	1991-06-05	1992-10-06	Eli Lilly And Company	Excitatory amino acid receptor antagonists and methods for the use thereof
US5182386A (en) *	1991-08-27	1993-01-26	Neurogen Corporation	Certain imidazoquinoxalinones; a new class of gaba brain receptor ligands
WO1993020077A1 (fr) *	1992-04-03	1993-10-14	Yamanouchi Pharmaceutical Co., Ltd.	Derive de quinoxalinone fondue et composition pharmaceutique le contenant
US5306819A (en) *	1992-08-27	1994-04-26	Neurogen Corporation	Certain aryl a cycloalkyl fused imidazopyrazinols; and new class of GABA brain receptor ligands
DE4310523A1 (de) *	1993-03-31	1994-10-06	Basf Ag	Imidazolo-chinoxalinone zur Behandlung zentralnervöser Erkrankungen
EP0743945B1 (en) *	1994-02-11	2002-03-06	Novo Nordisk A/S	Heterocyclic compounds and their preparation and use
US5536718A (en) *	1995-01-17	1996-07-16	American Cyanamid Company	Tricyclic benzazepine vasopressin antagonists

1995
- 1995-09-19 PL PL95319406A patent/PL319406A1/xx unknown
- 1995-09-19 AU AU36506/95A patent/AU3650695A/en not_active Abandoned
- 1995-09-19 US US08/809,170 patent/US6121265A/en not_active Expired - Fee Related
- 1995-09-19 JP JP8511334A patent/JPH10513435A/ja active Pending
- 1995-09-19 WO PCT/EP1995/003686 patent/WO1996010572A1/de not_active Ceased
- 1995-09-19 SI SI9520108A patent/SI9520108A/sl unknown
- 1995-09-19 CZ CZ97942A patent/CZ94297A3/cs unknown
- 1995-09-19 EP EP95934074A patent/EP0783506A1/de not_active Withdrawn
- 1995-09-19 CA CA002200358A patent/CA2200358A1/en not_active Abandoned
- 1995-09-19 CN CN95195396A patent/CN1046518C/zh not_active Expired - Fee Related
- 1995-09-19 BR BR9509055A patent/BR9509055A/pt not_active Application Discontinuation
- 1995-09-28 IL IL11544495A patent/IL115444A0/xx unknown
- 1995-09-29 HU HU9502847A patent/HUT73969A/hu unknown
1997
- 1997-03-14 BG BG101328A patent/BG101328A/xx unknown
- 1997-03-25 NO NO971424A patent/NO971424L/no unknown
- 1997-03-27 FI FI971317A patent/FI971317A7/fi unknown

Also Published As

Publication number	Publication date
AU3650695A (en)	1996-04-26
PL319406A1 (en)	1997-08-04
JPH10513435A (ja)	1998-12-22
US6121265A (en)	2000-09-19
WO1996010572A1 (de)	1996-04-11
CN1046518C (zh)	1999-11-17
CA2200358A1 (en)	1996-04-11
NO971424L (no)	1997-05-22
BG101328A (en)	1997-08-29
BR9509055A (pt)	1998-06-23
CN1159807A (zh)	1997-09-17
CZ94297A3 (en)	1997-08-13
FI971317A0 (fi)	1997-03-27
IL115444A0 (en)	1995-12-31
HU9502847D0 (en)	1995-11-28
HUT73969A (en)	1996-10-28
NO971424D0 (no)	1997-03-25
EP0783506A1 (de)	1997-07-16
FI971317A7 (fi)	1997-03-27

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EP0572852B1 (de)	1998-10-21	Chinoxalin-2,3(1H,4H)-dione als Arzneimittel
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SI9520108A (en)	1997-10-31	New heterocyclic substituted imidazoloquinoxalinones, their preparation and their use
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EP0691970B1 (de)	1998-11-11	Imidazolochinoxalinonderivate als eaa antagonisten
US3707539A (en)	1972-12-26	5-phenyl-7-trifluoromethyl-1h-1,5-benzodiazepine-2,4-diones
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WO1995021842A1 (en)	1995-08-17	Heterocyclic compounds and their preparation and use
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SI9520076A (en)	1997-08-31	Novel amido quinoxaline diones, their production and use
US5631261A (en)	1997-05-20	Triazoloquinazolines, their preparation and use
DE4329970A1 (de)	1994-10-06	Neue Imidazolo-chinoxalinone, ihre Hestellung und Verwendung
DE19503825A1 (de)	1996-04-04	Neue heterocyclische substituierte Imidazolo-chinoxalinone, ihre Herstellung und Verwendung
DE19611476A1 (de)	1997-09-25	Neue heterocyclische substituierte Imidazolo-chinoxalinone, ihre Herstellung und Verwendung
DE4201554A1 (de)	1993-07-29	Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
JPWO1993020077A1 (ja)	1994-04-07	縮合キノキサリノン誘導体及びその医薬組成物