CH478754A - Process for the preparation of 5-aminomethylated 5H-dibenzo (a, d) cycloheptene derivatives - Google Patents
Process for the preparation of 5-aminomethylated 5H-dibenzo (a, d) cycloheptene derivativesInfo
- Publication number
- CH478754A CH478754A CH1295767A CH1295767A CH478754A CH 478754 A CH478754 A CH 478754A CH 1295767 A CH1295767 A CH 1295767A CH 1295767 A CH1295767 A CH 1295767A CH 478754 A CH478754 A CH 478754A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dibenzo
- cycloheptene
- aminomethylated
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical class C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 7
- 150000001933 cycloheptenes Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LCVQTDUGLFVCGP-UHFFFAOYSA-N 11h-dibenzo[1,2-a:1',2'-e][7]annulene-11-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(C#N)C2=CC=CC=C21 LCVQTDUGLFVCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- -1 aminomethyl-11-methyl-5H-dibenzo [a, d] -cyclohepten- Hydrochloride Chemical compound 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- RZJLDZMIOKCPJA-UHFFFAOYSA-N cycloheptene;hydrochloride Chemical compound Cl.C1CCC=CCC1 RZJLDZMIOKCPJA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- WOMPUOBDXRIHFY-UHFFFAOYSA-N (5-methyl-11h-dibenzo[1,2-a:2',1'-e][7]annulen-11-yl)methanamine Chemical compound CC1=CC2=CC=CC=C2C(CN)C2=CC=CC=C12 WOMPUOBDXRIHFY-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RJPZIQRLRMWPRF-UHFFFAOYSA-N Dibenzepin hydrochloride Chemical compound [Cl-].C[NH+](C)CCN1C(=O)C2=CC=CC=C2N(C)C2=CC=CC=C21 RJPZIQRLRMWPRF-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960003075 dibenzepin Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004678 hydrides Chemical class 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 5-aminomethylierten 5DDibenzola, d] cyclohepten-Derivaten
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von neuen 5-aminomethylierten 5H-Diben- zo [a, d] cycloheptenen und 10, 11-Dihydro-SH-dibenzo [a, d] cycloheptenen der Formel :
EMI1.1
worin R eine Alkylgruppe mit höchstens 3 C-Atomen darstellt, sowie von Säure-Additionssalzen davon. Die gestrichelte Linie in Formel I bedeutet, dass die Verbin dungen an den betreffenden Stellungen gesättigt oder ungesättigt sein können.
Verbindungen gemäss Formel I sowie deren Säure-
Additionssalze zeigen pharmakologische Eigenschaften, welche auf Verwendbarkeit als Antidepressiva schliessen lassen und welche bekannten Verbindungen dieser Wir kungsrichtung überlegen sind.
Die nachfolgende Tabelle zeigt einen Wirkungs vergleich zwischen dem erfindungsgemässen 5 Aminomethyl-11-methyl-5H-dibenzo [a, d]-cyclohepten-
Hydrochlorid und 5-Aminomethyl-10, 11-dihydro-11- methyl-5H-dibenzo [a, d]-cyclohepten-Hydrochlorid einerseits und dem als Antidepressivum bekannten Dibenzepin-Hydrochlorid anderseits. Als Mass für die antidepressive Wirkung wird diejenige Wirkstoffmenge (in mg/kg i. p.) angegeben, welche an der Ratte die durch 60 Minuten später verabreichtes Tetrabenazin (10 mg/kg i. p.) hervorgerufene Haltestarre (Katalepsie) bei 50 ouzo der Versuchstiere auf weniger als 30 Sekunden herabsetzt (ED 50).
Zur Beurteilung des therapeutischen Index'sind in der Tabelle auch die oralen Toxizitäten bei der Maus als DL 50 angegeben.
Sabelle
EMI2.1
<SEP> Toxizität <SEP> Antitetrabenazin <SEP> W <SEP> i <SEP> r <SEP> k <SEP> s <SEP> t <SEP> o <SEP> f <SEP> f <SEP> (Maus) <SEP> Wirkung <SEP> (Ratte)
<tb> <SEP> DL <SEP> 50 <SEP> mg/kg <SEP> p. <SEP> o. <SEP> ED <SEP> 50 <SEP> mg/kg <SEP> i. <SEP> p.
<tb>
5-Aminomethylz <SEP> methyl-5H-dibenzo <SEP>
<tb> (api) <SEP> cyclohepten-Hydrochlorid <SEP> 240 <SEP> 17 <SEP>
<tb> 5-jUminomathyl-10, <SEP> 11-dihydro-11-meth. <SEP> yl- <SEP>
<tb> 5H <SEP> dibenzo <SEP> [a, <SEP> d] <SEP> cyclohepten-Hydrochlorid <SEP> 420 <SEP> 16
<tb> Dibenzepm-Hydrochlorid <SEP> 225 <SEP> 25 <SEP>
<tb>
Die gewünschten Verbindungen (I) werden erhalten durch Reduktion von 5-Cyano-5H-dibenzo [a, d] cycloheptenen oder 5-Cyano-10, 11-dihydro-5H-dibenzo [a, cycloheptenen der Formel.
EMI2.2
worin R die genannte Bedeutung hat. Die Reduktion erfolgt vorzugsweise durch Behandeln mit komplexen Hydriden, insbesondere Lithiumaluminiumhydrid.
Bei Verwendung von Lithiumaluminiumhydrid als Reduktionsmittel wird vorteilhaft in Aether und in Anwesenheit von wasserfreiem Aluminiumchlorid gearbeitet.
Die nach diesem Verfahren erhaltenen Verbindungen entsprechend Formel I können sowohl als freie Basen als auch in Form ihrer Additionssalze mit geeigneten Säuren, wie Halogenwasserstoffsäuren, Toluolsulfonsäuren, Schwefelsäure, Salpetersäure, Phosphorsäure, Essigsäure, Oxalsäure, Malonsäure, Bernsteinsäure, Äpfelsäure, Maleinsäure oder Weinsäure, gewonnen und verwendet werden.
Beispiel 1
Zu 2, 05 g Lithiumaluminiumhydrid und 7, 0 g Aluminiumchlorid in 150 ml Aether werden unter Rühren 10, 8 g 5-Cyano-11-methyl-5H-dibenzo [a, d] cyclohepten (Smp. 144-145 C) portionenweise zugegeben. Das Reaktionsgemisch wird anschliessend während 2 Stunden am Rückfluss erhitzt und dann über Nacht bei Zimmertemperatur stehengelassen. Das überschüssige Lithiumaluminiumhydrid wird hierauf sorgfältig mit Wasser zerstört, und das Reaktionsgemisch wird viermal mit 2n-Salzsäure ausgeschüttelt. Die vereinigten salzsauren Auszüge werden mit 2n-Natronlauge alkalisch gestellt und viermal mit Aether ausgeschüttelt. Die Aetherauszüge werden mit Wasser gewaschen, mit Natriumsul- fat getrocknet und eingedampft.
Man erhält 9,35 g (85 % der Theorie) 5-Aminomethyl-11-methyl-5H-dibenzo[a,d]cyclohepten, welches durch Behandeln mit 15 /0iger äthanolischer Salzsäure in das Hydrochlorid übergeführt wird. Das erhaltene 5-Aminomethyl-11- methyl-SH-dibenzo [a, d] cyclohepten-Hydrochlorid zeigt nach Kristallisation aus Methanol/Aether die Gestalt von farblosen Nadeln und einen Schmelzpunkt von 234-235 C.
Beispiel 2
Bei gleichem Vorgehen wie in Beispiel 1, jedoch unter Verwendung von 1, 45 g Lithiumaluminiumhydrid und 5, 1 g Aluminiumchlorid und ausgehend von 8, 0 g 5- Cyano-10, 11-dihydro-11-methyl-SH-dibenzo [a, d] cyclohepten (Smp. 167-169 C), erhalt man 7, 75 g (95 O/o der Theorie) S-Aminomethyl-10, 11-dihydro-11-methyl- 5H-dibenzo [a, d] cyclohepten welches wie in Beispiel 1 in das Hydrochlorid übergeführt wird.
Das erhaltene 5- Aminomethyl-10, 11-dihydro-11-methyl-5H-dibenzo [a, d] cyclohepten-Hydrochlorid zeigt nach Kristallisation aus Methanol/Aether die Gestalt von farblosen Nadeln und einen Schmelzpunkt von 248-251 C.
Process for the preparation of 5-aminomethylated 5D-dibenzola, d] cycloheptene derivatives
The invention relates to a process for the preparation of new 5-aminomethylated 5H-dibenzo [a, d] cycloheptenes and 10, 11-dihydro-SH-dibenzo [a, d] cycloheptenes of the formula:
EMI1.1
in which R represents an alkyl group having at most 3 carbon atoms, and acid addition salts thereof. The dashed line in formula I means that the connec tions at the positions in question can be saturated or unsaturated.
Compounds according to formula I and their acid
Addition salts show pharmacological properties which indicate their usefulness as antidepressants and which known compounds are superior to this direction of action.
The table below shows an activity comparison between the 5 aminomethyl-11-methyl-5H-dibenzo [a, d] -cyclohepten-
Hydrochloride and 5-aminomethyl-10, 11-dihydro-11-methyl-5H-dibenzo [a, d] -cycloheptene hydrochloride on the one hand and the dibenzepine hydrochloride known as an antidepressant on the other. As a measure of the antidepressant effect, that amount of active substance (in mg / kg ip) is given which reduces the rigid posture (catalepsy) caused by 60 minutes later administered tetrabenazine (10 mg / kg ip) in 50 ouzo of the test animals to less than 30 Seconds down (ED 50).
To assess the therapeutic index, the oral toxicities in the mouse are also given as DL 50 in the table.
Sabelle
EMI2.1
<SEP> Toxicity <SEP> Antitetrabenazine <SEP> W <SEP> i <SEP> r <SEP> k <SEP> s <SEP> t <SEP> o <SEP> f <SEP> f <SEP> (mouse) <SEP> effect <SEP> (rat)
<tb> <SEP> DL <SEP> 50 <SEP> mg / kg <SEP> p. <SEP> o. <SEP> ED <SEP> 50 <SEP> mg / kg <SEP> i. <SEP> p.
<tb>
5-aminomethylz <SEP> methyl-5H-dibenzo <SEP>
<tb> (api) <SEP> cycloheptene hydrochloride <SEP> 240 <SEP> 17 <SEP>
<tb> 5-jUminomathyl-10, <SEP> 11-dihydro-11-meth. <SEP> yl- <SEP>
<tb> 5H <SEP> dibenzo <SEP> [a, <SEP> d] <SEP> cycloheptene hydrochloride <SEP> 420 <SEP> 16
<tb> Dibenzepm hydrochloride <SEP> 225 <SEP> 25 <SEP>
<tb>
The desired compounds (I) are obtained by reducing 5-cyano-5H-dibenzo [a, d] cycloheptenes or 5-cyano-10,11-dihydro-5H-dibenzo [a, cycloheptenes of the formula.
EMI2.2
wherein R has the stated meaning. The reduction is preferably carried out by treatment with complex hydrides, in particular lithium aluminum hydride.
When using lithium aluminum hydride as reducing agent, it is advantageous to work in ether and in the presence of anhydrous aluminum chloride.
The compounds according to formula I obtained by this process can be obtained both as free bases and in the form of their addition salts with suitable acids, such as hydrohalic acids, toluenesulfonic acids, sulfuric acid, nitric acid, phosphoric acid, acetic acid, oxalic acid, malonic acid, succinic acid, malic acid, maleic acid or tartaric acid and used.
example 1
To 2.05 g of lithium aluminum hydride and 7.0 g of aluminum chloride in 150 ml of ether, 10.8 g of 5-cyano-11-methyl-5H-dibenzo [a, d] cycloheptene (melting point 144-145 C) are added in portions with stirring . The reaction mixture is then refluxed for 2 hours and then left to stand overnight at room temperature. The excess lithium aluminum hydride is then carefully destroyed with water, and the reaction mixture is extracted four times with 2N hydrochloric acid. The combined hydrochloric acid extracts are made alkaline with 2N sodium hydroxide solution and extracted four times with ether. The ether extracts are washed with water, dried with sodium sulfate and evaporated.
9.35 g (85% of theory) of 5-aminomethyl-11-methyl-5H-dibenzo [a, d] cycloheptene are obtained, which is converted into the hydrochloride by treatment with 15% strength ethanolic hydrochloric acid. The 5-aminomethyl-11-methyl-SH-dibenzo [a, d] cycloheptene hydrochloride obtained has the shape of colorless needles and a melting point of 234-235 ° C. after crystallization from methanol / ether.
Example 2
Using the same procedure as in Example 1, but using 1.45 g of lithium aluminum hydride and 5.1 g of aluminum chloride and starting from 8.0 g of 5-cyano-10, 11-dihydro-11-methyl-SH-dibenzo [a, d] cycloheptene (melting point 167-169 ° C.), 7.75 g (95% of theory) of S-aminomethyl-10, 11-dihydro-11-methyl-5H-dibenzo [a, d] cycloheptene are obtained as in Example 1 is converted into the hydrochloride.
The 5-aminomethyl-10, 11-dihydro-11-methyl-5H-dibenzo [a, d] cycloheptene hydrochloride obtained shows the shape of colorless needles and a melting point of 248-251 ° C. after crystallization from methanol / ether.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1295767A CH478754A (en) | 1967-09-15 | 1967-09-15 | Process for the preparation of 5-aminomethylated 5H-dibenzo (a, d) cycloheptene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1295767A CH478754A (en) | 1967-09-15 | 1967-09-15 | Process for the preparation of 5-aminomethylated 5H-dibenzo (a, d) cycloheptene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH478754A true CH478754A (en) | 1969-09-30 |
Family
ID=4387967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1295767A CH478754A (en) | 1967-09-15 | 1967-09-15 | Process for the preparation of 5-aminomethylated 5H-dibenzo (a, d) cycloheptene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH478754A (en) |
-
1967
- 1967-09-15 CH CH1295767A patent/CH478754A/en not_active IP Right Cessation
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |