DE955682C - Process for the production of new isonicotinic acid derivatives - Google Patents
Process for the production of new isonicotinic acid derivativesInfo
- Publication number
- DE955682C DE955682C DEH15448A DEH0015448A DE955682C DE 955682 C DE955682 C DE 955682C DE H15448 A DEH15448 A DE H15448A DE H0015448 A DEH0015448 A DE H0015448A DE 955682 C DE955682 C DE 955682C
- Authority
- DE
- Germany
- Prior art keywords
- isonicotinic acid
- parts
- formaldehyde
- new
- production
- 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.)
- Expired
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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung von neuen Isonicotinsäurederivaten Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Isonicotinsäurederivaten, welches darin besteht, daß man Isonicotinsäurehydrazid bzw. 2-Methyl-isonicotinsäurehydrazid mit Formaldehyd oder einer Formaldehyd abgebenden Verbindung, wie z. B. Paraformaldehyd, . umsetzt.Process for the production of new isonicotinic acid derivatives The invention relates to a method for the production of new isonicotinic acid derivatives, which consists in that isonicotinic acid hydrazide or 2-methyl-isonicotinic acid hydrazide with formaldehyde or a formaldehyde-releasing compound, such as. As paraformaldehyde. implements.
Zur Umsetzung der Reaktionspartner verwendet man zweckmäßig äquimolekulare #Mengen derselben. Ferner ist es empfehlenswert, ein Verdünnungsmittel, z. B. Wasser oder einen niederen Alkohol, wie z. B. Äthanol oder Isopropanot, zuzusetzen. Die Umsetzung kann bei gewöhnlicher oder erhöhter Temperatur vorgenommen werden. Die er.findungsgemäß gewonnenen Kondensationsprodukte aus Isonicotinsäurehydrazid bzw. :2-Methyl-isonicotinsäurehydrazid und Formaldehyd-oder Formaldehyd abgebenden Substanzen sind in der Regel polymere Verbindungen von unbestimmtem Molekulargewicht, in denen das Molverhältnis der Isonicotinsäurehydrazidkomponente zum Formaldehyd i : i beträgt. Sie sind in Wasser schwer löslich.To convert the reactants, it is expedient to use equimolecular amounts of the same. It is also advisable to use a diluent, e.g. B. water or a lower alcohol such. B. ethanol or isopropanol to add. The reaction can be carried out at ordinary or elevated temperature. The condensation products obtained according to the invention from isonicotinic acid hydrazide or: 2-methyl-isonicotinic acid hydrazide and formaldehyde- or formaldehyde-releasing substances are generally polymeric compounds of indeterminate molecular weight in which the molar ratio of isonicotinic acid hydrazide component to formaldehyde is i : i. They are sparingly soluble in water.
Diese Verbindungen besitzen bemerkenswerte chemotherapeutische Eigenschaften und können als Heilmittel, vor allem in der Tuberkulosebekämpfung, verwendet werden, wobei sie sich wegen ihrer Schwerlöslichkeit namentlich als Depotpräparate eignen.These compounds have remarkable chemotherapeutic properties and can be used as a remedy, especially in the fight against tuberculosis, used because of their poor solubility, they are particularly suitable as depot preparations suitable.
Beispiel i Eine Mischung von 45Gewichtsteilen Isonicotinoylhydrazin, 45 Raumteilen einer 351/oigen wäßrigen Formaldehydlösung und 2,5okaumteilen Isopropanol wird auf dem Wasserbad erwärmt, bis vollständige Lösung eintritt. Beim Kühlen der Reaktionsmischung scheidet sich ein mikrokristallinischer Niederschlag des Kondensationsproduktes aus Isonicotinoylhydrazin und Formaldehyd ab. Er wird abfiltriert und getrocknet. Der Schmelzpunkt liegt bei 167,5 bis 1745'. Eine weitere Menge der Verbindung erhält man beim Einengen des Filtrates auf etwa die Hälfte seines ursprünglichen Volumens und beim Kühlen des Konzentrates. Gesamtausbeute: 36 Gewichtsteile. Diese Verbindung ist in Wasser von Raumtemperatur zu 2o mg pro ioo cem löslich.EXAMPLE i A mixture of 45 parts by weight of isonicotinoyl hydrazine, 45 parts by volume of a 35% strength aqueous formaldehyde solution and 2.5 parts by weight of isopropanol is heated on a water bath until complete dissolution occurs. When the reaction mixture is cooled, a microcrystalline precipitate of the condensation product of isonicotinoyl hydrazine and formaldehyde separates out. It is filtered off and dried. The melting point is 167.5 to 1745 '. A further amount of the compound is obtained when the filtrate is concentrated to about half its original volume and when the concentrate is cooled. Total yield: 36 parts by weight. This compound is soluble in water at room temperature to the extent of 20 mg per 100 cem.
Beispiel -2 Eine Mischung von 45 Gewichtsteilen Isonicotinoylhydrazin, io Gewichtsteilen Paraformaldehyd und :25o Raumteilen Isopropanol, welches i Raumteil 3 n-SalzAäure enthält, wird 3/4 Stunde-n auf dem Wasserbad erwärmt. Das unlösliche Isonicotinoylhydrazin macht nach und nach einem weißen Niederschlag des gewünschten Kondensationsproduktes von Isonicotinoylhydrazin und Formaldehyd Platz. Dieser weiße Niederschlag wird abfiltriert, gewaschen und getrocknet; er hat die gleichen Eigenschaften wie das Produkt aus Beispiel i. Ausbeute: 42 Gewichtsteile.Example -2 A mixture of 45 parts by weight Isonicotinoylhydrazin, io weight parts paraformaldehyde, and: 25o parts by volume of isopropanol which contains 3 i space part n-SalzAäure is 3/4 hour n-heated on a water bath. The insoluble isonicotinoylhydrazine gradually gives way to a white precipitate of the desired condensation product of isonicotinoylhydrazine and formaldehyde. This white precipitate is filtered off, washed and dried; it has the same properties as the product from example i. Yield: 42 parts by weight.
Beispiel 3 Eine Mischung von 2oGewichtsteilen Isonicotinoylhydrazin, 45 Gewichtsteilen Paraformaldehyd und ioo Raumteilen Wasser wird etwa i Stunde auf dem Dampfbad erwärmt. Zunächst lösen sich die festen Anteile vollständig auf, dann scheidet sich ein weißer kristallinischer Niederschlag des Kondensationsproduktes aus Isonicotinoylhydrazin und Formaldehyd ab. Er wird abfiltriert, gewaschen und getrocknet; er besitzt die gleichen Eigenschaften wie das Produkt aus Beispiel i. Ausbeute: 18,5 Gewichtsteile.Example 3 A mixture of 20 parts by weight of isonicotinoyl hydrazine, 45 parts by weight of paraformaldehyde and 100 parts by volume of water is heated on the steam bath for about one hour. At first the solid components dissolve completely, then a white crystalline precipitate of the condensation product of isonicotinoylhydrazine and formaldehyde separates out. It is filtered off, washed and dried; it has the same properties as the product from example i. Yield: 18.5 parts by weight.
Beispiel 4 Eine Mischung von ioGewichtsteilen Isorficotinoylhydrazin, io Raumteilen wäßrigem Formalde-hyd (35"/0) und 4o Raumteilen Wasser wird '/2Stunde auf dem Dampfbad erwärmt. Es bildet sich ein Niederschlag des Kondensationsproduktes aus Isonicotinoylhydrazin und Formaldehyd, welcher abfiltriert, gewaschen und getrocknet wird und der die gleichen Eigenschaften wie das Produkt aus Beispiel i hat. Ausbeute: 8,5 Gewichtsteile.Example 4 heated A mixture of ioGewichtsteilen Isorficotinoylhydrazin, io parts by volume of aqueous formaldehyde (35 "/ 0) and 4o parts by volume of water is' / 2Stunde on the steam bath. It forms a precipitate the condensation product of Isonicotinoylhydrazin and formaldehyde, which was filtered, washed and is dried and which has the same properties as the product from Example I. Yield: 8.5 parts by weight.
Beispiel 5 Zu einer Lösung von 38 Gewichtsteilen 2-Methylisonicotinsäurehydrazid in 12o Raumteilen Wasser werden bei etwa 35' 22 Gewichtsteile wäßriger, 381/oiger Formaldehydlösung gefügt. Nach 2StÜndigem Rühren wird das ausgefallene Kondensationsprodukt abgenutscht, mit Wasser gewaschen und getrocknet. Die so erhaltene polymere Verbindung schmilzt bei 143' und besitzt die Summenformel (C.H.ON")". Ausbeute: 36Gewichtsteile. EXAMPLE 5 To a solution of 38 parts by weight of 2-methylisonicotinic acid hydrazide in 120 parts by volume of water, 22 parts by weight of 381% aqueous formaldehyde solution are added at about 35%. After stirring for 2 hours, the precipitated condensation product is filtered off with suction, washed with water and dried. The polymeric compound thus obtained melts at 143 'and has the empirical formula (CHON ")". Yield: 36 parts by weight.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US955682XA | 1952-03-07 | 1952-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE955682C true DE955682C (en) | 1957-01-10 |
Family
ID=22252593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH15448A Expired DE955682C (en) | 1952-03-07 | 1953-02-21 | Process for the production of new isonicotinic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE955682C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1238471B (en) * | 1962-08-01 | 1967-04-13 | Farmabion S A | Process for the preparation of soluble therapeutically effective compounds of the tetracycline series |
-
1953
- 1953-02-21 DE DEH15448A patent/DE955682C/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1238471B (en) * | 1962-08-01 | 1967-04-13 | Farmabion S A | Process for the preparation of soluble therapeutically effective compounds of the tetracycline series |
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