CH248637A - Process for the preparation of a basic amide of a 2-thioalkyl-cinchoninic acid. - Google Patents
Process for the preparation of a basic amide of a 2-thioalkyl-cinchoninic acid.Info
- Publication number
- CH248637A CH248637A CH248637DA CH248637A CH 248637 A CH248637 A CH 248637A CH 248637D A CH248637D A CH 248637DA CH 248637 A CH248637 A CH 248637A
- Authority
- CH
- Switzerland
- Prior art keywords
- thioalkyl
- preparation
- acid
- cinchoninic
- cinchoninic acid
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines basischen Amids-.einer 2-Thioalkyl-einehoninsäure. Es ist bekannt, dass Amide der 2-Alkogy- cinchoninsäuren, welche in der Säureamid- Seitenkette ein tertiäres Stickstoffatom tra gen, sich durch eine bedeutende anästhesie- rende Wirkung auszeichnen.
Dieser starken Wirkung auf die sensiblen Nerven geht nun aber bei dieser Körperklasse eine sehr bedeutende Giftigkeit parallel, welche be sonders bei paranteraler Applikation eine grosse Gefahrenquelle darstellt und der weiten Anwendungsmöglichkeit dieser Stoffe hin- dernd im Wege steht.
Demgegenüber wurde gefunden, dass basi- sehe Amide der 2-Thioalkyl-cinchoninsäuren bei guter anästhesierender Wirkung eine ver minderte Giftigkeit aufweisen. Verbindun gen dieser Art sind bisher in der Literatur nicht beschrieben.
Es wurde nun gefunden, dass man diese Verbindungen in guter Ausbeute erhält, wenn man basische Amide der 2-Halogen- cinchoninsäuren mit Salzen von Meroaptanen umsetzt. Als solche Salze eignen sich am besten die Natrium- oder Kalisalze. Vorzugs weise erfolgt die Umsetzung in Gegenwart eines Lösungsmittels; als solches verwendet man zweckmässigerweise absoluten oder auch gewöhnlichen Alkohol.
Die so erhaltenen Verbindungen stellen gewöhnlich beständige farblose Nadeln oder Blättchen dar, deren Chlorhydrate sich in Wasser leicht mit neutraler Reaktion lösen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines basi schen Amids einer 2-Thioalkyl-cinchonin- säure, welches dadurch gekennzeichnet ist, dass man ein Salz des Athylmercaptans mit 2-Halogen-cinchoninsäure-diäthylamino- äthylamid umsetzt.
Man erhält das 2-Thio- äthy 1- cinchoninsäure - diäthylamina -. äthyl- amid, das für therapeutische Zwecke be stimmt ist.
Beispiel: 0,8 Teile Natrium werden in 40 Teilen abs. Alkohol gelöst und die Lösung mit 4 Teilen Athylmercaptan versetzt. Nun wer den 10 Teile 2-Chlor-cinchoninsäure-diäthyl- amino-äthylamid zugefügt und die Lösung eine halbe Stunde zum Sieden erwärmt. Da Gemisch wird darauf in 200 Teile Wasser gerührt, wobei sich das Kondensationspro dukt als 01 abscheidet, das bald zu körnigen Kristallen erstarrt.
Es wird abgesaugt, in verdünnter Essigsäure aufgenommen, die Lösung mit Kohle filtriert und das Konden sationsprodukt durch Zusatz von Natron lauge abgeschieden, getrocknet und aus Petroläther umkristallisiert. Man erhält da: bei das neue Produkt, das 2-Thioäthyl- cinchoninsäure-diäthylamino-äthylamid, in Form weisser Nadeln.
Process for the preparation of a basic amide - a 2-thioalkyl-einhoninsäure. It is known that amides of 2-alkogycinchoninic acids, which carry a tertiary nitrogen atom in the acid amide side chain, are distinguished by a significant anesthetic effect.
This strong effect on the sensitive nerves is now paralleled by a very significant toxicity in this body class, which is a major source of danger, especially in paranteral application, and stands in the way of the broad application of these substances.
In contrast, it was found that basic amides of 2-thioalkyl-cinchoninic acids have a reduced toxicity with a good anesthetic effect. Compounds of this type have not yet been described in the literature.
It has now been found that these compounds are obtained in good yield if basic amides of 2-halo-cinchoninic acids are reacted with salts of meroaptans. Sodium or potassium salts are best suited as such salts. The reaction is preferably carried out in the presence of a solvent; as such, it is expedient to use absolute or ordinary alcohol.
The compounds obtained in this way are usually stable, colorless needles or flakes, the chlorohydrates of which dissolve easily in water with a neutral reaction.
The present patent relates to a process for the preparation of a basic amide of a 2-thioalkyl-cinchonic acid, which is characterized in that a salt of ethyl mercaptan is reacted with 2-halo-cinchoninic acid diethylamino-ethylamide.
The 2-thioäthy 1-cinchoninsäure - diethylamina - is obtained. ethyl amide, which is intended for therapeutic purposes.
Example: 0.8 parts of sodium are abs in 40 parts. Dissolved alcohol and added 4 parts of ethyl mercaptan to the solution. Now who the 10 parts of 2-chloro-cinchoninsäure-diethylamino-ethylamide are added and the solution is heated to the boil for half an hour. The mixture is then stirred into 200 parts of water, the condensation product separating out as 01, which soon solidifies to form granular crystals.
It is filtered off with suction, taken up in dilute acetic acid, the solution is filtered with charcoal and the condensation product is deposited by adding sodium hydroxide solution, dried and recrystallized from petroleum ether. The new product, 2-thioethyl cinchoninic acid diethylaminoethylamide, is obtained in the form of white needles.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH248637T | 1945-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH248637A true CH248637A (en) | 1947-05-15 |
Family
ID=4467057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH248637D CH248637A (en) | 1945-11-17 | 1945-11-17 | Process for the preparation of a basic amide of a 2-thioalkyl-cinchoninic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH248637A (en) |
-
1945
- 1945-11-17 CH CH248637D patent/CH248637A/en unknown
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