AP767A - Quinoxalinediones - Google Patents
Quinoxalinediones Download PDFInfo
- Publication number
- AP767A AP767A APAP/P/1997/000947A AP9700947A AP767A AP 767 A AP767 A AP 767A AP 9700947 A AP9700947 A AP 9700947A AP 767 A AP767 A AP 767A
- Authority
- AP
- ARIPO
- Prior art keywords
- triazol
- aryl
- methyl
- alkyl
- alkoxy
- Prior art date
Links
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 27
- 125000003118 aryl group Chemical group 0.000 abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 125000005843 halogen group Chemical group 0.000 abstract description 17
- 150000003839 salts Chemical class 0.000 abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 5
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 abstract description 2
- 208000012902 Nervous system disease Diseases 0.000 abstract description 2
- 208000025966 Neurological disease Diseases 0.000 abstract description 2
- 230000001154 acute effect Effects 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000001684 chronic effect Effects 0.000 abstract description 2
- 230000000626 neurodegenerative effect Effects 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- -1 pyrrol-1-yl-substituted 2,3(1 H,4H)-quinoxalinedione Chemical class 0.000 description 142
- 125000001309 chloro group Chemical group Cl* 0.000 description 25
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 5
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000002098 pyridazinyl group Chemical group 0.000 description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229960002989 glutamic acid Drugs 0.000 description 4
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 125000001425 triazolyl group Chemical group 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 235000013922 glutamic acid Nutrition 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 description 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 2
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 2
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 2
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical class C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 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 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- 102000003678 AMPA Receptors Human genes 0.000 description 2
- 108090000078 AMPA Receptors Proteins 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- 229940127337 Glycine Antagonists Drugs 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 208000016621 Hearing disease Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 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 1
- VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000007125 Neurotoxicity Syndromes Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 201000007737 Retinal degeneration Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 208000029650 alcohol withdrawal Diseases 0.000 description 1
- 229940124326 anaesthetic agent Drugs 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000002461 excitatory amino acid Effects 0.000 description 1
- 239000003257 excitatory amino acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 102000006239 metabotropic receptors Human genes 0.000 description 1
- 108020004083 metabotropic receptors Proteins 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9605027.3A GB9605027D0 (en) | 1996-03-09 | 1996-03-09 | Quinoxalinediones |
| PCT/EP1997/000995 WO1997032873A1 (en) | 1996-03-09 | 1997-02-27 | Quinoxalinediones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9700947A0 AP9700947A0 (en) | 1997-04-30 |
| AP767A true AP767A (en) | 1999-09-29 |
Family
ID=10790134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/000947A AP767A (en) | 1996-03-09 | 1997-03-06 | Quinoxalinediones |
Country Status (42)
| Country | Link |
|---|---|
| US (1) | US6376490B1 (no) |
| EP (1) | EP0885212B1 (no) |
| JP (1) | JP3110467B2 (no) |
| KR (1) | KR100288099B1 (no) |
| CN (1) | CN1103770C (no) |
| AP (1) | AP767A (no) |
| AR (1) | AR006119A1 (no) |
| AT (1) | ATE208773T1 (no) |
| AU (1) | AU717972B2 (no) |
| BG (1) | BG63340B1 (no) |
| BR (1) | BR9707851A (no) |
| CA (1) | CA2248366C (no) |
| CO (1) | CO4770976A1 (no) |
| CZ (1) | CZ292792B6 (no) |
| DE (1) | DE69708269T2 (no) |
| DK (1) | DK0885212T3 (no) |
| DZ (1) | DZ2188A1 (no) |
| EA (1) | EA001730B1 (no) |
| ES (1) | ES2163742T3 (no) |
| GB (1) | GB9605027D0 (no) |
| HN (1) | HN1998000034A (no) |
| HR (1) | HRP970132A2 (no) |
| HU (1) | HUP9900975A3 (no) |
| ID (1) | ID18112A (no) |
| IL (1) | IL125491A (no) |
| IS (1) | IS4811A (no) |
| MA (1) | MA26422A1 (no) |
| NO (1) | NO984058L (no) |
| NZ (1) | NZ331060A (no) |
| OA (1) | OA10850A (no) |
| PE (2) | PE43398A1 (no) |
| PL (1) | PL329032A1 (no) |
| PT (1) | PT885212E (no) |
| SI (1) | SI0885212T1 (no) |
| SK (1) | SK283467B6 (no) |
| TN (1) | TNSN97044A1 (no) |
| TR (1) | TR199801782T2 (no) |
| TW (1) | TW454004B (no) |
| UY (1) | UY24482A1 (no) |
| WO (1) | WO1997032873A1 (no) |
| YU (2) | YU39698A (no) |
| ZA (1) | ZA971987B (no) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR199902055T2 (xx) * | 1997-02-27 | 2000-07-21 | Pfizer Inc. | Kinoksalindiyonlar. |
| AP982A (en) * | 1997-02-27 | 2001-07-16 | Pfizer | Quinoxalinediones. |
| US6340758B1 (en) * | 1997-05-16 | 2002-01-22 | Warner-Lambert Company | Conformationally semi-constrained quinoxaline 2,3-diones as neuroprotective agents |
| DE10005150A1 (de) * | 2000-02-07 | 2001-08-09 | Merck Patent Gmbh | Verfahren zur Herstellung von 5-Arylnicotinaldehyden |
| BR0110961A (pt) * | 2000-05-19 | 2004-06-29 | Merck Patent Gmbh | Derivados de triazol |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
| WO2005006945A2 (en) * | 2003-07-03 | 2005-01-27 | The Salk Institute For Biological Studies | Methods for treating neural disorders and compounds useful therefor |
| MY145368A (en) * | 2004-01-13 | 2012-01-31 | Nissan Chemical Ind Ltd | Aminoquinoxaline compounds and polyaminoquinoxaline compounds, and use thereof |
| JP4827173B2 (ja) | 2004-02-06 | 2011-11-30 | 国立大学法人山口大学 | 電気二重層キャパシタ用電極及びその製造方法 |
| JP2007223901A (ja) * | 2004-03-24 | 2007-09-06 | Takeda Chem Ind Ltd | 複素環化合物およびその用途 |
| US20060211739A1 (en) * | 2005-02-08 | 2006-09-21 | Arturo Perez-Medrano | Use of selective P2X7 receptor antagonists |
| WO2007112347A1 (en) * | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| JP5379692B2 (ja) | 2006-11-09 | 2013-12-25 | プロビオドルグ エージー | 潰瘍、癌及び他の疾患の治療のためのグルタミニルシクラーゼの阻害薬としての３−ヒドロキシ−１，５−ジヒドロ−ピロール−２−オン誘導体 |
| US9126987B2 (en) | 2006-11-30 | 2015-09-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US8603980B2 (en) | 2007-01-16 | 2013-12-10 | The Johns Hopkins University | Glutamate receptor antagonists and methods of use |
| JP5930573B2 (ja) | 2007-03-01 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤の新規使用 |
| DK2142514T3 (da) | 2007-04-18 | 2015-03-23 | Probiodrug Ag | Thioureaderivater som glutaminylcyclase-inhibitorer |
| WO2008143019A1 (en) | 2007-05-17 | 2008-11-27 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, and light-emitting element, light-emitting device, and electronic device with the use of triazole derivative |
| EA022007B1 (ru) | 2009-09-11 | 2015-10-30 | Пробиодруг Аг | Гетероциклические производные в качестве ингибиторов глутаминилциклазы |
| EP2542549B1 (en) | 2010-03-03 | 2016-05-11 | Probiodrug AG | Inhibitors of glutaminyl cyclase |
| EA022420B1 (ru) | 2010-03-10 | 2015-12-30 | Пробиодруг Аг | Гетероциклические ингибиторы глутаминилциклазы (qc, ec 2.3.2.5) |
| JP5945532B2 (ja) | 2010-04-21 | 2016-07-05 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤としてのベンゾイミダゾール誘導体 |
| US8530670B2 (en) | 2011-03-16 | 2013-09-10 | Probiodrug Ag | Inhibitors |
| EP2953933A1 (en) * | 2013-02-07 | 2015-12-16 | Merck Patent GmbH | Substituted acetylene derivatives and their use as positive allosteric modulators of mglur4 |
| ES2812698T3 (es) | 2017-09-29 | 2021-03-18 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
| CN111548320B (zh) * | 2019-10-09 | 2023-03-24 | 贵州大学 | 一类1，3，4-噁二唑酰肼类化合物及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2095444C (en) * | 1990-11-06 | 2001-06-19 | Shuichi Sakamoto | Fused pyrazine derivatives |
| DE4217952A1 (de) * | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
| GB9418443D0 (en) | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
| DE4439492A1 (de) * | 1994-10-25 | 1996-05-02 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| TR199902055T2 (xx) * | 1997-02-27 | 2000-07-21 | Pfizer Inc. | Kinoksalindiyonlar. |
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1996
- 1996-03-09 GB GBGB9605027.3A patent/GB9605027D0/en active Pending
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1997
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- 1997-02-27 AT AT97908156T patent/ATE208773T1/de not_active IP Right Cessation
- 1997-02-27 SK SK1214-98A patent/SK283467B6/sk unknown
- 1997-02-27 BR BR9707851A patent/BR9707851A/pt not_active Application Discontinuation
- 1997-02-27 IL IL12549197A patent/IL125491A/xx not_active IP Right Cessation
- 1997-02-27 DK DK97908156T patent/DK0885212T3/da active
- 1997-02-27 DE DE69708269T patent/DE69708269T2/de not_active Expired - Fee Related
- 1997-02-27 HU HU9900975A patent/HUP9900975A3/hu unknown
- 1997-02-27 CA CA002248366A patent/CA2248366C/en not_active Expired - Fee Related
- 1997-02-27 PT PT97908156T patent/PT885212E/pt unknown
- 1997-02-27 EA EA199800702A patent/EA001730B1/ru not_active IP Right Cessation
- 1997-02-27 SI SI9730225T patent/SI0885212T1/xx unknown
- 1997-02-27 NZ NZ331060A patent/NZ331060A/xx unknown
- 1997-02-27 KR KR1019980707063A patent/KR100288099B1/ko not_active IP Right Cessation
- 1997-02-27 PL PL97329032A patent/PL329032A1/xx unknown
- 1997-02-27 ES ES97908156T patent/ES2163742T3/es not_active Expired - Lifetime
- 1997-02-27 CZ CZ19982864A patent/CZ292792B6/cs not_active IP Right Cessation
- 1997-02-27 EP EP97908156A patent/EP0885212B1/en not_active Expired - Lifetime
- 1997-02-27 JP JP09531429A patent/JP3110467B2/ja not_active Expired - Fee Related
- 1997-02-27 YU YU39698A patent/YU39698A/sh unknown
- 1997-02-27 TR TR1998/01782T patent/TR199801782T2/xx unknown
- 1997-02-27 WO PCT/EP1997/000995 patent/WO1997032873A1/en active IP Right Grant
- 1997-02-27 CN CN97192923A patent/CN1103770C/zh not_active Expired - Fee Related
- 1997-02-27 AU AU20231/97A patent/AU717972B2/en not_active Ceased
- 1997-03-05 TN TNTNSN97044A patent/TNSN97044A1/fr unknown
- 1997-03-05 DZ DZ970034A patent/DZ2188A1/fr active
- 1997-03-05 MA MA24514A patent/MA26422A1/fr unknown
- 1997-03-05 AR ARP970100888A patent/AR006119A1/es unknown
- 1997-03-06 AP APAP/P/1997/000947A patent/AP767A/en active
- 1997-03-06 UY UY24482A patent/UY24482A1/es not_active IP Right Cessation
- 1997-03-06 PE PE1997000162A patent/PE43398A1/es not_active Application Discontinuation
- 1997-03-07 ZA ZA971987A patent/ZA971987B/xx unknown
- 1997-03-07 ID IDP970725A patent/ID18112A/id unknown
- 1997-03-07 HR HR9605027.3A patent/HRP970132A2/xx not_active Application Discontinuation
- 1997-03-10 CO CO97012901A patent/CO4770976A1/es unknown
-
1998
- 1998-02-19 HN HN1998000034A patent/HN1998000034A/es unknown
- 1998-02-23 PE PE1998000128A patent/PE58199A1/es not_active Application Discontinuation
- 1998-02-24 YU YU41199A patent/YU41199A/sh unknown
- 1998-07-27 IS IS4811A patent/IS4811A/is unknown
- 1998-08-28 OA OA9800155A patent/OA10850A/en unknown
- 1998-09-03 NO NO984058A patent/NO984058L/no unknown
- 1998-09-04 US US09/157,806 patent/US6376490B1/en not_active Expired - Fee Related
- 1998-09-09 BG BG102760A patent/BG63340B1/bg unknown
Non-Patent Citations (1)
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| NONE * |
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