PL81057B1 - 1,2,2a,3,4,5-hexahydro-1-(2-imidazolin-2-ylamino)-benz(cd)indoles[us3674801a] - Google Patents
1,2,2a,3,4,5-hexahydro-1-(2-imidazolin-2-ylamino)-benz(cd)indoles[us3674801a] Download PDFInfo
- Publication number
- PL81057B1 PL81057B1 PL1970144024A PL14402470A PL81057B1 PL 81057 B1 PL81057 B1 PL 81057B1 PL 1970144024 A PL1970144024 A PL 1970144024A PL 14402470 A PL14402470 A PL 14402470A PL 81057 B1 PL81057 B1 PL 81057B1
- Authority
- PL
- Poland
- Prior art keywords
- hexahydro
- indole
- benz
- mixture
- methyl
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 72
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 29
- -1 2-imidazolin-2-ylamino Chemical group 0.000 claims description 24
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- ICISUXWQUUKZMT-UHFFFAOYSA-N 2,3,3a,4,5,9b-hexahydro-1h-benzo[g]indole Chemical class C1CC2=CC=CC=C2C2C1CCN2 ICISUXWQUUKZMT-UHFFFAOYSA-N 0.000 claims description 2
- LVTLJXBCOWXJOY-UHFFFAOYSA-N N-(4,5-dihydro-1H-imidazol-2-yl)-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound N1C(=NCC1)NN1CC2C=3C(=CC=CC13)CCC2 LVTLJXBCOWXJOY-UHFFFAOYSA-N 0.000 claims description 2
- DXXJWTQVIPIAAW-UHFFFAOYSA-N N-(4,5-dihydro-1H-imidazol-2-yl)-6-methylsulfanyl-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound N1C(=NCC1)NN1CC2C=3C(=C(C=CC13)SC)CCC2 DXXJWTQVIPIAAW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QZCFDMXHASMDAO-UHFFFAOYSA-N N-(4,5-dihydro-1H-imidazol-2-yl)-8-methyl-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound N1C(=NCC1)NN1CC2C=3C(=CC=C(C13)C)CCC2 QZCFDMXHASMDAO-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 58
- 150000001412 amines Chemical class 0.000 abstract description 13
- 230000009467 reduction Effects 0.000 abstract description 10
- 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 abstract description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 abstract description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 abstract description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 abstract description 2
- 229960003147 reserpine Drugs 0.000 abstract description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000699 topical effect Effects 0.000 abstract description 2
- UTCMYCAFVUUNBK-UHFFFAOYSA-N benzo[cd]indole Chemical class C1=CC(C=N2)=C3C2=CC=CC3=C1 UTCMYCAFVUUNBK-UHFFFAOYSA-N 0.000 abstract 2
- OVXDVWVMKICYBN-UHFFFAOYSA-N 1-(2a,3,4,5,5a,6-hexahydro-2H-benzo[cd]indol-1-yl)ethanone Chemical group C(C)(=O)N1CC2C=3C(CC=CC1=3)CCC2 OVXDVWVMKICYBN-UHFFFAOYSA-N 0.000 abstract 1
- FUHUCCZDQAURLS-UHFFFAOYSA-N 1-benzoyl-8-methyl-2,2a,3,4-tetrahydrobenzo[cd]indol-5-one Chemical group C(C1=CC=CC=C1)(=O)N1CC2C=3C(=CC=C(C13)C)C(CC2)=O FUHUCCZDQAURLS-UHFFFAOYSA-N 0.000 abstract 1
- YYXHPIFGGUHJGM-UHFFFAOYSA-N 1-nitroso-2H-benzo[cd]indole Chemical class N(=O)N1CC2=C3C(C=CC=C13)=CC=C2 YYXHPIFGGUHJGM-UHFFFAOYSA-N 0.000 abstract 1
- SSKDVCULXAVNIR-UHFFFAOYSA-N 2-(1-benzoyl-7-methyl-2,3-dihydroindol-3-yl)propanoic acid Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C2=CC=CC(=C12)C)C(C(=O)O)C SSKDVCULXAVNIR-UHFFFAOYSA-N 0.000 abstract 1
- BNEVEZKWKCEQQI-UHFFFAOYSA-N 2-(7-methyl-2,3-dihydro-1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C(C)C2=C1C(C(C)C(O)=O)CN2 BNEVEZKWKCEQQI-UHFFFAOYSA-N 0.000 abstract 1
- KGWPHCDTOLQQEP-UHFFFAOYSA-N 7-methylindole Chemical group CC1=CC=CC2=C1NC=C2 KGWPHCDTOLQQEP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 230000008485 antagonism Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- FHKVFVCJZLNCPU-UHFFFAOYSA-N methyl N'-(2H-benzo[cd]indol-1-yl)carbamimidothioate Chemical class CSC(NN1CC2=C3C(C=CC=C13)=CC=C2)=N FHKVFVCJZLNCPU-UHFFFAOYSA-N 0.000 abstract 1
- 210000004400 mucous membrane Anatomy 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 239000005526 vasoconstrictor agent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 124
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
- 238000009835 boiling Methods 0.000 description 25
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 24
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 10
- 235000010288 sodium nitrite Nutrition 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- DWDLGZNOVBIDAO-UHFFFAOYSA-N 3-(7-methyl-2,3-dihydro-1h-indol-3-yl)propanoic acid Chemical compound CC1=CC=CC2=C1NCC2CCC(O)=O DWDLGZNOVBIDAO-UHFFFAOYSA-N 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 2
- YVTNSFNVZGWNBR-UHFFFAOYSA-N C(C)(=O)N1CC2C=3C(=C(C=CC13)N)CCC2 Chemical compound C(C)(=O)N1CC2C=3C(=C(C=CC13)N)CCC2 YVTNSFNVZGWNBR-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 2
- 238000012360 testing method Methods 0.000 description 2
- MFVFAPQCEUCUSG-UHFFFAOYSA-N 1,2,2a,3,4,5-hexahydrobenzo[cd]indole Chemical compound C1CCC2CNC3=CC=CC1=C32 MFVFAPQCEUCUSG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YFJALWHBKKXHQG-UHFFFAOYSA-N 1-(2a,3,4,5-tetrahydro-2h-benzo[cd]indol-1-yl)ethanone Chemical compound C1CCC2=CC=CC3=C2C1CN3C(=O)C YFJALWHBKKXHQG-UHFFFAOYSA-N 0.000 description 1
- IHDGIKYJRJQLFP-UHFFFAOYSA-N 2-methylsulfanylbenzo[cd]indole Chemical compound C1=CC(C(SC)=N2)=C3C2=CC=CC3=C1 IHDGIKYJRJQLFP-UHFFFAOYSA-N 0.000 description 1
- VKUXHJHFMGQKGQ-UHFFFAOYSA-N 3-(1-benzoyl-7-methyl-2,3-dihydroindol-3-yl)propanoic acid Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C2=CC=CC(=C12)C)CCC(=O)O VKUXHJHFMGQKGQ-UHFFFAOYSA-N 0.000 description 1
- ITGAJZHXKNHAMK-UHFFFAOYSA-N 3-(7-methyl-1h-indol-3-yl)propanoic acid Chemical compound CC1=CC=CC2=C1NC=C2CCC(O)=O ITGAJZHXKNHAMK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XAAKBSKQJMVCFB-UHFFFAOYSA-N 6-chloro-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound NN1CC2C=3C(=C(C=CC13)Cl)CCC2 XAAKBSKQJMVCFB-UHFFFAOYSA-N 0.000 description 1
- YQYOKVANFUXFAL-UHFFFAOYSA-N 6-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound ClC1=C2C=3C(CN(C3C=C1)NC=1NCCN1)CCC2 YQYOKVANFUXFAL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- YDGMXUBYBUHXHX-UHFFFAOYSA-N C(C)(=O)N1CC2C=3C(=C(C=CC13)Cl)CCC2 Chemical compound C(C)(=O)N1CC2C=3C(=C(C=CC13)Cl)CCC2 YDGMXUBYBUHXHX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920006068 Minlon® Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- RDYSLOGGODYGJV-UHFFFAOYSA-N N-(4,5-dihydro-1H-imidazol-2-yl)-6-methyl-2a,3,4,5-tetrahydro-2H-benzo[cd]indol-1-amine Chemical compound N1C(=NCC1)NN1CC2C=3C(=C(C=CC13)C)CCC2 RDYSLOGGODYGJV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1585869A CH517757A (de) | 1969-10-24 | 1969-10-24 | Verfahren zur Herstellung neuer Imidazolin- Verbindungen |
| CH1018270 | 1970-07-06 | ||
| CH1018370A CH528524A (de) | 1970-07-06 | 1970-07-06 | Verfahren zur Herstellung neuer Benz(cd)indol-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81057B1 true PL81057B1 (en) | 1975-08-30 |
Family
ID=27176385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970144024A PL81057B1 (en) | 1969-10-24 | 1970-10-22 | 1,2,2a,3,4,5-hexahydro-1-(2-imidazolin-2-ylamino)-benz(cd)indoles[us3674801a] |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3674801A (https=) |
| JP (1) | JPS4833748B1 (https=) |
| BE (1) | BE757879A (https=) |
| DE (1) | DE2051062A1 (https=) |
| DK (1) | DK126944B (https=) |
| FR (1) | FR2070159B1 (https=) |
| GB (1) | GB1318944A (https=) |
| IL (1) | IL35504A (https=) |
| NL (1) | NL7015541A (https=) |
| NO (1) | NO129523B (https=) |
| PL (1) | PL81057B1 (https=) |
| SE (1) | SE377125B (https=) |
| SU (1) | SU461496A3 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI206974A7 (https=) * | 1973-07-16 | 1975-01-17 | Sandoz Ag | |
| JPS54151990A (en) * | 1978-04-17 | 1979-11-29 | Beiersdorf Ag | Novel condensated nitrogenncontained heterocyclic compound and its manufacture |
| US5302612A (en) * | 1990-02-26 | 1994-04-12 | Eli Lilly And Company | 6-substituted-hexahydrobenz[cd]indoles |
| US5229409A (en) * | 1990-08-15 | 1993-07-20 | Eli Lilly And Company | 6-substituted-tetrahydrobenz[cd]indoles |
| US5244912A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5364856A (en) * | 1991-03-28 | 1994-11-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles |
| US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
| US5648356A (en) * | 1991-03-28 | 1997-07-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[CD]indoles |
-
0
- BE BE757879D patent/BE757879A/xx unknown
-
1970
- 1970-10-05 GB GB4715970A patent/GB1318944A/en not_active Expired
- 1970-10-14 US US80748A patent/US3674801A/en not_active Expired - Lifetime
- 1970-10-15 SU SU1487459A patent/SU461496A3/ru active
- 1970-10-17 DE DE19702051062 patent/DE2051062A1/de active Pending
- 1970-10-21 SE SE7014152A patent/SE377125B/xx unknown
- 1970-10-21 IL IL35504A patent/IL35504A/en unknown
- 1970-10-22 PL PL1970144024A patent/PL81057B1/pl unknown
- 1970-10-22 DK DK539470AA patent/DK126944B/da unknown
- 1970-10-23 FR FR7038325A patent/FR2070159B1/fr not_active Expired
- 1970-10-23 JP JP45093394A patent/JPS4833748B1/ja active Pending
- 1970-10-23 NO NO04013/70A patent/NO129523B/no unknown
- 1970-10-23 NL NL7015541A patent/NL7015541A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL35504A (en) | 1973-10-25 |
| NL7015541A (https=) | 1971-04-27 |
| NO129523B (https=) | 1974-04-22 |
| SU461496A3 (ru) | 1975-02-25 |
| IL35504A0 (en) | 1970-12-24 |
| FR2070159A1 (https=) | 1971-09-10 |
| SE377125B (https=) | 1975-06-23 |
| US3674801A (en) | 1972-07-04 |
| GB1318944A (en) | 1973-05-31 |
| DK126944B (da) | 1973-09-03 |
| BE757879A (fr) | 1971-04-22 |
| DE2051062A1 (de) | 1971-05-06 |
| JPS4833748B1 (https=) | 1973-10-16 |
| FR2070159B1 (https=) | 1973-12-21 |
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