NO864061L - Hetrocykliske forbindelser og fremstilling og anvendelse av disse. - Google Patents
Hetrocykliske forbindelser og fremstilling og anvendelse av disse.Info
- Publication number
- NO864061L NO864061L NO864061A NO864061A NO864061L NO 864061 L NO864061 L NO 864061L NO 864061 A NO864061 A NO 864061A NO 864061 A NO864061 A NO 864061A NO 864061 L NO864061 L NO 864061L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- given above
- general formula
- meaning given
- ethyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 210000003169 central nervous system Anatomy 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- KBHRHYNROOOPRO-UHFFFAOYSA-N 5-(5,6-dihydro-4h-imidazo[1,5-a][1]benzazepin-3-yl)-3-ethyl-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C3N(C4=CC=CC=C4CCC3)C=N2)=N1 KBHRHYNROOOPRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- TYYNRNJZHIKVBH-UHFFFAOYSA-N 3-(5,6-dihydro-4h-imidazo[1,5-a][1]benzazepin-3-yl)-5-ethyl-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C2=C3N(C4=CC=CC=C4CCC3)C=N2)=N1 TYYNRNJZHIKVBH-UHFFFAOYSA-N 0.000 claims 1
- 230000007306 turnover Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 4
- 230000000949 anxiolytic effect Effects 0.000 abstract description 4
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 239000000642 acaricide Substances 0.000 abstract description 3
- 230000000507 anthelmentic effect Effects 0.000 abstract description 3
- 229940124339 anthelmintic agent Drugs 0.000 abstract description 3
- 239000000921 anthelmintic agent Substances 0.000 abstract description 3
- 229940125681 anticonvulsant agent Drugs 0.000 abstract description 3
- 239000002249 anxiolytic agent Substances 0.000 abstract description 3
- 229940005530 anxiolytics Drugs 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 239000002664 nootropic agent Substances 0.000 abstract description 2
- 230000001777 nootropic effect Effects 0.000 abstract description 2
- 239000003326 hypnotic agent Substances 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000027455 binding Effects 0.000 description 8
- -1 sleeping aids Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- FPULFENIJDPZBX-UHFFFAOYSA-N ethyl 2-isocyanoacetate Chemical compound CCOC(=O)C[N+]#[C-] FPULFENIJDPZBX-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000009870 specific binding Effects 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- PLGAAZZAJDBMMF-UHFFFAOYSA-N ethyl 5,6-dihydro-4h-imidazo[1,5-a][1]benzazepine-3-carboxylate Chemical compound C1CCC2=CC=CC=C2N2C=NC(C(=O)OCC)=C21 PLGAAZZAJDBMMF-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- OMCUPXRCMTUDHI-UHFFFAOYSA-N n'-hydroxycyclopropanecarboximidamide Chemical compound ON=C(N)C1CC1 OMCUPXRCMTUDHI-UHFFFAOYSA-N 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HRVRAYIYXRVAPR-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1-benzazepin-2-one Chemical compound N1C(=O)CCCC2=CC=CC=C21 HRVRAYIYXRVAPR-UHFFFAOYSA-N 0.000 description 2
- JOGGWBCSSCRGPG-UHFFFAOYSA-N 1,5-dihydro-4,1-benzothiazepin-2-one Chemical compound N1C(=O)CSCC2=CC=CC=C21 JOGGWBCSSCRGPG-UHFFFAOYSA-N 0.000 description 2
- BXCBUWKTXLWPSB-UHFFFAOYSA-N 1-(chloromethyl)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CCl BXCBUWKTXLWPSB-UHFFFAOYSA-N 0.000 description 2
- OHCLSGDNYDGHDE-UHFFFAOYSA-N 2-[(2-aminophenyl)methoxy]acetic acid Chemical compound NC1=CC=CC=C1COCC(O)=O OHCLSGDNYDGHDE-UHFFFAOYSA-N 0.000 description 2
- KFVVSDPKGPUSEL-UHFFFAOYSA-N 3-cyclopropyl-5-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound O1C(C[N+]#[C-])=NC(C2CC2)=N1 KFVVSDPKGPUSEL-UHFFFAOYSA-N 0.000 description 2
- WBFSHWXZTOEPNM-UHFFFAOYSA-N 4-methyl-3,5-dihydro-1h-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CN(C)CC2=CC=CC=C21 WBFSHWXZTOEPNM-UHFFFAOYSA-N 0.000 description 2
- GTFMIJNXNMDHAB-UHFFFAOYSA-N 4h-1,4-benzothiazin-3-one Chemical compound C1=CC=C2NC(=O)CSC2=C1 GTFMIJNXNMDHAB-UHFFFAOYSA-N 0.000 description 2
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 2
- BGHGVAKKIBOJGS-UHFFFAOYSA-N 5-cyclopropyl-3-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound [C-]#[N+]CC1=NOC(C2CC2)=N1 BGHGVAKKIBOJGS-UHFFFAOYSA-N 0.000 description 2
- YDQHQLYSPHGVPM-UHFFFAOYSA-N 5-ethyl-3-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound CCC1=NC(C[N+]#[C-])=NO1 YDQHQLYSPHGVPM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- SEJSKFBMCMOBCZ-UHFFFAOYSA-N ethyl 2-[(2-aminophenyl)methyl-methylamino]acetate Chemical compound CCOC(=O)CN(C)CC1=CC=CC=C1N SEJSKFBMCMOBCZ-UHFFFAOYSA-N 0.000 description 2
- RNIDDPLICCCRIC-UHFFFAOYSA-N ethyl 2-[(2-nitrophenyl)methoxy]acetate Chemical compound CCOC(=O)COCC1=CC=CC=C1[N+]([O-])=O RNIDDPLICCCRIC-UHFFFAOYSA-N 0.000 description 2
- HZOOVSDCIIZYPU-UHFFFAOYSA-N ethyl 4h-imidazo[5,1-c][1,4]benzothiazine-3-carboxylate Chemical compound C1=CC=C2N3C=NC(C(=O)OCC)=C3CSC2=C1 HZOOVSDCIIZYPU-UHFFFAOYSA-N 0.000 description 2
- SSSFDFPKMXSNSV-UHFFFAOYSA-N ethyl 4h-imidazo[5,1-c][1,4]benzoxazine-3-carboxylate Chemical compound C1=CC=C2N3C=NC(C(=O)OCC)=C3COC2=C1 SSSFDFPKMXSNSV-UHFFFAOYSA-N 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- SNUNDARWDNTCNX-UHFFFAOYSA-N methyl 2-[(2-aminophenyl)methylsulfanyl]acetate Chemical compound COC(=O)CSCC1=CC=CC=C1N SNUNDARWDNTCNX-UHFFFAOYSA-N 0.000 description 2
- LJWVXDQRFVJLJA-UHFFFAOYSA-N methyl 2-[(2-nitrophenyl)methylsulfanyl]acetate Chemical compound COC(=O)CSCC1=CC=CC=C1[N+]([O-])=O LJWVXDQRFVJLJA-UHFFFAOYSA-N 0.000 description 2
- UNKQCVYVFHGUTQ-UHFFFAOYSA-N n'-hydroxy-2-methoxyethanimidamide Chemical compound COCC(N)=NO UNKQCVYVFHGUTQ-UHFFFAOYSA-N 0.000 description 2
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- BWRBVBFLFQKBPT-UHFFFAOYSA-N (2-nitrophenyl)methanol Chemical compound OCC1=CC=CC=C1[N+]([O-])=O BWRBVBFLFQKBPT-UHFFFAOYSA-N 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- PBQINQSJWPGZAX-UHFFFAOYSA-N 1,5-dihydro-4,1-benzoxazepin-2-one Chemical compound N1C(=O)COCC2=CC=CC=C21 PBQINQSJWPGZAX-UHFFFAOYSA-N 0.000 description 1
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- QKPVEISEHYYHRH-UHFFFAOYSA-N 2-methoxyacetonitrile Chemical compound COCC#N QKPVEISEHYYHRH-UHFFFAOYSA-N 0.000 description 1
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 1
- PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 description 1
- OOHTWJGRUZYQST-UHFFFAOYSA-N 3-(isocyanomethyl)-5-(methoxymethyl)-1,2,4-oxadiazole Chemical compound COCC1=NC(C[N+]#[C-])=NO1 OOHTWJGRUZYQST-UHFFFAOYSA-N 0.000 description 1
- UNCHAYRENXIZBL-UHFFFAOYSA-N 3-(isocyanomethyl)-5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC(C[N+]#[C-])=NO1 UNCHAYRENXIZBL-UHFFFAOYSA-N 0.000 description 1
- OTFHPGNTKWFEHS-UHFFFAOYSA-N 3-ethyl-5-(4h-imidazo[5,1-c][1,4]benzothiazin-3-yl)-1,2,4-oxadiazole Chemical compound CCC1=NOC(C2=C3N(C4=CC=CC=C4SC3)C=N2)=N1 OTFHPGNTKWFEHS-UHFFFAOYSA-N 0.000 description 1
- BMCZADOABZFKMG-UHFFFAOYSA-N 3-ethyl-5-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound CCC1=NOC(C[N+]#[C-])=N1 BMCZADOABZFKMG-UHFFFAOYSA-N 0.000 description 1
- ZBJVPBPXJSMVLG-UHFFFAOYSA-N 4,5-dihydro-1,4-benzothiazepin-3-one Chemical compound C1NC(=O)CSC2=CC=CC=C21 ZBJVPBPXJSMVLG-UHFFFAOYSA-N 0.000 description 1
- GSQAJAIGMSUCKW-UHFFFAOYSA-N 5-(5,6-dihydro-4h-imidazo[1,5-a][1]benzazepin-3-yl)-3-phenyl-1,2,4-oxadiazole Chemical compound N1=CN2C3=CC=CC=C3CCCC2=C1C(ON=1)=NC=1C1=CC=CC=C1 GSQAJAIGMSUCKW-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- DHHFGQADZVYGIE-UHFFFAOYSA-N 9h-carbazole-1-carboxylic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)O DHHFGQADZVYGIE-UHFFFAOYSA-N 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102000005915 GABA Receptors Human genes 0.000 description 1
- 108010005551 GABA Receptors Proteins 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PIMZUZSSNYHVCU-OMKDEKJRSA-N Picrotoxinin Natural products O=C1O[C@@H]2[C@@H](C(=C)C)[C@H]1[C@@]1(O)[C@@]3(C)[C@@H]2OC(=O)[C@@]23O[C@H]2C1 PIMZUZSSNYHVCU-OMKDEKJRSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
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- 239000002671 adjuvant Substances 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- OPQRBXUBWHDHPQ-UHFFFAOYSA-N etazolate Chemical compound CCOC(=O)C1=CN=C2N(CC)N=CC2=C1NN=C(C)C OPQRBXUBWHDHPQ-UHFFFAOYSA-N 0.000 description 1
- 229950009329 etazolate Drugs 0.000 description 1
- NIDZUMSLERGAON-UHFFFAOYSA-N ethyl 2-(methylamino)acetate;hydron;chloride Chemical compound Cl.CCOC(=O)CNC NIDZUMSLERGAON-UHFFFAOYSA-N 0.000 description 1
- HBWXVCOFOBURKF-UHFFFAOYSA-N ethyl 5-methyl-4,6-dihydroimidazo[1,5-a][1,4]benzodiazepine-3-carboxylate Chemical compound C1N(C)CC2=CC=CC=C2N2C=NC(C(=O)OCC)=C21 HBWXVCOFOBURKF-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229960002200 flunitrazepam Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229960002418 ivermectin Drugs 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- JHRDEHLFNLLCQS-UHFFFAOYSA-N n'-hydroxy-2-methylpropanimidamide Chemical compound CC(C)C(N)=NO JHRDEHLFNLLCQS-UHFFFAOYSA-N 0.000 description 1
- YFDVQUUMKXZPLK-UHFFFAOYSA-N n-(3,4-dihydro-2h-naphthalen-1-ylidene)hydroxylamine Chemical compound C1=CC=C2C(=NO)CCCC2=C1 YFDVQUUMKXZPLK-UHFFFAOYSA-N 0.000 description 1
- HULPLKDCCLPDEX-UHFFFAOYSA-N n-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]formamide Chemical compound O1C(CNC=O)=NC(C2CC2)=N1 HULPLKDCCLPDEX-UHFFFAOYSA-N 0.000 description 1
- VVWSIHMDVHQTNC-UHFFFAOYSA-N n-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]formamide Chemical compound CCC1=NOC(CNC=O)=N1 VVWSIHMDVHQTNC-UHFFFAOYSA-N 0.000 description 1
- OYPIXUZKTODLAC-UHFFFAOYSA-N n-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]formamide Chemical compound O=CNCC1=NOC(C2CC2)=N1 OYPIXUZKTODLAC-UHFFFAOYSA-N 0.000 description 1
- RVHCGNUSTHNQRK-UHFFFAOYSA-N n-[(5-ethyl-1,2,4-oxadiazol-3-yl)methyl]formamide Chemical compound CCC1=NC(CNC=O)=NO1 RVHCGNUSTHNQRK-UHFFFAOYSA-N 0.000 description 1
- UGNUTYFQHHSKSG-UHFFFAOYSA-N n-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]formamide Chemical compound CC1=NC(CNC=O)=NO1 UGNUTYFQHHSKSG-UHFFFAOYSA-N 0.000 description 1
- DHQNLZOSPPTOAU-UHFFFAOYSA-N n-[[5-(methoxymethyl)-1,2,4-oxadiazol-3-yl]methyl]formamide Chemical compound COCC1=NC(CNC=O)=NO1 DHQNLZOSPPTOAU-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PIMZUZSSNYHVCU-YKWPQBAZSA-N picrotoxinin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2 PIMZUZSSNYHVCU-YKWPQBAZSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 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
- 239000012085 test solution Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Cosmetics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK476885A DK476885D0 (da) | 1985-10-17 | 1985-10-17 | Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO864061D0 NO864061D0 (no) | 1986-10-13 |
| NO864061L true NO864061L (no) | 1987-04-21 |
Family
ID=8136485
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864061A NO864061L (no) | 1985-10-17 | 1986-10-13 | Hetrocykliske forbindelser og fremstilling og anvendelse av disse. |
| NO864062A NO163776C (no) | 1985-10-17 | 1986-10-13 | Analogifremgangsmaate til fremstilling av terapeutisk aktive imidazoquinoksaliner. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864062A NO163776C (no) | 1985-10-17 | 1986-10-13 | Analogifremgangsmaate til fremstilling av terapeutisk aktive imidazoquinoksaliner. |
Country Status (18)
| Country | Link |
|---|---|
| US (5) | US4774245A (fi) |
| EP (2) | EP0225013B1 (fi) |
| JP (2) | JPS62155278A (fi) |
| KR (1) | KR940010034B1 (fi) |
| AT (1) | ATE48844T1 (fi) |
| AU (2) | AU591937B2 (fi) |
| CA (2) | CA1293723C (fi) |
| DE (1) | DE3667665D1 (fi) |
| DK (1) | DK476885D0 (fi) |
| ES (1) | ES2014234B3 (fi) |
| FI (2) | FI864124A (fi) |
| GR (1) | GR3000367T3 (fi) |
| IE (1) | IE59642B1 (fi) |
| IL (1) | IL80319A (fi) |
| NO (2) | NO864061L (fi) |
| NZ (2) | NZ217958A (fi) |
| PH (1) | PH22556A (fi) |
| PT (2) | PT83571B (fi) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK476885D0 (da) * | 1985-10-17 | 1985-10-17 | Ferrosan As | Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf |
| DE3664211D1 (en) * | 1985-10-17 | 1989-08-10 | Ferrosan As | Heterocyclic compounds and their preparation and use |
| DK174086D0 (da) * | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| DK155524C (da) * | 1987-03-18 | 1989-09-11 | Ferrosan As | Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse |
| DK160876C (da) * | 1987-12-08 | 1991-10-14 | Novo Nordisk As | Imidazoquinoxalinforbindelser, fremgangsmaade til deres fremstilling, anvendelse af forbindelserne og farmaceutiske praeparater, hvori forbindelserne indgaar |
| IL90315A0 (en) * | 1988-06-01 | 1989-12-15 | Ferrosan As | Imidazoquinoxaline compounds,their preparation and pharmaceutical compositions containing them |
| DK161148C (da) * | 1988-06-14 | 1991-11-18 | Novo Nordisk As | Imidazoquinoxalinforbindelser, fremgangsmaade til fremstilling deraf samt farmaceutiske praeprater indeholdende forbindelserne |
| GB8823475D0 (en) * | 1988-10-06 | 1988-11-16 | Merck Sharp & Dohme | Chemical compounds |
| DK626288D0 (da) * | 1988-11-10 | 1988-11-10 | Ferrosan As | Kemisk proces til fremstilling af imidazoquinoxaliner og mellemprodukter til brug i processen |
| ES2052172T3 (es) * | 1989-03-23 | 1994-07-01 | Pfizer | Agentes antialergicos basados en diazepina. |
| DK443589D0 (da) * | 1989-09-08 | 1989-09-08 | Ferrosan As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| DK588489D0 (da) * | 1989-11-22 | 1989-11-22 | Ferrosan As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| DK588389D0 (da) * | 1989-11-22 | 1989-11-22 | Ferrosan As | Heterocykliske forbindelser, deres fremstilling og anvendelse |
| DK151890D0 (da) * | 1990-06-22 | 1990-06-22 | Ferrosan As | Heterocykliske forbindelser deres fremstilling og brug |
| US5371080A (en) * | 1990-06-22 | 1994-12-06 | Novo Nordisk A/S | Imidazoquinazoline compounds and their use |
| US5276028A (en) * | 1990-06-22 | 1994-01-04 | Nordisk A/S | Imidazoquinoxaline compounds |
| DK41191D0 (da) * | 1991-03-07 | 1991-03-07 | Novo Nordisk As | Heterocycliske forbindelser, deres fremstilling og anvendelse |
| KR100207360B1 (ko) * | 1991-06-14 | 1999-07-15 | 돈 더블유. 슈미츠 | 이미다조[1,5,-a]퀸옥살린 |
| US5561227A (en) * | 1991-07-23 | 1996-10-01 | Schering Corporation | Process for the stereospecific synthesis of azetidinones |
| EP0524595A1 (en) * | 1991-07-23 | 1993-01-27 | Schering Corporation | Substituted beta-lactam compounds useful as hypocholesterolemic agents and processes for the preparation thereof |
| WO1993012113A1 (en) * | 1991-12-17 | 1993-06-24 | The Upjohn Company | 3-SUBSTITUTED IMIDAZO (1,5-a) AND IMIDAZO (1,5-a)-TRIAZOLO (1,5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY |
| US5244906A (en) * | 1992-01-23 | 1993-09-14 | Dowelanco | Insect control with substituted oxadiazole and thiadiazole compounds |
| ES2177539T3 (es) * | 1992-02-13 | 2002-12-16 | Upjohn Co | Benzoxacinas 4-oxo- y 4h-imidazo(5,1-c)(1,4) utilez como agentes de union de receptores de benzodiacepina. |
| GB9212486D0 (en) * | 1992-06-12 | 1992-07-22 | Erba Carlo Spa | Derivatives of substituted imidazo benzoxazin-1-one and process for their preparation |
| CA2143246C (en) * | 1994-03-16 | 2000-08-22 | Thierry Godel | Imidazodiazepines |
| GB2328940B (en) * | 1997-09-05 | 1999-12-08 | Dong Kook Pharm Co Ltd | A process for preparing benzodiazepine derivatives |
| EP1978966A4 (en) * | 2006-01-23 | 2010-11-10 | Amira Pharmaceuticals Inc | TRICYCLIC INHIBITORS OF 5-LIPOXYGENASE |
| CA2696703C (en) | 2007-08-20 | 2016-07-26 | Evotec Neurosciences Gmbh | Treatment of sleep disorders |
| US20090054412A1 (en) * | 2007-08-20 | 2009-02-26 | John Alan Kemp | Treatment of Sleep Disorders |
| TWI421252B (zh) | 2009-07-09 | 2014-01-01 | Irm Llc | 用於治療寄生蟲疾病之化合物及組合物 |
| AU2018260414A1 (en) | 2017-04-24 | 2019-10-17 | Novartis Ag | Therapeutic regimen of 2-amino-l-(2-(4-fluorophenyl)-3-(4-fluorophenylamino)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)ethanone and combinations thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118386A (en) * | 1977-04-04 | 1978-10-03 | Hoffmann-La Roche Inc. | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates |
| US4668678A (en) * | 1980-05-09 | 1987-05-26 | Usv Pharmaceutical Corporation | Triazoloquinoxalin-1,4-diones |
| CA1184175A (en) * | 1981-02-27 | 1985-03-19 | Walter Hunkeler | Imidazodiazepines |
| US4440929A (en) * | 1981-07-16 | 1984-04-03 | Usv Pharmaceutical Corporation | Imidazoquinoxaline compounds |
| DK151808C (da) * | 1982-11-16 | 1988-06-20 | Ferrosan As | Analogifremgangsmaade til fremstilling af oxadiazolylimidazo-oe1,4aa-benzodiazepinderivater |
| FI850191L (fi) * | 1984-01-19 | 1985-07-20 | Hoffmann La Roche | Imidazodiazepinderivat. |
| DK476885D0 (da) * | 1985-10-17 | 1985-10-17 | Ferrosan As | Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf |
| US4771051A (en) * | 1985-05-17 | 1988-09-13 | A/S Ferrosan | 3-substituted-4,5-dihydro-5-oxo imidazoquinazolines, their preparation, and their use in treating benzodiazepin receptor-related ailments |
| DE3664211D1 (en) * | 1985-10-17 | 1989-08-10 | Ferrosan As | Heterocyclic compounds and their preparation and use |
| FR2598147B1 (fr) * | 1986-04-30 | 1988-08-26 | Pasteur Institut | Immunogene isole de mollusques, son procede de preparation, reactifs de diagnostic des bilharzioses humaines, vaccins contre les schistosomiases et compositions immunisantes comprenant ledit immunogene. |
-
1985
- 1985-10-17 DK DK476885A patent/DK476885D0/da not_active Application Discontinuation
-
1986
- 1986-09-26 US US06/912,776 patent/US4774245A/en not_active Expired - Fee Related
- 1986-09-26 US US06/912,777 patent/US4870073A/en not_active Expired - Fee Related
- 1986-10-01 EP EP86307542A patent/EP0225013B1/en not_active Expired
- 1986-10-01 DE DE8686307542T patent/DE3667665D1/de not_active Expired - Lifetime
- 1986-10-01 AT AT86307542T patent/ATE48844T1/de not_active IP Right Cessation
- 1986-10-01 CA CA000519556A patent/CA1293723C/en not_active Expired - Lifetime
- 1986-10-01 ES ES86307542T patent/ES2014234B3/es not_active Expired - Lifetime
- 1986-10-01 CA CA000519557A patent/CA1275411C/en not_active Expired - Lifetime
- 1986-10-01 EP EP86307543A patent/EP0220845A1/en not_active Withdrawn
- 1986-10-13 NO NO864061A patent/NO864061L/no unknown
- 1986-10-13 FI FI864124A patent/FI864124A/fi not_active IP Right Cessation
- 1986-10-13 FI FI864125A patent/FI82050C/fi not_active IP Right Cessation
- 1986-10-13 NO NO864062A patent/NO163776C/no unknown
- 1986-10-15 IL IL80319A patent/IL80319A/xx not_active IP Right Cessation
- 1986-10-16 NZ NZ217958A patent/NZ217958A/xx unknown
- 1986-10-16 IE IE273386A patent/IE59642B1/en not_active IP Right Cessation
- 1986-10-16 PH PH34375A patent/PH22556A/en unknown
- 1986-10-16 NZ NZ217957A patent/NZ217957A/xx unknown
- 1986-10-17 JP JP61247306A patent/JPS62155278A/ja active Pending
- 1986-10-17 AU AU64179/86A patent/AU591937B2/en not_active Ceased
- 1986-10-17 JP JP61247307A patent/JPH0753731B2/ja not_active Expired - Lifetime
- 1986-10-17 PT PT83571A patent/PT83571B/pt unknown
- 1986-10-17 KR KR1019860008728A patent/KR940010034B1/ko not_active IP Right Cessation
- 1986-10-17 PT PT83572A patent/PT83572B/pt not_active IP Right Cessation
- 1986-10-17 AU AU64178/86A patent/AU6417886A/en not_active Abandoned
-
1987
- 1987-10-13 US US07/108,272 patent/US4795749A/en not_active Expired - Fee Related
-
1989
- 1989-02-02 US US07/305,969 patent/US4886797A/en not_active Expired - Fee Related
- 1989-02-02 US US07/305,970 patent/US4880799A/en not_active Expired - Fee Related
-
1990
- 1990-03-01 GR GR90400114T patent/GR3000367T3/el unknown
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