CH399469A - Verfahren zur Herstellung von neuen Azepinderivaten - Google Patents

Verfahren zur Herstellung von neuen Azepinderivaten

Info

Publication number: CH399469A
Authority: CH; Switzerland
Prior art keywords: parts; dibenz; formula; azepine; radical
Prior art date: 1960-08-05

Application number

CH894860A

Other languages

German (de)

English (en)

Inventor

Walter Dr Schindler

Blattner Hans

Original Assignee

Geigy Ag J R

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.)

1960-08-05

Filing date

1960-08-05

Publication date

1965-09-30

1960-08-05 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1960-08-05 Priority to CH894860A priority Critical patent/CH399469A/de

1960-08-05 Priority to CH1252665A priority patent/CH412908A/de

1960-11-15 Priority to ES0262489A priority patent/ES262489A1/es

1960-11-16 Priority to GB39271/60A priority patent/GB961444A/en

1960-12-14 Priority to BE598193A priority patent/BE598193A/fr

1965-09-30 Publication of CH399469A publication Critical patent/CH399469A/de

Links

150000001538 azepines Chemical class 0.000 title claims description 5
238000000034 method Methods 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 9
-1 hydroxyl compound Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 74
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 8
238000009835 boiling Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
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 5
239000011777 magnesium Substances 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000002440 hydroxy compounds Chemical class 0.000 description 4
YUBRTLUBFAJRHT-UHFFFAOYSA-N 5,6-dimethyl-11h-benzo[b][1]benzazepine Chemical compound CC1=C(C)C2=CC=CC=C2NC2=CC=CC=C12 YUBRTLUBFAJRHT-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
IXJXEQCOCIZUNT-UHFFFAOYSA-N 11-benzyl-5,6-dimethylbenzo[b][1]benzazepine Chemical compound C12=CC=CC=C2C(C)=C(C)C2=CC=CC=C2N1CC1=CC=CC=C1 IXJXEQCOCIZUNT-UHFFFAOYSA-N 0.000 description 2
HFGXUSVJYOFYHO-UHFFFAOYSA-N 5,11-dimethylbenzo[b][1]benzazepine Chemical compound C1=C(C)C2=CC=CC=C2N(C)C2=CC=CC=C21 HFGXUSVJYOFYHO-UHFFFAOYSA-N 0.000 description 2
ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LMXZWQIVFCRULO-UHFFFAOYSA-N C1(=CC=CC=C1)C1CC2=C(NC3=C1C=CC=C3)C=CC=C2 Chemical compound C1(=CC=CC=C1)C1CC2=C(NC3=C1C=CC=C3)C=CC=C2 LMXZWQIVFCRULO-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
239000000155 melt Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
WYGCMGHBEUGWNS-UHFFFAOYSA-N 11-methyl-6h-benzo[b][1]benzazepin-5-one Chemical compound C1C(=O)C2=CC=CC=C2N(C)C2=CC=CC=C21 WYGCMGHBEUGWNS-UHFFFAOYSA-N 0.000 description 1
WKMPLZAFPNQAMR-UHFFFAOYSA-N 11-methylbenzo[b][1]benzazepine Chemical compound C1=CC2=CC=CC=C2N(C)C2=CC=CC=C21 WKMPLZAFPNQAMR-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
SQFQJVQTJBLTSI-UHFFFAOYSA-N 5,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepine Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)C)C=CC=C2 SQFQJVQTJBLTSI-UHFFFAOYSA-N 0.000 description 1
YRVYIAFBLROBGH-UHFFFAOYSA-N 5,11-dimethyl-6H-benzo[b][1]benzazepin-5-ol Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)(O)C)C=CC=C2 YRVYIAFBLROBGH-UHFFFAOYSA-N 0.000 description 1
CXVNZQVWELHKLT-UHFFFAOYSA-N 5,6-dimethyl-6,11-dihydro-5H-benzo[b][1]benzazepine Chemical compound CC1C(C2=C(NC3=C1C=CC=C3)C=CC=C2)C CXVNZQVWELHKLT-UHFFFAOYSA-N 0.000 description 1
YVVYQLLVFFEKHJ-UHFFFAOYSA-N 5-ethyl-6,11-dihydro-5H-benzo[b][1]benzazepine Chemical compound C(C)C1CC2=C(NC3=C1C=CC=C3)C=CC=C2 YVVYQLLVFFEKHJ-UHFFFAOYSA-N 0.000 description 1
SNAXXYLGUQUSEB-UHFFFAOYSA-N 5-methoxy-11-methylbenzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2N(C)C2=CC=CC=C12 SNAXXYLGUQUSEB-UHFFFAOYSA-N 0.000 description 1
CRMKCEIXGVXGEO-UHFFFAOYSA-N 5-methyl-6,11-dihydro-5H-benzo[b][1]benzazepine Chemical compound CC1CC2=C(NC3=C1C=CC=C3)C=CC=C2 CRMKCEIXGVXGEO-UHFFFAOYSA-N 0.000 description 1
SJZUSSHIGOEGHX-UHFFFAOYSA-N C(C1=CC=CC=C1)N1C2=C(C=C(C3=C1C=CC=C3)OC)C=CC=C2 Chemical compound C(C1=CC=CC=C1)N1C2=C(C=C(C3=C1C=CC=C3)OC)C=CC=C2 SJZUSSHIGOEGHX-UHFFFAOYSA-N 0.000 description 1
CRPLICUGTIJHJP-UHFFFAOYSA-N CCC(C1)C(C=CC=C2)=C2N(C)C2=C1C=CC=C2 Chemical compound CCC(C1)C(C=CC=C2)=C2N(C)C2=C1C=CC=C2 CRPLICUGTIJHJP-UHFFFAOYSA-N 0.000 description 1
XEYSRYGOZSFHRK-UHFFFAOYSA-N CCC1=CC(C=CC=C2)=C2N(C)C2=C1C=CC=C2 Chemical compound CCC1=CC(C=CC=C2)=C2N(C)C2=C1C=CC=C2 XEYSRYGOZSFHRK-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1

Landscapes

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

CH894860A 1959-11-16 1960-08-05 Verfahren zur Herstellung von neuen Azepinderivaten CH399469A (de)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CH894860A CH399469A (de)	1960-08-05	1960-08-05	Verfahren zur Herstellung von neuen Azepinderivaten
CH1252665A CH412908A (de)	1960-08-05	1960-08-05	Verfahren zur Herstellung von neuen Azepinderivaten
ES0262489A ES262489A1 (es)	1959-11-16	1960-11-15	Procedimiento para la preparaciën de nuevos derivados azepinicos
GB39271/60A GB961444A (en)	1959-11-16	1960-11-16	Dibenz[b,f]-azepine derivatives and processes for the preparation thereof
BE598193A BE598193A (fr)	1960-08-05	1960-12-14	Nouvelles dibenzo-azépines et leur préparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH894860A CH399469A (de)	1960-08-05	1960-08-05	Verfahren zur Herstellung von neuen Azepinderivaten

Publications (1)

Publication Number	Publication Date
CH399469A true CH399469A (de)	1965-09-30

Family

ID=4346618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH894860A CH399469A (de)	1959-11-16	1960-08-05	Verfahren zur Herstellung von neuen Azepinderivaten

Country Status (2)

Country	Link
BE (1)	BE598193A (fr)
CH (1)	CH399469A (fr)

1960
- 1960-08-05 CH CH894860A patent/CH399469A/de unknown
- 1960-12-14 BE BE598193A patent/BE598193A/fr unknown

Also Published As

Publication number	Publication date
BE598193A (fr)	1961-06-14

Publication	Publication Date	Title
DE3010195C2 (fr)	1990-10-25
DE1961778A1 (de)	1970-06-18	Verfahren zur Herstellung von Brenzcatechin-Derivaten
CH651289A5 (de)	1985-09-13	Verfahren zur herstellung der d-2-(6-methoxy-2-naphthyl)-propionsaeure.
CH637363A5 (en)	1983-07-29	Process for preparing novel 2-aminotetralins
DE3300522C2 (fr)	1992-01-09
CH399469A (de)	1965-09-30	Verfahren zur Herstellung von neuen Azepinderivaten
CH591415A5 (en)	1977-09-15	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
AT223204B (de)	1962-09-10	Verfahren zur Herstellung von neuen Azepinderivaten
AT200579B (de)	1958-11-10	Verfahren zur Herstellung der neuen 5-Dibenzo[b,f]azepine
CH412908A (de)	1966-05-15	Verfahren zur Herstellung von neuen Azepinderivaten
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DE1142870B (de)	1963-01-31	Verfahren zur Herstellung von Azepinderivaten
AT344153B (de)	1978-07-10	Verfahren zur herstellung neuer 2-alkyl-5-indanessigsaeure- und -alkylester-derivate
AT226724B (de)	1963-04-10	Verfahren zur Herstellung von neuen 1-Aza-thioxanthen-Derivaten
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AT210435B (de)	1960-08-10	Verfahren zur Herstellung von neuen Ferrocenderivaten
AT283364B (de)	1970-08-10	Verfahren zur Herstellung neuer Zimtsäureamide
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AT217470B (de)	1961-10-10	Verfahren zur Herstellung von neuen 3-Alkyl- bzw. 3-Alkanoyl-10, 11-dihydro-5-dibenzo [b,f] azepinen und 3-Alkyl-5-dibenzo [b,f] azepinen
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AT247847B (de)	1966-06-27	Verfahren zur Herstellung von neuen 5-(3'-Aminopropyliden)-5H-dibenzo [a, d] cycloheptenen bzw. den 10, 11-Dihydroderivaten derselben
AT219604B (de)	1962-02-12	Verfahren zur Herstellung von neuen Iminodibenzylderivaten und deren Salzen
AT219037B (de)	1962-01-10	Verfahren zur Herstellung neuer, basischer Indol-Derivate
AT243268B (de)	1965-11-10	Verfahren zur Herstellung von neuen Benzochinolizin-Derivaten
AT222116B (de)	1962-07-10	Verfahren zur Herstellung von neuen, 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen