CH373757A - Verfahren zur Herstellung von Dibenzazepinen - Google Patents

Verfahren zur Herstellung von Dibenzazepinen

Info

Publication number: CH373757A
Authority: CH; Switzerland
Prior art keywords: azepine; dibenz; diphenyldialdehyde; dihydro; solution
Prior art date: 1958-07-04

Application number

CH6137958A

Other languages

German (de)

English (en)

Inventor

Arthur Dr Boller

Andor Dr Fuerst

Werner Dr Meier

Original Assignee

Hoffmann La Roche

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.)

1958-07-04

Filing date

1958-07-04

Publication date

1963-12-15

1958-07-04 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1958-07-04 Priority to CH6137958A priority Critical patent/CH373757A/de

1959-07-01 Priority to BE580291A priority patent/BE580291A/fr

1959-07-03 Priority to ES0250509A priority patent/ES250509A1/es

1963-12-15 Publication of CH373757A publication Critical patent/CH373757A/de

Links

238000000034 method Methods 0.000 title claims description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
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 15
235000019253 formic acid Nutrition 0.000 claims description 15
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 10
-1 alicychic Chemical group 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 8
230000002829 reductive effect Effects 0.000 claims description 8
FHYFQRCUSZETDW-UHFFFAOYSA-N 6,7-dihydro-5h-benzo[d][2]benzazepine Chemical compound C1NCC2=CC=CC=C2C2=CC=CC=C12 FHYFQRCUSZETDW-UHFFFAOYSA-N 0.000 claims description 7
239000000047 product Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
150000003141 primary amines Chemical class 0.000 claims 2
XCFNJQFEOFKMOS-UHFFFAOYSA-N 7h-benzo[d][2]benzazepine Chemical compound C1N=CC2=CC=CC=C2C2=CC=CC=C12 XCFNJQFEOFKMOS-UHFFFAOYSA-N 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229930195734 saturated hydrocarbon Natural products 0.000 claims 1
229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
239000000243 solution Substances 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
239000003921 oil Substances 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
239000000155 melt Substances 0.000 description 13
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
230000001476 alcoholic effect Effects 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
239000001569 carbon dioxide Substances 0.000 description 10
229910002092 carbon dioxide Inorganic materials 0.000 description 10
239000007789 gas Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
238000001816 cooling Methods 0.000 description 7
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
229910003446 platinum oxide Inorganic materials 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000012452 mother liquor Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000010452 phosphate Substances 0.000 description 5
MMNUZQLGYHBLAD-UHFFFAOYSA-N 5h-benzo[d][2]benzazepin-5-ol Chemical compound OC1N=CC2=CC=CC=C2C2=CC=CC=C12 MMNUZQLGYHBLAD-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
DUUCAGQAOMZIGC-UHFFFAOYSA-N 6-butyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1N(CCCC)CC2=CC=CC=C2C2=CC=CC=C21 DUUCAGQAOMZIGC-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
NYGHGTMKALXFIA-UHFFFAOYSA-N azapetine Chemical compound C1N(CC=C)CC2=CC=CC=C2C2=CC=CC=C21 NYGHGTMKALXFIA-UHFFFAOYSA-N 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
LSPRUQXPQKPRDQ-UHFFFAOYSA-N 5,7-dihydrobenzo[d][2]benzazepine-6-carbaldehyde Chemical compound C1N(C=O)CC2=CC=CC=C2C2=CC=CC=C21 LSPRUQXPQKPRDQ-UHFFFAOYSA-N 0.000 description 2
JQNQBWAAUPNGJU-UHFFFAOYSA-N 6-benzyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1C2=CC=CC=C2C2=CC=CC=C2CN1CC1=CC=CC=C1 JQNQBWAAUPNGJU-UHFFFAOYSA-N 0.000 description 2
IUWNEWJWRCZZLG-UHFFFAOYSA-N 6-cyclohexyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1CCCCC1N1CC2=CC=CC=C2C2=CC=CC=C2C1 IUWNEWJWRCZZLG-UHFFFAOYSA-N 0.000 description 2
HAISSBBARJYERH-UHFFFAOYSA-N 6-phenyl-5,7-dihydrobenzo[d][2]benzazepine Chemical compound C1C2=CC=CC=C2C2=CC=CC=C2CN1C1=CC=CC=C1 HAISSBBARJYERH-UHFFFAOYSA-N 0.000 description 2
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000001177 diphosphate Substances 0.000 description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
238000001035 drying Methods 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
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
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 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
125000002723 alicyclic group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000003974 aralkylamines Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000002785 azepinyl group Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
SHIGCAOWAAOWIG-UHFFFAOYSA-N n-prop-2-enylformamide Chemical compound C=CCNC=O SHIGCAOWAAOWIG-UHFFFAOYSA-N 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012071 phase Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CH6137958A 1958-07-04 1958-07-04 Verfahren zur Herstellung von Dibenzazepinen CH373757A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH6137958A CH373757A (de)	1958-07-04	1958-07-04	Verfahren zur Herstellung von Dibenzazepinen
BE580291A BE580291A (fr)	1958-07-04	1959-07-01	Procédé pour la préparation de composés de dibenzazépine.
ES0250509A ES250509A1 (es)	1958-07-04	1959-07-03	UN PROCEDIMIENTO PARA LA PRODUCCIoN DE COMPUESTOS DE DIBENZAZEPINA

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6137958A CH373757A (de)	1958-07-04	1958-07-04	Verfahren zur Herstellung von Dibenzazepinen

Publications (1)

Publication Number	Publication Date
CH373757A true CH373757A (de)	1963-12-15

Family

ID=4523593

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6137958A CH373757A (de)	1958-07-04	1958-07-04	Verfahren zur Herstellung von Dibenzazepinen

Country Status (3)

Country	Link
BE (1)	BE580291A (fr)
CH (1)	CH373757A (fr)
ES (1)	ES250509A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4766115A (en) *	1985-01-10	1988-08-23	Hoffmann-La Roche Inc.	5,6-dihydro-6H-dibenz[c,e]azepine-6-(thio)carboximidic acid esters and insecticidal use thereof

1958
- 1958-07-04 CH CH6137958A patent/CH373757A/de unknown
1959
- 1959-07-01 BE BE580291A patent/BE580291A/fr unknown
- 1959-07-03 ES ES0250509A patent/ES250509A1/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4766115A (en) *	1985-01-10	1988-08-23	Hoffmann-La Roche Inc.	5,6-dihydro-6H-dibenz[c,e]azepine-6-(thio)carboximidic acid esters and insecticidal use thereof

Also Published As

Publication number	Publication date
BE580291A (fr)	1960-01-04
ES250509A1 (es)	1960-01-16

Publication	Publication Date	Title
DE2806909C2 (fr)	1988-04-07
CH373757A (de)	1963-12-15	Verfahren zur Herstellung von Dibenzazepinen
DE2337126C3 (de)	1980-07-31	Iminodibenzyl-Derivate und Verfahren zu deren Herstellung
DE2352632B2 (de)	1980-06-19	Berbinderivate, Verfahren zu deren Herstellung und Arzneimittel
CH301670A (de)	1954-09-15	Verfahren zur Herstellung eines Morphinanabkömmlings.
AT212325B (de)	1960-12-12	Verfahren zur Herstellung von Dibenzazepinverbindungen
DE1802297C3 (de)	1974-10-17	Isopropylaminderivate und Verfahren zu ihrer Herstellung
DE2013729A1 (fr)	1970-12-17
DE1107231B (de)	1961-05-25	Verfahren zur Herstellung von 6, 7-Dihydro-5H-dibenz[c, e]azepinen, deren Salzen undquaternaeren Ammoniumverbindungen
DE1670019C3 (de)	1975-06-05	N-Aminoalkenyl- und -alkinylsuccinimide und sie enthaltende MIttel
DE908138C (de)	1954-04-01	Verfahren zur Herstellung von 1-Benzyl-2-alkyl-1,2,3,4,5,6,7,8,-octa-hydroisochinolinen und ihren Salzen
CH642617A5 (de)	1984-04-30	Verfahren zur herstellung von bromhexin.
DE2058237C (fr)	1973-02-08
DE1470065C3 (de)	1980-07-17	Verfahren zur Herstellung von Chinolizinderivaten
AT238174B (de)	1965-01-25	Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen
DE825840C (de)	1951-12-20	Verfahren zur Herstellung substituierter Piperazine
AT200134B (de)	1958-10-25	Verfahren zur Herstellung von a-Amino-b-oxycarbonsäureamiden
AT219041B (de)	1962-01-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
AT299207B (de)	1972-06-12	Verfahren zur Herstellung neuer Benzodiazepin-Derivaten und ihren Salzen
AT238186B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT213885B (de)	1961-03-10	Verfahren zur Herstellung von neuen Indol-Derivaten
DE2624042A1 (de)	1976-12-23	Verfahren zur herstellung von n-substituierten oder n,n'-disubstituierten piperazinen
DE2139084B2 (de)	1978-06-29	Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen
AT227690B (de)	1963-06-10	Verfahren zur Herstellung neuer, basisch substituierter Succinimide
AT300787B (de)	1972-08-10	Verfahren zur Herstellung von neuen 1-Aminoäthyl-indolderivaten und ihren Salzen

CH373757A - Verfahren zur Herstellung von Dibenzazepinen - Google Patents

Info

Links

Landscapes

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4523593

Family Applications (1)

Country Status (3)

Cited By (1)

Cited By (1)

Also Published As

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