CH402838A - Verfahren zur Herstellung von neuen basischen Verbindungen - Google Patents

Verfahren zur Herstellung von neuen basischen Verbindungen

Info

Publication number: CH402838A
Authority: CH; Switzerland
Prior art keywords: dibenzo; solution; cycloheptatriene; hydroxy; tetrahydrofuran
Prior art date: 1961-07-06

Application number

CH794061A

Other languages

German (de)

English (en)

Inventor

Ernst Dr Jucker

Anton Dr Ebnoether

Original Assignee

Sandoz Ag

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.)

1961-07-06

Filing date

1961-07-06

Publication date

1965-11-30

1961-07-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1961-07-06 Priority to CH469965A priority Critical patent/CH421942A/de

1961-07-06 Priority to CH794061A priority patent/CH402838A/de

1962-06-26 Priority to GB24452/62A priority patent/GB1012619A/en

1962-07-05 Priority to ES0278944A priority patent/ES278944A1/es

1962-07-05 Priority to DK300162A priority patent/DK105918C/da

1962-10-01 Priority to FR910912A priority patent/FR2093M/fr

1965-11-30 Publication of CH402838A publication Critical patent/CH402838A/de

Links

238000000034 method Methods 0.000 title claims description 13
150000007514 bases Chemical class 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 3
150000003951 lactams Chemical class 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
239000000243 solution Substances 0.000 description 58
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000155 melt Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
-1 example Chemical class 0.000 description 14
239000000203 mixture Substances 0.000 description 13
150000001993 dienes Chemical class 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
239000012280 lithium aluminium hydride Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000000725 suspension Substances 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
QVWDCTQRORVHHT-UHFFFAOYSA-N tropone Chemical compound O=C1C=CC=CC=C1 QVWDCTQRORVHHT-UHFFFAOYSA-N 0.000 description 6
BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 4
238000009835 boiling Methods 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
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 3
LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
YJVMEQIJDPMNHT-UHFFFAOYSA-N cyclohepta-1,3,5-triene;hydrochloride Chemical compound Cl.C1C=CC=CC=C1 YJVMEQIJDPMNHT-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
206010013781 dry mouth Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract 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
238000005187 foaming Methods 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000003867 tiredness Effects 0.000 description 1
208000016255 tiredness Diseases 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH794061A 1961-07-06 1961-07-06 Verfahren zur Herstellung von neuen basischen Verbindungen CH402838A (de)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
CH469965A CH421942A (de)	1961-07-06	1961-07-06	Verfahren zur Herstellung von neuen basischen Verbindungen
CH794061A CH402838A (de)	1961-07-06	1961-07-06	Verfahren zur Herstellung von neuen basischen Verbindungen
GB24452/62A GB1012619A (en)	1961-07-06	1962-06-26	Improvements in or relating to dibenzocyclohepta-diene and -triene derivatives
ES0278944A ES278944A1 (es)	1961-07-06	1962-07-05	Procedimiento para la obtenciën de nuevos compuestos ciclicos basicos
DK300162A DK105918C (da)	1961-07-06	1962-07-05	Fremgangsmåde til fremstilling af i 5-stilling med en basisk gruppe substituerede dibenzocycloheptadien- og dibenzocycloheptatrienderivater eller salte heraf.
FR910912A FR2093M (fr)	1961-07-06	1962-10-01	Médicament a base de dérivé d'hydroxy-dibenzocycloheptane.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH794061A CH402838A (de)	1961-07-06	1961-07-06	Verfahren zur Herstellung von neuen basischen Verbindungen

Publications (1)

Publication Number	Publication Date
CH402838A true CH402838A (de)	1965-11-30

Family

ID=4332700

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH794061A CH402838A (de)	1961-07-06	1961-07-06	Verfahren zur Herstellung von neuen basischen Verbindungen

Country Status (5)

Country	Link
CH (1)	CH402838A (fr)
DK (1)	DK105918C (fr)
ES (1)	ES278944A1 (fr)
FR (1)	FR2093M (fr)
GB (1)	GB1012619A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1543035A1 (de) *	1965-01-06	1969-09-25	Hoffmann La Roche	Verfahren zur Herstellung von Dibenzocycloheptenverbindungen

1961
- 1961-07-06 CH CH794061A patent/CH402838A/de unknown
1962
- 1962-06-26 GB GB24452/62A patent/GB1012619A/en not_active Expired
- 1962-07-05 DK DK300162A patent/DK105918C/da active
- 1962-07-05 ES ES0278944A patent/ES278944A1/es not_active Expired
- 1962-10-01 FR FR910912A patent/FR2093M/fr not_active Expired

Also Published As

Publication number	Publication date
FR2093M (fr)	1963-10-21
DK105918C (da)	1966-11-28
ES278944A1 (es)	1963-03-01
GB1012619A (en)	1965-12-08

Publication	Publication Date	Title
DE2419970C3 (de)	1980-06-12	3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung
DE1695836B2 (de)	1977-03-31	4-phenyl-4-hydroxypiperidinopropylthianaphthene und diese verbindungen enthaltende arzneimittel
CH402838A (de)	1965-11-30	Verfahren zur Herstellung von neuen basischen Verbindungen
AT231425B (de)	1964-01-27	Verfahren zur Herstellung von neuen basischen Verbindungen und deren Salzen
DE1182664B (de)	1964-12-03	Verfahren zur Herstellung von basisch substituierten Dibenzocycloheptanderivaten und deren Salzen
AT218526B (de)	1961-12-11	Verfahren zur Herstellung von neuen Phenthiazinderivaten
AT229290B (de)	1963-09-10	Verfahren zur Herstellung von 5-(3'-Aminopropyliden)-dibenzo-[a, d]-cyclohepta-[1, 4]-dienen und ihren Säureadditionssalzen
AT233552B (de)	1964-05-11	Verfahren zur Herstellung von neuen Dibenzocycloheptadien-Derivaten und ihren Salzen
AT226706B (de)	1963-04-10	Verfahren zur Herstellung neuer Derivate der Nicotinsäure
AT208867B (de)	1960-05-10	Verfahren zur Herstellung von neuen substituierten heterocyclischen Säurehydraziden
CH511840A (de)	1971-08-31	Verfahren zur Herstellung von neuen Indolderivaten
AT253494B (de)	1967-04-10	Verfahren zur Herstellung von neuen Dibenzo[a, d] cycloheptadien-Derivaten
AT228218B (de)	1963-07-10	Verfahren zur Herstellung von neuen Thioxanthen-Verbindungen
AT262271B (de)	1968-06-10	Verfahren zur Herstellung neuer 9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate und ihrer Salze
AT263026B (de)	1968-07-10	Verfahren zur Herstellung von neuen Phenthiazinderivaten
AT256834B (de)	1967-09-11	Verfahren zur Herstellung von neuen Aminoalkyl-substituierten 5-gliedrigen Heterocyclen und ihren Salzen
AT252234B (de)	1967-02-10	Verfahren zur Herstellung von neuen Aminoalkyl-substituierten Thiadiazolen
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
AT343119B (de)	1978-05-10	Verfahren zur herstellung neuer 10h-thieno (3,2-c) (1) benzazepin-derivate und deren saureadditionssalze
AT258298B (de)	1967-11-10	Verfahren zur Herstellung von neuen Derivaten des 5,6-Dihydromorphantridins
AT210886B (de)	1960-08-25	Verfahren zur Herstellung von neuen, basisch substituierten Diphenylcarbinolestern und deren Salzen
AT226696B (de)	1963-04-10	Verfahren zur Herstellung von neuen Derivaten des Phthalimidins bzw. deren quaternären Ammoniumverbindungen
AT219600B (de)	1962-02-12	Verfahren zur Herstellung von neuen Pyrido-benzthiazin-Derivaten
AT273972B (de)	1969-09-10	Verfahren zur Herstellung von neuen 1-(2-Aminophenyl)-1,2,3,4-tetrahydroisochinolinen sowie von deren Salzen
DE1445858C3 (de)	1976-02-26	7-Cyan-5-phenyl-1,2-dihydro-3H-l,4benzodiazepin-2-on-Derivate