CH622792A5 - - Google Patents
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- Publication number
- CH622792A5 CH622792A5 CH1599475A CH1599475A CH622792A5 CH 622792 A5 CH622792 A5 CH 622792A5 CH 1599475 A CH1599475 A CH 1599475A CH 1599475 A CH1599475 A CH 1599475A CH 622792 A5 CH622792 A5 CH 622792A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- radical
- formula
- alkyl
- component
- Prior art date
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- -1 alkyl radical Chemical class 0.000 claims description 135
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 231100000252 nontoxic Toxicity 0.000 claims description 13
- 230000003000 nontoxic effect Effects 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 5
- 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 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 239000002262 Schiff base Substances 0.000 claims description 2
- 150000004753 Schiff bases Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002081 enamines Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 35
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000935 antidepressant agent Substances 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WKULXSQWEYBIOG-UHFFFAOYSA-N 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholine Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CC1CNCCO1 WKULXSQWEYBIOG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- DXLIEDFAJMIORI-UHFFFAOYSA-N 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)-4-(2-methylpropyl)morpholine Chemical compound C1N(CC(C)C)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 DXLIEDFAJMIORI-UHFFFAOYSA-N 0.000 description 2
- UHUDXXGZXPDPTD-UHFFFAOYSA-N 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)-4-ethylmorpholine Chemical compound C1N(CC)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 UHUDXXGZXPDPTD-UHFFFAOYSA-N 0.000 description 2
- ROOCBJKEADQQIM-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)morpholine Chemical compound C12=CC=CC=C2C=CC2=CC=CC=C2N1CC1CNCCO1 ROOCBJKEADQQIM-UHFFFAOYSA-N 0.000 description 2
- HTGVMMRLONLRPK-UHFFFAOYSA-N 2-[(2-ethyl-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]-4-methylmorpholine Chemical compound C12=CC(CC)=CC=C2CCC2=CC=CC=C2N1CC1CN(C)CCO1 HTGVMMRLONLRPK-UHFFFAOYSA-N 0.000 description 2
- NGZAOXLFHKCEOI-UHFFFAOYSA-N 2-[(2-ethyl-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(CC)=CC=C2CCC2=CC=CC=C2N1CC1CNCCO1 NGZAOXLFHKCEOI-UHFFFAOYSA-N 0.000 description 2
- KQAYQQSNRBHUCQ-UHFFFAOYSA-N 2-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholin-4-yl]ethanol Chemical compound C1N(CCO)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 KQAYQQSNRBHUCQ-UHFFFAOYSA-N 0.000 description 2
- FBLGRLFNLCIMSV-UHFFFAOYSA-N 4-benzyl-2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholine Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 FBLGRLFNLCIMSV-UHFFFAOYSA-N 0.000 description 2
- NJPYPZKMCLREQP-UHFFFAOYSA-N 4-benzyl-6-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholin-3-one Chemical compound O=C1COC(CN2C3=CC=CC=C3CCC3=CC=CC=C32)CN1CC1=CC=CC=C1 NJPYPZKMCLREQP-UHFFFAOYSA-N 0.000 description 2
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- HKVMPMPKDBEBNS-UHFFFAOYSA-N 1-(benzylamino)-3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propan-2-ol Chemical compound C12=CC=CC=C2CCC2=CC=CC=C2N1CC(O)CNCC1=CC=CC=C1 HKVMPMPKDBEBNS-UHFFFAOYSA-N 0.000 description 1
- SOLSOWLPTBIRMO-UHFFFAOYSA-N 1-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholin-4-yl]ethanone Chemical compound C1N(C(=O)C)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 SOLSOWLPTBIRMO-UHFFFAOYSA-N 0.000 description 1
- WQMWGXBJFYSUJA-UHFFFAOYSA-N 1-[2-(benzo[b][1]benzazepin-11-ylmethyl)morpholin-4-yl]ethanone Chemical compound C1N(C(=O)C)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 WQMWGXBJFYSUJA-UHFFFAOYSA-N 0.000 description 1
- JSUAJTLKVREZHV-UHFFFAOYSA-N 1-[4-(1-pyrrolidinyl)but-2-ynyl]pyrrolidine Chemical compound C1CCCN1CC#CCN1CCCC1 JSUAJTLKVREZHV-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- GOIWZZQXWJVDOG-UHFFFAOYSA-N 2,2,2-trifluoroethyl trichloromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(Cl)(Cl)Cl GOIWZZQXWJVDOG-UHFFFAOYSA-N 0.000 description 1
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 description 1
- KTICDWYHOWWALA-UHFFFAOYSA-N 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)-4-methylmorpholine Chemical compound C1N(C)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 KTICDWYHOWWALA-UHFFFAOYSA-N 0.000 description 1
- UACNFGYIMGTVPW-UHFFFAOYSA-N 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)-4-propan-2-ylmorpholine Chemical compound C1N(C(C)C)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 UACNFGYIMGTVPW-UHFFFAOYSA-N 0.000 description 1
- RVIJHJXBVPEKKI-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-3-methylmorpholine Chemical compound CC1NCCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 RVIJHJXBVPEKKI-UHFFFAOYSA-N 0.000 description 1
- WQZFGHZUBQLXGW-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-(2,2,2-trifluoroethyl)morpholine Chemical compound C1N(CC(F)(F)F)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 WQZFGHZUBQLXGW-UHFFFAOYSA-N 0.000 description 1
- ZRUUNYNWFSGUOL-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-(cyclopropylmethyl)morpholine Chemical compound C1COC(CN2C3=CC=CC=C3C=CC3=CC=CC=C32)CN1CC1CC1 ZRUUNYNWFSGUOL-UHFFFAOYSA-N 0.000 description 1
- HZKRQCDULCACFU-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-(trifluoromethyl)morpholine Chemical compound C1N(C(F)(F)F)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 HZKRQCDULCACFU-UHFFFAOYSA-N 0.000 description 1
- YIQVHNWFTXVYIL-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-benzylmorpholine Chemical compound C12=CC=CC=C2C=CC2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 YIQVHNWFTXVYIL-UHFFFAOYSA-N 0.000 description 1
- ZPYNNPPFKZKNAD-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-ethylmorpholine Chemical compound C1N(CC)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 ZPYNNPPFKZKNAD-UHFFFAOYSA-N 0.000 description 1
- FIIYVVYKTFXDKC-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-prop-2-ynylmorpholine Chemical compound C1N(CC#C)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 FIIYVVYKTFXDKC-UHFFFAOYSA-N 0.000 description 1
- QIWRPYBOTIADLA-UHFFFAOYSA-N 2-(benzo[b][1]benzazepin-11-ylmethyl)-4-propan-2-ylmorpholine Chemical compound C1N(C(C)C)CCOC1CN1C2=CC=CC=C2C=CC2=CC=CC=C21 QIWRPYBOTIADLA-UHFFFAOYSA-N 0.000 description 1
- HZCSTPNNGZODII-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]-4-methylmorpholine Chemical compound C1N(C)CCOC1CN1C2=CC(Cl)=CC=C2CCC2=CC=CC=C21 HZCSTPNNGZODII-UHFFFAOYSA-N 0.000 description 1
- MMTPWEREVHNHAB-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CC1CNCCO1 MMTPWEREVHNHAB-UHFFFAOYSA-N 0.000 description 1
- FLPGAHBFYVCLDD-UHFFFAOYSA-N 2-[(2-chlorobenzo[b][1]benzazepin-11-yl)methyl]-4-methylmorpholine Chemical compound C1N(C)CCOC1CN1C2=CC(Cl)=CC=C2C=CC2=CC=CC=C21 FLPGAHBFYVCLDD-UHFFFAOYSA-N 0.000 description 1
- NFDNFVUMDVEXIZ-UHFFFAOYSA-N 2-[(2-chlorobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(Cl)=CC=C2C=CC2=CC=CC=C2N1CC1CNCCO1 NFDNFVUMDVEXIZ-UHFFFAOYSA-N 0.000 description 1
- MGPFXFCAACSNDV-UHFFFAOYSA-N 2-[(2-methoxy-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(OC)=CC=C2CCC2=CC=CC=C2N1CC1CNCCO1 MGPFXFCAACSNDV-UHFFFAOYSA-N 0.000 description 1
- AGFLOYQQWLUQTL-UHFFFAOYSA-N 2-[(2-nitrobenzo[b][1]benzazepin-11-yl)methyl]-4-propan-2-ylmorpholine Chemical compound C1N(C(C)C)CCOC1CN1C2=CC([N+]([O-])=O)=CC=C2C=CC2=CC=CC=C21 AGFLOYQQWLUQTL-UHFFFAOYSA-N 0.000 description 1
- NODMSEZHQPFCIL-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)-5,6-dihydrobenzo[b][1]benzazepin-11-yl]methyl]morpholine Chemical compound C12=CC(C(F)(F)F)=CC=C2CCC2=CC=CC=C2N1CC1CNCCO1 NODMSEZHQPFCIL-UHFFFAOYSA-N 0.000 description 1
- HJRWSASSHIYEPP-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)benzo[b][1]benzazepin-11-yl]methyl]morpholine Chemical compound C12=CC(C(F)(F)F)=CC=C2C=CC2=CC=CC=C2N1CC1CNCCO1 HJRWSASSHIYEPP-UHFFFAOYSA-N 0.000 description 1
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- OFPXUACPEABKNO-UHFFFAOYSA-N 4-benzyl-2-[(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(Cl)=CC=C2CCC2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 OFPXUACPEABKNO-UHFFFAOYSA-N 0.000 description 1
- JUIVCEWCGJZZOA-UHFFFAOYSA-N 4-benzyl-2-[(2-chlorobenzo[b][1]benzazepin-11-yl)methyl]morpholine Chemical compound C12=CC(Cl)=CC=C2C=CC2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 JUIVCEWCGJZZOA-UHFFFAOYSA-N 0.000 description 1
- WSEIXKFRGJOVSI-UHFFFAOYSA-N 6-(benzo[b][1]benzazepin-11-ylmethyl)-4-benzylmorpholin-3-one Chemical compound O=C1COC(CN2C3=CC=CC=C3C=CC3=CC=CC=C32)CN1CC1=CC=CC=C1 WSEIXKFRGJOVSI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
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- 208000020401 Depressive disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000003833 Wallach reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
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- 231100001259 acute cardiotoxicity Toxicity 0.000 description 1
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- 238000005917 acylation reaction Methods 0.000 description 1
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- 239000003513 alkali Substances 0.000 description 1
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- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- UFKDESIUZHMUGL-UHFFFAOYSA-N boron;formonitrile;sodium Chemical compound [B].[Na].N#C UFKDESIUZHMUGL-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- DIPRRGKGEKHRAO-UHFFFAOYSA-N ethyl 2-(5,6-dihydrobenzo[b][1]benzazepin-11-ylmethyl)morpholine-4-carboxylate Chemical compound C1N(C(=O)OCC)CCOC1CN1C2=CC=CC=C2CCC2=CC=CC=C21 DIPRRGKGEKHRAO-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000003102 mental depression Diseases 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RMCDUNHIVVEEDD-UHFFFAOYSA-N methylcyclopropane Chemical compound [CH2]C1CC1 RMCDUNHIVVEEDD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/26—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a double bond between positions 10 and 11
-
- 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
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14169174A JPS5833875B2 (ja) | 1974-12-09 | 1974-12-09 | シンキナルモルホリンユウドウタイ オヨビ ソノサンフカエンノセイゾウホウ |
| JP291175A JPS5939433B2 (ja) | 1974-12-27 | 1974-12-27 | 新規なるモルホリン誘導体及びその酸付加塩の製造法 |
| JP4989175A JPS5939435B2 (ja) | 1975-04-23 | 1975-04-23 | 新規なるモルホリン誘導体及びその酸付加塩の製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622792A5 true CH622792A5 (it) | 1981-04-30 |
Family
ID=27275587
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1599475A CH622792A5 (it) | 1974-12-09 | 1975-12-09 | |
| CH401880A CH626083A5 (it) | 1974-12-09 | 1980-05-22 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH401880A CH626083A5 (it) | 1974-12-09 | 1980-05-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4017621A (it) |
| AR (2) | AR213082A1 (it) |
| AT (1) | AT348532B (it) |
| CA (1) | CA1064924A (it) |
| CH (2) | CH622792A5 (it) |
| DE (1) | DE2555351A1 (it) |
| DK (1) | DK551175A (it) |
| ES (1) | ES443333A1 (it) |
| FI (1) | FI753414A (it) |
| FR (1) | FR2293936A1 (it) |
| GB (1) | GB1510669A (it) |
| HU (1) | HU170641B (it) |
| NL (1) | NL7514348A (it) |
| NO (1) | NO145074C (it) |
| SE (1) | SE419985B (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW248556B (it) * | 1993-01-18 | 1995-06-01 | Takeda Pharm Industry Co | |
| US6214816B1 (en) * | 1998-03-17 | 2001-04-10 | Novo Nordisk A/S | Heterocyclic compounds |
| JP2002506863A (ja) * | 1998-03-17 | 2002-03-05 | ノボ ノルディスク アクティーゼルスカブ | 新規ヘテロ環式化合物 |
| EP1956906A4 (en) | 2005-11-09 | 2009-12-30 | Combinatorx Inc | METHODS, COMPOSITIONS AND KITS FOR THE TREATMENT OF PATHOLOGIES |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2976281A (en) * | 1961-03-21 | Substituted iminostilbenes | ||
| NL110232C (it) * | 1958-12-06 | |||
| CH542210A (de) * | 1969-06-20 | 1973-09-30 | Takeda Chemical Industries Ltd | Verfahren zur Herstellung neuer Dibenzazepinderivate |
-
1975
- 1975-11-26 US US05/635,355 patent/US4017621A/en not_active Expired - Lifetime
- 1975-12-02 SE SE7513577A patent/SE419985B/xx unknown
- 1975-12-04 FI FI753414A patent/FI753414A/fi not_active Application Discontinuation
- 1975-12-05 GB GB50019/75A patent/GB1510669A/en not_active Expired
- 1975-12-05 DK DK551175A patent/DK551175A/da not_active Application Discontinuation
- 1975-12-08 CA CA241,209A patent/CA1064924A/en not_active Expired
- 1975-12-08 NO NO75754126A patent/NO145074C/no unknown
- 1975-12-09 FR FR7537633A patent/FR2293936A1/fr active Granted
- 1975-12-09 ES ES75443333A patent/ES443333A1/es not_active Expired
- 1975-12-09 AT AT931175A patent/AT348532B/de not_active IP Right Cessation
- 1975-12-09 DE DE19752555351 patent/DE2555351A1/de not_active Withdrawn
- 1975-12-09 NL NL7514348A patent/NL7514348A/xx not_active Application Discontinuation
- 1975-12-09 AR AR261527A patent/AR213082A1/es active
- 1975-12-09 HU HUSU907A patent/HU170641B/hu unknown
- 1975-12-09 CH CH1599475A patent/CH622792A5/de not_active IP Right Cessation
-
1976
- 1976-09-20 AR AR264773A patent/AR212970A1/es active
-
1980
- 1980-05-22 CH CH401880A patent/CH626083A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO145074C (no) | 1982-01-06 |
| AR212970A1 (es) | 1978-11-30 |
| FR2293936A1 (fr) | 1976-07-09 |
| DK551175A (da) | 1976-06-10 |
| CA1064924A (en) | 1979-10-23 |
| CH626083A5 (it) | 1981-10-30 |
| FR2293936B1 (it) | 1978-11-10 |
| NL7514348A (nl) | 1976-06-11 |
| DE2555351A1 (de) | 1976-06-10 |
| SE7513577L (sv) | 1976-06-10 |
| ES443333A1 (es) | 1978-02-01 |
| NO145074B (no) | 1981-09-28 |
| AU8734175A (en) | 1977-06-16 |
| US4017621A (en) | 1977-04-12 |
| SE419985B (sv) | 1981-09-07 |
| ATA931175A (de) | 1978-07-15 |
| AT348532B (de) | 1979-02-26 |
| NO754126L (it) | 1976-06-10 |
| AR213082A1 (es) | 1978-12-15 |
| GB1510669A (en) | 1978-05-10 |
| FI753414A (it) | 1976-06-10 |
| HU170641B (it) | 1977-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |