DE2629877A1 - Pyrrolo eckige klammer auf 2,1-b eckige klammer zu eckige klammer auf 3 eckige klammer zu benzazepine - Google Patents
Pyrrolo eckige klammer auf 2,1-b eckige klammer zu eckige klammer auf 3 eckige klammer zu benzazepineInfo
- Publication number
- DE2629877A1 DE2629877A1 DE19762629877 DE2629877A DE2629877A1 DE 2629877 A1 DE2629877 A1 DE 2629877A1 DE 19762629877 DE19762629877 DE 19762629877 DE 2629877 A DE2629877 A DE 2629877A DE 2629877 A1 DE2629877 A1 DE 2629877A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- alkyl
- pyrrolo
- perhalo
- hydrogen atom
- 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.)
- Granted
Links
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 title description 4
- -1 1-piperidyl Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 36
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 13
- 235000019253 formic acid Nutrition 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229910000838 Al alloy Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 229910000990 Ni alloy Inorganic materials 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000020335 dealkylation Effects 0.000 claims 1
- 238000006900 dealkylation reaction Methods 0.000 claims 1
- 239000005022 packaging material Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 113
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- 239000000203 mixture Substances 0.000 description 80
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 125000001246 bromo group Chemical group Br* 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- 238000001704 evaporation Methods 0.000 description 25
- 239000000284 extract Substances 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 24
- 235000011152 sodium sulphate Nutrition 0.000 description 24
- 230000008020 evaporation Effects 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- YGLDQFWPUCURIP-UHFFFAOYSA-N 3h-3-benzazepine Chemical compound C1=CNC=CC2=CC=CC=C21 YGLDQFWPUCURIP-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 235000006408 oxalic acid Nutrition 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- VONGYFFEWFJHNP-UHFFFAOYSA-N methyl 1h-pyrrole-2-carboxylate Chemical compound COC(=O)C1=CC=CN1 VONGYFFEWFJHNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XYWDPYKBIRQXQS-UHFFFAOYSA-N Diisopropyl sulfide Chemical compound CC(C)SC(C)C XYWDPYKBIRQXQS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- QHACEJBZGFEEJE-UHFFFAOYSA-L bis(trifluoromethylsulfanyl)mercury Chemical compound [Hg+2].FC(F)(F)[S-].FC(F)(F)[S-] QHACEJBZGFEEJE-UHFFFAOYSA-L 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 208000007101 Muscle Cramp Diseases 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 208000013403 hyperactivity Diseases 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 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 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WFEMZZIWWBHTKO-UHFFFAOYSA-N 5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CN21 WFEMZZIWWBHTKO-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 239000003158 myorelaxant agent Substances 0.000 description 4
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 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 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 208000008238 Muscle Spasticity Diseases 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 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 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 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 3
- 238000000926 separation method Methods 0.000 description 3
- 229940125706 skeletal muscle relaxant agent Drugs 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 208000018198 spasticity Diseases 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 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
- 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
- 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
- FGGAASXIAPOHHG-UHFFFAOYSA-N 2-pentanoylpyrrolo[2,1-b][3]benzazepin-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(C(=O)CCCC)=CN21 FGGAASXIAPOHHG-UHFFFAOYSA-N 0.000 description 2
- KRBHNLFMZDOLGK-UHFFFAOYSA-N 4-cyano-1-(2-phenylethyl)pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1CCC1=CC=CC=C1 KRBHNLFMZDOLGK-UHFFFAOYSA-N 0.000 description 2
- VPXXZDSCPQEDGD-VOTSOKGWSA-N 4-cyano-1-[(e)-2-phenylethenyl]pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1\C=C\C1=CC=CC=C1 VPXXZDSCPQEDGD-VOTSOKGWSA-N 0.000 description 2
- SAEZQFNKTQKVSM-UHFFFAOYSA-N 4-cyano-1h-pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC(C#N)=CN1 SAEZQFNKTQKVSM-UHFFFAOYSA-N 0.000 description 2
- YXRLPVJSSFLHNN-UHFFFAOYSA-N 9-amino-5,6-dihydropyrrolo[1,2-c][3]benzazepin-11-one Chemical compound C1CN2C=CC=C2C(=O)C2=CC(N)=CC=C21 YXRLPVJSSFLHNN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
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- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
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- 239000012259 ether extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DNPVFFXTLHXSKX-UHFFFAOYSA-N ethyl n-[11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepin-9-yl]carbamate Chemical compound C1=CN2C=CC=C2C(=CCCN(C)C)C2=CC(NC(=O)OCC)=CC=C21 DNPVFFXTLHXSKX-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 150000004795 grignard reagents Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- LKPMWMYULCMFBX-UHFFFAOYSA-N methyl 4-cyano-1-phenacylpyrrole-2-carboxylate Chemical compound COC(=O)C1=CC(C#N)=CN1CC(=O)C1=CC=CC=C1 LKPMWMYULCMFBX-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
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- 229940035363 muscle relaxants Drugs 0.000 description 1
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- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- ZAPVAUYFFBWFEV-UHFFFAOYSA-N n-[11-[3-(dimethylamino)propylidene]pyrrolo[2,1-b][3]benzazepin-9-yl]acetamide Chemical compound C1=CC2=CC=C(NC(C)=O)C=C2C(=CCCN(C)C)C2=CC=CN21 ZAPVAUYFFBWFEV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- 229960002601 protriptyline Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- VITRLXDSBBVNCZ-UHFFFAOYSA-K trichloroiron;hydrate Chemical compound O.Cl[Fe](Cl)Cl VITRLXDSBBVNCZ-UHFFFAOYSA-K 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
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)
- Anesthesiology (AREA)
- Psychiatry (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 |
|---|---|
| DE2629877A1 true DE2629877A1 (de) | 1977-01-20 |
| DE2629877C2 DE2629877C2 (forum.php) | 1989-01-05 |
Family
ID=24370639
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2661014A Expired DE2661014C2 (forum.php) | 1975-07-02 | 1976-07-02 | |
| DE19762629877 Granted DE2629877A1 (de) | 1975-07-02 | 1976-07-02 | Pyrrolo eckige klammer auf 2,1-b eckige klammer zu eckige klammer auf 3 eckige klammer zu benzazepine |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2661014A Expired DE2661014C2 (forum.php) | 1975-07-02 | 1976-07-02 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS527996A (forum.php) |
| AU (1) | AU499122B2 (forum.php) |
| BE (1) | BE843678A (forum.php) |
| CA (1) | CA1092105A (forum.php) |
| CH (5) | CH626366A5 (forum.php) |
| CY (1) | CY1091A (forum.php) |
| DE (2) | DE2661014C2 (forum.php) |
| ES (1) | ES449432A1 (forum.php) |
| FR (1) | FR2315935A1 (forum.php) |
| GB (1) | GB1499047A (forum.php) |
| GR (1) | GR60851B (forum.php) |
| HK (1) | HK60580A (forum.php) |
| HU (1) | HU177866B (forum.php) |
| MY (1) | MY8100227A (forum.php) |
| NL (1) | NL188287C (forum.php) |
| PT (1) | PT65295B (forum.php) |
| SE (1) | SE424076B (forum.php) |
| ZA (1) | ZA763990B (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0708090A1 (en) | 1994-10-07 | 1996-04-24 | Rhone-Poulenc Agrochimie | Intermediates useful for the synthesis of pesticides |
Families Citing this family (2)
| 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 (forum.php) * | 1990-12-06 | 1992-07-29 |
Citations (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 ES ES449432A patent/ES449432A1/es not_active Expired
- 1976-07-01 AU AU15488/76A patent/AU499122B2/en not_active Expired
- 1976-07-01 GR GR51162A patent/GR60851B/el unknown
- 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 CY CY1091A patent/CY1091A/xx unknown
- 1976-07-01 GB GB27487/76A patent/GB1499047A/en not_active Expired
- 1976-07-01 BE BE168549A patent/BE843678A/xx not_active IP Right Cessation
- 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
- 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
-
1980
- 1980-05-16 CH CH386080A patent/CH626616A5/de not_active IP Right Cessation
- 1980-05-16 CH CH385980A patent/CH626893A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386280A patent/CH626618A5/de not_active IP Right Cessation
- 1980-05-16 CH CH386180A patent/CH626617A5/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
Patent Citations (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 |
Non-Patent Citations (5)
| Title |
|---|
| CA 54 (1960), Spalte 9888f * |
| CA 54, 1960, Sp. 9888 f |
| CA 70 (1969), Ref. 77667a * |
| CA 71 (1969), Ref. 91169s * |
| CA 79 (1973), Ref. 42570x * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0708090A1 (en) | 1994-10-07 | 1996-04-24 | Rhone-Poulenc Agrochimie | Intermediates useful for the synthesis of pesticides |
| US6271392B1 (en) | 1994-10-07 | 2001-08-07 | Rhone-Poulenc Inc. | Intermediates useful for the synthesis of 1-arylpyrrole pesticides |
Also Published As
| Publication number | Publication date |
|---|---|
| HK60580A (en) | 1980-11-07 |
| SE424076B (sv) | 1982-06-28 |
| NL188287B (nl) | 1991-12-16 |
| NL7607347A (nl) | 1977-01-04 |
| CH626618A5 (en) | 1981-11-30 |
| AU1548876A (en) | 1978-01-05 |
| CA1092105A (en) | 1980-12-23 |
| FR2315935A1 (fr) | 1977-01-28 |
| GB1499047A (en) | 1978-01-25 |
| HU177866B (en) | 1982-01-28 |
| SE7607534L (sv) | 1977-01-03 |
| CH626617A5 (en) | 1981-11-30 |
| DE2661014A1 (forum.php) | 1985-07-04 |
| PT65295A (en) | 1976-07-01 |
| CH626366A5 (en) | 1981-11-13 |
| GR60851B (en) | 1978-08-31 |
| DE2629877C2 (forum.php) | 1989-01-05 |
| JPH0132225B2 (forum.php) | 1989-06-29 |
| PT65295B (en) | 1978-05-10 |
| ES449432A1 (es) | 1977-12-16 |
| CY1091A (en) | 1980-12-27 |
| NL188287C (nl) | 1992-05-18 |
| JPS527996A (en) | 1977-01-21 |
| BE843678A (fr) | 1977-01-03 |
| MY8100227A (en) | 1981-12-31 |
| FR2315935B1 (forum.php) | 1978-11-17 |
| CH626616A5 (en) | 1981-11-30 |
| DE2661014C2 (forum.php) | 1989-01-05 |
| AU499122B2 (en) | 1979-04-05 |
| ZA763990B (en) | 1978-02-22 |
| CH626893A5 (en) | 1981-12-15 |
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