JPH0132225B2 - - Google Patents
Info
- Publication number
- JPH0132225B2 JPH0132225B2 JP51077992A JP7799276A JPH0132225B2 JP H0132225 B2 JPH0132225 B2 JP H0132225B2 JP 51077992 A JP51077992 A JP 51077992A JP 7799276 A JP7799276 A JP 7799276A JP H0132225 B2 JPH0132225 B2 JP H0132225B2
- Authority
- JP
- Japan
- Prior art keywords
- benzazepine
- pyrrolo
- dihydro
- cyano
- dimethylaminopropylidene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 claims description 65
- -1 carboxy, carbamoyl Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 97
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 74
- 239000000243 solution Substances 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
- 238000002844 melting Methods 0.000 description 49
- 230000008018 melting Effects 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 31
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000010992 reflux Methods 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000284 extract Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 229960000583 acetic acid Drugs 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 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 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003039 volatile agent Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000006408 oxalic acid Nutrition 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- VONGYFFEWFJHNP-UHFFFAOYSA-N pyrrolecarboxylic acid methyl ester Natural products COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 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 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- ZVJHKYFQORNKRJ-UHFFFAOYSA-N 11h-pyrrolo[2,1-b][3]benzazepine Chemical compound C1=CC2=CC=CC=C2CC2=CC=CN21 ZVJHKYFQORNKRJ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 208000007101 Muscle Cramp Diseases 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 208000005392 Spasm Diseases 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000003891 oxalate salts Chemical class 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- PLKKXWBJOVTVEU-UHFFFAOYSA-N pyrrolo[2,3-i][1]benzazepine Chemical class C1=CC=NC2=C3C=CN=C3C=CC2=C1 PLKKXWBJOVTVEU-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- UVJURAVPWNZIFR-UHFFFAOYSA-N 11-oxopyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(C#N)=CN21 UVJURAVPWNZIFR-UHFFFAOYSA-N 0.000 description 5
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 208000013403 hyperactivity Diseases 0.000 description 5
- 239000003158 myorelaxant agent Substances 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XYWDPYKBIRQXQS-UHFFFAOYSA-N Diisopropyl sulfide Chemical group CC(C)SC(C)C XYWDPYKBIRQXQS-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000008038 benzoazepines Chemical class 0.000 description 4
- QHACEJBZGFEEJE-UHFFFAOYSA-L bis(trifluoromethylsulfanyl)mercury Chemical compound [Hg+2].FC(F)(F)[S-].FC(F)(F)[S-] QHACEJBZGFEEJE-UHFFFAOYSA-L 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 238000013375 chromatographic separation Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KLLCRUMWQRYULP-UHFFFAOYSA-N methyl 4-cyano-1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C#N)=CN1 KLLCRUMWQRYULP-UHFFFAOYSA-N 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- MVNSDNLKXSKZPJ-UHFFFAOYSA-N pyrrolo[2,1-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=CN21 MVNSDNLKXSKZPJ-UHFFFAOYSA-N 0.000 description 4
- 210000002027 skeletal muscle Anatomy 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000003204 tranquilizing agent Substances 0.000 description 4
- 230000002936 tranquilizing effect Effects 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- RLOSTJFTJFPCOV-UHFFFAOYSA-N 1-(2-chloro-2-phenylethyl)-4-cyanopyrrole-2-carbonyl chloride Chemical compound C=1C=CC=CC=1C(Cl)CN1C=C(C#N)C=C1C(Cl)=O RLOSTJFTJFPCOV-UHFFFAOYSA-N 0.000 description 3
- ZXBHYCRVSIUNAJ-UHFFFAOYSA-N 1-(2-phenylethyl)pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1CCC1=CC=CC=C1 ZXBHYCRVSIUNAJ-UHFFFAOYSA-N 0.000 description 3
- PWJLKYMVJVBEPD-UHFFFAOYSA-N 11-[3-(dimethylamino)propyl]-5,6-dihydropyrrolo[2,1-b][3]benzazepin-11-ol Chemical compound C1CC2=CC=CC=C2C(CCCN(C)C)(O)C2=CC=CN21 PWJLKYMVJVBEPD-UHFFFAOYSA-N 0.000 description 3
- JWBQFKXZFXSLAZ-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbaldehyde Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C=O)=CN21 JWBQFKXZFXSLAZ-UHFFFAOYSA-N 0.000 description 3
- KNGKKWYLKSIFIS-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-9-carbaldehyde Chemical compound C1CN2C=CC=C2C(=O)C2=CC(C=O)=CC=C21 KNGKKWYLKSIFIS-UHFFFAOYSA-N 0.000 description 3
- SCHRRVXSPNLRMS-UHFFFAOYSA-N 3h-pyrrolo[2,1-b][3]benzazepine Chemical compound C1=CN2CC=CC2=CC2=CC=CC=C21 SCHRRVXSPNLRMS-UHFFFAOYSA-N 0.000 description 3
- DBTQJMCUZNZBPA-VOTSOKGWSA-N 4-cyano-1-[(e)-2-phenylethenyl]pyrrole-2-carbonyl chloride Chemical compound ClC(=O)C1=CC(C#N)=CN1\C=C\C1=CC=CC=C1 DBTQJMCUZNZBPA-VOTSOKGWSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 3
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MXLKNLNJTRYHKU-UHFFFAOYSA-N 1-(2-chloro-2-phenylethyl)pyrrole-2-carbonyl chloride Chemical compound C=1C=CC=CC=1C(Cl)CN1C=CC=C1C(Cl)=O MXLKNLNJTRYHKU-UHFFFAOYSA-N 0.000 description 2
- IRTONNFUETYNTE-UHFFFAOYSA-N 1-(2-phenylethenyl)pyrrole Chemical compound C=1C=CC=CC=1C=CN1C=CC=C1 IRTONNFUETYNTE-UHFFFAOYSA-N 0.000 description 2
- WHASPLKNGUEKGD-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbonitrile Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C#N)=CN21 WHASPLKNGUEKGD-UHFFFAOYSA-N 0.000 description 2
- WPVYEXRMHZRXEV-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-9-carbaldehyde Chemical compound C1CC2=CC=C(C=O)C=C2C(=CCCN(C)C)C2=CC=CN21 WPVYEXRMHZRXEV-UHFFFAOYSA-N 0.000 description 2
- ONXFWZYTSMEDPR-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]-5,6-dihydropyrrolo[1,2-c][3]benzazepine-9-carbonitrile Chemical compound C1CC2=CC=C(C#N)C=C2C(=CCCN(C)C)C2=CC=CN21 ONXFWZYTSMEDPR-UHFFFAOYSA-N 0.000 description 2
- DDVNVKNPJUMLOO-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepin-9-amine Chemical compound C1=CC2=CC=C(N)C=C2C(=CCCN(C)C)C2=CC=CN21 DDVNVKNPJUMLOO-UHFFFAOYSA-N 0.000 description 2
- UYRDUBJWJJTYLS-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepine-2-carbaldehyde Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C=O)=CN21 UYRDUBJWJJTYLS-UHFFFAOYSA-N 0.000 description 2
- BJIZXECRDHHTFL-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepine-2-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC(C#N)=CN21 BJIZXECRDHHTFL-UHFFFAOYSA-N 0.000 description 2
- OHGVSQDDCTUFIS-UHFFFAOYSA-N 11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepine-9-carbaldehyde Chemical compound C1=CC2=CC=C(C=O)C=C2C(=CCCN(C)C)C2=CC=CN21 OHGVSQDDCTUFIS-UHFFFAOYSA-N 0.000 description 2
- XDGFSERHJUTNJD-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carbonitrile Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(C#N)=CN21 XDGFSERHJUTNJD-UHFFFAOYSA-N 0.000 description 2
- PSBGNXGVXQKOBH-UHFFFAOYSA-N 11-oxo-5,6-dihydropyrrolo[1,2-c][3]benzazepine-2-carboxylic acid Chemical compound C1CN2C=C(C(=O)O)C=C2C(=O)C2=CC=CC=C21 PSBGNXGVXQKOBH-UHFFFAOYSA-N 0.000 description 2
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59243675A | 1975-07-02 | 1975-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS527996A JPS527996A (en) | 1977-01-21 |
| JPH0132225B2 true JPH0132225B2 (en:Method) | 1989-06-29 |
Family
ID=24370639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51077992A Granted JPS527996A (en) | 1975-07-02 | 1976-07-02 | Pyroro *2*11b* *3** benzazepine |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527996A (en:Method) |
| AU (1) | AU499122B2 (en:Method) |
| BE (1) | BE843678A (en:Method) |
| CA (1) | CA1092105A (en:Method) |
| CH (5) | CH626366A5 (en:Method) |
| CY (1) | CY1091A (en:Method) |
| DE (2) | DE2629877A1 (en:Method) |
| ES (1) | ES449432A1 (en:Method) |
| FR (1) | FR2315935A1 (en:Method) |
| GB (1) | GB1499047A (en:Method) |
| GR (1) | GR60851B (en:Method) |
| HK (1) | HK60580A (en:Method) |
| HU (1) | HU177866B (en:Method) |
| MY (1) | MY8100227A (en:Method) |
| NL (1) | NL188287C (en:Method) |
| PT (1) | PT65295B (en:Method) |
| SE (1) | SE424076B (en:Method) |
| ZA (1) | ZA763990B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148903A (en) * | 1977-07-28 | 1979-04-10 | Merck & Co., Inc. | Antipsychotic, antiserotonin and antihistaminic pyrrolo[2,1-b][3]benzazepines |
| JPH0487401U (en:Method) * | 1990-12-06 | 1992-07-29 | ||
| US6271392B1 (en) | 1994-10-07 | 2001-08-07 | Rhone-Poulenc Inc. | Intermediates useful for the synthesis of 1-arylpyrrole pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428677A (en) * | 1962-09-24 | 1969-02-18 | Merck & Co Inc | Chemical compounds and methods of preparing same |
| US3499037A (en) * | 1966-05-31 | 1970-03-03 | Merck & Co Inc | Preparation of trifluoromethyl substituted dibenzocycloheptenes |
-
1976
- 1976-06-30 PT PT65295A patent/PT65295B/pt unknown
- 1976-06-30 CA CA256,080A patent/CA1092105A/en not_active Expired
- 1976-06-30 FR FR7619897A patent/FR2315935A1/fr active Granted
- 1976-07-01 SE SE7607534A patent/SE424076B/xx not_active IP Right Cessation
- 1976-07-01 CH CH844376A patent/CH626366A5/de not_active IP Right Cessation
- 1976-07-01 ES ES449432A patent/ES449432A1/es not_active Expired
- 1976-07-01 GB GB27487/76A patent/GB1499047A/en not_active Expired
- 1976-07-01 AU AU15488/76A patent/AU499122B2/en not_active Expired
- 1976-07-01 BE BE168549A patent/BE843678A/xx not_active IP Right Cessation
- 1976-07-01 GR GR51162A patent/GR60851B/el unknown
- 1976-07-01 CY CY1091A patent/CY1091A/xx unknown
- 1976-07-02 ZA ZA00763990A patent/ZA763990B/xx unknown
- 1976-07-02 JP JP51077992A patent/JPS527996A/ja active Granted
- 1976-07-02 DE DE19762629877 patent/DE2629877A1/de active Granted
- 1976-07-02 HU HU76ME2001A patent/HU177866B/hu unknown
- 1976-07-02 DE DE2661014A patent/DE2661014C2/de not_active Expired
- 1976-07-02 NL NLAANVRAGE7607347,A patent/NL188287C/xx not_active IP Right Cessation
-
1980
- 1980-05-16 CH CH386280A patent/CH626618A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386080A patent/CH626616A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386180A patent/CH626617A5/de not_active IP Right Cessation
- 1980-05-16 CH CH385980A patent/CH626893A5/de not_active IP Right Cessation
- 1980-10-30 HK HK605/80A patent/HK60580A/xx unknown
-
1981
- 1981-12-30 MY MY227/81A patent/MY8100227A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1091A (en) | 1980-12-27 |
| SE7607534L (sv) | 1977-01-03 |
| JPS527996A (en) | 1977-01-21 |
| PT65295A (en) | 1976-07-01 |
| SE424076B (sv) | 1982-06-28 |
| NL188287C (nl) | 1992-05-18 |
| HU177866B (en) | 1982-01-28 |
| NL7607347A (nl) | 1977-01-04 |
| DE2661014A1 (en:Method) | 1985-07-04 |
| FR2315935B1 (en:Method) | 1978-11-17 |
| DE2629877C2 (en:Method) | 1989-01-05 |
| FR2315935A1 (fr) | 1977-01-28 |
| GR60851B (en) | 1978-08-31 |
| CA1092105A (en) | 1980-12-23 |
| ZA763990B (en) | 1978-02-22 |
| HK60580A (en) | 1980-11-07 |
| PT65295B (en) | 1978-05-10 |
| MY8100227A (en) | 1981-12-31 |
| DE2629877A1 (de) | 1977-01-20 |
| CH626893A5 (en) | 1981-12-15 |
| AU499122B2 (en) | 1979-04-05 |
| CH626616A5 (en) | 1981-11-30 |
| NL188287B (nl) | 1991-12-16 |
| AU1548876A (en) | 1978-01-05 |
| DE2661014C2 (en:Method) | 1989-01-05 |
| CH626618A5 (en) | 1981-11-30 |
| CH626617A5 (en) | 1981-11-30 |
| CH626366A5 (en) | 1981-11-13 |
| BE843678A (fr) | 1977-01-03 |
| GB1499047A (en) | 1978-01-25 |
| ES449432A1 (es) | 1977-12-16 |
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