SK25298A3 - Novel 2,3-dioxo-1,2,3,4-tetrahydro-quinoyxalinyl derivatives - Google Patents
Novel 2,3-dioxo-1,2,3,4-tetrahydro-quinoyxalinyl derivatives Download PDFInfo
- Publication number
- SK25298A3 SK25298A3 SK252-98A SK25298A SK25298A3 SK 25298 A3 SK25298 A3 SK 25298A3 SK 25298 A SK25298 A SK 25298A SK 25298 A3 SK25298 A3 SK 25298A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- dioxo
- ylmethyl
- nitro
- tetrahydroquinoxalin
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 652
- -1 2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalinyl Chemical class 0.000 claims abstract description 602
- 125000002252 acyl group Chemical group 0.000 claims abstract description 132
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 125
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 117
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 112
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 111
- 150000003839 salts Chemical class 0.000 claims abstract description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 79
- 239000001257 hydrogen Substances 0.000 claims abstract description 75
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 71
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 67
- 150000002367 halogens Chemical class 0.000 claims abstract description 64
- 239000002253 acid Substances 0.000 claims abstract description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 54
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 23
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000004122 cyclic group Chemical class 0.000 claims abstract description 21
- 230000027455 binding Effects 0.000 claims abstract description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001450 anions Chemical class 0.000 claims abstract description 14
- 239000004471 Glycine Substances 0.000 claims abstract description 12
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims abstract description 11
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims abstract description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 8
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 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 claims abstract description 7
- 230000000903 blocking effect Effects 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 150000003008 phosphonic acid esters Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 459
- 125000003545 alkoxy group Chemical group 0.000 claims description 279
- 150000001875 compounds Chemical class 0.000 claims description 188
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 121
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
- 125000001118 alkylidene group Chemical group 0.000 claims description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 96
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 91
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 86
- 125000005843 halogen group Chemical group 0.000 claims description 78
- 150000003254 radicals Chemical class 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 65
- 125000003277 amino group Chemical group 0.000 claims description 56
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 125000003386 piperidinyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 36
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 35
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 27
- 125000004450 alkenylene group Chemical group 0.000 claims description 27
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 26
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 26
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
- 125000002541 furyl group Chemical group 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 15
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical group OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 13
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- WIQNHLFZBWOETQ-UHFFFAOYSA-N 5-(bromomethyl)-2,3-dimethoxy-7-nitroquinoxaline Chemical compound [O-][N+](=O)C1=CC(CBr)=C2N=C(OC)C(OC)=NC2=C1 WIQNHLFZBWOETQ-UHFFFAOYSA-N 0.000 claims description 11
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 11
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000001041 indolyl group Chemical group 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 11
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical group C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 9
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 9
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000002785 azepinyl group Chemical group 0.000 claims description 8
- 125000005605 benzo group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000005352 carboxycycloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 7
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- 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 7
- ULFNAOHBWGRYLW-UHFFFAOYSA-N 1-cyclononylazonane Chemical group C1CCCCCCCC1N1CCCCCCCC1 ULFNAOHBWGRYLW-UHFFFAOYSA-N 0.000 claims description 6
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical group ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
- 125000006294 amino alkylene group Chemical group 0.000 claims description 6
- 125000005124 aminocycloalkyl group Chemical group 0.000 claims description 6
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 6
- NPYSGAQZDKLFNW-UHFFFAOYSA-N (2,3-dimethoxy-7-nitroquinoxalin-5-yl)methanamine Chemical compound [O-][N+](=O)C1=CC(CN)=C2N=C(OC)C(OC)=NC2=C1 NPYSGAQZDKLFNW-UHFFFAOYSA-N 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
- UICIJOHWFFTRLI-UHFFFAOYSA-N n-phenylpiperidine-1-carboxamide Chemical group C1CCCCN1C(=O)NC1=CC=CC=C1 UICIJOHWFFTRLI-UHFFFAOYSA-N 0.000 claims description 5
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical class C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 claims description 4
- NKOGCJIYHZVBDR-UHFFFAOYSA-N 1-phenylpiperidin-2-one Chemical group O=C1CCCCN1C1=CC=CC=C1 NKOGCJIYHZVBDR-UHFFFAOYSA-N 0.000 claims description 4
- XGUOQIARSDZLAZ-UHFFFAOYSA-N 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methoxy]acetic acid Chemical compound OC1=C(O)N=C2C(COCC(=O)O)=CC(Br)=CC2=N1 XGUOQIARSDZLAZ-UHFFFAOYSA-N 0.000 claims description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- SEWARTPIJFHCRP-UHFFFAOYSA-N N-hydroxypipecolic acid Chemical group ON1CCCCC1C(O)=O SEWARTPIJFHCRP-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 4
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 4
- QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical group O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 claims description 4
- DQAKJEWZWDQURW-UHFFFAOYSA-N pyrrolidonecarboxylic acid Chemical compound OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical group ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 claims description 3
- KSALZGBIPLGHSV-UHFFFAOYSA-N 1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1=CC(Br)=CC2=C1NC(=O)C(=O)N2 KSALZGBIPLGHSV-UHFFFAOYSA-N 0.000 claims description 3
- YXTROGRGRSPWKL-UHFFFAOYSA-N 1-benzoylpiperidine Chemical group C=1C=CC=CC=1C(=O)N1CCCCC1 YXTROGRGRSPWKL-UHFFFAOYSA-N 0.000 claims description 3
- LUNCTSDANKHFSS-UHFFFAOYSA-N 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylsulfanyl]acetic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CSCC(=O)O LUNCTSDANKHFSS-UHFFFAOYSA-N 0.000 claims description 3
- IOTAZFKOEYHBTR-UHFFFAOYSA-N 4-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-4-oxobut-2-enoic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)C=CC(=O)O IOTAZFKOEYHBTR-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- UTZKZNGQZSXEMU-UHFFFAOYSA-N carboxymethylazanium;bromide Chemical compound Br.NCC(O)=O UTZKZNGQZSXEMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 3
- QOSNBBDHQFUXEP-UHFFFAOYSA-N ethyl 4-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-4-oxobut-2-enoate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)C=CC(=O)OCC QOSNBBDHQFUXEP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical group [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- ZPZMPJXQGUTTFQ-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-2-thiophen-3-ylacetamide Chemical compound C=12N=C(O)C(O)=NC2=CC(Br)=CC=1CNC(=O)CC=1C=CSC=1 ZPZMPJXQGUTTFQ-UHFFFAOYSA-N 0.000 claims description 3
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical group ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical group O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical compound O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- DLZOLLNNKYSSHM-UHFFFAOYSA-N 1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-n-phenylpiperidine-2-carboxamide Chemical compound C=12NC(=O)C(=O)NC2=CC(Br)=CC=1CN1CCCCC1C(=O)NC1=CC=CC=C1 DLZOLLNNKYSSHM-UHFFFAOYSA-N 0.000 claims description 2
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- CUDSZNYENLEESG-UHFFFAOYSA-N 1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1CC1=CC(Br)=CC2=C1NC(=O)C(=O)N2 CUDSZNYENLEESG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- GWHMOMLPZOCSRX-UHFFFAOYSA-N 2,2-diamino-3-hydroxy-N-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]propanamide Chemical compound NC(N)(CO)C(=O)NCC1=C2NC(C(NC2=CC(=C1)[N+](=O)[O-])=O)=O GWHMOMLPZOCSRX-UHFFFAOYSA-N 0.000 claims description 2
- SRELFGFNBLSMOA-UHFFFAOYSA-N 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methoxy]-n-phenylacetamide Chemical compound C=12NC(=O)C(=O)NC2=CC(Br)=CC=1COCC(=O)NC1=CC=CC=C1 SRELFGFNBLSMOA-UHFFFAOYSA-N 0.000 claims description 2
- VPXGMWADLVSTFS-UHFFFAOYSA-N 2-hydroxy-n-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]benzamide Chemical compound OC1=CC=CC=C1C(=O)NCC1=CC([N+]([O-])=O)=CC2=NC(O)=C(O)N=C12 VPXGMWADLVSTFS-UHFFFAOYSA-N 0.000 claims description 2
- BRTOBRXUIDUFCF-UHFFFAOYSA-N 2-methoxy-n-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]acetamide Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)COC BRTOBRXUIDUFCF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- ATVMBTCWAFQXKC-UHFFFAOYSA-N 3,3-dimethyl-n-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]butanamide Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)CC(C)(C)C ATVMBTCWAFQXKC-UHFFFAOYSA-N 0.000 claims description 2
- NUAVKAPDVFGXTQ-UHFFFAOYSA-N 3,4,5-trimethoxy-n-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=3NC(=O)C(=O)NC=3C=C(C=2)[N+]([O-])=O)=C1 NUAVKAPDVFGXTQ-UHFFFAOYSA-N 0.000 claims description 2
- KKYCYMMMVWQQMI-UHFFFAOYSA-N 4-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-4-oxobutanoic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)CCC(=O)O KKYCYMMMVWQQMI-UHFFFAOYSA-N 0.000 claims description 2
- GCFBEWCSVASKNU-UHFFFAOYSA-N 4-hydroxy-3,5-dimethoxy-n-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]benzamide Chemical compound COC1=C(O)C(OC)=CC(C(=O)NCC=2C=3NC(=O)C(=O)NC=3C=C(C=2)[N+]([O-])=O)=C1 GCFBEWCSVASKNU-UHFFFAOYSA-N 0.000 claims description 2
- JYVFVXGWMACTAY-UHFFFAOYSA-N 7-nitro-5-(piperazin-1-ylmethyl)-1,4-dihydroquinoxaline-2,3-dione;dihydrobromide Chemical compound Br.Br.C=12NC(=O)C(=O)NC2=CC([N+](=O)[O-])=CC=1CN1CCNCC1 JYVFVXGWMACTAY-UHFFFAOYSA-N 0.000 claims description 2
- VLOJPMOYHVYDAX-UHFFFAOYSA-N [3-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylcarbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(C(=O)NCC=2C=3NC(=O)C(=O)NC=3C=C(C=2)[N+]([O-])=O)=C1 VLOJPMOYHVYDAX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000320 amidine group Chemical group 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- MPVDGANTIKPFNK-UHFFFAOYSA-N ethyl 1-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-6-yl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(C(=C1)[N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 MPVDGANTIKPFNK-UHFFFAOYSA-N 0.000 claims description 2
- JWGWORCNBSCZSW-UHFFFAOYSA-N ethyl 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methoxy]acetate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2COCC(=O)OCC JWGWORCNBSCZSW-UHFFFAOYSA-N 0.000 claims description 2
- PGGVHJIVPUYORO-UHFFFAOYSA-N ethyl 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-2-oxoacetate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)C(=O)OCC PGGVHJIVPUYORO-UHFFFAOYSA-N 0.000 claims description 2
- OVSIGOBKQOKMOI-UHFFFAOYSA-N ethyl 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylsulfanyl]acetate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CSCC(=O)OCC OVSIGOBKQOKMOI-UHFFFAOYSA-N 0.000 claims description 2
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims description 2
- MVNWQJWZFTYXOO-UHFFFAOYSA-N methyl 2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-2-oxoacetate Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(=O)C(=O)OC MVNWQJWZFTYXOO-UHFFFAOYSA-N 0.000 claims description 2
- ZSDZBAIQNCPIQX-UHFFFAOYSA-N methyl 3-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-3-oxopropanoate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)CC(=O)OC ZSDZBAIQNCPIQX-UHFFFAOYSA-N 0.000 claims description 2
- QOAFGTQFFLOFGM-UHFFFAOYSA-N methyl 5-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-5-oxopentanoate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)CCCC(=O)OC QOAFGTQFFLOFGM-UHFFFAOYSA-N 0.000 claims description 2
- RMOZLMCDJNUJJP-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-2,2,2-trifluoroacetamide Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)C(F)(F)F RMOZLMCDJNUJJP-UHFFFAOYSA-N 0.000 claims description 2
- OPCFSDCUKYIAHK-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NCC=2C3=NC(O)=C(O)N=C3C=C(Br)C=2)=C1 OPCFSDCUKYIAHK-UHFFFAOYSA-N 0.000 claims description 2
- WOGATXNLOVWIQG-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-2-phenylacetamide Chemical compound C=12N=C(O)C(O)=NC2=CC(Br)=CC=1CNC(=O)CC1=CC=CC=C1 WOGATXNLOVWIQG-UHFFFAOYSA-N 0.000 claims description 2
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- PCARITKDGLENBQ-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-3-phenylpropanamide Chemical compound C=12N=C(O)C(O)=NC2=CC(Br)=CC=1CNC(=O)CCC1=CC=CC=C1 PCARITKDGLENBQ-UHFFFAOYSA-N 0.000 claims description 2
- CCRLGBIOCNHFTM-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-n'-phenylbut-2-enediamide Chemical compound C=12NC(=O)C(=O)NC2=CC(Br)=CC=1CNC(=O)C=CC(=O)NC1=CC=CC=C1 CCRLGBIOCNHFTM-UHFFFAOYSA-N 0.000 claims description 2
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- IFHCAXFRPOBMJG-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]benzamide Chemical compound C=12NC(=O)C(=O)NC2=CC(Br)=CC=1CNC(=O)C1=CC=CC=C1 IFHCAXFRPOBMJG-UHFFFAOYSA-N 0.000 claims description 2
- HDTQVDKGKMQQJM-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]methanesulfonamide Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNS(=O)(=O)C HDTQVDKGKMQQJM-UHFFFAOYSA-N 0.000 claims description 2
- QAKGVBTUMLAEFY-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]thiophene-2-carboxamide Chemical compound C=12N=C(O)C(O)=NC2=CC(Br)=CC=1CNC(=O)C1=CC=CS1 QAKGVBTUMLAEFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006308 propyl amino group Chemical group 0.000 claims description 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical group OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 7
- 229960002449 glycine Drugs 0.000 claims 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- AAPBRENFFPZBFN-UHFFFAOYSA-N 2-(2,3-dimethoxy-7-nitroquinoxalin-5-yl)ethyl methanesulfonate Chemical compound [O-][N+](=O)C1=CC(CCOS(C)(=O)=O)=C2N=C(OC)C(OC)=NC2=C1 AAPBRENFFPZBFN-UHFFFAOYSA-N 0.000 claims 2
- FPNCIRXCHYQYDB-UHFFFAOYSA-N 2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methoxy]acetic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2COCC(=O)O FPNCIRXCHYQYDB-UHFFFAOYSA-N 0.000 claims 2
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- ZCYVIXJEEJFRHV-UHFFFAOYSA-N 5-[(4-aminopyridin-1-ium-1-yl)methyl]-7-nitro-1,4-dihydroquinoxaline-2,3-dione;bromide Chemical compound [Br-].C1=CC(N)=CC=[N+]1CC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 ZCYVIXJEEJFRHV-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
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- 229960003767 alanine Drugs 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- VGYGEGNFYUUKHV-UHFFFAOYSA-N dimethyl 1-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]triazole-4,5-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)N=NN1CC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 VGYGEGNFYUUKHV-UHFFFAOYSA-N 0.000 claims 2
- NXZYKAQUSVAAIV-UHFFFAOYSA-N n-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-n-methyl-2-phenylacetamide Chemical compound C=1C(Br)=CC=2NC(=O)C(=O)NC=2C=1CN(C)C(=O)CC1=CC=CC=C1 NXZYKAQUSVAAIV-UHFFFAOYSA-N 0.000 claims 2
- 125000005968 oxazolinyl group Chemical group 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical group OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
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- PVRVLLIRLHEDJB-UHFFFAOYSA-N (2,3-dimethoxy-7-nitroquinoxalin-5-yl)methanol Chemical compound [O-][N+](=O)C1=CC(CO)=C2N=C(OC)C(OC)=NC2=C1 PVRVLLIRLHEDJB-UHFFFAOYSA-N 0.000 claims 1
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- HNGZQOWTVFQEQF-JTQLQIEISA-N (2s)-1-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1CC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 HNGZQOWTVFQEQF-JTQLQIEISA-N 0.000 claims 1
- OPMXEQOTZUDBNS-QMMMGPOBSA-N (2s)-2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]pentanedioic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CN[C@@H](CCC(=O)O)C(O)=O OPMXEQOTZUDBNS-QMMMGPOBSA-N 0.000 claims 1
- FXOIXZSMYHAWRZ-AWEZNQCLSA-N (2s)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NCC=1C=2NC(=O)C(=O)NC=2C=C(C=1)[N+]([O-])=O)C1=CC=CC=C1 FXOIXZSMYHAWRZ-AWEZNQCLSA-N 0.000 claims 1
- SQQDZMZVQFRDNJ-QMMMGPOBSA-N (2s)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]pentanedioic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CN[C@@H](CCC(=O)O)C(O)=O SQQDZMZVQFRDNJ-QMMMGPOBSA-N 0.000 claims 1
- MRIFAJFUJAFNCH-AWEZNQCLSA-N (2s)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-6-yl)methylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NCC=1C(=CC=2NC(=O)C(=O)NC=2C=1)[N+]([O-])=O)C1=CC=CC=C1 MRIFAJFUJAFNCH-AWEZNQCLSA-N 0.000 claims 1
- KJNRHPCVCJUBRQ-HNNXBMFYSA-N (2s)-2-[[2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]acetyl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CNCC=1C=2NC(=O)C(=O)NC=2C=C(C=1)[N+]([O-])=O)C1=CC=CC=C1 KJNRHPCVCJUBRQ-HNNXBMFYSA-N 0.000 claims 1
- JVEIVYKQYMEKGN-AWEZNQCLSA-N (2s)-3-(4-hydroxyphenyl)-2-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NCC=1C=2NC(=O)C(=O)NC=2C=C(C=1)[N+]([O-])=O)C1=CC=C(O)C=C1 JVEIVYKQYMEKGN-AWEZNQCLSA-N 0.000 claims 1
- UXNNSZSFVJSWSD-UHFFFAOYSA-N (7-bromo-2,3-dimethoxy-3,4-dihydro-2h-quinoxalin-1-yl)methanamine Chemical compound C1=C(Br)C=C2N(CN)C(OC)C(OC)NC2=C1 UXNNSZSFVJSWSD-UHFFFAOYSA-N 0.000 claims 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- IGZOSUKLRRIVRV-UHFFFAOYSA-N 1-(2,3-dimethoxy-7-nitroquinoxalin-5-yl)ethanone Chemical compound [O-][N+](=O)C1=CC(C(C)=O)=C2N=C(OC)C(OC)=NC2=C1 IGZOSUKLRRIVRV-UHFFFAOYSA-N 0.000 claims 1
- GOAIZLWIPJCIDR-UHFFFAOYSA-N 1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]-n-phenylpiperidine-3-carboxamide Chemical compound C=12NC(=O)C(=O)NC2=CC(Br)=CC=1CN(C1)CCCC1C(=O)NC1=CC=CC=C1 GOAIZLWIPJCIDR-UHFFFAOYSA-N 0.000 claims 1
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- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- 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
- C07D401/02—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
- C07D401/06—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 linked by a carbon chain containing only aliphatic 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
- 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
- A61P25/28—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D401/02—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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH247995 | 1995-08-31 | ||
CH273495 | 1995-09-27 | ||
CH274795 | 1995-09-28 | ||
CH121396 | 1996-05-10 | ||
CH163096 | 1996-06-28 | ||
PCT/EP1996/003644 WO1997008155A1 (en) | 1995-08-31 | 1996-08-19 | Novel 2,3-dioxo-1,2,3,4-tetrahydro-quinoyxalinyl derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
SK25298A3 true SK25298A3 (en) | 1998-09-09 |
Family
ID=27508939
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK252-98A SK25298A3 (en) | 1995-08-31 | 1996-08-19 | Novel 2,3-dioxo-1,2,3,4-tetrahydro-quinoyxalinyl derivatives |
Country Status (26)
Country | Link |
---|---|
US (1) | US6080743A (cs) |
EP (1) | EP0853617B1 (cs) |
JP (1) | JP3159711B2 (cs) |
KR (1) | KR100462337B1 (cs) |
CN (1) | CN1137886C (cs) |
AR (1) | AR005229A1 (cs) |
AT (1) | ATE260902T1 (cs) |
AU (1) | AU705871B2 (cs) |
BR (1) | BRPI9603626B8 (cs) |
CA (1) | CA2227851C (cs) |
CZ (1) | CZ56298A3 (cs) |
DE (1) | DE69631774T2 (cs) |
DK (1) | DK0853617T3 (cs) |
ES (1) | ES2217324T3 (cs) |
HK (1) | HK1010196A1 (cs) |
HU (1) | HUP9801676A3 (cs) |
IL (1) | IL122987A (cs) |
MY (1) | MY132385A (cs) |
NO (1) | NO310236B1 (cs) |
NZ (1) | NZ316497A (cs) |
PL (1) | PL189637B1 (cs) |
PT (1) | PT853617E (cs) |
SI (1) | SI0853617T1 (cs) |
SK (1) | SK25298A3 (cs) |
TR (1) | TR199800349T2 (cs) |
WO (1) | WO1997008155A1 (cs) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1997046539A1 (en) * | 1996-06-05 | 1997-12-11 | Warner-Lambert Company | Amide derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
WO1998017672A1 (de) * | 1996-10-24 | 1998-04-30 | Novartis Ag | Substituierte aminoalkanphosphonsäuren |
WO1998023599A1 (en) * | 1996-11-25 | 1998-06-04 | Warner-Lambert Company | Urea and thiourea derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
GB9702194D0 (en) | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
US6172065B1 (en) * | 1997-03-04 | 2001-01-09 | Warner-Lambert Company | Urea and thiourea derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
US6340758B1 (en) | 1997-05-16 | 2002-01-22 | Warner-Lambert Company | Conformationally semi-constrained quinoxaline 2,3-diones as neuroprotective agents |
US6096744A (en) * | 1998-05-04 | 2000-08-01 | Warner-Lambert Company | Sulfonamide derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
US6677332B1 (en) | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
WO2001092226A1 (en) * | 2000-05-25 | 2001-12-06 | Sepracor, Inc. | Heterocyclic analgesic compounds and method of use thereof |
AU2002250256B2 (en) * | 2001-03-08 | 2008-04-03 | Emory University | pH-dependent NMDA receptor antagonists |
TW200403066A (en) * | 2002-04-30 | 2004-03-01 | Novartis Ag | New uses of substituted aminoalkanephosphonic acids |
WO2004101533A1 (en) * | 2003-05-12 | 2004-11-25 | Janssen Pharmaceutica, N.V. | 1, 3, 4-benzotriazepin-2-one salts and their use as cck receptor ligands |
GB0310868D0 (en) * | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
JP2007507514A (ja) * | 2003-09-30 | 2007-03-29 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノキサリン化合物 |
US20060020029A1 (en) * | 2004-07-02 | 2006-01-26 | Shimasaki Craig D | Pharmaceutical compositions from ethnobotanicals |
UA95788C2 (en) * | 2005-12-15 | 2011-09-12 | Ф. Хоффманн-Ля Рош Аг | Fused pyrrole derivatives |
MX2009014216A (es) * | 2007-06-29 | 2010-07-05 | Univ Emory | Antagonistas del receptor nmda para neuroproteccion. |
US20130053381A1 (en) | 2010-05-20 | 2013-02-28 | Novartis Ag | 2,4-dioxo-1,4-dihydro-2h-quinazolin-3-yl-sulfonamide derivatives |
US9737531B2 (en) | 2012-07-12 | 2017-08-22 | Glytech, Llc | Composition and method for treatment of depression and psychosis in humans |
JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
CN103435561B (zh) * | 2013-08-19 | 2016-08-10 | 上海交通大学 | 一种新型d-氨基酸氧化酶抑制剂及其制备和应用 |
EP3573960B1 (en) * | 2017-01-27 | 2023-08-16 | Genfit | N-{[2-(piperidin-1-yl)phenyl](phenyl)methyl}-2-(3-oxo-3,4-dihydro-2h-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ror-gamma modulators for treating autoimmune diseases |
CA3067162A1 (en) | 2017-06-12 | 2018-12-20 | Glytech Llc. | Treatment of depression with nmda antagonists and d2/5ht2a or selective 5ht2a antagonists |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US4156734A (en) * | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
CA2002864C (en) * | 1988-11-29 | 1999-11-16 | Eddy J. E. Freyne | (1h-azol-1-ylmethyl) substituted quinoline, quinazoline or quinoxaline derivatives |
JPH04506967A (ja) * | 1989-07-27 | 1992-12-03 | ジー.ディー.サール アンド カンパニー | 高血圧症治療用腎選択性生成物 |
US5631373A (en) * | 1993-11-05 | 1997-05-20 | 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, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
GB9418443D0 (en) * | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
GB9419318D0 (en) * | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
-
1996
- 1996-08-12 MY MYPI96003300A patent/MY132385A/en unknown
- 1996-08-19 SI SI9630678T patent/SI0853617T1/xx unknown
- 1996-08-19 US US09/029,525 patent/US6080743A/en not_active Expired - Lifetime
- 1996-08-19 HU HU9801676A patent/HUP9801676A3/hu unknown
- 1996-08-19 SK SK252-98A patent/SK25298A3/sk unknown
- 1996-08-19 CA CA002227851A patent/CA2227851C/en not_active Expired - Fee Related
- 1996-08-19 EP EP96929275A patent/EP0853617B1/en not_active Expired - Lifetime
- 1996-08-19 DK DK96929275T patent/DK0853617T3/da active
- 1996-08-19 TR TR1998/00349T patent/TR199800349T2/xx unknown
- 1996-08-19 KR KR10-1998-0701511A patent/KR100462337B1/ko not_active IP Right Cessation
- 1996-08-19 IL IL12298796A patent/IL122987A/en not_active IP Right Cessation
- 1996-08-19 NZ NZ316497A patent/NZ316497A/xx unknown
- 1996-08-19 WO PCT/EP1996/003644 patent/WO1997008155A1/en not_active Application Discontinuation
- 1996-08-19 CZ CZ98562A patent/CZ56298A3/cs unknown
- 1996-08-19 DE DE69631774T patent/DE69631774T2/de not_active Expired - Lifetime
- 1996-08-19 ES ES96929275T patent/ES2217324T3/es not_active Expired - Lifetime
- 1996-08-19 PL PL96324992A patent/PL189637B1/pl not_active IP Right Cessation
- 1996-08-19 PT PT96929275T patent/PT853617E/pt unknown
- 1996-08-19 CN CNB961965819A patent/CN1137886C/zh not_active Expired - Fee Related
- 1996-08-19 AU AU68742/96A patent/AU705871B2/en not_active Ceased
- 1996-08-19 JP JP50980197A patent/JP3159711B2/ja not_active Expired - Fee Related
- 1996-08-19 AT AT96929275T patent/ATE260902T1/de active
- 1996-08-30 AR ARP960104160A patent/AR005229A1/es active IP Right Grant
- 1996-08-30 BR BRPI9603626A patent/BRPI9603626B8/pt not_active IP Right Cessation
-
1998
- 1998-02-26 NO NO19980814A patent/NO310236B1/no unknown
- 1998-10-16 HK HK98111287A patent/HK1010196A1/xx not_active IP Right Cessation
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