CH305265A - Process for preparing a novel quaternary ammonium derivative. - Google Patents
Process for preparing a novel quaternary ammonium derivative.Info
- Publication number
- CH305265A CH305265A CH305265DA CH305265A CH 305265 A CH305265 A CH 305265A CH 305265D A CH305265D A CH 305265DA CH 305265 A CH305265 A CH 305265A
- Authority
- CH
- Switzerland
- Prior art keywords
- quaternary ammonium
- preparing
- ammonium derivative
- novel quaternary
- bis
- Prior art date
Links
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J23/00—Details of transit-time tubes of the types covered by group H01J25/00
- H01J23/16—Circuit elements, having distributed capacitance and inductance, structurally associated with the tube and interacting with the discharge
- H01J23/24—Slow-wave structures, e.g. delay systems
- H01J23/26—Helical slow-wave structures; Adjustment therefor
Landscapes
- Microwave Tubes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation d'un nouveau dérivé d'ammonium quaternaire.
La présente invention a pour objet un procédé de préparation d'un nouveau dérivé d'ammonium quaternaire.
Il est bien connu que les sels d'hexaméthylene-bis (triméthvlammonium)-1, 6 et de pentaméthylene-bis (triméthylammonium)-1, 5 (par exemple le bromure d'hexaméthonium et de pentaméthonium) ont une application théra- peutique intéressante comme agents ganglio plegiques. On a aussi montré que les sels de his (éthyl-diméthylammonium) correspondants ont une activité plus marquée que les composés voisins. Cependant, pour toutes ces substances, le rapport entre l'activité ganglio plégique sympathique et l'activité ganglioplé gique parasympathique est à peu près le même quand on détermine ces activités par des méthodes connues, respectivement sur le ganglion cervical supérieur du chat et l'intestin isolé du cobaye.
Le nouveau sel d'ammonium quaternaire que l'on peut obtenir par le procédé selon la présente invention, à savoir le dibromure de tétraméthylene-bis (diéthyl-méthyla. mmonium)- 1, 4, qui répond à la formule :
EMI1.1
et est un solide fondant à 284-287 , présente une action ganglioplégique parasympathique sélective et, de ce fait, présente un avantage dans les traitements où l'activité ganglioplé- gique sympathique pourrait produire des effets secondaires indésirables.
Par exemple, en clinique, on a constaté que ce corps était efficace dans le cas d'ulcères gastriques, sans avoir sur le système nerveux sympathique les effets secondaires provoqués par les composés de structure chimique analogue connus.
Selon l'invention, on prépare ce composé par condensation du dibromo-1, 4-butane avec la méthyldiéthylamine.
Ce composé peut également servir d'inter médiaire pour la préparation des bitartrate et phosphate correspondants, soit par métathèse directe, soit par l'intermédiaire de l'hydroxyde.
Le procédé objet de la présente invention est illustré par l'exemple suivant :
Exemple :
On chauffe à reflux pendant quelques heures des quantités stoéchiométriques de dibromo-1, 4-butane et de méthyldiéthylamine en solution dans l'alcool éthylique. On élimine l'excès d'alcool par distillation et on verse le résidu dans l'acétone. Le solide cristallin blane qui se forme est séparé par filtration et on le fait cristalliser dans le mélange alcool éthyli- que (acétone. On obtient du dibromure de tétraméthylene-bis (diéthvl-méthylammonium)- 1, 4 sous forme de microprismes irréguliers hygroscopiques, P. F. = 284-287¯.
Process for preparing a novel quaternary ammonium derivative.
The present invention relates to a process for preparing a novel quaternary ammonium derivative.
It is well known that the salts of hexamethylene-bis (trimethylammonium) -1, 6 and of pentamethylene-bis (trimethylammonium) -1, 5 (for example hexamethonium and pentamethonium bromide) have interesting therapeutic application. as ganglio plegic agents. It has also been shown that the corresponding his (ethyl-dimethylammonium) salts have a more marked activity than the neighboring compounds. However, for all these substances, the ratio between sympathetic ganglio plegic activity and parasympathetic ganglioplegic activity is about the same when these activities are determined by known methods, respectively on the upper cervical ganglion of the cat and the isolated gut of guinea pig.
The new quaternary ammonium salt which can be obtained by the process according to the present invention, namely tetramethylene-bis (diethyl-methyla. Mmonium) dibromide - 1, 4, which corresponds to the formula:
EMI1.1
and is a 284-287 solid flux, exhibits selective parasympathetic ganglioplegic action and, therefore, has an advantage in treatments where sympathetic ganglioplegic activity could produce unwanted side effects.
For example, clinically, this body has been found to be effective in gastric ulcers, without having the side effects on the sympathetic nervous system caused by known compounds of similar chemical structure.
According to the invention, this compound is prepared by condensation of dibromo-1,4-butane with methyldiethylamine.
This compound can also serve as an intermediary for the preparation of the corresponding bitartrate and phosphate, either by direct metathesis or via the hydroxide.
The method which is the subject of the present invention is illustrated by the following example:
Example:
Stoichiometric amounts of dibromo-1, 4-butane and methyldiethylamine in solution in ethyl alcohol are heated under reflux for a few hours. The excess alcohol is removed by distillation and the residue is poured into acetone. The white crystalline solid which forms is separated by filtration and it is crystallized in an ethyl alcohol mixture (acetone. Tetramethylene bis (diethyl-methylammonium) dibromide - 1, 4 is obtained in the form of hygroscopic irregular microprisms, PF = 284-287¯.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34/52A GB764681A (en) | 1952-01-01 | 1952-01-01 | Improvements in travelling wave tubes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH305265A true CH305265A (en) | 1955-02-15 |
Family
ID=32302972
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH305265D CH305265A (en) | 1952-01-01 | 1952-12-19 | Process for preparing a novel quaternary ammonium derivative. |
| CH310060D CH310060A (en) | 1952-01-01 | 1952-12-30 | Traveling wave tube with a conductive screw. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310060D CH310060A (en) | 1952-01-01 | 1952-12-30 | Traveling wave tube with a conductive screw. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2757310A (en) |
| CH (2) | CH305265A (en) |
| DE (1) | DE933352C (en) |
| FR (1) | FR1078434A (en) |
| GB (1) | GB764681A (en) |
| NL (1) | NL174893B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB767190A (en) * | 1953-11-17 | 1957-01-30 | Mullard Radio Valve Co Ltd | Improvements in or relating to travelling wave tubes |
| NL203186A (en) * | 1954-12-31 | |||
| LU34572A1 (en) * | 1955-08-12 | |||
| US2853644A (en) * | 1956-07-30 | 1958-09-23 | California Inst Res Found | Traveling-wave tube |
| US3121819A (en) * | 1959-12-30 | 1964-02-18 | Itt | Arrangement for reducing high voltage breakdown between helical windings in traveling wave tubes |
| US3209198A (en) * | 1961-06-28 | 1965-09-28 | Sylvania Electric Prod | Resilient helix mount for traveling wave tube |
| US4041438A (en) * | 1976-02-17 | 1977-08-09 | Odette Landeroin Duvernois | Electric heating device |
| FR2422265A2 (en) * | 1976-09-21 | 1979-11-02 | Thomson Csf | Wave propagation tube with hyperfrequency delay line - having triangular section with three equally inclined flat plates and is supported in tube by bars |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2110911A (en) * | 1933-07-31 | 1938-03-15 | Telefunken Gmbh | Electron tube |
| US2064469A (en) * | 1933-10-23 | 1936-12-15 | Rca Corp | Device for and method of controlling high frequency currents |
| NL62817C (en) * | 1940-05-04 | |||
| US2351055A (en) * | 1941-11-21 | 1944-06-13 | Henry S Blum | Tube for producing multiple wave lengths |
| GB623537A (en) * | 1944-06-08 | 1949-05-19 | Rudolf Kompfner | Improvements in or relating to electron discharge devices |
| US2489082A (en) * | 1944-07-01 | 1949-11-22 | Forest Lee De | High-voltage generator |
| US2452572A (en) * | 1944-10-20 | 1948-11-02 | John L Jago | Delay line |
| US2672572A (en) * | 1947-07-18 | 1954-03-16 | Philco Corp | Traveling wave tube |
| FR984595A (en) * | 1949-02-14 | 1951-07-09 | Csf | Wave propagation tube comprising a helical-shaped delay line coated with glass or quartz |
| FR993156A (en) * | 1949-06-08 | 1951-10-29 | Thomson Houston Comp Francaise | Structure ensuring a reduction in the propagation speed of an electromagnetic wave |
-
1952
- 1952-01-01 GB GB34/52A patent/GB764681A/en not_active Expired
- 1952-12-19 CH CH305265D patent/CH305265A/en unknown
- 1952-12-24 NL NLAANVRAGE7217713,A patent/NL174893B/en not_active IP Right Cessation
- 1952-12-30 US US328582A patent/US2757310A/en not_active Expired - Lifetime
- 1952-12-30 CH CH310060D patent/CH310060A/en unknown
- 1952-12-30 FR FR1078434D patent/FR1078434A/en not_active Expired
-
1953
- 1953-01-01 DE DEN6579A patent/DE933352C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE933352C (en) | 1955-09-22 |
| GB764681A (en) | 1957-01-02 |
| US2757310A (en) | 1956-07-31 |
| NL84206C (en) | 1957-02-15 |
| NL174893B (en) | 1956-09-15 |
| CH310060A (en) | 1955-09-30 |
| FR1078434A (en) | 1954-11-18 |
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