DE1158055B - Process for the preparation of hypertensive 2-propyl-3, 3-diphenyl-propen- (2) -yl-amine - Google Patents
Process for the preparation of hypertensive 2-propyl-3, 3-diphenyl-propen- (2) -yl-amineInfo
- Publication number
- DE1158055B DE1158055B DEG34038A DEG0034038A DE1158055B DE 1158055 B DE1158055 B DE 1158055B DE G34038 A DEG34038 A DE G34038A DE G0034038 A DEG0034038 A DE G0034038A DE 1158055 B DE1158055 B DE 1158055B
- Authority
- DE
- Germany
- Prior art keywords
- diphenyl
- propyl
- amine
- propen
- blood pressure
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Description
Gegenstand der deutschen Auslegeschrift 1 122 514 ist ein Verfahren zur Herstellung von blutdrucksteigerndem 2-Äthyl-3,3-diphenyl-propen-(2)-yl-amin.The subject of German Auslegeschrift 1 122 514 is a process for the production of blood pressure-increasing 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine.
Es hat sich nun gezeigt, daß man auf analogem Wege, nämlich durch Hydrierung von l-Propyl-2-hydroxy-2,2-diphenyl-propionitril und anschließende Abspaltung von Wasser aus dem entstandenen 2-Propyl-3,3-diphenyl-3-hydroxy-propyl-amin das 2-Propyl-3,3-diphenyl-propen-(2)-yl-amin erhält. Dieser Stoff besitzt die gleichen pharmakologischen Eigenschaften, insbesondere die anhaltende blutdrucksteigernde Wirkung, nur ist diese Wirkung sehr viel ausgeprägter. Diese langanhaltende blutdrucksteigernde Wirkung geht aus folgender Gegenüberstellung hervor:It has now been shown that an analogous route, namely by hydrogenation of 1-propyl-2-hydroxy-2,2-diphenyl-propionitrile and subsequent elimination of water from the 2-propyl-3,3-diphenyl-3-hydroxypropylamine formed the 2-propyl-3,3-diphenyl-propen- (2) -yl-amine is obtained. This substance has the same pharmacological properties especially the sustained antihypertensive effect, but this effect is much more pronounced. This long-lasting blood pressure-increasing effect can be seen from the following comparison:
Wirkung auf den Blutdruck der Katze
in Urethan-Chloralose-Narkose bei Anwendung von:Effect on cat's blood pressure
under urethane-chloralose anesthesia when using:
a) 2-Propyl-3,3-diphenyl-propen-(2)-yl-amin als Hydrochlorid, Gluconat und Methansulfonat:a) 2-propyl-3,3-diphenyl-propen- (2) -yl-amine as hydrochloride, gluconate and methanesulfonate:
0,5 mg/kg i. v., Blutdrucksteigerung von 40 bis0.5 mg / kg i.v. v., increase in blood pressure from 40 to
60 mm Hg etwa 30 bis 40 Minuten anhaltend, 1,0 mg/kg i. v., Blutdrucksteigerung von 45 bis60 mm Hg sustained for about 30 to 40 minutes, 1.0 mg / kg i.p. v., increase in blood pressure from 45 to
60 mm Hg etwa 2 bis 3 Stunden anhaltend, 2,0 mg/kg i. v., Blutdrucksteigerung von 70 bis 90 mm Hg etwa 3 bis 4 Stunden und länger anhaltend.60 mm Hg sustained for about 2 to 3 hours, 2.0 mg / kg i.p. v., increase in blood pressure from 70 to 90 mm Hg for about 3 to 4 hours and longer.
Bei erniedrigtem Ausgangsblutdruck ist die blutdrucksteigernde Wirkung stärker und länger anhaltend als bei überhöhtem oder normalem Ausgangsblutdruck.If the initial blood pressure is reduced, the blood pressure-increasing effect is stronger and longer-lasting than with excessive or normal initial blood pressure.
b) l-(3'-Hydroxyphenyl)-l-hydroxy-2-N-äthylaminoäthanhydrochlorid von der Strukturformelb) l- (3'-hydroxyphenyl) -l-hydroxy-2-N-ethylaminoethane hydrochloride of the structural formula
Verfahren zur HerstellungMethod of manufacture
von blutdrucksteigerndemof hypertensive
2-Propyl-3,3-diphenyl-propen-(2)-yl-amin2-propyl-3,3-diphenyl-propen- (2) -yl-amine
Anmelder:Applicant:
Gebrüder GiuliniGiulini brothers
Gesellschaft mit beschränkter Haftung,
Ludwigshafen/Rhein, Giulinistr. 2Company with limited liability,
Ludwigshafen / Rhine, Giulinistr. 2
DipL-Chem. Dr. Werner Heinrich
und Dipl.-Chem. Dr. Walter Heigel,DipL-Chem. Dr. Werner Heinrich
and Dipl.-Chem. Dr. Walter Heigel,
Ludwigshafen/Rhein,
sind als Erfinder genannt wordenLudwigshafen / Rhine,
have been named as inventors
p— CHOH — CH2- NHC2H5 · HCl p - CHOH - CH 2 - NHC 2 H 5 • HCl
OHOH
1 mg/kg i. v., Blutdrucksteigerung von etwa 20 mm Hg etwa 4 bis 8 Minuten anhaltend,1 mg / kg i.v. v., increase in blood pressure of about 20 mm Hg lasting about 4 to 8 minutes,
2 mg/kg i. v., Blutdrucksteigerung von 20 bis 30 mm Hg etwa 4 bis 8 Minuten anhaltend,2 mg / kg i.v. v., increase in blood pressure of 20 to 30 mm Hg lasting about 4 to 8 minutes,
3 mg/kg i. v., Blutdrucksteigerung von 40 bis 60 mm Hg etwa 4 bis 8 Minuten anhaltend,3 mg / kg i.v. v., increase in blood pressure of 40 to 60 mm Hg lasting about 4 to 8 minutes,
4 mg/kg i. v., Blutdrucksteigerung von 40 bis 60 mm Hg etwa 4 bis 8 Minuten anhaltend.4 mg / kg i.p. v., increase in blood pressure of 40 to 60 mm Hg lasting about 4 to 8 minutes.
c) Ephedrinc) ephedrine
1 mg/kg i. v., Blutdrucksteigerung von 20 bis 40 mm Hg etwa 30 bis 40 Minuten anhaltend,1 mg / kg i.v. v., increase in blood pressure of 20 to 40 mm Hg lasting about 30 to 40 minutes,
2 mg/kg i. v., Blutdrucksteigerung von 40 bis 50 mm Hg etwa 30 bis 40 Minuten anhaltend,2 mg / kg i.v. v., increase in blood pressure of 40 to 50 mm Hg lasting about 30 to 40 minutes,
3 mg/kg i. v., Blutdrucksteigerung von 40 bis 50 mm Hg etwa 30 bis 40 Minuten anhaltend.3 mg / kg i.v. v., increase in blood pressure of 40 to 50 mm Hg lasting about 30 to 40 minutes.
In allen Fällen wurde jeweils darauf geachtet, daß der Ausgangsblutdruck in etwa der gleiche war und zwischen 80 und 100 mm Hg lag.In all cases, care was taken to ensure that the starting blood pressure was approximately the same and was between 80 and 100 mm Hg.
Beispiel
a) 2-Propyl-3,3-diphenyl-3-hydroxy-propyl-aminexample
a) 2-Propyl-3,3-diphenyl-3-hydroxy-propyl-amine
13,1 g l-PropyW-hydroxy^^-diphenyl-propionitril werden in 400 ml Eisessig gelöst, 200 mg Platinkontakt werden hinzugefügt, und anschließend wird hydriert. Nach Beendigung der Wasserstoffaufnahme wird vom Kontakt abfiltriert und das Filtrat im Vakuum zur Trockene eingedampft. Der Rückstand wird in Wasser gelöst, mit Salzsäure bis zur sauren Reaktion versetzt, vom Ungelösten abfiltriert und das Filtrat in 20%ige Natronlauge eingetropft. Das ausgefällte 2-Propyl-3,3-diphenyl-3-hydroxy-propyl-amin wird abgesaugt. Schmp. 108 bis 1100C.13.1 g of l-PropyW-hydroxy ^^ - diphenyl-propionitrile are dissolved in 400 ml of glacial acetic acid, 200 mg of platinum contact are added, and then it is hydrogenated. After the uptake of hydrogen has ended, the contact is filtered off and the filtrate is evaporated to dryness in vacuo. The residue is dissolved in water, hydrochloric acid is added until the reaction is acidic, the undissolved material is filtered off and the filtrate is added dropwise to 20% sodium hydroxide solution. The precipitated 2-propyl-3,3-diphenyl-3-hydroxypropyl-amine is filtered off with suction. Mp. 108 to 110 0 C.
309 750/399309 750/399
b) 2-Propyl-3,3-diphenyl-propen-(2)-yl-amin-b) 2-propyl-3,3-diphenyl-propen- (2) -yl-amine-
hydrochloridhydrochloride
4,8 g 2-Propyl-3,3-diphenyl-3-hydroxy-propyl-amin werden in 50 nil Eisessig gelöst. Diese Lösung wird mit Chlorwasserstoffgas gesättigt und anschließend 3 Stunden auf 1000C erhitzt. Die Essigsäure wird im Vakuum abdestilliert. Die zurückbleibenden Kristalle werden in Methanol gelöst und das 2-Propyl-3,3-diphenyl-propen-(2)-yl-amin-hydrochlorid durch Zugabe von absolutem Äther ausgefällt. Schmp. 213 bis 215°C.4.8 g of 2-propyl-3,3-diphenyl-3-hydroxypropyl-amine are dissolved in 50 ml of glacial acetic acid. This solution is saturated with hydrogen chloride gas and then heated to 100 ° C. for 3 hours. The acetic acid is distilled off in vacuo. The remaining crystals are dissolved in methanol and the 2-propyl-3,3-diphenyl-propen (2) -yl-amine hydrochloride is precipitated by adding absolute ether. Mp 213-215 ° C.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG34038A DE1158055B (en) | 1962-01-17 | 1962-01-17 | Process for the preparation of hypertensive 2-propyl-3, 3-diphenyl-propen- (2) -yl-amine |
| FR19981A FR1398726A (en) | 1962-01-17 | 1962-12-08 | Process for the manufacture of 2-propyl-3, 3-diphenyl-propene- (2) -yl-amine |
| GB140763A GB964308A (en) | 1962-01-17 | 1963-01-11 | Propenylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG34038A DE1158055B (en) | 1962-01-17 | 1962-01-17 | Process for the preparation of hypertensive 2-propyl-3, 3-diphenyl-propen- (2) -yl-amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1158055B true DE1158055B (en) | 1963-11-28 |
Family
ID=7124836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG34038A Pending DE1158055B (en) | 1962-01-17 | 1962-01-17 | Process for the preparation of hypertensive 2-propyl-3, 3-diphenyl-propen- (2) -yl-amine |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1158055B (en) |
| FR (1) | FR1398726A (en) |
| GB (1) | GB964308A (en) |
-
1962
- 1962-01-17 DE DEG34038A patent/DE1158055B/en active Pending
- 1962-12-08 FR FR19981A patent/FR1398726A/en not_active Expired
-
1963
- 1963-01-11 GB GB140763A patent/GB964308A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB964308A (en) | 1964-07-22 |
| FR1398726A (en) | 1965-05-14 |
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