CH434241A - Process for the preparation of bicyclically substituted aminoalkanes - Google Patents

Process for the preparation of bicyclically substituted aminoalkanes

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Publication number
CH434241A
CH434241A CH1638166A CH1638166A CH434241A CH 434241 A CH434241 A CH 434241A CH 1638166 A CH1638166 A CH 1638166A CH 1638166 A CH1638166 A CH 1638166A CH 434241 A CH434241 A CH 434241A
Authority
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Switzerland
Prior art keywords
sep
compounds
preparation
formula
aminoalkanes
Prior art date
Application number
CH1638166A
Other languages
German (de)
Inventor
Helmut Kraft
Wilfried Klavehn
Original Assignee
Knoll 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.)
Filing date
Publication date
Application filed by Knoll Ag filed Critical Knoll Ag
Publication of CH434241A publication Critical patent/CH434241A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

  



  Verfahren zur Herstellung   bicyclisch    substituierter Aminoalkane
Gegenstand der Erfindung ist ein Verfahren zur Herstellung neuer   bicyclisch    substituierter Aminoalkane der Formeln
EMI1.1     
 bzw. deren Salzen und quartären Ammoniumverbindun gen, wobei A einen niedermolekularen Alkylenrest mit
2 oder 3 Kohlenstoffatomen in der Hauptkette, B ein
Wasserstoffatom, einen niedermolekularen Alkyl-oder Alkoxyrest oder ein Chloratom und Ri und R2 niedermolekulare Alkylreste oder zusammen mit dem Stickstoffatom einen gegebenenfalls substituierten   hetero-      cyclischen    Rest, wie den Pyrrolidin-, Piperidin-oder Morpholinrest, oder Ri und A zusammen mit dem Stickstoffatom einen   N-Alkylpiperidinrest    bedeuten.



   Die neuen Verbindungen besitzen wertvolle thera  peutische    Eigenschaften und sollen als Arzneimittel Verwendung finden. Insbesondere kommen ihnen analgetische, spasmolytische,   hustendämpfende    und   entzün-      dungshemmende    Wirkungen zu.



   Die neuen   bicyclisch    substituierten Aminoalkane werden erfindungsgemäss erhalten, indem man   bicyclisch    substituierte   Aminopropanole    der Formel
EMI1.2     
 durch Einwirkung wasserbindender Mittel dehydratisiert und die erhaltenen Verbindungen der Formel I gege benenfalls durch katalytische Hydrierung in Verbin dungen der Formel II überführt und/oder aus den Ver fahrensprodukten deren Salze mit anorganischen oder organischen Säuren bzw. deren quaternäre Ammonium verbindungen bildet.



   Die Ausgangsverbindungen der Formel III lassen sich nach dem Verfahren der schweizerischen Patent schrift Nr. 330 310 herstellen. Als wasserbindende Mit tel kommen beispielsweise Gemische aus Eisessig und konzentrierter Schwefelsäure, sirupöse Phosphorsäure,
Acetanhydrid, Eisessig oder Zinkchlorid oder deren
Mischungen in Betracht.



   Die erhaltenen Verbindungen der Formel I können, wie erwähnt, gegebenenfalls durch katalytische Hydrierung z. B. mit Wasserstoff in Gegenwart von Platinoxyd in essigsaurer Lösung oder mit Raney-Nickel in organischen Lösungsmitteln in Verbindungen der Formel II überführt werden.



   Die auf dem erfindungsgemässen Wege erhältlichen   bicyclisch    substituierten Aminoalkane sind im Vakuum destillierbare, ölige Flüssigkeiten, welche mit anorganischen und organischen Säuren gut kristallisierte wasserlösliche Salze bilden. Durch Umsetzung mit Alkylhalo geniden oder Alkylsulfaten werden die kristallisierten, quartären Ammoniumverbindungen erhalten.



   Die Erfindung wird nachstehend anhand von Ausführungsbeispielen erläutert.



   Beispiel 1    l-Phenyl-1-[bicyclo-(2,    2,1)-heptyliden-2]-3-piperi   dino-propan   
Zu einer Lösung von 27,4 g   1-Phenyl-l-[bicyclo-    (2,2,1)-heptyl-2]-3-piperidino-propanol-1 in 22 g Eisessig wird unter Rühren bei 50 bis   60  C    eine Mischung von 22 g konzentrierter Schwefelsäure und 11 g Eisessig innerhalb 30 Minuten zugetropft. Die Reaktionslösung wird   11/2    Stunden unter Rühren auf   50  ge-    halten, alsdann in eine Mischung von Eis und 350 cm3 2n Natronlauge eingegossen und die   ölig    abgeschiedene Base in   Ather    aufgenommen. Nach Trocknen mit Natriumsulfat wird unter vermindertem Druck destilliert.



     Kp4mm 159-162  C    ; Ausbeute an   1-Phenyl-l-[bicyclo-    (2,2,1)-heptyliden-2]-3-piperidino-propan 21,2 g entsprechend 83 % der Theorie.



   Durch entsprechende Umsetzung wird auf 1- (2 Methoxy-phenyl)-l- [bicyclo- (2, 2,1) heptyl-2]-3-piperi  dino-propanol-1    das   1- (2-Methoxy-phenyl)-l- [bicyclo-    (2,2,1)-heptyliden-2]-3-piperidino-propan vom Kpo,   4mm    166-172  C erhalten.   C22H3tNO. Eydroclílorid    F 168 bis   170     C (aus Methyläthylketon).



   Aus   1-(4-Chlorphenyl)-l-[bicyclo-(2,    2,1)-heptyl-2]  3-piperidinopropanol-1    wird in analoger Weise das   1- (4-      Chlorphenyl)-1- [bicyclo-(2,2,1)-heptyliden-2]-3-piperi-    dino-propan vom   Kpo,      2mm    160 bis   162     C erhalten.



  Hydrochlorid F 240 bis 241  C (aus Methyläthylketon).



   In analoger Weise erhält man auch die folgenden Derivate :
EMI2.1     


<tb>  <SEP> Kp <SEP> Base <SEP> F <SEP> Hydrochlorid
<tb>  <SEP> /C2H5
<tb>  <SEP> 1. <SEP> C-CHz-CHz-N <SEP> 4mm/145-149 C <SEP> 137-138  <SEP> C
<tb>  <SEP> \CzHs
<tb>  <SEP> /'C. <SEP> zii6
<tb>  <SEP> 2. <SEP> C-CHs-CHz-N <SEP> 4mm/162-164 C <SEP> 225-226  <SEP> C
<tb>  <SEP> /
<tb> 3. <SEP> C-CHz-CH2-N <SEP> 2 <SEP> mm/180-185  <SEP> C <SEP> 248-250  <SEP> C
<tb> 4. <SEP> CCH2CH2CH2N <SEP> 4 <SEP> mm/177-181  <SEP> C <SEP> 202-203  <SEP> C
<tb>  <SEP> \CHs
<tb>  <SEP>  < Zx <SEP> 
<tb> 5. <SEP> C/\NCH3 <SEP> 3 <SEP> mm/168-171  <SEP> C <SEP> 258-260 C
<tb>  <SEP> CH
<tb> 6. <SEP> C-CH-CH.-N <SEP> 0,5 <SEP> mm/165-169  <SEP> C <SEP> 235  <SEP> C
<tb>  <SEP> /
<tb>  <SEP>  <  <SEP> CH
<tb>  <SEP> /CH3
<tb> 7. <SEP> CCH2CHN/0, <SEP> 6 <SEP> mm/124-130  <SEP> C <SEP> 198-199  <SEP> C
<tb>  <SEP> s.

   <SEP> G <SEP> CHs <SEP> CHa
<tb>  
Durch katalytische Hydrierung dieser Bicycloheptyliden-Verbindungen gemäss Beispiel   2    oder 3 sind die entsprechenden gesättigten Derivate erhältlich. Man erhält auf diese Weise :
EMI3.1     


<tb>  <SEP> Kp <SEP> Base
<tb>  <SEP> /zHs
<tb> 8. <SEP> CH-CH2-CH2-N <SEP> 0, <SEP> 05 <SEP> mm/135-137  <SEP> C
<tb> 9. <SEP> CH-CHz-CH2-N <SEP> 0,1 <SEP> mm/146-148  <SEP> C
<tb>  <SEP> x <SEP> 
<tb> 10. <SEP> CH-CH2-CH2-N <SEP> O <SEP> 0,2 <SEP> mm/160-163 <SEP> C
<tb>  <SEP>  < S <SEP> CH
<tb> 11. <SEP> CH-CHz-CHz-CH2-N <SEP> 0,05 <SEP> mm/132-135  <SEP> C
<tb>  <SEP> CH3
<tb>  <SEP> //
<tb> 12.

   <SEP> CH/N-CH3 <SEP> 0, <SEP> 05 <SEP> mm/147-149  <SEP> C
<tb> 
Beispiel 2    1-Phenyl-l-[bicyclo-(2,    2,1)-heptyl-2]-3-dimethyl aminopropan
10 g   1-Phenyl-l-[bicyclo-(2,    2,1)-heptyliden-2]-3-dimethylaminopropan werden in 100 cm3 Eisessig gelöst und in Gegenwart von 0,2-0,5 g   Platinoxyd-Katalysator    und Wasserstoff bei gewöhnlicher Temperatur und Atmosphärendruck hydriert, bis die berechnete Wasserstoffmenge von 880 cm3 aufgenommen ist. Nach dem Abdampfen des Eisessigs im Vakuum wird der   Rück-    stand in Wasser gelöst, mit Natronlauge alkalisch gemacht und die abgeschiedene Base in Äther aufgenommen. Nach dem Trocknen über Natriumsulfat wird im Vakuum destilliert.   Kp4mm      122-124  C    ;   Ct8H2TN.   



   Beispiel 3    l-Phenyl-l-[bicyclo-(2,    2,1)-heptyl-2]-3 piperidino-propan
10 g   1-Phenyl-1-[bicyclo-(2,    2,1)-heptyliden-2]-3piperidino-propan werden in 100 cm3 Methanol gelöst und mit 5 g Raney-Nickel bei   80     C und 80   atü    Wasserstoffdruck bis zur Aufnahme der berechneten Menge Wasserstoff (760 cm3) hydriert. Nach Abdampfen des Methanols unter vermindertem Druck wird der   Rück-    stand im Vakuum destilliert.   Kapo, 4mu    176 bis   179  C.   



  Hydrochlorid F 214 bis 215  C (aus   Athanol/Ather).  



  



  Process for the preparation of bicyclically substituted aminoalkanes
The invention relates to a process for the preparation of new bicyclically substituted aminoalkanes of the formulas
EMI1.1
 or their salts and quaternary ammonium compounds, where A is a low molecular weight alkylene radical
2 or 3 carbon atoms in the main chain, B.
Hydrogen atom, a low molecular weight alkyl or alkoxy group or a chlorine atom and Ri and R2 low molecular weight alkyl groups or, together with the nitrogen atom, an optionally substituted heterocyclic group, such as the pyrrolidine, piperidine or morpholine group, or Ri and A together with the nitrogen atom an N -Alkylpiperidine radical.



   The new compounds have valuable therapeutic properties and are intended to be used as drugs. In particular, they have analgesic, spasmolytic, cough suppressant and anti-inflammatory effects.



   The new bicyclically substituted aminoalkanes are obtained according to the invention by adding bicyclically substituted aminopropanols of the formula
EMI1.2
 dehydrated by the action of water-binding agents and the resulting compounds of the formula I, if necessary, converted into compounds of the formula II by catalytic hydrogenation and / or their salts with inorganic or organic acids or their quaternary ammonium compounds are formed from the process products.



   The starting compounds of the formula III can be prepared by the process of Swiss Patent No. 330 310. As water-binding agents, for example, mixtures of glacial acetic acid and concentrated sulfuric acid, syrupy phosphoric acid,
Acetic anhydride, glacial acetic acid or zinc chloride or their
Mixtures into consideration.



   The compounds of formula I obtained can, as mentioned, optionally by catalytic hydrogenation, for. B. with hydrogen in the presence of platinum oxide in acetic acid solution or with Raney nickel in organic solvents in compounds of formula II.



   The bicyclically substituted aminoalkanes obtainable by the route according to the invention are oily liquids which can be distilled in vacuo and which form well-crystallized water-soluble salts with inorganic and organic acids. The crystallized quaternary ammonium compounds are obtained by reaction with alkyl halides or alkyl sulfates.



   The invention is explained below on the basis of exemplary embodiments.



   Example 1 1-Phenyl-1- [bicyclo- (2, 2,1) -heptylidene-2] -3-piperidino-propane
A solution of 27.4 g of 1-phenyl-l- [bicyclo- (2,2,1) -heptyl-2] -3-piperidino-1-propanol in 22 g of glacial acetic acid is added at 50 to 60 ° C. with stirring Mixture of 22 g of concentrated sulfuric acid and 11 g of glacial acetic acid was added dropwise over 30 minutes. The reaction solution is kept at 50 for 11/2 hours with stirring, then poured into a mixture of ice and 350 cm 3 of 2N sodium hydroxide solution and the oily base which has separated out is taken up in ether. After drying with sodium sulfate, it is distilled under reduced pressure.



     Kp4mm 159-162 C; Yield of 1-phenyl-l- [bicyclo- (2,2,1) -heptylidene-2] -3-piperidino-propane 21.2 g corresponding to 83% of theory.



   By appropriate reaction, 1- (2-methoxyphenyl) -l- [bicyclo- (2, 2,1) heptyl-2] -3-piperi dino-propanol-1 is 1- (2-methoxyphenyl) - I- [bicyclo- (2,2,1) -heptylidene-2] -3-piperidino-propane obtained from Kpo, 4mm 166-172 ° C. C22H3tNO. Eydroclílorid F 168 to 170 C (from methyl ethyl ketone).



   1- (4-chlorophenyl) -1- [bicyclo- (2, 2,1) -heptyl-2] 3-piperidinopropanol-1 is converted in an analogous manner to 1- (4-chlorophenyl) -1- [bicyclo- ( 2,2,1) -heptylidene-2] -3-piperidino-propane obtained from Kpo, 2mm 160 to 162 ° C.



  Hydrochloride F 240 to 241 C (from methyl ethyl ketone).



   The following derivatives are also obtained in an analogous manner:
EMI2.1


<tb> <SEP> Kp <SEP> Base <SEP> F <SEP> hydrochloride
<tb> <SEP> / C2H5
<tb> <SEP> 1. <SEP> C-CHz-CHz-N <SEP> 4mm / 145-149 C <SEP> 137-138 <SEP> C
<tb> <SEP> \ CzHs
<tb> <SEP> / 'C. <SEP> zii6
<tb> <SEP> 2. <SEP> C-CHs-CHz-N <SEP> 4mm / 162-164 C <SEP> 225-226 <SEP> C
<tb> <SEP> /
<tb> 3. <SEP> C-CHz-CH2-N <SEP> 2 <SEP> mm / 180-185 <SEP> C <SEP> 248-250 <SEP> C
<tb> 4. <SEP> CCH2CH2CH2N <SEP> 4 <SEP> mm / 177-181 <SEP> C <SEP> 202-203 <SEP> C
<tb> <SEP> \ CHs
<tb> <SEP> <Zx <SEP>
<tb> 5. <SEP> C / \ NCH3 <SEP> 3 <SEP> mm / 168-171 <SEP> C <SEP> 258-260 C
<tb> <SEP> CH
<tb> 6. <SEP> C-CH-CH.-N <SEP> 0.5 <SEP> mm / 165-169 <SEP> C <SEP> 235 <SEP> C
<tb> <SEP> /
<tb> <SEP> <<SEP> CH
<tb> <SEP> / CH3
<tb> 7. <SEP> CCH2CHN / 0, <SEP> 6 <SEP> mm / 124-130 <SEP> C <SEP> 198-199 <SEP> C
<tb> <SEP> s.

   <SEP> G <SEP> CHs <SEP> CHa
<tb>
The corresponding saturated derivatives can be obtained by catalytic hydrogenation of these bicycloheptylidene compounds according to Example 2 or 3. In this way you get:
EMI3.1


<tb> <SEP> Kp <SEP> Base
<tb> <SEP> / zHs
<tb> 8. <SEP> CH-CH2-CH2-N <SEP> 0, <SEP> 05 <SEP> mm / 135-137 <SEP> C
<tb> 9. <SEP> CH-CHz-CH2-N <SEP> 0.1 <SEP> mm / 146-148 <SEP> C
<tb> <SEP> x <SEP>
<tb> 10. <SEP> CH-CH2-CH2-N <SEP> O <SEP> 0.2 <SEP> mm / 160-163 <SEP> C
<tb> <SEP> <S <SEP> CH
<tb> 11. <SEP> CH-CHz-CHz-CH2-N <SEP> 0.05 <SEP> mm / 132-135 <SEP> C
<tb> <SEP> CH3
<tb> <SEP> //
<tb> 12.

   <SEP> CH / N-CH3 <SEP> 0, <SEP> 05 <SEP> mm / 147-149 <SEP> C
<tb>
Example 2 1-Phenyl-1- [bicyclo- (2, 2,1) -heptyl-2] -3-dimethyl aminopropane
10 g of 1-phenyl-l- [bicyclo- (2, 2,1) -heptylidene-2] -3-dimethylaminopropane are dissolved in 100 cm3 of glacial acetic acid and in the presence of 0.2-0.5 g of platinum oxide catalyst and hydrogen hydrogenated at normal temperature and atmospheric pressure until the calculated amount of hydrogen of 880 cm3 is absorbed. After the glacial acetic acid has evaporated in vacuo, the residue is dissolved in water, made alkaline with sodium hydroxide solution and the base which has separated out is taken up in ether. After drying over sodium sulfate, it is distilled in vacuo. Kp4mm 122-124 C; Ct8H2TN.



   Example 3 l-Phenyl-l- [bicyclo- (2, 2,1) -heptyl-2] -3-piperidino-propane
10 g of 1-phenyl-1- [bicyclo- (2, 2,1) -heptylidene-2] -3piperidino-propane are dissolved in 100 cm3 of methanol and treated with 5 g of Raney nickel at 80 ° C. and 80 atm. Hydrogen pressure until absorption the calculated amount of hydrogen (760 cm3) hydrogenated. After the methanol has been evaporated off under reduced pressure, the residue is distilled in vacuo. Kapo, 4mu 176 to 179 C.



  Hydrochloride F 214 to 215 C (from ethanol / ether).

Claims (1)

PATENTANSPRÜCHE I. Verfahren zur Herstellung bicyclisch substituierter Aminoalkane der Formel EMI3.2 worin A einen niedermolekularen Alkylenrest mit 2 oder 3 Kohlenstoffatomen in der Hauptkette, B ein Wasserstoffatom, einen niedermolekularen Alkyl-oder Alkoxyrest oder ein Chloratom und Ri und R2 niedermolekulare Alkylreste oder zusammen mit dem Stickstoffatom einen N-Alkyl-piperidin-Rest bedeuten, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI3.3 durch Einwirkung wasserbindender Mittel dehydratisiert. PATENT CLAIMS I. Process for the preparation of bicyclically substituted aminoalkanes of the formula EMI3.2 wherein A is a low molecular weight alkylene radical with 2 or 3 carbon atoms in the main chain, B is a hydrogen atom, a low molecular weight alkyl or alkoxy radical or a chlorine atom and Ri and R2 are low molecular weight alkyl radicals or together with the nitrogen atom an N-alkylpiperidine radical, characterized that you can get a compound of the formula EMI3.3 dehydrated by the action of water-binding agents. II. Verwendung der nach dem Verfahren nach Pa tentanspruch I hergestellten Verbindungen zur Henstellung der entsprechenden quartären Ammoniumverbindungen. II. Use of the compounds prepared according to the method according to Pa tent claims I for the preparation of the corresponding quaternary ammonium compounds. UNTERANSPRUCH Verfahren nach Patentanspruch I, dadurch gekennzeichnet, dass man die erhaltenen Verbindungen durch katalytische Hydrierung in Verbindungen der Formel EMI4.1 iiberfiihrt. SUBClaim Process according to patent claim I, characterized in that the compounds obtained are converted into compounds of the formula by catalytic hydrogenation EMI4.1 transferred.
CH1638166A 1962-06-09 1963-05-21 Process for the preparation of bicyclically substituted aminoalkanes CH434241A (en)

Applications Claiming Priority (1)

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DEK46969A DE1284421B (en) 1962-06-09 1962-06-09 Bicyclically substituted aminoalkanes and processes for their preparation

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CH434241A true CH434241A (en) 1967-04-30

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Publication number Priority date Publication date Assignee Title
CA1130318A (en) * 1978-10-11 1982-08-24 Peter M. Muller Cyclohexadiene derivatives

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1088484B (en) * 1958-03-10 1960-09-08 Bayer Ag Process for the production of bicyclically substituted carbinamines or their non-toxic salts with an effect on blood pressure
DE1110159B (en) * 1959-08-01 1961-07-06 Merck Ag E Process for the preparation of analeptically active N-substituted amino orcamphan derivatives or of their acid addition salts and quaternary ammonium compounds
BE598255A (en) * 1959-12-19 1961-06-16 Knoll Ag New amines and their preparation

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DE1284421B (en) 1968-12-05
FR2641M (en) 1964-07-06
CH435250A (en) 1967-05-15

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