DE716807C - Process for the preparation of therapeutically valuable salts of the ª ‰ -position di- and tirialkyl-substituted AEthylamines with at least 11 and at most 18 carbon atoms - Google Patents

Process for the preparation of therapeutically valuable salts of the ª ‰ -position di- and tirialkyl-substituted AEthylamines with at least 11 and at most 18 carbon atoms

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Publication number
DE716807C
DE716807C DESCH120033D DESC120033D DE716807C DE 716807 C DE716807 C DE 716807C DE SCH120033 D DESCH120033 D DE SCH120033D DE SC120033 D DESC120033 D DE SC120033D DE 716807 C DE716807 C DE 716807C
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salts
carbon atoms
substituted
water
preparation
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DESCH120033D
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German (de)
Inventor
Dr Hans-Georg Allardt
Dr Karl Junkmann
Dr Ernst Neuhoff
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Bayer Pharma AG
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Schering AG
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Priority to DESCH120033D priority Critical patent/DE716807C/en
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Description

Verfahren zur Herstellung therapeutisch wertvoller Salze der in ß-Stellung di- und trialkylsubstituierten Äthylamine mit mindestens 11 und höchstens 18 Kohlenstoffatomen Die wasserlöslichen Salze, z. B. die Chlorhydrate der nach dem Verfahren der Patente 688 zig und 709 539 herstellbaren, in ß-Stellung di- und trialkylsubstituierten Äthylaminverbindungen mit mindestens z i und höchstens 18 Kohlenstoffatomen, welche bekanntlich eine ausgezeichnete spasmolytische Wirkung besitzen, haben :den Nachteil, daß sie bei peroraler Verabreichung starke Reizungen der Mund- und Magenschleimhäute und in größeren Dosen sogar Übelkeit und Erbrechen hervorrufen.Process for the preparation of therapeutically valuable salts in the ß-position di- and trialkyl-substituted ethylamines with at least 11 and at most 18 carbon atoms The water soluble salts, e.g. B. the chlorohydrates of the method of the patents 688 umpteen and 709 539 producible, di- and trialkyl-substituted in the ß-position Ethylamine compounds with at least z i and at most 18 carbon atoms, which are known to have an excellent spasmolytic effect, have: the disadvantage that they cause severe irritation of the oral and gastric mucous membranes when administered orally and even cause nausea and vomiting in larger doses.

Eis wurde nun gefunden, daß dieser Nachteil behoben ist bei Verwendung von bislang unbekannten wasserunlöslichen Salzen, die aus diesen ß-alkylsubstituierten Äthylaminen und aromatischen Mono- oder Disulfonsäuren der Naphthalin- oder Anthracenreihe, insbesondere Naphtholdi- und Anthrachinonmonosulfonsäuren, zweckmäßig ß-Naphthol-3₧6-disulfonsäure und Anthrachinon I- oder 2-monosulfonsäure gebildet sind. Dä:e Herstellung dieser Salze erfolgt nach :den für die Gewinnung vorn Salzen üblichen Methoden, z. B. durch direkte Umsetzung der Komponenten in Gegenwart :oder Abwesenheit vom Lösungsmitteln oder durch doppelte Umsetzung geeigneter Salze. ` Beispiel i 252g ß # ß # ß - Tri - n - butyläthylamin # H Cl (F.= i36°) werden in 21 kochendem- Wasser gelöst und zu der Lösung unter Rühren eine durch Kochen mit Tierkohle ,entfärbte Lösung von 332 g 2-naphthol-3#6-disulfonsaurem Natrium (53%iges R-salz) in 21 Wasser hinzugegeben. Das ausgefallene Salz wird heiß abgesaugt und mit heißem Wasser ausgewaschen. Es stellt ein weißes, kristallisiertes .Pulver dar, welches sich aus Alkohol umkristallisieren läßt, von der Zusammensetzung [(C4H9)3C₧CH2₧NH2]2-C10H5 (G H) (SO3H)2 Ausbeute 367 g.Ice has now been found that this disadvantage is remedied when using hitherto unknown water-insoluble salts, which are expediently ß-naphthol-3 ₧ from these ß-alkyl-substituted ethylamines and aromatic mono- or disulfonic acids of the naphthalene or anthracene series, in particular naphthol and anthraquinone monosulfonic acids 6-disulfonic acid and anthraquinone I or 2-monosulfonic acid are formed. The production of these salts takes place according to: the methods customary for the production of salts, e.g. B. by direct reaction of the components in the presence: or absence of solvents or by double conversion of suitable salts. Example i 252g ß # ß # ß - tri - n - butylethylamine # H Cl (F. = i36 °) are dissolved in 21 boiling water and, while stirring, a solution of 332 g of 2 -naphthol-3 # 6-disulfonic acid sodium (53% R-salt) in 21 water added. The precipitated salt is suctioned off while hot and washed out with hot water. It is a white, crystallized powder, which can be recrystallized from alcohol, of the composition [(C4H9) 3C ₧ CH2 ₧ NH2] 2-C10H5 (GH) (SO3H) 2, yield 367 g.

Beispiel 2 Zu einer Lösung von 3, i Teilen α-anthrachinonmonosulfonsaurem Natrium in Ioo Teilen heißem Wasser wird unter Rühren eine heiße Lösung von ß # ß #ß-Tri-n-butyläthylamin# H Cl in 25 cm3 Wasser hinzugegeben, das seich kristallisiert ausscheidende, schwach gelbgefärbte α-anthrachinonmonosulfonsaure Tri- n -butyläthylamin nach einigem Stehen ,abgesaugt und mit Wasser chlorfrei gewaschen. Es schmilzt oberhalb 270''. Beispiel 3 Zu einer Lösung von 2,87 Teilen ß-Anthrachinonmonosulfonsäure in 5o Teilen Wasser wird .eine Lösung von a, i 3 Teilen Tri-n-butyläthylamin in wenig Äthanol gelöst gegeben, das ausgefallene 3-anthrachinonmonosulfonsaure Tributyläthylamin .abgesaugt und mit wenig 2o%igem Alkohol ausgewaschen.Example 2 To a solution of 3.1 parts of α-anthraquinone monosulfonic acid Sodium in 100 parts of hot water is stirred into a hot solution of ß # ß # ß-Tri-n-butylethylamine # H Cl in 25 cm3 of water was added, which crystallized seich Pale yellow-colored α-anthraquinone monosulfonic acid tri-n -butylethylamine which precipitates after standing for a while, suctioned off and washed free of chlorine with water. It melts above 270 ''. Example 3 To a solution of 2.87 parts of β-anthraquinone monosulfonic acid in 5o parts of water. a solution of a, i 3 parts of tri-n-butylethylamine in given a little dissolved ethanol, the precipitated 3-anthraquinone monosulfonic acid tributylethylamine .sucked off and washed out with a little 20% alcohol.

In gleicher Weise oder auch durch direkte Umsetzung in Gegenwart oder in Abwesenheit von Lösungsmitteln erhält man aus anderen f-alkylsubstituierten Äthylaminen der genannten Art und Naphtholdisulfonsäuren oder Anthrachinonmonosulfonsäuren die entsprechenden wasserunlöslichen Salze.In the same way or by direct reaction in the presence or in the absence of solvents, other f-alkyl-substituted ethylamines are obtained of the type mentioned and naphthol disulfonic acids or anthraquinone monosulfonic acids corresponding water-insoluble salts.

Die auf die beschriebene Weise erhaltenen neuen Salze sind geschmacklos und reizen die Schleimhäute nicht. Nur bei ihrer Verwendung ist es möglich, die guten spasmolytischen Eigenschaften der Äthylaminbasen richtig zur Wirkung zu bringen, da sie trotz ihrer Wasserunlöslichkeit bei per oraler Verabreichung, wie Tierversuche zeigen, in vollkommen ausreichendem Maße resorbiert werden.The new salts obtained in the manner described are tasteless and do not irritate the mucous membranes. It is only possible to use the to bring the good spasmolytic properties of the ethylamine bases to effect properly, because, despite their insolubility in water, when administered orally, as in animal experiments show to be absorbed to a perfectly adequate extent.

Claims (3)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung therapeutisch wertvoller Salze der in ß-Stellung di-und trialkylsubstituierten Äthylamine mit mindesteins i i und höchstens i 8 Kohlenstoffatomen, dadurch gekennzeichnet, daß man die genannten Amine bzw. ihre wasserlöslichen Salze nach ,an sich üblichen Methoden in die Salze aromatischer Mono-oder Disulfonsäuren der Naphthalin- oder Anthracenreihe überführt. PATENT CLAIMS: i. Process for the preparation of therapeutically valuable salts of the ß-position di- and trialkyl-substituted ethylamines with at least ii and at most i 8 carbon atoms, characterized in that the said amines or their water-soluble salts are converted into the salts of aromatic mono- or disulfonic acids of the naphthalene or anthracene series. 2. Verfahren nach Anspruch i. dadurch gekennzeichnet, daß als Ausgangsmaterial ß #f#3-Tri-n-butyläthylamin bzw. dessen wasserlösliche Salze verwendet werden. 2. The method according to claim i. characterized in that as the starting material ß # f # 3-tri-n-butylethylamine or its water-soluble salts can be used. 3. Verfahren nach Anspruch i und 2 dadurch gekennzeichnet, daß zur Umsetzung Naphtholdisulfonsäuren, insbesondere 2-Naphthol-3 # 6-disulfonsäure bzw. ihre wasserlöslichen Salze verwendet werden.3. Process according to claim 1 and 2, characterized in that naphthol disulphonic acids, in particular 2-naphthol-3 # 6-disulfonic acid or its water-soluble salts are used will.
DESCH120033D 1940-02-28 1940-02-28 Process for the preparation of therapeutically valuable salts of the ª ‰ -position di- and tirialkyl-substituted AEthylamines with at least 11 and at most 18 carbon atoms Expired DE716807C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH120033D DE716807C (en) 1940-02-28 1940-02-28 Process for the preparation of therapeutically valuable salts of the ª ‰ -position di- and tirialkyl-substituted AEthylamines with at least 11 and at most 18 carbon atoms

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Application Number Priority Date Filing Date Title
DESCH120033D DE716807C (en) 1940-02-28 1940-02-28 Process for the preparation of therapeutically valuable salts of the ª ‰ -position di- and tirialkyl-substituted AEthylamines with at least 11 and at most 18 carbon atoms

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DE716807C true DE716807C (en) 1943-04-06

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