DD296915A5 - Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze - Google Patents

Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze Download PDF

Info

Publication number: DD296915A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; salts; mol; amine; compounds
Prior art date: 1989-06-30

Application number

DD89330175A

Other languages

German (de)

English (en)

Inventor

Helmut Wunderlich

Andreas Stark

Dieter Lohmann

Lothar Zenker

Reni Bartsch

Hildegard Poppe

Aleksandr P Skoldinov

Natalja V Kaverina

Anna N Grizenko

Valentin V Lyskovzev

Ekaterina K Grigoreva

Original Assignee

Arzneimittelwerk Dresden Gmbh,De

Inst. Fuer Pharmakologie Der Akademie Der Medizin. Wissenschaften Der Udssr,Su

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-06-30

Filing date

1989-06-30

Publication date

1991-12-19

1989-06-30 Application filed by Arzneimittelwerk Dresden Gmbh,De, Inst. Fuer Pharmakologie Der Akademie Der Medizin. Wissenschaften Der Udssr,Su filed Critical Arzneimittelwerk Dresden Gmbh,De

1989-06-30 Priority to DD89330175A priority Critical patent/DD296915A5/de

1990-06-15 Priority to EP19900111337 priority patent/EP0405255A3/de

1990-06-27 Priority to JP2169656A priority patent/JPH0338570A/ja

1990-06-29 Priority to US07/546,375 priority patent/US5192760A/en

1991-12-19 Publication of DD296915A5 publication Critical patent/DD296915A5/de

Links

150000003839 salts Chemical class 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000001538 azepines Chemical class 0.000 title description 4
150000001412 amines Chemical class 0.000 claims abstract description 22
150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
150000007524 organic acids Chemical class 0.000 claims abstract description 5
235000005985 organic acids Nutrition 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
150000001875 compounds Chemical class 0.000 claims description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
239000002585 base Substances 0.000 claims description 20
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
239000012433 hydrogen halide Substances 0.000 claims description 8
229910000039 hydrogen halide Inorganic materials 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
239000000370 acceptor Substances 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
229940072033 potash Drugs 0.000 claims description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
235000015320 potassium carbonate Nutrition 0.000 claims description 2
239000011877 solvent mixture Substances 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
206010003119 arrhythmia Diseases 0.000 abstract description 10
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 9
238000000921 elemental analysis Methods 0.000 description 24
239000000243 solution Substances 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 15
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
238000001816 cooling Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000002035 prolonged effect Effects 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
229960004194 lidocaine Drugs 0.000 description 3
229960003404 mexiletine Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 2
241000173529 Aconitum napellus Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700157 Rattus norvegicus Species 0.000 description 2
229940023019 aconite Drugs 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 2
230000036983 biotransformation Effects 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000005252 haloacyl group Chemical group 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
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 2
239000000376 reactant Substances 0.000 description 2
238000000611 regression analysis Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
HAAZMOAXEMIBAJ-UHFFFAOYSA-N 4-chloro-2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC(Cl)=C21 HAAZMOAXEMIBAJ-UHFFFAOYSA-N 0.000 description 1
-1 5 -cyclohexyl Chemical group 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
SKVSEUUZNPBOJB-UHFFFAOYSA-N C12=CC=CC=C2CCC=2C(C(C)=O)=CC(NC(=O)OCC)=CC=2N1NC1CCCCC1 Chemical compound C12=CC=CC=C2CCC=2C(C(C)=O)=CC(NC(=O)OCC)=CC=2N1NC1CCCCC1 SKVSEUUZNPBOJB-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
208000009729 Ventricular Premature Complexes Diseases 0.000 description 1
206010047289 Ventricular extrasystoles Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003929 acidic solution Substances 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
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000037007 arousal Effects 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
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 1
238000004140 cleaning Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
UVTNFZQICZKOEM-UHFFFAOYSA-N disopyramide Chemical compound C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 UVTNFZQICZKOEM-UHFFFAOYSA-N 0.000 description 1
229960001066 disopyramide Drugs 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
JFYBNHBSKIKGQF-UHFFFAOYSA-N ethyl n-[11-[3-(ethylamino)propanoyl]-5,6-dihydrobenzo[b][1]benzazepin-2-yl]carbamate;hydrochloride Chemical compound Cl.C1CC2=CC=C(NC(=O)OCC)C=C2N(C(=O)CCNCC)C2=CC=CC=C21 JFYBNHBSKIKGQF-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical group 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 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
XJWABFCDXKZWPV-UHFFFAOYSA-N n-{2-[2-(dimethylamino)acetyl]-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl}ethoxycarboximidic acid hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 XJWABFCDXKZWPV-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
229960000203 propafenone Drugs 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000001020 rhythmical effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
238000005406 washing Methods 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
- 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
- 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

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DD89330175A 1989-06-30 1989-06-30 Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze DD296915A5 (de)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
DD89330175A DD296915A5 (de)	1989-06-30	1989-06-30	Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze
EP19900111337 EP0405255A3 (en)	1989-06-30	1990-06-15	3-carbalkoxyamino-5-aminoacyl-5h-dibenzo(b,f)-azepines, their salts and process for their preparation
JP2169656A JPH0338570A (ja)	1989-06-30	1990-06-27	新規な３―カルボアルコキシアミノ―５―アミノアシル―５Ｈ―ジベンズ［ｂ、ｆ］アゼピン、その塩およびそれらの製造方法
US07/546,375 US5192760A (en)	1989-06-30	1990-06-29	3-carbalkoxyamino-5-(alpha-aminopropionyl)-5H-dibenz[b,f]azepines and method for their making

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD89330175A DD296915A5 (de)	1989-06-30	1989-06-30	Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze

Publications (1)

Publication Number	Publication Date
DD296915A5 true DD296915A5 (de)	1991-12-19

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ID=5610382

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89330175A DD296915A5 (de)	1989-06-30	1989-06-30	Verfahren zur herstellung von neuen 3-carbalkoxyamino-5-aminoacyl-5h-dibenz[b,f]azepine und ihrer salze

Country Status (4)

Country	Link
US (1)	US5192760A (fr)
EP (1)	EP0405255A3 (fr)
JP (1)	JPH0338570A (fr)
DD (1)	DD296915A5 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4843069B2 (ja) *	2009-05-29	2011-12-21	東生加美野	二重管式熱交換器

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD152782B1 (de) *	1979-11-05	1988-11-30	Ernst Carstens	Verfahren zur herstellung neuer 10.11-dihydro-5h-dibenz[b,f]azepine und ihrer salze
FR2493314A1 (fr) *	1980-11-05	1982-05-07	Inst Farmakologii Akademii	Derives de 5-(o-aminoacyl)-3-carbalcoxyamino-10,11-dihydro-5h-dibenzo (b, f) azepine, leur procede de preparation et leur application therapeutique
DD258224B3 (de) *	1987-03-05	1992-12-17	Dresden Arzneimittel	Verfahren zur herstellung von 3-carbethoxyamino-5-dimethylaminoacetyl-10,11-dihydro-5h-dibenz\|b,f¨azepin

1989
- 1989-06-30 DD DD89330175A patent/DD296915A5/de not_active IP Right Cessation
1990
- 1990-06-15 EP EP19900111337 patent/EP0405255A3/de not_active Withdrawn
- 1990-06-27 JP JP2169656A patent/JPH0338570A/ja active Pending
- 1990-06-29 US US07/546,375 patent/US5192760A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0405255A2 (fr)	1991-01-02
US5192760A (en)	1993-03-09
EP0405255A3 (en)	1991-08-07
JPH0338570A (ja)	1991-02-19

Legal Events

Date	Code	Title	Description
1994-06-23	VZ	Disclaimer of patent (art. 11 and 12 extension act)

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