KR100262371B1 - 퀴스퀄레이트 수용체에 대한 친화성이 있는 퀴녹살린 유도체 - Google Patents
퀴스퀄레이트 수용체에 대한 친화성이 있는 퀴녹살린 유도체 Download PDFInfo
- Publication number
- KR100262371B1 KR100262371B1 KR1019930701948A KR930701948A KR100262371B1 KR 100262371 B1 KR100262371 B1 KR 100262371B1 KR 1019930701948 A KR1019930701948 A KR 1019930701948A KR 930701948 A KR930701948 A KR 930701948A KR 100262371 B1 KR100262371 B1 KR 100262371B1
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- dioxo
- tetrahydroquinoxalin
- alkyl
- nitro
- Prior art date
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- 102000003678 AMPA Receptors Human genes 0.000 title description 6
- 108090000078 AMPA Receptors Proteins 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 63
- -1 6-nitro-2, 3-dioxo-1, 2, 3, 4-tetra Hydroquinoxalin-1-ylmethyl Chemical group 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- QOMQWUVIIVYNHO-UHFFFAOYSA-N (6-amino-2,3-dioxo-4h-quinoxalin-1-yl)methylphosphonic acid Chemical compound OP(=O)(O)CN1C(=O)C(=O)NC2=CC(N)=CC=C21 QOMQWUVIIVYNHO-UHFFFAOYSA-N 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- BWJLAJURYPUBJI-UHFFFAOYSA-N (6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(=O)N(CP(O)(=O)O)C2=C1 BWJLAJURYPUBJI-UHFFFAOYSA-N 0.000 claims description 4
- LLPWERCBDBEKLS-UHFFFAOYSA-N 1-[2,3-dioxo-6-(trifluoromethyl)-4h-quinoxalin-1-yl]ethylphosphonic acid Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C(=O)N(C(C)P(O)(O)=O)C2=C1 LLPWERCBDBEKLS-UHFFFAOYSA-N 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 150000002912 oxalic acid derivatives Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- TUVFMMNANXKTRP-UHFFFAOYSA-N Ethenamine, N-methylene- Chemical compound C=CN=C TUVFMMNANXKTRP-UHFFFAOYSA-N 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- VTYNPKUTIPZLEI-UHFFFAOYSA-N 4-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)butylphosphonic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(=O)N(CCCCP(O)(=O)O)C2=C1 VTYNPKUTIPZLEI-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- FIZJZOZMVQFGPM-UHFFFAOYSA-N [2,3-dioxo-6-(trifluoromethyl)-4h-quinoxalin-1-yl]methylphosphonic acid Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C(=O)N(CP(O)(=O)O)C2=C1 FIZJZOZMVQFGPM-UHFFFAOYSA-N 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 claims description 2
- 229960000911 benserazide Drugs 0.000 claims description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- QTMTWUTZSOSQGM-UHFFFAOYSA-N ethyl 2-[[4-[(2-ethoxycarbonylphenyl)methyl]-6-nitro-2,3-dioxoquinoxalin-1-yl]methyl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CN1C(=O)C(=O)N(CC=2C(=CC=CC=2)C(=O)OCC)C2=CC([N+]([O-])=O)=CC=C21 QTMTWUTZSOSQGM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- DPIWGGWBUSWCKU-UHFFFAOYSA-N 4-[(4-diethoxyphosphorylphenyl)methyl]-7-nitro-1h-quinoxaline-2,3-dione Chemical compound C1=CC(P(=O)(OCC)OCC)=CC=C1CN1C(=O)C(=O)NC2=CC([N+]([O-])=O)=CC=C21 DPIWGGWBUSWCKU-UHFFFAOYSA-N 0.000 claims 1
- LCNOYMDSDJSTBX-UHFFFAOYSA-N [1-[2,3-dioxo-6-(trifluoromethyl)-4h-quinoxalin-1-yl]-1-phenylethyl]phosphonic acid Chemical compound C12=CC=C(C(F)(F)F)C=C2NC(=O)C(=O)N1C(P(O)(O)=O)(C)C1=CC=CC=C1 LCNOYMDSDJSTBX-UHFFFAOYSA-N 0.000 claims 1
- HDJUELSXFKOAMB-UHFFFAOYSA-N [3-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)phenyl]phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC(N2C(C(=O)NC3=CC(=CC=C32)[N+]([O-])=O)=O)=C1 HDJUELSXFKOAMB-UHFFFAOYSA-N 0.000 claims 1
- RCONJPQATQKYKG-UHFFFAOYSA-N [6-(2-ethoxycarbonylimidazol-1-yl)-2,3-dioxo-4H-quinoxalin-1-yl]methylphosphonic acid Chemical compound C(=O)(OCC)C=1N(C=CN1)C=1C=C2NC(C(N(C2=CC1)CP(O)(=O)O)=O)=O RCONJPQATQKYKG-UHFFFAOYSA-N 0.000 claims 1
- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 59
- 230000008018 melting Effects 0.000 description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000000746 purification Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- UYCUMNRCCJNSBR-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid;hydrochloride Chemical compound Cl.CCOC(=O)C(O)=O UYCUMNRCCJNSBR-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QVQRFNNFBQRNPM-UHFFFAOYSA-N (6-bromo-2,3-dioxo-4h-quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=C(Br)C=C2NC(=O)C(=O)N(CP(O)(=O)O)C2=C1 QVQRFNNFBQRNPM-UHFFFAOYSA-N 0.000 description 3
- SAUYTDLSSGZDMZ-UHFFFAOYSA-N (6-iodo-2,3-dioxo-4h-quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=C(I)C=C2NC(=O)C(=O)N(CP(O)(=O)O)C2=C1 SAUYTDLSSGZDMZ-UHFFFAOYSA-N 0.000 description 3
- TZAFLAJENIMHJK-UHFFFAOYSA-N 1-[2-amino-4-(trifluoromethyl)anilino]ethylphosphonic acid Chemical compound OP(=O)(O)C(C)NC1=CC=C(C(F)(F)F)C=C1N TZAFLAJENIMHJK-UHFFFAOYSA-N 0.000 description 3
- XPRXSVUVVFZBIB-UHFFFAOYSA-N 1-[2-nitro-4-(trifluoromethyl)anilino]ethylphosphonic acid Chemical compound OP(=O)(O)C(C)NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O XPRXSVUVVFZBIB-UHFFFAOYSA-N 0.000 description 3
- RQEIUNRFWLZDPY-UHFFFAOYSA-N 2-(2,4-dinitroanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RQEIUNRFWLZDPY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- WOUUXKDUWGWFPD-UHFFFAOYSA-N ethyl 4-(2-amino-4-nitroanilino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1N WOUUXKDUWGWFPD-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IZFPMHONRRSWFK-UHFFFAOYSA-N 1-(6-bromo-2,3-dioxo-4h-quinoxalin-1-yl)ethylphosphonic acid Chemical compound C1=C(Br)C=C2NC(=O)C(=O)N(C(C)P(O)(O)=O)C2=C1 IZFPMHONRRSWFK-UHFFFAOYSA-N 0.000 description 2
- BXPOWJYKHYHGHI-UHFFFAOYSA-N 1-(6-iodo-2,3-dioxo-4h-quinoxalin-1-yl)ethylphosphonic acid Chemical compound C1=C(I)C=C2NC(=O)C(=O)N(C(C)P(O)(O)=O)C2=C1 BXPOWJYKHYHGHI-UHFFFAOYSA-N 0.000 description 2
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 2
- PWWSBXCEIIQXQB-UHFFFAOYSA-N 2-(2-amino-4-nitroanilino)benzoic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1NC1=CC=CC=C1C(O)=O PWWSBXCEIIQXQB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PMCPRCXYFGNSSL-UHFFFAOYSA-N 3-(2-amino-4-nitroanilino)propanoic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1NCCC(O)=O PMCPRCXYFGNSSL-UHFFFAOYSA-N 0.000 description 2
- MBLWYSINCMBQRP-UHFFFAOYSA-N 3-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)propanoic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(=O)N(CCC(=O)O)C2=C1 MBLWYSINCMBQRP-UHFFFAOYSA-N 0.000 description 2
- ADLCESCCZRIIAR-UHFFFAOYSA-N 3-[(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CN2C(C(=O)NC3=CC(=CC=C32)[N+]([O-])=O)=O)=C1 ADLCESCCZRIIAR-UHFFFAOYSA-N 0.000 description 2
- RYMLSFWVYNAKAR-UHFFFAOYSA-N 6-nitro-1,4-dihydroquinoxaline-2,3-dione Chemical compound N1C(=O)C(=O)NC2=CC([N+](=O)[O-])=CC=C21 RYMLSFWVYNAKAR-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Biochemistry (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4135871.6 | 1991-10-26 | ||
| DE4135871A DE4135871A1 (de) | 1991-10-26 | 1991-10-26 | Chinoxalinderivate, deren herstellung und verwendung in arzneimitteln |
| DEP4224200.2 | 1992-07-17 | ||
| DE4224200 | 1992-07-17 | ||
| PCT/DE1992/000895 WO1993008173A1 (fr) | 1991-10-26 | 1992-10-25 | Derives de quinoxaline ayant une affinite pour les recepteurs de quisqualate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR930703271A KR930703271A (ko) | 1993-11-29 |
| KR100262371B1 true KR100262371B1 (ko) | 2000-08-01 |
Family
ID=25908683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930701948A KR100262371B1 (ko) | 1991-10-26 | 1992-10-25 | 퀴스퀄레이트 수용체에 대한 친화성이 있는 퀴녹살린 유도체 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0565683A1 (fr) |
| JP (1) | JP3258008B2 (fr) |
| KR (1) | KR100262371B1 (fr) |
| CN (1) | CN1038840C (fr) |
| AU (1) | AU664212B2 (fr) |
| CA (1) | CA2099270A1 (fr) |
| CZ (1) | CZ286351B6 (fr) |
| FI (1) | FI932959A0 (fr) |
| HU (1) | HUT64756A (fr) |
| IL (1) | IL103538A (fr) |
| NO (1) | NO304693B1 (fr) |
| NZ (1) | NZ244896A (fr) |
| PL (1) | PL171125B1 (fr) |
| PT (1) | PT101004B (fr) |
| RU (1) | RU2117663C1 (fr) |
| SK (1) | SK281518B6 (fr) |
| WO (1) | WO1993008173A1 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK162491D0 (da) * | 1991-09-20 | 1991-09-20 | Novo Nordisk As | Heterocycliske forbindelser, deres fremstilling og farmaceutiske praeparater indeholdende forbindelserne |
| ATE404201T1 (de) * | 1992-06-22 | 2008-08-15 | Univ California | Glycinrezeptorantagonisten und ihre verwendung |
| DE4314592A1 (de) * | 1993-04-28 | 1994-11-03 | Schering Ag | Benzo(f)chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| IL109397A0 (en) * | 1993-04-28 | 1994-07-31 | Schering Ag | Quinoxalinedione derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
| DE4428152A1 (de) * | 1994-06-22 | 1996-01-04 | Basf Ag | Neue Amido-chinoxalindione, ihrer Herstellung und Verwendung |
| GB9419318D0 (en) * | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
| HU223945B1 (hu) * | 1994-09-27 | 2005-03-29 | Yamanouchi Pharmaceutical Co., Ltd. | 1,2,3,4-Tetrahidro-kinoxalin-dion-származékok és ezeket tartalmazó gyógyszerkészítmények |
| DE4439492A1 (de) * | 1994-10-25 | 1996-05-02 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| DE4439493A1 (de) * | 1994-10-25 | 1996-05-02 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| US6110911A (en) * | 1995-06-07 | 2000-08-29 | Warner-Lambert Company | Cyclic amine derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
| DE19521058A1 (de) * | 1995-06-09 | 1996-12-12 | Basf Ag | Verfahren zur Herstellung von Aromaten enthaltenden Polyetherpolyolen |
| DE19545251A1 (de) * | 1995-11-24 | 1997-05-28 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| TW448171B (en) * | 1996-06-06 | 2001-08-01 | Yamanouchi Pharma Co Ltd | Imidazole-substituted quinoxalinedione derivatives |
| DE19624808A1 (de) | 1996-06-21 | 1998-01-02 | Basf Ag | Pyrrolylchinoxalindione, ihre Herstellung und Verwendung |
| DE19728326A1 (de) * | 1997-06-27 | 1999-01-07 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| US6015800A (en) * | 1997-09-03 | 2000-01-18 | Warner-Lambert Company | Substituted quinoxaline-2-ones as glutamate receptor antagonists |
| EP0900567A3 (fr) * | 1997-09-05 | 2001-05-02 | Pfizer Products Inc. | Quinazoline-4-ones antagonistes d'AMPA pour le traitement des dyscinésies associées à la thérapie aux agonistes de la dopamine |
| IL125950A0 (en) * | 1997-09-05 | 1999-04-11 | Pfizer Prod Inc | Methods of administering ampa receptor antagonists to treat dyskinesias associated with dopamine agonist therapy |
| FR2769309B1 (fr) | 1997-10-08 | 2001-06-15 | Oreal | Composition de teinture d'oxydation des fibres keratiniques comprenant un derive d'aminoacide en tant que base d'oxydation et nouveaux derives d'aminoacides |
| GB0311406D0 (en) * | 2003-05-17 | 2003-06-25 | Queen Mary & Westfield College | Substituted phosphonate fluorescent sensors,and use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991013878A1 (fr) * | 1990-03-16 | 1991-09-19 | Novo Nordisk A/S | Composes de quinoxaline, preparation et utilisation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0118982A1 (fr) * | 1983-02-01 | 1984-09-19 | Sumitomo Chemical Company, Limited | Composés organo-phosphorés de la quinoxalinone, leur production et utilisation |
| NO179551C (no) * | 1987-11-10 | 1996-10-30 | Novo Nordisk As | Analogifremgangsmåte for fremstilling av terapeutisk virksomme kinoxalinforbindelser |
-
1992
- 1992-10-23 PT PT101004A patent/PT101004B/pt not_active IP Right Cessation
- 1992-10-25 WO PCT/DE1992/000895 patent/WO1993008173A1/fr not_active Application Discontinuation
- 1992-10-25 JP JP50735393A patent/JP3258008B2/ja not_active Expired - Fee Related
- 1992-10-25 CZ CZ19931387A patent/CZ286351B6/cs not_active IP Right Cessation
- 1992-10-25 SK SK727-93A patent/SK281518B6/sk unknown
- 1992-10-25 PL PL92299929A patent/PL171125B1/pl unknown
- 1992-10-25 CA CA002099270A patent/CA2099270A1/fr not_active Abandoned
- 1992-10-25 RU RU93044489A patent/RU2117663C1/ru active
- 1992-10-25 IL IL10353892A patent/IL103538A/en not_active IP Right Cessation
- 1992-10-25 HU HU9301877A patent/HUT64756A/hu unknown
- 1992-10-25 AU AU28894/92A patent/AU664212B2/en not_active Ceased
- 1992-10-25 EP EP92922676A patent/EP0565683A1/fr not_active Withdrawn
- 1992-10-25 KR KR1019930701948A patent/KR100262371B1/ko not_active IP Right Cessation
- 1992-10-26 CN CN92113338A patent/CN1038840C/zh not_active Expired - Fee Related
- 1992-10-27 NZ NZ244896A patent/NZ244896A/en unknown
-
1993
- 1993-06-24 FI FI932959A patent/FI932959A0/fi unknown
- 1993-06-25 NO NO932116A patent/NO304693B1/no not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991013878A1 (fr) * | 1990-03-16 | 1991-09-19 | Novo Nordisk A/S | Composes de quinoxaline, preparation et utilisation |
Also Published As
| Publication number | Publication date |
|---|---|
| FI932959A (fi) | 1993-06-24 |
| NZ244896A (en) | 1995-07-26 |
| CZ138793A3 (en) | 1994-01-19 |
| NO304693B1 (no) | 1999-02-01 |
| AU2889492A (en) | 1993-05-21 |
| SK281518B6 (sk) | 2001-04-09 |
| SK72793A3 (en) | 1993-10-06 |
| CZ286351B6 (cs) | 2000-03-15 |
| EP0565683A1 (fr) | 1993-10-20 |
| PL299929A1 (en) | 1994-04-05 |
| HUT64756A (en) | 1994-02-28 |
| CN1072929A (zh) | 1993-06-09 |
| IL103538A0 (en) | 1993-03-15 |
| CA2099270A1 (fr) | 1993-04-27 |
| AU664212B2 (en) | 1995-11-09 |
| WO1993008173A1 (fr) | 1993-04-29 |
| NO932344L (no) | 1993-06-25 |
| IL103538A (en) | 2001-07-24 |
| JPH06503583A (ja) | 1994-04-21 |
| NO932344D0 (no) | 1993-06-25 |
| KR930703271A (ko) | 1993-11-29 |
| PT101004B (pt) | 1999-10-29 |
| PL171125B1 (pl) | 1997-03-28 |
| JP3258008B2 (ja) | 2002-02-18 |
| FI932959A0 (fi) | 1993-06-24 |
| RU2117663C1 (ru) | 1998-08-20 |
| HU9301877D0 (en) | 1993-09-28 |
| CN1038840C (zh) | 1998-06-24 |
| PT101004A (pt) | 1994-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |