SK131795A3 - Benzo£f|quinoxalindione derivatives, their preparation and their use in drugs - Google Patents

Benzo£f|quinoxalindione derivatives, their preparation and their use in drugs Download PDF

Info

Publication number: SK131795A3
Authority: SK; Slovakia
Prior art keywords: nitro; dioxo; acid; benzo; group
Prior art date: 1993-04-28

Application number

SK1317-95A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Holscher

Lechoslaw Turski

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-04-28

Filing date

1994-04-28

Publication date

1996-07-03

1994-04-28 Application filed by Schering Ag filed Critical Schering Ag

1996-07-03 Publication of SK131795A3 publication Critical patent/SK131795A3/sk

Links

239000003814 drug Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
229940079593 drug Drugs 0.000 title description 2
125000005605 benzo group Chemical group 0.000 title 1
-1 quinoxalin-1-yl Chemical group 0.000 claims description 114
150000001875 compounds Chemical class 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 27
238000000034 method Methods 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
150000002912 oxalic acid derivatives Chemical class 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
235000006408 oxalic acid Nutrition 0.000 claims description 6
NPNXFGJTBMDAMA-UHFFFAOYSA-N 6-nitro-1,4-dihydrobenzo[f]quinoxaline-2,3-dione Chemical compound C1=CC=CC2=C(N=C(C(O)=N3)O)C3=CC([N+]([O-])=O)=C21 NPNXFGJTBMDAMA-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
230000002829 reductive effect Effects 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 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
125000005843 halogen group Chemical group 0.000 claims description 4
150000003536 tetrazoles Chemical class 0.000 claims description 4
XVZJRBVJWZIGJD-UHFFFAOYSA-N (6-nitro-2,3-dioxo-4h-benzo[h]quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=CC=C2C(N(C(C(=O)N3)=O)CP(O)(=O)O)=C3C=C([N+]([O-])=O)C2=C1 XVZJRBVJWZIGJD-UHFFFAOYSA-N 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
RITZOZAQQBAFAW-UHFFFAOYSA-N benzo[f]quinoxaline-2,3-dione Chemical class C1=CC=C2C3=NC(=O)C(=O)N=C3C=CC2=C1 RITZOZAQQBAFAW-UHFFFAOYSA-N 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
WFUBFGMCIYTQFY-UHFFFAOYSA-N 2-(6-nitro-2,3-dioxo-7-sulfamoyl-4h-benzo[h]quinoxalin-1-yl)acetic acid Chemical compound N1C(=O)C(=O)N(CC(O)=O)C2=C1C=C([N+]([O-])=O)C1=C2C=CC=C1S(=O)(=O)N WFUBFGMCIYTQFY-UHFFFAOYSA-N 0.000 claims 1
CKDZEXUCUNHQIY-UHFFFAOYSA-N 2h-tetrazole-5-carbonitrile Chemical group N#CC=1N=NNN=1 CKDZEXUCUNHQIY-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 3
239000008177 pharmaceutical agent Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
239000000047 product Substances 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000000243 solution Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 11
239000012043 crude product Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000012267 brine Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
125000005322 morpholin-1-yl group Chemical group 0.000 description 7
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
SSHIVHKMGVBXTJ-UHFFFAOYSA-N 1-nitronaphthalen-2-ol Chemical compound C1=CC=CC2=C([N+]([O-])=O)C(O)=CC=C21 SSHIVHKMGVBXTJ-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 4
102000003678 AMPA Receptors Human genes 0.000 description 4
108090000078 AMPA Receptors Proteins 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
FCQJEPASRCXVCB-UHFFFAOYSA-N flavianic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FCQJEPASRCXVCB-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003513 alkali Substances 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
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
UIBCDEFKKLRXHR-UHFFFAOYSA-N diethoxyphosphorylmethanamine Chemical compound CCOP(=O)(CN)OCC UIBCDEFKKLRXHR-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 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
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
SABMKLHBCKBYJA-UHFFFAOYSA-N (6,10-dinitro-2,3-dioxo-4h-benzo[h]quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(N(C(C(=O)N3)=O)CP(O)(=O)O)=C3C=C([N+]([O-])=O)C2=C1 SABMKLHBCKBYJA-UHFFFAOYSA-N 0.000 description 2
SSCNRKWRQSHMNE-UHFFFAOYSA-N (6-amino-2,3-dioxo-4h-benzo[h]quinoxalin-1-yl)methylphosphonic acid Chemical compound C12=CC=CC=C2C(N)=CC2=C1N(CP(O)(O)=O)C(=O)C(=O)N2 SSCNRKWRQSHMNE-UHFFFAOYSA-N 0.000 description 2
HFVBPMRHDRZVIP-UHFFFAOYSA-N (6-nitro-2,3-dioxo-1h-benzo[f]quinoxalin-4-yl)methylphosphonic acid Chemical compound C1=CC=CC2=C(NC(=O)C(N3CP(O)(=O)O)=O)C3=CC([N+]([O-])=O)=C21 HFVBPMRHDRZVIP-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RCYYZRIUOQUYFD-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-6-nitro-4h-benzo[f]quinoxaline-2,3-dione Chemical compound C1=CC=C2C(N(C(C(=O)N3)=O)CP(=O)(OCC)OCC)=C3C=C([N+]([O-])=O)C2=C1 RCYYZRIUOQUYFD-UHFFFAOYSA-N 0.000 description 2
LRZGNMJOLRIZHM-UHFFFAOYSA-N 1-[diethoxyphosphoryl(phenyl)methyl]-2,3-dioxo-4h-benzo[f]quinoxaline-7-sulfonamide Chemical compound C1=CC2=C(S(N)(=O)=O)C=CC=C2C2=C1NC(=O)C(=O)N2C(P(=O)(OCC)OCC)C1=CC=CC=C1 LRZGNMJOLRIZHM-UHFFFAOYSA-N 0.000 description 2
NYYLZXREFNYPKB-UHFFFAOYSA-N 1-[ethoxy(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)OCC NYYLZXREFNYPKB-UHFFFAOYSA-N 0.000 description 2
SKKUAUZTZZRYPW-UHFFFAOYSA-N 1-chloro-2,4-dinitronaphthalene Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CC([N+]([O-])=O)=C21 SKKUAUZTZZRYPW-UHFFFAOYSA-N 0.000 description 2
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
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GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 2
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208000024827 Alzheimer disease Diseases 0.000 description 2
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CTLDPADAWAUPCW-UHFFFAOYSA-N C(C)(=O)NN1C(C(NC=2C=C(C3=C(C12)C=CC=C3)[N+](=O)[O-])=O)=O Chemical compound C(C)(=O)NN1C(C(NC=2C=C(C3=C(C12)C=CC=C3)[N+](=O)[O-])=O)=O CTLDPADAWAUPCW-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003008 phosphonic acid esters Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-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
150000003252 quinoxalines Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 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
150000003335 secondary amines Chemical class 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000000344 soap Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
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 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
150000007944 thiolates Chemical class 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
QQMMVNKVUROQMN-UHFFFAOYSA-N trifluoromethylsulfonylmethylphosphonic acid Chemical compound OP(O)(=O)CS(=O)(=O)C(F)(F)F QQMMVNKVUROQMN-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
238000009736 wetting Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- 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
- 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
- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

SK1317-95A 1993-04-28 1994-04-28 Benzo£f|quinoxalindione derivatives, their preparation and their use in drugs SK131795A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4314592A DE4314592A1 (de)	1993-04-28	1993-04-28	Benzo(f)chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln
PCT/DE1994/000495 WO1994025470A1 (de)	1993-04-28	1994-04-28	Benzo[f]chinoxalindionderivative, deren herstellung und verwendung in arzneimitteln

Publications (1)

Publication Number	Publication Date
SK131795A3 true SK131795A3 (en)	1996-07-03

Family

ID=6487059

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1317-95A SK131795A3 (en)	1993-04-28	1994-04-28	Benzo£f\|quinoxalindione derivatives, their preparation and their use in drugs

Country Status (23)

Country	Link
US (1)	US5710138A (da)
EP (1)	EP0696289B1 (da)
JP (1)	JPH08512289A (da)
KR (1)	KR960701883A (da)
CN (1)	CN1041935C (da)
AT (1)	ATE150026T1 (da)
AU (1)	AU683258B2 (da)
CA (1)	CA2161426A1 (da)
CZ (1)	CZ276395A3 (da)
DE (2)	DE4314592A1 (da)
DK (1)	DK0696289T3 (da)
ES (1)	ES2101531T3 (da)
FI (1)	FI955142A0 (da)
GR (1)	GR3022867T3 (da)
HU (1)	HUT72439A (da)
IL (1)	IL109398A (da)
NO (1)	NO305519B1 (da)
NZ (1)	NZ265601A (da)
PL (1)	PL174292B1 (da)
RU (1)	RU2140421C1 (da)
SK (1)	SK131795A3 (da)
WO (1)	WO1994025470A1 (da)
ZA (1)	ZA942971B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6057304A (en) *	1992-10-26	2000-05-02	Schering Aktiengesellschaft	Quinoxaline-phosphonic acid derivatives
DE19728326A1 (de) *	1997-06-27	1999-01-07	Schering Ag	Neue Chinoxalindionderivate, deren Herstellung und Verwendung in Arzneimitteln
CN113620890B (zh) *	2020-05-07	2024-06-28	普济生物科技（台州）有限公司	苯并喹喔啉酮化合物及其合成方法和用途

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO179551C (no) *	1987-11-10	1996-10-30	Novo Nordisk As	Analogifremgangsmåte for fremstilling av terapeutisk virksomme kinoxalinforbindelser
DK716188D0 (da) *	1988-12-22	1988-12-22	Ferrosan As	Quinoxalinforbindelser, deres fremstilling og anvendelse
DK69790D0 (da) *	1990-03-16	1990-03-16	Novo Nordisk As	Heterocykliske forbindelser, deres fremstilling af anvendelse
DK73091D0 (da) *	1991-04-22	1991-04-22	Novo Nordisk As	Quinoxalinforbindelser, deres fremstilling og anvendelse
PT101004B (pt) *	1991-10-26	1999-10-29	Schering Ag	Derivados da quinoxalina, processo para a sua preparacao e composicoes farmaceuticas que os contem
DK31093D0 (da) *	1993-03-19	1993-03-19	Novo Nordisk As

1993
- 1993-04-28 DE DE4314592A patent/DE4314592A1/de not_active Withdrawn
1994
- 1994-04-01 ZA ZA942971A patent/ZA942971B/xx unknown
- 1994-04-22 IL IL10939894A patent/IL109398A/xx active IP Right Grant
- 1994-04-28 JP JP6523753A patent/JPH08512289A/ja active Pending
- 1994-04-28 NZ NZ265601A patent/NZ265601A/en unknown
- 1994-04-28 CN CN94191945A patent/CN1041935C/zh not_active Expired - Fee Related
- 1994-04-28 SK SK1317-95A patent/SK131795A3/sk unknown
- 1994-04-28 AU AU66757/94A patent/AU683258B2/en not_active Ceased
- 1994-04-28 KR KR1019950704706A patent/KR960701883A/ko not_active Application Discontinuation
- 1994-04-28 CZ CZ952763A patent/CZ276395A3/cs unknown
- 1994-04-28 EP EP94914315A patent/EP0696289B1/de not_active Expired - Lifetime
- 1994-04-28 WO PCT/DE1994/000495 patent/WO1994025470A1/de not_active Application Discontinuation
- 1994-04-28 ES ES94914315T patent/ES2101531T3/es not_active Expired - Lifetime
- 1994-04-28 PL PL94311296A patent/PL174292B1/pl unknown
- 1994-04-28 AT AT94914315T patent/ATE150026T1/de not_active IP Right Cessation
- 1994-04-28 CA CA002161426A patent/CA2161426A1/en not_active Abandoned
- 1994-04-28 DE DE59402079T patent/DE59402079D1/de not_active Expired - Lifetime
- 1994-04-28 HU HU9502647A patent/HUT72439A/hu unknown
- 1994-04-28 DK DK94914315.0T patent/DK0696289T3/da active
- 1994-04-28 RU RU95120090A patent/RU2140421C1/ru active
- 1994-04-28 US US08/537,895 patent/US5710138A/en not_active Expired - Fee Related
1995
- 1995-10-27 FI FI955142A patent/FI955142A0/fi unknown
- 1995-10-27 NO NO954316A patent/NO305519B1/no unknown
1997
- 1997-03-18 GR GR970400542T patent/GR3022867T3/el unknown

Also Published As

Publication number	Publication date
EP0696289A1 (de)	1996-02-14
RU2140421C1 (ru)	1999-10-27
DE59402079D1 (de)	1997-04-17
HU9502647D0 (en)	1995-11-28
WO1994025470A1 (de)	1994-11-10
EP0696289B1 (de)	1997-03-12
JPH08512289A (ja)	1996-12-24
CZ276395A3 (en)	1996-02-14
FI955142A (fi)	1995-10-27
NO954316L (no)	1995-12-28
NO954316D0 (no)	1995-10-27
PL311296A1 (en)	1996-02-05
DK0696289T3 (da)	1997-09-22
AU6675794A (en)	1994-11-21
KR960701883A (ko)	1996-03-28
ZA942971B (en)	1995-01-19
IL109398A0 (en)	1994-07-31
AU683258B2 (en)	1997-11-06
CA2161426A1 (en)	1994-11-10
ES2101531T3 (es)	1997-07-01
NZ265601A (en)	1996-09-25
NO305519B1 (no)	1999-06-14
FI955142A0 (fi)	1995-10-27
IL109398A (en)	1999-12-22
HUT72439A (en)	1996-04-29
CN1041935C (zh)	1999-02-03
US5710138A (en)	1998-01-20
CN1122136A (zh)	1996-05-08
PL174292B1 (pl)	1998-07-31
DE4314592A1 (de)	1994-11-03
ATE150026T1 (de)	1997-03-15
GR3022867T3 (en)	1997-06-30

Publication	Publication Date	Title
SK282851B6 (sk)	2002-12-03	Deriváty chinoxalíndiónu, spôsob ich výroby a ich použitie v liečivách
US6200970B1 (en)	2001-03-13	2,3-benzodiazepine derivatives and their use as AMPA-receptor inhibitors
SK281518B6 (sk)	2001-04-09	Deriváty chinoxalínu, spôsob ich výroby a ich použitie v liečivách
EP1025100B1 (de)	2002-01-23	3-substituierte tetrahydropyridopyrimidinon-derivate, ihre herstellung und verwendung
SK19212000A3 (sk)	2001-07-10	Spôsob prípravy morfolínových derivátov
FI113177B (fi)	2004-03-15	Uusia 1,3-dioksolo[4,5-h]-, 1,4-dioksano[2,3-h]- ja 1,5-dioksepino[2,3-h] [2,3]bentsodiatsepiinijohdannaisia, niiden valmistus ja käyttö lääkkeenä
US4612312A (en)	1986-09-16	Glutarimide antianxiety and antihypertensive agents
SK131795A3 (en)	1996-07-03	Benzo£f\|quinoxalindione derivatives, their preparation and their use in drugs
JPH0372061B2 (da)	1991-11-15
FI76075C (fi)	1988-09-09	Foerfarande foer framstaellning av farmaceutiskt vaerdefulla bensazepinderivat.
RU2140924C1 (ru)	1999-11-10	Производные пиридо(1,2,3-de)хиноксалина, способы их получения, лекарственное средство
JPS6130588A (ja)	1986-02-12	ベンゾ〔ｃ〕〔１，８〕ナフチリジン、その製造方法及びその使用、並びにこれらの化合物を含有する調製剤
EP1200433B1 (en)	2006-03-22	C-6 RING-SUBSTITUTED PYRIDO[1,2-a]BENZIMIDAZOLE DERIVATIVES USEFUL IN TREATING CENTRAL NERVOUS SYSTEM DISORDERS
SK286680B6 (sk)	2009-03-05	Deriváty 2,3-benzodiazepínu, spôsob ich prípravy a ich použitie, farmaceutická kompozícia s ich obsahom a spôsob jej prípravy
US3642791A (en)	1972-02-15	Morpholino-1-substituted-2(1h)-quinazolinones
PL171652B1 (pl)	1997-05-30	Nowe pochodne 2-[4-[4-(2-chinolino)-1-piperazynylo]butylo]- lH-izoindolo-1,3(2H)-dionu i sposób otrzymywania nowych pochodnych2-[4-[4-(2-chinolino)-1 -piperazynylo]butylo]-1Hizoindolo- 1,3(2H)-dionu