NO813074L - Imidazolderivater. - Google Patents
Imidazolderivater.Info
- Publication number
- NO813074L NO813074L NO813074A NO813074A NO813074L NO 813074 L NO813074 L NO 813074L NO 813074 A NO813074 A NO 813074A NO 813074 A NO813074 A NO 813074A NO 813074 L NO813074 L NO 813074L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- imino
- lower alkyl
- oxide
- methyl
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 65
- -1 hydroxy, methyl Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- CLWRFNUKIFTVHQ-UHFFFAOYSA-N [N].C1=CC=NC=C1 Chemical group [N].C1=CC=NC=C1 CLWRFNUKIFTVHQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005661 deetherification reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- KBVBBBSPBXUVAR-UHFFFAOYSA-N n-(2,3-dichlorophenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound [O-][N+]1=CC=CC=C1CON(CCN1)C1=NC1=CC=CC(Cl)=C1Cl KBVBBBSPBXUVAR-UHFFFAOYSA-N 0.000 claims description 3
- JTKZHEFBOYARLQ-UHFFFAOYSA-N OC1=CC=[N+]([O-])C(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=C1 Chemical compound OC1=CC=[N+]([O-])C(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=C1 JTKZHEFBOYARLQ-UHFFFAOYSA-N 0.000 claims description 2
- NFTZLFMZLWLHHM-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(4-methyl-1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=[N+]([O-])C(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=C1 NFTZLFMZLWLHHM-UHFFFAOYSA-N 0.000 claims description 2
- JNQIPSMWZPNPHZ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(5-methyl-1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound [O-][N+]1=CC(C)=CC=C1CON(CCN1)C1=NC1=C(Cl)C=CC=C1Cl JNQIPSMWZPNPHZ-UHFFFAOYSA-N 0.000 claims description 2
- YANFMRSMXAYQPE-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(6-methyl-1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=[N+]1[O-] YANFMRSMXAYQPE-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
- 238000002844 melting Methods 0.000 description 70
- 230000008018 melting Effects 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- MOAMWFWIEPZLRO-UHFFFAOYSA-N 2-(chloromethyl)-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1CCl MOAMWFWIEPZLRO-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- AGWXBBFKRUVIBC-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=C(Cl)C=CC=C1Cl AGWXBBFKRUVIBC-UHFFFAOYSA-N 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 4
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- RUAMSCROJQFLKO-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound [O-][N+]1=CC=CC=C1CON(CCN1)C1=NC1=C(Cl)C=CC=C1Cl RUAMSCROJQFLKO-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003054 catalyst Substances 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
- 239000008120 corn starch Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229940126601 medicinal product Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 3
- JDZWRQMOGDEJQA-UHFFFAOYSA-N 1,1-dibromo-n-(3,5-dichloro-4-methoxyphenyl)methanimine Chemical compound COC1=C(Cl)C=C(N=C(Br)Br)C=C1Cl JDZWRQMOGDEJQA-UHFFFAOYSA-N 0.000 description 2
- ACCHSVJRZUEVLG-UHFFFAOYSA-N 1,3-dichloro-2-isocyano-5-methoxybenzene Chemical compound COC1=CC(Cl)=C([N+]#[C-])C(Cl)=C1 ACCHSVJRZUEVLG-UHFFFAOYSA-N 0.000 description 2
- OZHQNQWAQJETQG-UHFFFAOYSA-N 1,3-dichloro-2-isothiocyanato-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C(N=C=S)=C1Cl OZHQNQWAQJETQG-UHFFFAOYSA-N 0.000 description 2
- NOHBAFVNPWPORE-UHFFFAOYSA-N 1,3-dichloro-4-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(Cl)C([N+]([O-])=O)=C1Cl NOHBAFVNPWPORE-UHFFFAOYSA-N 0.000 description 2
- HAIBRTRWRXXIDR-UHFFFAOYSA-N 2,6-dichloro-3-methoxyaniline Chemical compound COC1=CC=C(Cl)C(N)=C1Cl HAIBRTRWRXXIDR-UHFFFAOYSA-N 0.000 description 2
- JRQUBDLRTVYZED-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)imino-3-[(5-methoxypyridin-2-yl)methoxy]imidazolidine-1-carbaldehyde Chemical compound N1=CC(OC)=CC=C1CON(CCN1C=O)C1=NC1=C(Cl)C=CC=C1Cl JRQUBDLRTVYZED-UHFFFAOYSA-N 0.000 description 2
- RQUYAAVBWANDBO-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)imino-3-[(6-methylpyridin-2-yl)methoxy]imidazolidine-1-carbaldehyde Chemical compound CC1=CC=CC(CON2C(N(C=O)CC2)=NC=2C(=CC=CC=2Cl)Cl)=N1 RQUYAAVBWANDBO-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LLSXLHOEFSZLRY-UHFFFAOYSA-N 2-[2-(phenylmethoxyamino)ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCNOCC1=CC=CC=C1 LLSXLHOEFSZLRY-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000036592 analgesia Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- ZUYFWHPUNSUGMO-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=CC(Cl)=CC=C1Cl ZUYFWHPUNSUGMO-UHFFFAOYSA-N 0.000 description 1
- AYKFQYBDJZNMIP-UHFFFAOYSA-N n-(2,6-dibromophenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound [O-][N+]1=CC=CC=C1CON(CCN1)C1=NC1=C(Br)C=CC=C1Br AYKFQYBDJZNMIP-UHFFFAOYSA-N 0.000 description 1
- IRPMBIDRAWSLOF-UHFFFAOYSA-N n-(2,6-dichloro-3-methoxyphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C(Cl)C(N=C2N(CCN2)O)=C1Cl IRPMBIDRAWSLOF-UHFFFAOYSA-N 0.000 description 1
- ICIFIZXBOFXDID-UHFFFAOYSA-N n-(2,6-dichloro-3-methoxyphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound COC1=CC=C(Cl)C(N=C2N(CCN2)OCC=2C=CC=CC=2)=C1Cl ICIFIZXBOFXDID-UHFFFAOYSA-N 0.000 description 1
- NVVGXUNPKKXSDG-UHFFFAOYSA-N n-(2,6-dichloro-3-methoxyphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=C(Cl)C(N=C2N(CCN2)OCC=2C=CC=CC=2)=C1Cl NVVGXUNPKKXSDG-UHFFFAOYSA-N 0.000 description 1
- MOUHYWWKXOBQNF-UHFFFAOYSA-N n-(2,6-dichloro-4-methoxyphenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC(OC)=CC(Cl)=C1N=C1N(OCC=2[N+](=CC=CC=2)[O-])CCN1 MOUHYWWKXOBQNF-UHFFFAOYSA-N 0.000 description 1
- CRKFDCVRUYSVQJ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(pyridin-2-ylmethoxy)-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC=2N=CC=CC=2)CCN1 CRKFDCVRUYSVQJ-UHFFFAOYSA-N 0.000 description 1
- QRNNGXDOYHVDIA-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(1-oxidopyridin-1-ium-3-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrochloride Chemical compound Cl.Cl.[O-][N+]1=CC=CC(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=C1 QRNNGXDOYHVDIA-UHFFFAOYSA-N 0.000 description 1
- JLVOGSVUEBWORD-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(3-methoxy-1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrobromide Chemical compound Br.Br.COC1=CC=C[N+]([O-])=C1CON(CCN1)C1=NC1=C(Cl)C=CC=C1Cl JLVOGSVUEBWORD-UHFFFAOYSA-N 0.000 description 1
- NGRZFZNPTLKAGT-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(3-methoxypyridin-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrobromide Chemical compound Br.Br.COC1=CC=CN=C1CON1C(NC=2C(=CC=CC=2Cl)Cl)=NCC1 NGRZFZNPTLKAGT-UHFFFAOYSA-N 0.000 description 1
- SIQASOCFUZHTPL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(5-methoxy-1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrochloride Chemical compound Cl.Cl.[O-][N+]1=CC(OC)=CC=C1CON(CCN1)C1=NC1=C(Cl)C=CC=C1Cl SIQASOCFUZHTPL-UHFFFAOYSA-N 0.000 description 1
- ZMFIMXHNYGZBJV-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-[(6-methylpyridin-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC(CON2C(NCC2)=NC=2C(=CC=CC=2Cl)Cl)=N1 ZMFIMXHNYGZBJV-UHFFFAOYSA-N 0.000 description 1
- VPMQORITTGBKGL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-methyl-3-[(1-oxidopyridin-1-ium-2-yl)methoxy]imidazolidin-2-imine;dihydrochloride Chemical compound Cl.Cl.ClC=1C=CC=C(Cl)C=1N=C1N(C)CCN1OCC1=CC=CC=[N+]1[O-] VPMQORITTGBKGL-UHFFFAOYSA-N 0.000 description 1
- GJTJRMWWLOGXIH-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound ClC1=CC=CC(Cl)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 GJTJRMWWLOGXIH-UHFFFAOYSA-N 0.000 description 1
- JYWMJERMCUTOTJ-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-n-methyl-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.ClC=1C=CC=C(Cl)C=1N(C)C1=NCCN1OCC1=CC=CC=C1 JYWMJERMCUTOTJ-UHFFFAOYSA-N 0.000 description 1
- OPHRDYGFCZBRTI-UHFFFAOYSA-N n-(2,6-diethylphenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine Chemical compound CCC1=CC=CC(CC)=C1N=C1N(OCC=2[N+](=CC=CC=2)[O-])CCN1 OPHRDYGFCZBRTI-UHFFFAOYSA-N 0.000 description 1
- YNAKWJDDMXZXBA-UHFFFAOYSA-N n-(2,6-diethylphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound CCC1=CC=CC(CC)=C1N=C1N(O)CCN1 YNAKWJDDMXZXBA-UHFFFAOYSA-N 0.000 description 1
- CKCJSQITRUNCDK-UHFFFAOYSA-N n-(2,6-difluorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=C(F)C=CC=C1F CKCJSQITRUNCDK-UHFFFAOYSA-N 0.000 description 1
- HXEYBUMHAZKYIU-UHFFFAOYSA-N n-(2,6-difluorophenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine;hydrochloride Chemical compound Cl.FC1=CC=CC(F)=C1N=C1N(OCC=2C=CC=CC=2)CCN1 HXEYBUMHAZKYIU-UHFFFAOYSA-N 0.000 description 1
- ZZLFMERDKNWFCL-UHFFFAOYSA-N n-(2-chloro-5-methoxyphenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrobromide Chemical compound Br.Br.COC1=CC=C(Cl)C(N=C2N(CCN2)OCC=2[N+](=CC=CC=2)[O-])=C1 ZZLFMERDKNWFCL-UHFFFAOYSA-N 0.000 description 1
- SYQQEEJYVDUVKC-UHFFFAOYSA-N n-(2-chloro-5-methoxyphenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound COC1=CC=C(Cl)C(N=C2N(CCN2)O)=C1 SYQQEEJYVDUVKC-UHFFFAOYSA-N 0.000 description 1
- WGKRNXKSIBFMCN-UHFFFAOYSA-N n-(2-chloro-5-methoxyphenyl)-1-phenylmethoxy-4,5-dihydroimidazol-2-amine Chemical compound COC1=CC=C(Cl)C(N=C2N(CCN2)OCC=2C=CC=CC=2)=C1 WGKRNXKSIBFMCN-UHFFFAOYSA-N 0.000 description 1
- VMNHUPFZMJIYBB-UHFFFAOYSA-N n-(2-chlorophenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;hydrobromide Chemical compound Br.[O-][N+]1=CC=CC=C1CON(CCN1)C1=NC1=CC=CC=C1Cl VMNHUPFZMJIYBB-UHFFFAOYSA-N 0.000 description 1
- YSDIAVWNYCLIPC-UHFFFAOYSA-N n-(2-chlorophenyl)-1-hydroxy-4,5-dihydroimidazol-2-amine Chemical compound ON1CCNC1=NC1=CC=CC=C1Cl YSDIAVWNYCLIPC-UHFFFAOYSA-N 0.000 description 1
- LOFXPUURWPFXIS-UHFFFAOYSA-N n-(2-methylphenyl)-1-[(1-oxidopyridin-1-ium-2-yl)methoxy]-4,5-dihydroimidazol-2-amine;dihydrobromide Chemical compound Br.Br.CC1=CC=CC=C1N=C1N(OCC=2[N+](=CC=CC=2)[O-])CCN1 LOFXPUURWPFXIS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003401 opiate antagonist Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 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 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 208000024891 symptom Diseases 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- KNRQKQMCUXJVDY-UHFFFAOYSA-K trimethyl(phenyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)C1=CC=CC=C1.C[N+](C)(C)C1=CC=CC=C1.C[N+](C)(C)C1=CC=CC=C1 KNRQKQMCUXJVDY-UHFFFAOYSA-K 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- GQDDNDAYOVNZPG-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C[C]2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3N=C21 GQDDNDAYOVNZPG-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH679880 | 1980-09-10 | ||
| CH417581 | 1981-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO813074L true NO813074L (no) | 1982-03-11 |
Family
ID=25694852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO813074A NO813074L (no) | 1980-09-10 | 1981-09-09 | Imidazolderivater. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4366160A (es) |
| EP (1) | EP0048363B1 (es) |
| AR (1) | AR229164A1 (es) |
| AU (1) | AU7504281A (es) |
| CA (1) | CA1175434A (es) |
| DE (2) | DE3171582D1 (es) |
| DK (1) | DK393581A (es) |
| ES (2) | ES8206515A1 (es) |
| FI (1) | FI812756L (es) |
| FR (1) | FR2489822A1 (es) |
| GB (1) | GB2083475A (es) |
| IL (1) | IL63742A0 (es) |
| IT (1) | IT1138510B (es) |
| LU (1) | LU83618A1 (es) |
| MC (1) | MC1419A1 (es) |
| NL (1) | NL8103721A (es) |
| NO (1) | NO813074L (es) |
| NZ (1) | NZ198265A (es) |
| PH (1) | PH16887A (es) |
| PT (1) | PT73643B (es) |
| SE (1) | SE8105297L (es) |
| ZW (1) | ZW18881A1 (es) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3236857A (en) * | 1961-10-09 | 1966-02-22 | Boehringer Sohn Ingelheim | 2-(phenyl-amino)-1, 3-diazacyclopentene-(2) substitution products |
| NL123037C (es) | 1963-10-04 | |||
| DE1545628A1 (de) | 1965-10-01 | 1970-06-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von blutdrucksenkend und sedativ wirksamen Derivaten des 2-(2-Halogenanilino)-1,3-diazacyclopentens-(2) |
| DE1670230A1 (de) | 1967-05-26 | 1971-01-21 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von in 2-Stellung substituierten 1,3-Diazacycloalkenen(2) |
| ES352379A1 (es) | 1967-05-26 | 1969-08-01 | Boehringer Sohn Ingelheim | Procedimiento para la preparacion de 1,3-diazaciclopenteno-(2) sustituido en posicion 2. |
| DE1770872A1 (de) | 1968-08-26 | 1972-01-13 | Dresden Arzneimittel | Verfahren zur Herstellung von Imidazolin-2-Derivaten |
| BE721781A (es) | 1968-10-03 | 1969-04-03 | ||
| DE2220906A1 (de) * | 1972-04-28 | 1973-11-15 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2457979A1 (de) | 1974-12-07 | 1976-06-16 | Beiersdorf Ag | 2-n-aryl-hydroxyamino-imidazoline-(2) und verfahren zu deren herstellung |
| DE2709720A1 (de) | 1977-03-05 | 1978-09-07 | Beiersdorf Ag | N-substituierte 2-arylamino-imidazoline-(2), verfahren zu deren herstellung und neue hydroxylamine als zwischenprodukte |
| MTP837B (en) * | 1977-11-07 | 1979-10-22 | Hoffman La Roche And Co Aktien | Derivatives 2 finino-imidazolidire |
| DE2756269A1 (de) * | 1977-12-16 | 1979-06-21 | Bayer Ag | Azolylalkyl-pyridinyl-aether, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1981
- 1981-08-04 CA CA000383138A patent/CA1175434A/en not_active Expired
- 1981-08-05 ZW ZW188/81A patent/ZW18881A1/xx unknown
- 1981-08-06 NL NL8103721A patent/NL8103721A/nl not_active Application Discontinuation
- 1981-08-21 PH PH26079A patent/PH16887A/en unknown
- 1981-08-26 IT IT23655/81A patent/IT1138510B/it active
- 1981-08-26 US US06/296,596 patent/US4366160A/en not_active Expired - Fee Related
- 1981-09-03 EP EP81106900A patent/EP0048363B1/de not_active Expired
- 1981-09-03 NZ NZ198265A patent/NZ198265A/en unknown
- 1981-09-03 DE DE8181106900T patent/DE3171582D1/de not_active Expired
- 1981-09-03 DE DE19813134956 patent/DE3134956A1/de not_active Withdrawn
- 1981-09-04 IL IL63742A patent/IL63742A0/xx unknown
- 1981-09-04 AR AR286648A patent/AR229164A1/es active
- 1981-09-07 MC MC811537A patent/MC1419A1/xx unknown
- 1981-09-07 DK DK393581A patent/DK393581A/da not_active Application Discontinuation
- 1981-09-07 SE SE8105297A patent/SE8105297L/xx not_active Application Discontinuation
- 1981-09-07 FI FI812756A patent/FI812756L/fi not_active Application Discontinuation
- 1981-09-08 AU AU75042/81A patent/AU7504281A/en not_active Abandoned
- 1981-09-08 LU LU83618A patent/LU83618A1/de unknown
- 1981-09-08 FR FR8116998A patent/FR2489822A1/fr active Pending
- 1981-09-09 GB GB8127225A patent/GB2083475A/en not_active Withdrawn
- 1981-09-09 NO NO813074A patent/NO813074L/no unknown
- 1981-09-09 ES ES505322A patent/ES8206515A1/es not_active Expired
- 1981-09-09 PT PT73643A patent/PT73643B/pt unknown
-
1982
- 1982-03-25 ES ES510795A patent/ES8306370A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1138510B (it) | 1986-09-17 |
| US4366160A (en) | 1982-12-28 |
| PT73643B (en) | 1983-10-19 |
| SE8105297L (sv) | 1982-03-11 |
| ES505322A0 (es) | 1982-08-16 |
| MC1419A1 (fr) | 1982-10-18 |
| ES510795A0 (es) | 1983-06-01 |
| ES8206515A1 (es) | 1982-08-16 |
| EP0048363B1 (de) | 1985-07-31 |
| IT8123655A0 (it) | 1981-08-26 |
| FI812756L (fi) | 1982-03-11 |
| ES8306370A1 (es) | 1983-06-01 |
| EP0048363A3 (en) | 1982-05-26 |
| EP0048363A2 (de) | 1982-03-31 |
| CA1175434A (en) | 1984-10-02 |
| GB2083475A (en) | 1982-03-24 |
| ZW18881A1 (en) | 1982-05-05 |
| NZ198265A (en) | 1985-02-28 |
| DE3171582D1 (en) | 1985-09-05 |
| AU7504281A (en) | 1982-03-18 |
| LU83618A1 (de) | 1983-06-08 |
| IL63742A0 (en) | 1981-12-31 |
| NL8103721A (nl) | 1982-04-01 |
| PT73643A (en) | 1981-10-01 |
| DK393581A (da) | 1982-03-11 |
| AR229164A1 (es) | 1983-06-30 |
| PH16887A (en) | 1984-04-02 |
| FR2489822A1 (fr) | 1982-03-12 |
| DE3134956A1 (de) | 1982-04-15 |
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