DE1122514B - Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine - Google Patents

Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine

Info

Publication number
DE1122514B
DE1122514B DEG27898A DEG0027898A DE1122514B DE 1122514 B DE1122514 B DE 1122514B DE G27898 A DEG27898 A DE G27898A DE G0027898 A DEG0027898 A DE G0027898A DE 1122514 B DE1122514 B DE 1122514B
Authority
DE
Germany
Prior art keywords
diphenyl
ethyl
amine
hydroxy
propen
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
Application number
DEG27898A
Other languages
German (de)
Inventor
Dr Werner Heinrich
Dr Walter Heigel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BK Giulini Chemie GmbH
Original Assignee
Giulini Gebrueder GmbH
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 Giulini Gebrueder GmbH filed Critical Giulini Gebrueder GmbH
Priority to DEG27898A priority Critical patent/DE1122514B/en
Priority to BE594835A priority patent/BE594835A/en
Priority to GB3099160A priority patent/GB936041A/en
Priority to FR19000A priority patent/FR1352805A/en
Publication of DE1122514B publication Critical patent/DE1122514B/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Es ist bekannt, daß man durch Grignardierung von ß-Aminopropionsäureestern mit Phenylmagnesiumbromid zu 3-Hydroxy-3,3-diphenyI-propyl-aminen gelangen kann. Dieses Verfahren eignet sich besonders zur Herstellung von Verbindungen, die am Stickstoff tertiär sind. Es ist weiterhin bekannt, daß man aus diesen Aminoalkoholen durch Wasserabspaltung die entsprechenden 3,3-Diphenyl-propen-(2)-yl-amine erhält (D. W. Adamson, J. Chem. Soc. Supplement, 1949, S. 144 ff.).It is known that by Grignardation of ß-aminopropionic acid esters with phenylmagnesium bromide can reach 3-hydroxy-3,3-diphenyl-propyl-amines. This method is particularly suitable for the production of compounds that are tertiary at nitrogen. It is also known that one can get out the corresponding 3,3-diphenyl-propen- (2) -yl-amines are obtained from these amino alcohols by splitting off water (D. W. Adamson, J. Chem. Soc. Supplement, 1949, pp. 144 ff.).

C6H5 C 6 H 5

C6H5 C 6 H 5

C6H5 C 6 H 5

C8H6 C 8 H 6

OHOH

: — CH-CH2-NR2R,: - CH-CH 2 -NR 2 R,

R1 R 1

= C —CH2-NR2R,= C-CH 2 -NR 2 R,

R1 R 1

II.II.

Eine große Anzahl von Substanzen obiger Formeln, in denen R1 = Wasserstoff, R2 und R3 = Wasserstoff oder Alkyl sind, wurden hergestellt und insbesondere auf ihre spasmolytische Wirkung untersucht.A large number of substances of the above formulas, in which R 1 = hydrogen, R 2 and R 3 = hydrogen or alkyl, were produced and examined in particular for their spasmolytic effect.

Überraschenderweise hat sich nun gezeigt, daß in den Fällen, in denen die Kohlenstoffkette verzweigt und das Stickstoffatom primär ist, man eine Substanz erhält, die andere wertvolle pharmakologische Eigenschäften besitzt. Das von Adamson angegebene Verfahren ist zur Herstellung dieses Produktes wenig geeignet, weil das primäre Stickstoffatom zwei bewegliche Wasserstoffatome enthält, die 2 Mol Grignardverbindungen verbrauchen, bevor die eigentliche Um-Setzung der Estergruppe eintritt. Die Ausbeuten sind dementsprechend sehr gering, was sich mit den Angaben von Adamson deckt. Außerdem ist das Ausgangsprodukt, nämlich der primäre Aminopropionsäureester, schwer erhältlich, denn beim Umsetzen mit Ammoniak bildet sich aus dem Acrylsäureester ähnlich wie mit Methylamin eine Bis-Verbindung (s. Adamson, S. 145, letzter Absatz).Surprisingly, it has now been shown that in those cases in which the carbon chain is branched and the nitrogen atom is primary, a substance is obtained which has other valuable pharmacological properties owns. The process indicated by Adamson is little for making this product suitable because the primary nitrogen atom contains two mobile hydrogen atoms, the 2 moles of Grignard compounds consume before the actual conversion of the ester group occurs. The yields are accordingly very low, which is consistent with Adamson's statements. Besides, this is The starting product, namely the primary aminopropionic acid ester, is difficult to obtain because it is converted With ammonia, a bis-compound is formed from the acrylic acid ester in a similar way to that with methylamine (See Adamson, p. 145, last paragraph).

Es wurde nun gefunden, daß man in an sich bekannter Weise durch Hydrierung von 1-Äthyl-2-hydroxy-2,2-diphenyl-propionitril in guter Ausbeute das 2-Äthyl-3-hydroxy-3,3-diphenyl-propyl-amin erhält, das man dann in an sich bekannter Weise durch Wasserabspaltung in das 2-Äthyl-3,3-diphenyl-propen-(2)-yl-amin überführt.It has now been found that 1-ethyl-2-hydroxy-2,2-diphenyl-propionitrile can be hydrogenated in a manner known per se 2-ethyl-3-hydroxy-3,3-diphenyl-propyl-amine is obtained in good yield, which is then carried out in a manner known per se Dehydration is converted into 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine.

Das so hergestellte 2-Äthyl-3,3-diphenyl-propen-(2)-yl-amin besitzt eine starke, langanhaltende Blutdruck-Verfahren zur HerstellungThe 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine prepared in this way possesses a strong, long-lasting blood pressure production process

von blutdrucksteigerndem 2-Äthyl-of hypertensive 2-ethyl-

3,3-diphenyl-propen-( 2)-yl-amin3,3-diphenyl-propen- (2) -yl-amine

Anmelder:Applicant:

Gebrüder Giulini G. m. b. H.,
Ludwigshafen/Rhein, Giulinistr. 2Giulini brothers G. mb H.,
Ludwigshafen / Rhine, Giulinistr. 2

Dr. Werner Heinrich und Dr. Walter Heigel,Dr. Werner Heinrich and Dr. Walter Heigel,

Ludwigshafen/Rhein,
sind als Erfinder genannt wordenLudwigshafen / Rhine,
have been named as inventors

steigerung, eine anregende Wirkung auf die Atmung, eine kollapsverhütende Wirkung und eine Abnahme bzw. Beseitigung der schädigenden Wirkung des Morphins auf die Atmung. Die so hergestellte Substanz ist neu.increase, a stimulating effect on breathing, a collapse preventive effect and a decrease or elimination of the harmful effects of morphine on breathing. The substance made in this way is new.

Die langanhaltende blutdrucksteigernde Wirkung geht aus folgender Gegenüberstellung hervor:The long-lasting blood pressure-increasing effect can be seen from the following comparison:

Wirkung auf den Blutdruck der Katze in Urethan-ChIoralose-Narkose bei Anwendung von:Effect on cat blood pressure under urethane chioralose anesthesia when using:

a) 2-Äthyl-3,3-diphenyl-propen-(2)-yl-amin als Hydrochlorid, Gluconat, Nicotinat, Methansulfonat 0,5 mg/kg i. v.a) 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine as hydrochloride, Gluconate, nicotinate, methanesulfonate 0.5 mg / kg i.p. v.

Blutdrucksteigerung von 40 bis 60 mm HgIncrease in blood pressure from 40 to 60 mm Hg

etwa 6 bis 8 Minuten anhaltend,
1,0 mg/kg i.v.lasting about 6 to 8 minutes,
1.0 mg / kg iv

Blutdrucksteigerung von 45 bis 60 mm HgBlood pressure increase from 45 to 60 mm Hg

etwa 1 Stunde anhaltend,
2,0 mg/kg i. v.lasting about 1 hour,
2.0 mg / kg iv

Blutdrucksteigerung von 40 bis 60 mm HgIncrease in blood pressure from 40 to 60 mm Hg

länger anhaltend, 1V2 bis 3 Stunden.longer lasting, 1V 2 to 3 hours.

Bei erniedrigtem Ausgangsblutdruck ist die blutdrucksteigernde Wirkung stärker und länger anhaltend als bei normalem oder überhöhtem Ausgangsblutdruck. Erste klinische Versuche haben diese Wirkungen bestätigt. Darüber hinaus hat sich gezeigt, daß keine Tachykardie auftritt, aber eindeutig eine Zunahme des Minutenvolumens. If the initial blood pressure is lowered, the blood pressure-increasing effect is stronger and longer persistent than with normal or excessive initial blood pressure. First clinical trials have confirmed these effects. In addition, it has been shown that tachycardia does not occur, but clearly an increase in minute volume.

109 787/417109 787/417

b) 1 -(3 '-Hydroxyphenyl)-1 -hydroxy-2-N-äthylaminoäthan-hydrochlorid von der Strukturformel:b) 1- (3'-hydroxyphenyl) -1-hydroxy-2-N-ethylaminoethane hydrochloride from the structural formula:

CHOH-CH2NHC2H, HClCHOH-CH 2 NHC 2 H, HCl

OHOH

mg/kg i. v.mg / kg i.v. v.

Blutdrucksteigerung von etwa 20 mm Hg etwa 4 bis 8 Minuten anhaltend, mg/kg i. v.Blood pressure increase of about 20 mm Hg lasting about 4 to 8 minutes, mg / kg i.v. v.

Blutdrucksteigerung von 20 bis 30 mm Hg etwa 4 bis 8 Minuten anhaltend, mg/kg i. v.Blood pressure increase of 20 to 30 mm Hg lasting about 4 to 8 minutes, mg / kg i.v. v.

Blutdrucksteigerung von 40 bis 60 mm Hg etwa 4 bis 8 Minuten anhaltend, mg/kg i. v.Blood pressure increase of 40 to 60 mm Hg lasting about 4 to 8 minutes, mg / kg i.v. v.

Blutdrucksteigerung von 40 bis 60 mm Hg etwa 4 bis 8 Minuten anhaltend, c) EphedrinBlood pressure increase of 40 to 60 mm Hg lasting about 4 to 8 minutes, c) ephedrine

mg/kg i. v.mg / kg i.v. v.

Blutdrucksteigerung von 20 bis 40 mm Hg etwa 30 bis 40 Minuten anhaltend, mg/kg i. v.Blood pressure increase of 20 to 40 mm Hg lasting about 30 to 40 minutes, mg / kg i.v. v.

Blutdrucksteigerung von 40 bis 50 mm Hg etwa 30 bis 40 Minuten anhaltend, mg kg i. v.Blood pressure increase of 40 to 50 mm Hg lasting about 30 to 40 minutes, mg kg i. v.

Blutdrucksteigerung von 40 bis 50 mm Hg etwa 30 bis 40 Minuten anhaltend.Blood pressure increase of 40 to 50 mm Hg lasting about 30 to 40 minutes.

Filtrat im Vakuum zur Trockne eingedampft. Der Rückstand wird in Wasser gelöst, mit 1 ml Salzsäure versetzt und die Lösung ausgeäthert. Der saure Ätherteil wird verworfen. Der Wasserteil wird daraufhin mit Ammoniak alkalisch gemacht. Hierbei kristallisiert die Base aus. Sie wird aus Methanol umkristallisiert und schmilzt bei 1320C. Ausbeute: 65% der Theorie.The filtrate was evaporated to dryness in vacuo. The residue is dissolved in water, 1 ml of hydrochloric acid is added and the solution is extracted with ether. The acidic ether part is discarded. The water part is then made alkaline with ammonia. The base crystallizes out in the process. It is recrystallized from methanol and melts at 132 ° C. Yield: 65% of theory.

b) 2-Äthyl-3,3-diphenyl-propen-(2)-yl-aminhydrochlorid b) 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine hydrochloride

5 g 2-Äthyl-3-hydroxy-3,3-diphenyl-propyl-amin werden in 50 ml Eisessig gelöst. In die Lösung leitet man 10 Minuten lang trockenes Salzsäuregas und kocht anschließend 1 Stunde am Rückfluß. Daraufhin destilliert man zur Trockne. Der Rückstand wird in Wasser gelöst und die saure Lösung ausgeäthert. Der Wasserteil wird mit Ammoniak alkalisch gemacht und dann ausgeäthert, der Ätherteil wird mit Natriumsulfat getrocknet, der Äther abdestilliert und der so erhaltene Rückstand in methanolischer Salzsäure gelöst. Beim Zufügen von absolutem Äther kristallisiert das Hydrochlorid des 2-Äthyl-3,3-diphenyl-aminopropens-(2) aus. Die Substanz schmilzt bei 232° C. Ausbeute: 80% der Theorie.5 g of 2-ethyl-3-hydroxy-3,3-diphenyl-propyl-amine are dissolved in 50 ml of glacial acetic acid. Leads into the solution dry hydrochloric acid gas for 10 minutes and then reflux for 1 hour. Thereupon is distilled to dryness. The residue is dissolved in water and the acidic solution is extracted with ether. Of the The water part is made alkaline with ammonia and then etherified, the ether part is made with sodium sulphate dried, the ether was distilled off and the residue thus obtained in methanolic hydrochloric acid solved. When adding absolute ether, the hydrochloride of 2-ethyl-3,3-diphenyl-aminopropens- (2) crystallizes the end. The substance melts at 232 ° C. Yield: 80% of theory.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Herstellung von blutdrucksteigerndem 2 - Äthyl - 3,3 - diphenyl - propen - (2) - ylamin der FormelProcess for the production of hypertensive 2 - ethyl - 3,3 - diphenyl - propen - (2) - ylamine the formula In allen drei Fällen a), b) und c) wurde jeweils darauf geachtet, daß der Ausgangsblutdruck in etwa der gleiche war und zwischen 80 und 100 mm Hg lag.In all three cases a), b) and c), care was taken that the starting blood pressure was approximately the was the same and was between 80 and 100 mm Hg. Die bisher in der Literatur beschriebenen Verbindungen, in denen R1 = Wasserstoff, R2 und R3 = Wasserstoff oder Alkyl sind, weisen andere pharmakologische, insbesondere spasmolytische Eigenschaften auf.The compounds described so far in the literature, in which R 1 = hydrogen, R 2 and R 3 = hydrogen or alkyl, have different pharmacological, in particular spasmolytic, properties. Beispiel
a) 2-Äthyl-3-hydroxy-3,3-diphenyl-propyl-aminexample
a) 2-ethyl-3-hydroxy-3,3-diphenyl-propyl-amine 4040 g 1-Äthyl-2-hydroxy-2,2-diphenyl-propionitril werden in 200 ml Methanol gelöst. 10 ml Eisessig sowie der Platinkontakt werden hinzugefügt und anschließend hydriert. Nach Beendigung der Wasserstorfaufnahme wird vom Kontakt abfiltriert und das C8H5 g of 1-ethyl-2-hydroxy-2,2-diphenyl-propionitrile are dissolved in 200 ml of methanol. 10 ml of glacial acetic acid and the platinum contact are added and then hydrogenated. After the hydrogen uptake has ended, the contact is filtered off and the C 8 H 5 C6H5 C 6 H 5 !C = C-CH2-NH8 ! C = C-CH 2 -NH 8 C2H5 C 2 H 5 dadurch gekennzeichnet, daß man zunächst in an sich bekannter Weise das l-Äthyl-2-hydroxy-2,2-diphenyl-propionitril hydriert und darauf das entstandene 2-Äthyl-3,3-diphenyl-3-hydroxy-propyl-amin in an sich bekannter Weise durch Wasserabspaltung in das 2-Äthyl-3,3-diphenyl-propen-(2)-yl-amin überführt.characterized in that the l-ethyl-2-hydroxy-2,2-diphenyl-propionitrile is first used in a manner known per se hydrogenated and then the resulting 2-ethyl-3,3-diphenyl-3-hydroxy-propyl-amine in a manner known per se by splitting off water to form 2-ethyl-3,3-diphenyl-propen- (2) -yl-amine convicted. In Betracht gezogene Druckschriften:
Deutsche Patentschrift Nr. 887 649;
deutsche Auslegeschrift Nr. 1 051 281;
britische Patentschrift Nr. 689 288.Considered publications:
German Patent No. 887,649;
German Auslegeschrift No. 1 051 281;
British Patent No. 689 288. 1 109 787/417 1.621 109 787/417 1.62
DEG27898A 1959-09-08 1959-09-08 Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine Pending DE1122514B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DEG27898A DE1122514B (en) 1959-09-08 1959-09-08 Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine
BE594835A BE594835A (en) 1959-09-08 1960-09-08 Process for preparing (2-ethyl-3-hydroxy-3,3-diphenyl-propyl) amine and (2-ethyl-3,3-diphenyl-propene- (2)) -amine as well as monoalkylation products.
GB3099160A GB936041A (en) 1959-09-08 1960-09-08 Amino compounds
FR19000A FR1352805A (en) 1959-09-08 1960-09-08 Process for the manufacture of (2-ethyl-3-hydroxy-3, 3-diphenyl-propyl) -amine, and [2-ethyl-3, 3-diphenyl-propene (2)] - amine and monoalkylation products

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEG27898A DE1122514B (en) 1959-09-08 1959-09-08 Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine

Publications (1)

Publication Number Publication Date
DE1122514B true DE1122514B (en) 1962-01-25

Family

ID=7123328

Family Applications (1)

Application Number Title Priority Date Filing Date
DEG27898A Pending DE1122514B (en) 1959-09-08 1959-09-08 Process for the preparation of hypertensive 2-AEthyl-3,3-diphenyl-propen- (2) -yl-amine

Country Status (4)

Country Link
BE (1) BE594835A (en)
DE (1) DE1122514B (en)
FR (1) FR1352805A (en)
GB (1) GB936041A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422203A (en) * 1966-02-24 1969-01-14 Geistlich Ed Sohne Ag Fur Chem Treatment of depression with diphenyl prop-2-enylamine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL6511116A (en) * 1964-08-26 1966-02-28

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB689288A (en) * 1948-07-20 1953-03-25 Wellcome Found Improvements in and relating to the preparation of tertiary allylamines
DE887649C (en) * 1949-04-07 1953-08-24 Lundbeck Corp Process for the preparation of unsaturated amines suitable as antispasmodics
DE1051281B (en) * 1955-07-05 1959-02-26 Bayer Ag Process for the preparation of derivatives of 1-aryl-3-aminopropan-1-ols

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB689288A (en) * 1948-07-20 1953-03-25 Wellcome Found Improvements in and relating to the preparation of tertiary allylamines
DE887649C (en) * 1949-04-07 1953-08-24 Lundbeck Corp Process for the preparation of unsaturated amines suitable as antispasmodics
DE1051281B (en) * 1955-07-05 1959-02-26 Bayer Ag Process for the preparation of derivatives of 1-aryl-3-aminopropan-1-ols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422203A (en) * 1966-02-24 1969-01-14 Geistlich Ed Sohne Ag Fur Chem Treatment of depression with diphenyl prop-2-enylamine derivatives

Also Published As

Publication number Publication date
FR1352805A (en) 1964-02-21
GB936041A (en) 1963-09-04
BE594835A (en) 1961-01-02

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