DE1028997B - Process for the preparation of halogenated pyridone derivatives of aliphatic carboxylic acids - Google Patents
Process for the preparation of halogenated pyridone derivatives of aliphatic carboxylic acidsInfo
- Publication number
- DE1028997B DE1028997B DEF9619A DEF0009619A DE1028997B DE 1028997 B DE1028997 B DE 1028997B DE F9619 A DEF9619 A DE F9619A DE F0009619 A DEF0009619 A DE F0009619A DE 1028997 B DE1028997 B DE 1028997B
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acids
- aliphatic
- halogenated
- aliphatic carboxylic
- preparation
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von halogenierten Pyridonderivaten von aliphatischen Carbonsäuren In den deutschen Patentschriften 579 224, 570 860 und 646 116 sind am Stickstoffatom mit aliphatischen Carbonsäureresten substituierte Halogenpyridone, z. B. 3,5-Dijod-4-pyridon-N-essigsäure, beschrieben, die sich besonders für die röntgenographische Darstellung der Harnwege bewährt haben.Process for the preparation of halogenated pyridone derivatives of aliphatic Carboxylic acids In German patents 579 224, 570 860 and 646 116 are Halogenpyridones substituted on the nitrogen atom with aliphatic carboxylic acid residues, z. B. 3,5-Diiodo-4-pyridone-N-acetic acid described, which is particularly suitable for Radiographic representation of the urinary tract have proven effective.
Es wurde nun gefunden, daß Carbonsäuren, die eine Carboxylgruppe und zwei Halogenpyridonreste im Molekül enthalten, sich dadurch herstellen lassen, daß etwa 2 Mol eines Halogenpyridons als solchen oder in Form seiner Salze mit etwa 1 Mol einer aliphatischen Dihalogencarbonsäure nach an sich bekannten Methoden in Gegenwart säurebindender Mittel umgesetzt werden.It has now been found that carboxylic acids containing a carboxyl group and contain two halopyridone radicals in the molecule, can be produced in that about 2 moles of a halopyridone as such or in the form of its salts with about 1 mol of an aliphatic dihalocarboxylic acid according to methods known per se in The presence of acid-binding agents are implemented.
An Stelle von 2 Mol Halogenpyridon kann man auch etwa 2 Mol eines halogenfreien Pyridons mit etwa 1 Mol einer aliphatischen Dihalogencarbonsäure umsetzen und die so erhaltenen Verbindungen nachträglich halogenieren.Instead of 2 moles of halopyridone, about 2 moles of one can also be used React halogen-free pyridons with about 1 mole of an aliphatic dihalocarboxylic acid and subsequently halogenate the compounds obtained in this way.
An Stelle einer aliphatischen Dihalogencarbonsäure kann man auch etwa 1 Mol einer anderen aliphatischen Dihalogenverbindung, die einen in eine Carboxylgruppe umwandelbaren Substituenten enthält, mit etwa 2 Mol eines Halogenpyridons umsetzen und in den so erhaltenen Stoffen nachträglich die Carboxylgruppe in an sich bekannter Weise herstellen. Gegebenenfalls können beide Maßnahmen gleichzeitig durchgeführt werden.Instead of an aliphatic dihalocarboxylic acid, one can also use about 1 mole of another aliphatic dihalo compound that converts one into a carboxyl group contains convertible substituents, react with about 2 moles of a halopyridone and in the substances obtained in this way, the carboxyl group is subsequently known per se Manufacture way. If necessary, both measures can be carried out at the same time will.
Die erfindungsgemäß erhältlichen neuen halogenierten Pyridonderivate von aliphatischen Carbonsäuren können als Heilmittel, insbesondere als Choleretika, Verwendung finden.The novel halogenated pyridone derivatives obtainable according to the invention of aliphatic carboxylic acids can be used as remedies, especially as choleretics, Find use.
Bei der Anwendung der erfindungsgemäß hergestellten Verbindungen als Heilmittel sind wasserlösliche Produkte erwünscht. Zu diesem Zweck werden die Verbindungen mit Hilfe anorganischer oder organischer Basen in ihre Salze verwandelt.When using the compounds prepared according to the invention as Remedies, water-soluble products are desirable. For this purpose the connections transformed into their salts with the help of inorganic or organic bases.
Unter den neuen Verbindungen haben sich diejenigen Carbonsäuren bzw. deren Salze, die als Halogenpyridonreste die Reste des 3,5-Dijod-4-pyridons enthalten, als besonders geeignet erwiesen. Die neue a,E-Bis-[3,5-dijod-N-pyridon-(4)]-capronsäure zeigt bei Tierversuchen eine bedeutend stärkere choleretische Wirkung als das Natriumsalz der Nicotinsäure, das nach Literaturangaben erhebliche Gallensekretion herbeiführen soll.Among the new compounds, those carboxylic acids or their salts, which contain the residues of 3,5-diiodo-4-pyridone as halopyridone residues, proved to be particularly suitable. The new a, E-bis- [3,5-diiodo-N-pyridon- (4)] - caproic acid In animal experiments shows a significantly stronger choleretic effect than the sodium salt nicotinic acid, which, according to the literature, cause considerable bile secretion target.
Beispiel 1 69,4g 3,5-Dijod-4-pyridon werden mit etwa der berechneten Menge n-Natronlauge versetzt und unter Erwärmen im Wasserbad gelöst. Dazu gibt man 27,5 g a,s-Dibrom-capronsäure, gelöst in einer Lösung von 12 g Ätznatron in 300 ccm Wasser, und erhitzt 4 Stunden im Wasserbad. Nach dem Kühlen wird das nicht umgesetzte 3,5-Dijod-4-pyridon durch Ansäuern mit Essigsäure auf pH 8,5 bis 9 oder durch Einleiten von Kohlensäure auf pH 8,5 bis 9 ausgefällt. Die ausgefallene Substanz saugt man ab und säuert das Filtrat -eeebenenfalls unter Küh-Jung mit 2 n-Salzsäure an. Dabei fällt a,E-Bis-[3,5-dijod-N-pyridon-(4)]-capronsäure als weißes Pulver aus, das durch Umkristallisation oder Umfällen gereinigt werden kann. Die Ausbeute beträgt 30 g. Die Substanz bildet farblose Kristalle und schmilzt bei 192°C.Example 1 69.4 g of 3,5-diiodo-4-pyridone are used with approximately the calculated Amount of sodium hydroxide solution added and dissolved in a water bath while warming. In addition one gives 27.5 g of a, s-dibromo-caproic acid, dissolved in a solution of 12 g of caustic soda in 300 ccm of water, and heated for 4 hours in a water bath. After cooling, this will not be reacted 3,5-Diiodo-4-pyridone by acidification with acetic acid to pH 8.5 to 9 or by introducing precipitated from carbonic acid to pH 8.5 to 9. The precipitated substance is sucked up and acidify the filtrate -ee also under Küh-Jung with 2N hydrochloric acid. Included a, E-bis- [3,5-diiodo-N-pyridon- (4)] - caproic acid precipitates out as a white powder that passes through Recrystallization or reprecipitation can be purified. The yield is 30 g. The substance forms colorless crystals and melts at 192 ° C.
Für die Anwendung als Heilmittel wurden 57,5 g a,a-Bis-[3,5-dijod-N-pyridon-(4)]-capronsäure mit der berechneten Menge 2 n-Natronlauge versetzt und durch Auffüllen mit Wasser auf 100 ccm in Lösung gebracht. Die Lösung des Natriumsalzes kann, wenn notwendig, noch konzentrierter hergestellt werden.57.5 g of a, a-bis- [3,5-diiodo-N-pyridon- (4)] -caproic acid were used as medicinal products mixed with the calculated amount of 2N sodium hydroxide solution and topped up with water brought into solution to 100 cc. The solution of the sodium salt can, if necessary, can be produced even more concentrated.
In analoger Weise kann man für therapeutische Zwecke eine 35o/oige Lösung des entsprechenden Äthanolaminsalzes und eine 36o/oige Lösung des entsprechenden Diäthanolaminsalzes herstellen.In an analogous way one can use a 35% for therapeutic purposes Solution of the corresponding ethanolamine salt and a 36o / o solution of the corresponding Make diethanolamine salt.
Beispiel 2 In der gleichen Weise wie im Beispiel 1 werden 69,4 g 3,5-Dijod-4-pyridon mit 28,6 g a,8-Dibrom-valeriansäure umgesetzt. Die gereinigte a,8-Bis-[3,5-dijod-N-pyridon-(4)]-valeriansäure schmilzt bei 218 bis 220°C.Example 2 In the same way as in Example 1, 69.4 g of 3,5-diiodo-4-pyridone are obtained reacted with 28.6 g of α, 8-dibromo-valeric acid. The purified α, 8-bis- [3,5-diiodo-N-pyridon- (4)] -valeric acid melts at 218 to 220 ° C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF9619A DE1028997B (en) | 1952-07-31 | 1952-07-31 | Process for the preparation of halogenated pyridone derivatives of aliphatic carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF9619A DE1028997B (en) | 1952-07-31 | 1952-07-31 | Process for the preparation of halogenated pyridone derivatives of aliphatic carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1028997B true DE1028997B (en) | 1958-04-30 |
Family
ID=7086201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF9619A Pending DE1028997B (en) | 1952-07-31 | 1952-07-31 | Process for the preparation of halogenated pyridone derivatives of aliphatic carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1028997B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2842943A1 (en) * | 2013-08-30 | 2015-03-04 | Université de Strasbourg | New molecules presenting white light emission properties |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE506425C (en) * | 1927-05-12 | 1930-09-05 | Schering Kahlbaum Ag | Process for increasing the solubility of halogen-substituted oxpyridines in water |
| US2505634A (en) * | 1947-10-03 | 1950-04-25 | Sterling Drug Inc | 4-pyridone-nu-carboxylic acids |
-
1952
- 1952-07-31 DE DEF9619A patent/DE1028997B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE506425C (en) * | 1927-05-12 | 1930-09-05 | Schering Kahlbaum Ag | Process for increasing the solubility of halogen-substituted oxpyridines in water |
| US2505634A (en) * | 1947-10-03 | 1950-04-25 | Sterling Drug Inc | 4-pyridone-nu-carboxylic acids |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2842943A1 (en) * | 2013-08-30 | 2015-03-04 | Université de Strasbourg | New molecules presenting white light emission properties |
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