CA2099270A1 - Derives quinoxaliniques a affinite pour les recepteurs du quisqualate - Google Patents
Derives quinoxaliniques a affinite pour les recepteurs du quisqualateInfo
- Publication number
- CA2099270A1 CA2099270A1 CA002099270A CA2099270A CA2099270A1 CA 2099270 A1 CA2099270 A1 CA 2099270A1 CA 002099270 A CA002099270 A CA 002099270A CA 2099270 A CA2099270 A CA 2099270A CA 2099270 A1 CA2099270 A1 CA 2099270A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- dioxo
- nitro
- alkyl
- tetrahydroquinoxalin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
- 102000003678 AMPA Receptors Human genes 0.000 title description 7
- 108090000078 AMPA Receptors Proteins 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 29
- -1 COR13 Chemical group 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 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 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 5
- 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 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 150000002912 oxalic acid derivatives Chemical class 0.000 claims description 4
- QZOMEIASLFQZRK-UHFFFAOYSA-N 3-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)propylphosphonic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(=O)N(CCCP(O)(=O)O)C2=C1 QZOMEIASLFQZRK-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 compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- SZNFRIYTANUCHN-UHFFFAOYSA-N methyl 3-[(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C(C(=O)NC3=CC(=CC=C32)[N+]([O-])=O)=O)=C1 SZNFRIYTANUCHN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 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 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- OIZZRIOPPNDAKF-UHFFFAOYSA-N 1-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)ethylphosphonic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C(=O)N(C(C)P(O)(O)=O)C2=C1 OIZZRIOPPNDAKF-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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 description 2
- TUVFMMNANXKTRP-UHFFFAOYSA-N Ethenamine, N-methylene- Chemical compound C=CN=C TUVFMMNANXKTRP-UHFFFAOYSA-N 0.000 claims description 2
- AWSMICWCRIGNGU-UHFFFAOYSA-N [4-[(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]phenyl]phosphonic acid Chemical compound C1=CC(P(O)(=O)O)=CC=C1CN1C(=O)C(=O)NC2=CC([N+]([O-])=O)=CC=C21 AWSMICWCRIGNGU-UHFFFAOYSA-N 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
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 229940052760 dopamine agonists Drugs 0.000 claims description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 2
- BLMRCWDANZSHDG-UHFFFAOYSA-N ethyl 4-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1C(=O)C(=O)NC2=CC([N+]([O-])=O)=CC=C21 BLMRCWDANZSHDG-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
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 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 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
- 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 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
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 3
- 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 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 14
- 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
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 9
- 239000005711 Benzoic acid Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 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
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 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
- 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
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229940086542 triethylamine Drugs 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 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
- 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 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000003257 excitatory amino acid Substances 0.000 description 3
- 230000002461 excitatory amino acid Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 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 description 3
- 238000006722 reduction reaction Methods 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
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
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- HHBALKJHXDQCFF-UHFFFAOYSA-N ethoxy-[3-(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)phenyl]phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=CC(N2C(C(=O)NC3=CC(=CC=C32)[N+]([O-])=O)=O)=C1 HHBALKJHXDQCFF-UHFFFAOYSA-N 0.000 description 1
- CVBXBASSOWKOPD-UHFFFAOYSA-N ethoxy-[4-[(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]phenyl]phosphinic acid Chemical compound C1=CC(P(O)(=O)OCC)=CC=C1CN1C(=O)C(=O)NC2=CC([N+]([O-])=O)=CC=C21 CVBXBASSOWKOPD-UHFFFAOYSA-N 0.000 description 1
- GCGAOPMRWYDYIV-UHFFFAOYSA-N ethyl 2-[(6-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CN1C(=O)C(=O)NC2=CC([N+]([O-])=O)=CC=C21 GCGAOPMRWYDYIV-UHFFFAOYSA-N 0.000 description 1
- KINVHGBFZKMEAW-UHFFFAOYSA-N ethyl 3-(2-amino-4-nitroanilino)benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C(=CC(=CC=2)[N+]([O-])=O)N)=C1 KINVHGBFZKMEAW-UHFFFAOYSA-N 0.000 description 1
- DXAQPHQILRAIEW-UHFFFAOYSA-N ethyl 4-(2,4-dinitroanilino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O DXAQPHQILRAIEW-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
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- 208000028867 ischemia Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 229960004640 memantine Drugs 0.000 description 1
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- KOPWXFNKGLVFNL-UHFFFAOYSA-N methyl 3-[(7-nitro-2,3-dioxo-4h-quinoxalin-1-yl)methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C(C(=O)NC3=CC=C(C=C32)[N+]([O-])=O)=O)=C1 KOPWXFNKGLVFNL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- XRPITCBWOUOJTH-UHFFFAOYSA-N n,n-diethylpyridin-2-amine Chemical compound CCN(CC)C1=CC=CC=N1 XRPITCBWOUOJTH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical class N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical compound C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940043230 sarcosine Drugs 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960004558 terguride Drugs 0.000 description 1
- GSRBHDHXDPTIDH-UHFFFAOYSA-N tert-butyl 2-[2,3-dioxo-6-(trifluoromethyl)-4h-quinoxalin-1-yl]acetate Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C(=O)N(CC(=O)OC(C)(C)C)C2=C1 GSRBHDHXDPTIDH-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000001960 triggered effect 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
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Classifications
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4135871A DE4135871A1 (de) | 1991-10-26 | 1991-10-26 | Chinoxalinderivate, deren herstellung und verwendung in arzneimitteln |
| DEP4135871.6 | 1991-10-26 | ||
| DE4224200 | 1992-07-17 | ||
| DEP4224200.2 | 1992-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2099270A1 true CA2099270A1 (fr) | 1993-04-27 |
Family
ID=25908683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002099270A Abandoned CA2099270A1 (fr) | 1991-10-26 | 1992-10-25 | Derives quinoxaliniques a affinite pour les recepteurs du quisqualate |
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) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773439A (en) * | 1994-06-22 | 1998-06-30 | Basf Aktiengesellschaft | Amido-quinoxalinediones, the preparation and use thereof |
| US5895824A (en) * | 1995-06-09 | 1999-04-20 | Basf Aktiengesellschaft | Preparation of polyether polyols containing aromatics |
| US6277850B1 (en) | 1996-06-21 | 2001-08-21 | Abbott Laboratories | Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists |
Families Citing this family (17)
| 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 |
| AU672617B2 (en) * | 1992-06-22 | 1996-10-10 | Regents Of The University Of California, The | Glycine receptor antagonists and the use thereof |
| 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 |
| GB9419318D0 (en) * | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
| US6096743A (en) * | 1994-09-27 | 2000-08-01 | Yamanouchi Pharmaceuticals Co., Ltd. | 1,2,3,4-tetrahydroquinoxalinedione derivative |
| DE4439493A1 (de) * | 1994-10-25 | 1996-05-02 | Schering Ag | Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln |
| DE4439492A1 (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 |
| 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 |
| 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 |
Family Cites Families (3)
| 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 |
| DK69790D0 (da) * | 1990-03-16 | 1990-03-16 | Novo Nordisk As | Heterocykliske forbindelser, deres fremstilling af anvendelse |
-
1992
- 1992-10-23 PT PT101004A patent/PT101004B/pt not_active IP Right Cessation
- 1992-10-25 EP EP92922676A patent/EP0565683A1/fr not_active Withdrawn
- 1992-10-25 WO PCT/DE1992/000895 patent/WO1993008173A1/fr not_active Application Discontinuation
- 1992-10-25 IL IL10353892A patent/IL103538A/en not_active IP Right Cessation
- 1992-10-25 CA CA002099270A patent/CA2099270A1/fr not_active Abandoned
- 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 PL PL92299929A patent/PL171125B1/pl unknown
- 1992-10-25 AU AU28894/92A patent/AU664212B2/en not_active Ceased
- 1992-10-25 KR KR1019930701948A patent/KR100262371B1/ko not_active IP Right Cessation
- 1992-10-25 HU HU9301877A patent/HUT64756A/hu unknown
- 1992-10-25 RU RU93044489A patent/RU2117663C1/ru active
- 1992-10-25 SK SK727-93A patent/SK281518B6/sk unknown
- 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773439A (en) * | 1994-06-22 | 1998-06-30 | Basf Aktiengesellschaft | Amido-quinoxalinediones, the preparation and use thereof |
| US5895824A (en) * | 1995-06-09 | 1999-04-20 | Basf Aktiengesellschaft | Preparation of polyether polyols containing aromatics |
| US6277850B1 (en) | 1996-06-21 | 2001-08-21 | Abbott Laboratories | Pyrrolyl quinoxalindiones their production and use as AMPA receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| NO932344D0 (no) | 1993-06-25 |
| FI932959A (fi) | 1993-06-24 |
| NZ244896A (en) | 1995-07-26 |
| NO932344L (no) | 1993-06-25 |
| HU9301877D0 (en) | 1993-09-28 |
| PT101004A (pt) | 1994-01-31 |
| IL103538A (en) | 2001-07-24 |
| PT101004B (pt) | 1999-10-29 |
| RU2117663C1 (ru) | 1998-08-20 |
| IL103538A0 (en) | 1993-03-15 |
| PL171125B1 (pl) | 1997-03-28 |
| JP3258008B2 (ja) | 2002-02-18 |
| FI932959A0 (fi) | 1993-06-24 |
| KR100262371B1 (ko) | 2000-08-01 |
| CZ286351B6 (cs) | 2000-03-15 |
| KR930703271A (ko) | 1993-11-29 |
| AU2889492A (en) | 1993-05-21 |
| WO1993008173A1 (fr) | 1993-04-29 |
| CN1038840C (zh) | 1998-06-24 |
| NO304693B1 (no) | 1999-02-01 |
| CZ138793A3 (en) | 1994-01-19 |
| JPH06503583A (ja) | 1994-04-21 |
| AU664212B2 (en) | 1995-11-09 |
| SK281518B6 (sk) | 2001-04-09 |
| EP0565683A1 (fr) | 1993-10-20 |
| HUT64756A (en) | 1994-02-28 |
| CN1072929A (zh) | 1993-06-09 |
| PL299929A1 (en) | 1994-04-05 |
| SK72793A3 (en) | 1993-10-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |