DD152782B1 - Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze - Google Patents
Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze Download PDFInfo
- Publication number
- DD152782B1 DD152782B1 DD79216679A DD21667979A DD152782B1 DD 152782 B1 DD152782 B1 DD 152782B1 DD 79216679 A DD79216679 A DD 79216679A DD 21667979 A DD21667979 A DD 21667979A DD 152782 B1 DD152782 B1 DD 152782B1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- found
- calculated
- dihydro
- general formula
- azepine
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 10
- 150000001538 azepines Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 42
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkyl radical Chemical class 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- SQWQJTDHBAWIMQ-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepin-2-amine Chemical compound C1CC2=CC=CC=C2NC2=CC(N)=CC=C21 SQWQJTDHBAWIMQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 claims 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 206010003119 arrhythmia Diseases 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 8
- 230000003288 anthiarrhythmic effect Effects 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 208000003663 ventricular fibrillation Diseases 0.000 description 6
- 230000006793 arrhythmia Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 4
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 4
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- DTRJAYJJIYBWRG-UHFFFAOYSA-N ethyl n-(6,11-dihydro-5h-benzo[b][1]benzazepin-2-yl)carbamate Chemical compound C1CC2=CC=CC=C2NC2=CC(NC(=O)OCC)=CC=C21 DTRJAYJJIYBWRG-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229960004194 lidocaine Drugs 0.000 description 4
- 229940072033 potash Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229960001404 quinidine Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- DHTRYSLFWJKCCA-UHFFFAOYSA-N ethyl n-[11-(3-chloropropanoyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCCl)C2=CC(NC(=O)OCC)=CC=C21 DHTRYSLFWJKCCA-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- DPYFPVDOCCROID-UHFFFAOYSA-N methyl n-[11-(3-chloropropanoyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCCl)C2=CC(NC(=O)OC)=CC=C21 DPYFPVDOCCROID-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 2
- 208000001778 Coronary Occlusion Diseases 0.000 description 2
- 206010011086 Coronary artery occlusion Diseases 0.000 description 2
- 206010015856 Extrasystoles Diseases 0.000 description 2
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 2
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 2
- 206010049418 Sudden Cardiac Death Diseases 0.000 description 2
- 208000009729 Ventricular Premature Complexes Diseases 0.000 description 2
- 206010047289 Ventricular extrasystoles Diseases 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- JGBHZKBZBKTGGI-UHFFFAOYSA-N propan-2-yl n-[11-(3-chloropropanoyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCCl)C2=CC(NC(=O)OC(C)C)=CC=C21 JGBHZKBZBKTGGI-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- 206010047302 ventricular tachycardia Diseases 0.000 description 2
- BVXNSTQKLRXXEA-UHFFFAOYSA-N 10h-phenothiazin-2-amine Chemical compound C1=CC=C2NC3=CC(N)=CC=C3SC2=C1 BVXNSTQKLRXXEA-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 206010042602 Supraventricular extrasystoles Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XFSBVAOIAHNAPC-NPVHKAFCSA-N aconitin Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45[C@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-NPVHKAFCSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000037024 effective refractory period Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- OCKSRDBEORWEDN-UHFFFAOYSA-N ethyl n-[11-(2-chloroacetyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCl)C2=CC(NC(=O)OCC)=CC=C21 OCKSRDBEORWEDN-UHFFFAOYSA-N 0.000 description 1
- JGWVBMHOYLTWLC-UHFFFAOYSA-N ethyl n-[11-(3-piperidin-1-ylpropanoyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C12=CC(NC(=O)OCC)=CC=C2CCC2=CC=CC=C2N1C(=O)CCN1CCCCC1 JGWVBMHOYLTWLC-UHFFFAOYSA-N 0.000 description 1
- QWZNTHPYWMQGTC-UHFFFAOYSA-N ethyl n-[11-[3-(dimethylamino)propanoyl]-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCN(C)C)C2=CC(NC(=O)OCC)=CC=C21 QWZNTHPYWMQGTC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 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
- 238000000338 in vitro Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WOEGGBRWIKORFL-UHFFFAOYSA-N methyl n-(6,11-dihydro-5h-benzo[b][1]benzazepin-2-yl)carbamate Chemical compound C1CC2=CC=CC=C2NC2=CC(NC(=O)OC)=CC=C21 WOEGGBRWIKORFL-UHFFFAOYSA-N 0.000 description 1
- OZAIYDAHOMNNGT-UHFFFAOYSA-N methyl n-[11-[3-(dimethylamino)propanoyl]-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C1CC2=CC=CC=C2N(C(=O)CCN(C)C)C2=CC(NC(=O)OC)=CC=C21 OZAIYDAHOMNNGT-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229960002608 moracizine Drugs 0.000 description 1
- FUBVWMNBEHXPSU-UHFFFAOYSA-N moricizine Chemical compound C12=CC(NC(=O)OCC)=CC=C2SC2=CC=CC=C2N1C(=O)CCN1CCOCC1 FUBVWMNBEHXPSU-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- YJXOMYBLVRMVSB-UHFFFAOYSA-N propan-2-yl n-(6,11-dihydro-5h-benzo[b][1]benzazepin-2-yl)carbamate Chemical compound C1CC2=CC=CC=C2NC2=CC(NC(=O)OC(C)C)=CC=C21 YJXOMYBLVRMVSB-UHFFFAOYSA-N 0.000 description 1
- PGRJZCQJNBSGHM-UHFFFAOYSA-N propan-2-yl n-[11-(3-piperidin-1-ylpropanoyl)-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate Chemical compound C12=CC(NC(=O)OC(C)C)=CC=C2CCC2=CC=CC=C2N1C(=O)CCN1CCCCC1 PGRJZCQJNBSGHM-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD79216679A DD152782B1 (de) | 1979-11-05 | 1979-11-05 | Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze |
| AT0511980A AT380010B (de) | 1979-11-05 | 1980-10-15 | Verfahren zur herstellung neuer 10.11-dihydro-5h- -dibenz(b,f)azepine und ihrer salze |
| DE19803040085 DE3040085A1 (de) | 1979-11-05 | 1980-10-24 | Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz (b,f) azepine und ihrer salze |
| GB8035229A GB2065105B (en) | 1979-11-05 | 1980-11-03 | Dibenzazepines |
| CH819580A CH646153A5 (de) | 1979-11-05 | 1980-11-04 | 10,11-dihydro-5h-dibenz(b,f)azepine, ihre salze und ihre herstellung. |
| JP55155753A JPS6017789B2 (ja) | 1979-11-05 | 1980-11-05 | ５−（ω−アミノアシル）−３−カルボアルコキシアミノ−１０，１１−ジヒドロ−５Ｈ−ジベンゾ−〔ｂ，ｆ〕−アゼピン、その塩及びそれらの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD79216679A DD152782B1 (de) | 1979-11-05 | 1979-11-05 | Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD152782A1 DD152782A1 (de) | 1981-12-09 |
| DD152782B1 true DD152782B1 (de) | 1988-11-30 |
Family
ID=5520915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216679A DD152782B1 (de) | 1979-11-05 | 1979-11-05 | Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6017789B2 (enrdf_load_stackoverflow) |
| AT (1) | AT380010B (enrdf_load_stackoverflow) |
| CH (1) | CH646153A5 (enrdf_load_stackoverflow) |
| DD (1) | DD152782B1 (enrdf_load_stackoverflow) |
| DE (1) | DE3040085A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2065105B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61159986U (enrdf_load_stackoverflow) * | 1985-03-25 | 1986-10-03 | ||
| DD296914A5 (de) * | 1989-06-30 | 1991-12-19 | �������@������������@��k�� | Verfahren zur herstellung von 3-carbalkoxyamino-5-(alpha-aminopropionyl)-5h-dibenz[b,f]azepinen und deren physiologisch vertraegliche salze |
| DD296915A5 (de) * | 1989-06-30 | 1991-12-19 | Arzneimittelwerk Dresden Gmbh,De | Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR205239A1 (es) * | 1974-07-29 | 1976-04-12 | Searle & Co | Procedimiento para la preparacion de un grupo de n-(omega-hexametilenimina-alquilen c2-c6)-5h-benzo(b,f)-azepina-5-carbozamidas |
-
1979
- 1979-11-05 DD DD79216679A patent/DD152782B1/de not_active IP Right Cessation
-
1980
- 1980-10-15 AT AT0511980A patent/AT380010B/de not_active IP Right Cessation
- 1980-10-24 DE DE19803040085 patent/DE3040085A1/de active Granted
- 1980-11-03 GB GB8035229A patent/GB2065105B/en not_active Expired
- 1980-11-04 CH CH819580A patent/CH646153A5/de not_active IP Right Cessation
- 1980-11-05 JP JP55155753A patent/JPS6017789B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT380010B (de) | 1986-03-25 |
| GB2065105B (en) | 1984-01-25 |
| GB2065105A (en) | 1981-06-24 |
| ATA511980A (de) | 1985-08-15 |
| JPS6017789B2 (ja) | 1985-05-07 |
| DE3040085A1 (de) | 1981-06-04 |
| CH646153A5 (de) | 1984-11-15 |
| JPS5690062A (en) | 1981-07-21 |
| DE3040085C2 (enrdf_load_stackoverflow) | 1989-11-16 |
| DD152782A1 (de) | 1981-12-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| VZ | Disclaimer of patent (art. 11 and 12 extension act) |