NO811671L - Benzazepinderivater. - Google Patents
Benzazepinderivater.Info
- Publication number
- NO811671L NO811671L NO811671A NO811671A NO811671L NO 811671 L NO811671 L NO 811671L NO 811671 A NO811671 A NO 811671A NO 811671 A NO811671 A NO 811671A NO 811671 L NO811671 L NO 811671L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- chloro
- formula
- chlorine
- benzazepine
- Prior art date
Links
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000000460 chlorine Chemical group 0.000 claims abstract description 25
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052794 bromium Chemical group 0.000 claims abstract description 19
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 239000011737 fluorine Chemical group 0.000 claims abstract description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000005123 3H-2-benzazepines Chemical class 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 37
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000005544 phthalimido group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- MMAZIPBCTHYOBH-UHFFFAOYSA-N 8-chloro-2-oxido-1-phenyl-3h-2-benzazepin-2-ium Chemical compound C12=CC(Cl)=CC=C2C=CC[N+]([O-])=C1C1=CC=CC=C1 MMAZIPBCTHYOBH-UHFFFAOYSA-N 0.000 claims description 5
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 5
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000002940 palladium Chemical class 0.000 claims description 3
- UJTZKEOOWSWGHU-UHFFFAOYSA-N 3-(8-chloro-1-phenyl-3h-2-benzazepin-5-yl)prop-2-yn-1-amine Chemical compound C12=CC(Cl)=CC=C2C(C#CCN)=CCN=C1C1=CC=CC=C1 UJTZKEOOWSWGHU-UHFFFAOYSA-N 0.000 claims description 2
- CXNFCUKSQIJUEO-UHFFFAOYSA-N 3-[8-chloro-1-(2-fluorophenyl)-3h-2-benzazepin-5-yl]prop-2-yn-1-amine Chemical compound C12=CC(Cl)=CC=C2C(C#CCN)=CCN=C1C1=CC=CC=C1F CXNFCUKSQIJUEO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- DYZHOSWEDZDNCK-UHFFFAOYSA-N 3-[8-chloro-1-(2-fluorophenyl)-3h-2-benzazepin-5-yl]-n,n-dimethylprop-2-yn-1-amine Chemical compound C12=CC(Cl)=CC=C2C(C#CCN(C)C)=CCN=C1C1=CC=CC=C1F DYZHOSWEDZDNCK-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000001430 anti-depressive effect Effects 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- GFXAUMBEMYXIPK-UHFFFAOYSA-N 4,5-dihydro-3h-2-benzazepine Chemical class C1CCN=CC2=CC=CC=C21 GFXAUMBEMYXIPK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000049 anti-anxiety effect Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 230000002040 relaxant effect Effects 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 207
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 170
- 239000000203 mixture Substances 0.000 description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- 238000001953 recrystallisation Methods 0.000 description 32
- 239000007787 solid Substances 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000003480 eluent Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000012467 final product Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- MPXCXAKEUVBVIE-UHFFFAOYSA-N 2-[3-(2-benzoyl-4-chlorophenyl)prop-2-ynyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(C#CCN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 MPXCXAKEUVBVIE-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- AQDOLAWKRIYYAT-UHFFFAOYSA-N (5-chloro-2-iodophenyl)-phenylmethanone Chemical compound ClC1=CC=C(I)C(C(=O)C=2C=CC=CC=2)=C1 AQDOLAWKRIYYAT-UHFFFAOYSA-N 0.000 description 5
- LNSQAJGEVZJVJA-UHFFFAOYSA-N 5-bromo-8-chloro-1-phenyl-3h-2-benzazepine Chemical compound C=1C(Cl)=CC=C(C(=CCN=2)Br)C=1C=2C1=CC=CC=C1 LNSQAJGEVZJVJA-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- YDUKXANHBVTTJW-UHFFFAOYSA-N [2-(3-aminoprop-1-ynyl)-5-chlorophenyl]-phenylmethanone Chemical compound NCC#CC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 YDUKXANHBVTTJW-UHFFFAOYSA-N 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- ZCFKAMQTTUUNBY-UHFFFAOYSA-N 2-[3-[4-chloro-2-(2-fluorobenzoyl)phenyl]prop-2-ynyl]isoindole-1,3-dione Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1C#CCN1C(=O)C2=CC=CC=C2C1=O ZCFKAMQTTUUNBY-UHFFFAOYSA-N 0.000 description 4
- RGBONZYGHPARAC-UHFFFAOYSA-N 4-prop-2-ynylisoindole-1,3-dione Chemical compound C1=CC=C(CC#C)C2=C1C(=O)NC2=O RGBONZYGHPARAC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000004992 fission Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 229960004801 imipramine Drugs 0.000 description 4
- ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- JIZUQBOBEOPLRI-UHFFFAOYSA-N 2-[3-(2-benzoyl-4-chlorophenyl)prop-2-enyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(C=CCN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 JIZUQBOBEOPLRI-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- OKPBOBHXVKAQSG-UHFFFAOYSA-N 4,5-dibromo-8-chloro-1-(2-chlorophenyl)-4,5-dihydro-3h-2-benzazepine Chemical compound C12=CC(Cl)=CC=C2C(Br)C(Br)CN=C1C1=CC=CC=C1Cl OKPBOBHXVKAQSG-UHFFFAOYSA-N 0.000 description 3
- ZSTQDXRDUODDGA-UHFFFAOYSA-N 5-bromo-8-chloro-1-phenyl-3h-2-benzazepine;hydrochloride Chemical compound Cl.C=1C(Cl)=CC=C(C(=CCN=2)Br)C=1C=2C1=CC=CC=C1 ZSTQDXRDUODDGA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- SRRJQZXMKVFJKL-UHFFFAOYSA-N [2-(3-aminoprop-1-ynyl)phenyl]-(2-chlorophenyl)methanone Chemical compound NCC#CC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl SRRJQZXMKVFJKL-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002920 convulsive effect Effects 0.000 description 3
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- ZSYPPOBHGIGJOD-UHFFFAOYSA-N (2-chlorophenyl)-(2-iodophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1I ZSYPPOBHGIGJOD-UHFFFAOYSA-N 0.000 description 2
- MEIFVWINIHKENC-UHFFFAOYSA-N (2-iodophenyl)-phenylmethanone Chemical compound IC1=CC=CC=C1C(=O)C1=CC=CC=C1 MEIFVWINIHKENC-UHFFFAOYSA-N 0.000 description 2
- 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
- GHDUWHHOYQOLEI-UHFFFAOYSA-N (5-chloro-2-iodophenyl)-(2-fluorophenyl)methanone Chemical compound FC1=CC=CC=C1C(=O)C1=CC(Cl)=CC=C1I GHDUWHHOYQOLEI-UHFFFAOYSA-N 0.000 description 2
- CHEJRHVSNMAUCH-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-oxido-3h-2-benzazepin-2-ium Chemical compound C12=CC=CC=C2C=CC[N+]([O-])=C1C1=CC=CC=C1Cl CHEJRHVSNMAUCH-UHFFFAOYSA-N 0.000 description 2
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- GHUURDQYRGVEHX-UHFFFAOYSA-N prop-1-ynylbenzene Chemical compound CC#CC1=CC=CC=C1 GHUURDQYRGVEHX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15050880A | 1980-05-16 | 1980-05-16 | |
| US25157981A | 1981-04-06 | 1981-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811671L true NO811671L (no) | 1981-11-17 |
Family
ID=26847744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811671A NO811671L (no) | 1980-05-16 | 1981-05-15 | Benzazepinderivater. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0041627B1 (es) |
| AR (2) | AR228355A1 (es) |
| AU (1) | AU542482B2 (es) |
| CA (1) | CA1157856A (es) |
| DE (1) | DE3165365D1 (es) |
| DK (1) | DK216581A (es) |
| ES (2) | ES502211A0 (es) |
| FI (1) | FI811489L (es) |
| HU (1) | HU184957B (es) |
| IE (1) | IE51286B1 (es) |
| IL (1) | IL62872A (es) |
| MC (1) | MC1388A1 (es) |
| NO (1) | NO811671L (es) |
| NZ (1) | NZ197103A (es) |
| PT (1) | PT73047B (es) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4022800A (en) * | 1974-06-03 | 1977-05-10 | Ciba-Geigy Corporation | 2-Pyrazolyl-benzophenones |
| ZA786230B (en) * | 1977-12-21 | 1979-10-31 | Smithkline Corp | 8 and/or 9 substituted 2-benzazepine compounds |
| NZ192775A (en) * | 1979-02-07 | 1982-12-07 | Hoffmann La Roche | Preparation of 1-phenyl-3,4-dihydro-5h-2-benzazepin-5-ones and precursors therein |
-
1981
- 1981-05-12 DE DE8181103659T patent/DE3165365D1/de not_active Expired
- 1981-05-12 EP EP81103659A patent/EP0041627B1/de not_active Expired
- 1981-05-14 IL IL62872A patent/IL62872A/xx unknown
- 1981-05-14 FI FI811489A patent/FI811489L/fi not_active Application Discontinuation
- 1981-05-14 DK DK216581A patent/DK216581A/da not_active Application Discontinuation
- 1981-05-14 CA CA000377541A patent/CA1157856A/en not_active Expired
- 1981-05-14 ES ES502211A patent/ES502211A0/es active Granted
- 1981-05-14 NZ NZ197103A patent/NZ197103A/en unknown
- 1981-05-15 MC MC811514A patent/MC1388A1/xx unknown
- 1981-05-15 PT PT73047A patent/PT73047B/pt unknown
- 1981-05-15 HU HU811359A patent/HU184957B/hu unknown
- 1981-05-15 IE IE1095/81A patent/IE51286B1/en unknown
- 1981-05-15 AU AU70639/81A patent/AU542482B2/en not_active Ceased
- 1981-05-15 AR AR285347A patent/AR228355A1/es active
- 1981-05-15 NO NO811671A patent/NO811671L/no unknown
-
1982
- 1982-03-01 ES ES510003A patent/ES8304938A1/es not_active Expired
- 1982-04-12 AR AR289063A patent/AR230627A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| IE51286B1 (en) | 1986-11-26 |
| AR230627A1 (es) | 1984-05-31 |
| HU184957B (en) | 1984-11-28 |
| AU7063981A (en) | 1981-11-19 |
| DK216581A (da) | 1981-11-17 |
| IL62872A0 (en) | 1981-07-31 |
| DE3165365D1 (en) | 1984-09-13 |
| AU542482B2 (en) | 1985-02-21 |
| ES8302663A1 (es) | 1983-02-01 |
| NZ197103A (en) | 1984-07-31 |
| MC1388A1 (fr) | 1982-04-27 |
| ES510003A0 (es) | 1983-04-01 |
| IL62872A (en) | 1984-10-31 |
| ES8304938A1 (es) | 1983-04-01 |
| AR228355A1 (es) | 1983-02-28 |
| PT73047A (en) | 1981-06-01 |
| EP0041627B1 (de) | 1984-08-08 |
| EP0041627A2 (de) | 1981-12-16 |
| IE811095L (en) | 1981-11-16 |
| CA1157856A (en) | 1983-11-29 |
| ES502211A0 (es) | 1983-02-01 |
| EP0041627A3 (en) | 1982-02-24 |
| FI811489L (fi) | 1981-11-17 |
| PT73047B (en) | 1983-04-29 |
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