DE919351C - Process for the preparation of new derivatives of isonicotinic acid amide - Google Patents

Process for the preparation of new derivatives of isonicotinic acid amide

Info

Publication number
DE919351C
DE919351C DEF8546A DEF0008546A DE919351C DE 919351 C DE919351 C DE 919351C DE F8546 A DEF8546 A DE F8546A DE F0008546 A DEF0008546 A DE F0008546A DE 919351 C DE919351 C DE 919351C
Authority
DE
Germany
Prior art keywords
acid amide
isonicotinic acid
preparation
new derivatives
formaldehyde
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
Application number
DEF8546A
Other languages
German (de)
Inventor
Dr Hans-Albert Offe
Dr Werner Siefken
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to DEF8546A priority Critical patent/DE919351C/en
Application granted granted Critical
Publication of DE919351C publication Critical patent/DE919351C/en
Expired legal-status Critical Current

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
    • C07D213/81—Amides; Imides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

Verfahren zur Herstellung neuer Derivate des Isonicotinsäureamids Es ist bekannt, daß das Methylolamid der Nieotinsäure zur Bekämpfung der Enterococceninfektion der Gallenwege verwendet werden kann. Die Darstellung dieses Methylolamids geschieht, z. B. durch Umsetzung von Nicotinsäureamid mit wäßriger Formaldehydlösung in neutraler bis. schwachalkalischer Lösung. Derartigen Abkömmlingen der Nicotinsäure haftet der Nachteil an, daß sie, in Gegenwart von Serum einen erheblichen. Teil ihrer Wirksamkeit einbüßen.Process for the preparation of new derivatives of isonicotinic acid amide It is known that the methylolamide of nieotinic acid is used to combat enterococcal infection the biliary tract can be used. The representation of this methylolamide happens z. B. by reacting nicotinic acid amide with aqueous formaldehyde solution in neutral until. weakly alkaline solution. Such derivatives of nicotinic acid adheres the disadvantage is that, in the presence of serum, they produce a considerable amount. Part of their effectiveness forfeit.

Es wurde nun gefunden, daß man zu neuen Derivaten des Isornicotinsäurea.mids gelangt, wenn man Formaldehyd oder Formaldehyd abgebende Ver-Verbindungen auf Amide der Isonicotinsäure, in denen mindestens ein Wasserstoffatom der Säureamidgruppe unsubstituiert ist, nach den zur Methylolamidbildung üblichen Methoden einwirken läßt. Die neuen Derivate des Isonicotinsäureamids besitzen dem Nicotinsäure-methylolamid gegenüber den nicht vorauszusehenden Vorteil, in ihrer Wirkung auf Enterococcen nicht wie dieses von Blut, Serum oder p-Aminobenzoesäure beeinträchtigt zu -,werden.It has now been found that new derivatives of Isornicotinsäurea.mids if you get formaldehyde or formaldehyde-releasing Ver compounds on amides of isonicotinic acid, in which at least one hydrogen atom of the acid amide group is unsubstituted, act according to the usual methods for methylolamide formation leaves. The new derivatives of isonicotinic acid amide have nicotinic acid methylolamide compared to the unforeseeable advantage in their effect on enterococci not to be affected by blood, serum or p-aminobenzoic acid like this.

Zur Darstellung der neuen, chemotherapeutisch wirksameren Verbindungen kann man sich der üb- lichen Methoden zur Herstellung von Methylolverbindungen der Säureamide bedienen. Vorteilhaft arbeitet man in wäßriger Lösung oder im Gemisch von Wasser mit niederen Alkoholen, wobei es zweckmäßig ist, eine schwachbasische Reaktion der Lösung aufrechtzuerhalten. The usual methods for the preparation of methylol compounds of the acid amides can be used to prepare the new, chemotherapeutically more effective compounds. It is advantageous to work in an aqueous solution or in a mixture of water with lower alcohols, it being advantageous to maintain a weakly basic reaction of the solution.

Beispiel 122 g Isonicotinsäureamid vom F. i58° werden in 5oo ccm Wasser gelöst und mit 1o g Natriumhydrogencarbonat und 100 ccm 3oa/o-iger wäßriger Formaldehydlösung versetzt. Die Lösung wird a Stunden auf einer Temperatur von q.o bis 50° gehalten und sodann bei dieser Temperatur bis zur reichlichen Kristallabscheidung eingeengt. Nach dem Trocknen lassen sich die nadelförmigen Kristalle aus Alkohol-Benzin, umkristall.isieren. Das Isonicotinsä.ure-methylolamid schmilzt bei 13z° unter Zersetzung, um dann zu erstarren und bei r56° erneut zu schmelzen. Die Ausbeute beträgt 8o '/o der Theorie.Example 122 g of isonicotinic acid amide with a temperature of 158 ° are dissolved in 500 cc of water dissolved and with 1o g sodium hydrogen carbonate and 100 ccm 3oa / o-iger aqueous Formaldehyde solution offset. The solution is kept at a temperature of q.o to 50 ° for a hour and then concentrated at this temperature to the point of abundant crystal separation. After drying, the needle-shaped crystals can be recrystallized from alcohol-gasoline. Isonicotinsä.ure-methylolamid melts at 130 ° with decomposition, and then to solidify and melt again at r56 °. The yield is 80% of theory.

Claims (1)

PATENTANSPRUCIi: Verfahren zur Herstellung neuer Derivate des Isonicotinsäureamids, dadurch gekennzeichnet, daß man Formaldehyd oder Formaldehyd abgebendeVerbindungen auf Amide der Isonicotinsäure, in. denen. mindestens ein Wasserstoffatom der Säureamidgruppe unsubstituiert ist, nach den zur Methylolamidbildung üblichen Methoden einwirken läBt.PATENT CLAIMS: Process for the preparation of new derivatives of isonicotinic acid amide, characterized in that formaldehyde or formaldehyde-releasing compounds are used on amides of isonicotinic acid, in which. at least one hydrogen atom of the acid amide group is unsubstituted, act according to the usual methods for methylolamide formation lets.
DEF8546A 1952-03-11 1952-03-11 Process for the preparation of new derivatives of isonicotinic acid amide Expired DE919351C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF8546A DE919351C (en) 1952-03-11 1952-03-11 Process for the preparation of new derivatives of isonicotinic acid amide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF8546A DE919351C (en) 1952-03-11 1952-03-11 Process for the preparation of new derivatives of isonicotinic acid amide

Publications (1)

Publication Number Publication Date
DE919351C true DE919351C (en) 1954-10-21

Family

ID=7085867

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF8546A Expired DE919351C (en) 1952-03-11 1952-03-11 Process for the preparation of new derivatives of isonicotinic acid amide

Country Status (1)

Country Link
DE (1) DE919351C (en)

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