CH382759A - Verfahren zur Herstellung neuer 1-Acyl-1-(B-chloräthyl)-2-(5'-nitrofurfuryliden)-hydrazine - Google Patents

Verfahren zur Herstellung neuer 1-Acyl-1-(B-chloräthyl)-2-(5'-nitrofurfuryliden)-hydrazine

Info

Publication number
CH382759A
CH382759A CH205061A CH205061A CH382759A CH 382759 A CH382759 A CH 382759A CH 205061 A CH205061 A CH 205061A CH 205061 A CH205061 A CH 205061A CH 382759 A CH382759 A CH 382759A
Authority
CH
Switzerland
Prior art keywords
nitrofurfurylidene
chloroethyl
acyl
hydrazines
new
Prior art date
Application number
CH205061A
Other languages
English (en)
Inventor
F Ebetino Frank
Original Assignee
Norwich Pharma Co
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 Norwich Pharma Co filed Critical Norwich Pharma Co
Publication of CH382759A publication Critical patent/CH382759A/de

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
    • C07D307/75—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carboxylic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. hydrazides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
    • C07D307/76—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals having carbonic acyl radicals or their thio or nitrogen analogues directly attached to the hydrazino or hydrazono radical, e.g. semicarbazides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Saccharide Compounds (AREA)

Description


  



  Verfahren zur Herstellung neuer   1-Acyl-1-(p-chloräthyl)-2-(S'-nitrofurfuryliden)-hydrazine   
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von   l-Acyl-l-(ss-chloräthyl)-2-(S'-    nitrofurfuryliden)-hydrazinen der allgemeinen Formel
EMI1.1     
 in welcher X eine Amino-oder Methylgruppe bedeutet.



   Diese neuen Nitrofuran-Derivate besitzen   hervor-    ragende chemotherapeutische Eigenschaften. Verabreicht man z. B. Küken, welche mit Eimeria tenella, dem Erreger der Coccidiose, infiziert wurden, ein mit den neuen Verbindungen (0,011 Gew.    /b)    vermischtes Futter, so wird völlige Heilung erzielt. Auch Mäuse, welche mit   tödlichen    Mengen Staphylococcus aureus infiziert wurden, können mit den neuen Verbindungen erfolgreich behandelt werden ; bereits bei Verabreichung einer Einzeldosis von 210   mglkg über-    leben   60 /o    der Tiere.



   Die Verträglichkeit der erfindungsgemäss hergestellten Nitrofuran-Derivate ist gut ; bei ihrer Verabreichung konnten keine schädlichen Nebenwirkungen beobachtet werden. Die Verbindungen lassen sich mit den üblichen pharmazeutischen   Träger-    substanzen und Adjuvantien zu Tabletten, Suspensionen, Kapseln usw. verarbeiten ; zur Behandlung von Tieren werden sie in üblicher Weise mit dem Futter oder Trinkwasser vermischt.



   Die Herstellung der neuen   l-Acyl-l-(ss-chlor-      äthyl)-2- (5'-nitrofurfuryliden)-hydrazine    erfolgt erfindungsgemäss durch Chlorierung der entsprechenden    1-Acyl-1- (sshydroxyäthyl)-2-(5'-nitrofurfuryliden)-    hydrazine.



   Beispiel 1    l-Carbamyl-l- (ss-chloräthyl)-2-(5'-nitrofurfurylidet    hydrazin
Eine Suspension von 200 g   5-Nitrofurfurol-2-(ss-      hydroxyäthyl)-semicarbazon    in trockenem Benzol wird in der Wärme unter Rühren mit Thionylchlorid versetzt, wobei die Geschwindigkeit der Zugabe so gewählt wird, dass eine Temperatur von   40-45     C im Reaktionsgefäss aufrechterhalten bleibt. Nach Be endigung der Gasentwicklung erhitzt man die Suspen sion   1    Stunde lang auf 55-65  C, lässt abkühlen und filtriert ab. Der Niederschlag [186 g   3- (5'Nitrofurfu-      rylidenamino)-2-imino-oxazolidin-hydrochlorid]    wird in 2 1 Xylol aufgenommen und etwa 30 Minuten lang unter Rückfluss erhitzt.

   Man filtriert den orangefarbenen Niederschlag ab und wäscht ihn mit Ather, Wasser und Äthanol. Auf diese Weise erhält man
178 g   1-Carbamyl-l-(ss-chloräthyl)-2-(5'-nitrofurfu-    ryliden)-hydrazin vom Smp.   194-196  C    ; die Verbindung kann aus Acetonitril umkristallisiert werden.



   Beispiel 2    l-Acetyl-l- (ss-chloräthyl)-2-(5'-nitrofurfuryliden)-    hydrazin
10 g   1-Acetyl-1-      (-hydroxyäthyl)-2- (5'-nitro-    furfuryliden)-hydrazin werden unter Rühren innerhalb 10 Minuten in 25   cm3    Thionylchlorid gegeben.



  Hierbei bildet sich alsbald ein Niederschlag. Man giesst das Reaktionsgemisch in   100    cm3 Benzol, filtriert den Niederschlag ab, wäscht ihn mit Benzol und trocknet. Auf diese Weise erhält man 8,5 g   (=      79e/o    d. Th.)   l-Acetyl-l-(ss-chloräthyl)-2-(5'-nitro-    furfuryliden)-hydrazin vom Smp.   141-1466 C    ; durch Umkristallisieren aus Isopropanol oder Benzol erhöht sich der Schmelzpunkt auf 145,5-146,5    C.

Claims (1)

  1. PATENTANSPRUCH Verfahren zur Herstellung neuer 1-Acyl-1- (p- chloräthyl)-2- (5'-nitrofurfuryliden)-hydrazine der allgemeinen Formel EMI2.1 in welcher X eine Amino-oder Methylgruppe bedeutet, dadurch gekennzeichnet, dass man die ent- sprechenden l-Acyl-l-(ss-hydroxyäthyl)-2-(5'-nitro- furfuryliden)-hydrazine chloriert.
CH205061A 1960-02-23 1961-02-21 Verfahren zur Herstellung neuer 1-Acyl-1-(B-chloräthyl)-2-(5'-nitrofurfuryliden)-hydrazine CH382759A (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10039A US3108122A (en) 1960-02-23 1960-02-23 New 1-acyl-1-(2-chloroethyl)-2-(5-nitrofurfurylidene) hydrazines

Publications (1)

Publication Number Publication Date
CH382759A true CH382759A (de) 1964-10-15

Family

ID=21743498

Family Applications (2)

Application Number Title Priority Date Filing Date
CH205061A CH382759A (de) 1960-02-23 1961-02-21 Verfahren zur Herstellung neuer 1-Acyl-1-(B-chloräthyl)-2-(5'-nitrofurfuryliden)-hydrazine
CH205161A CH382760A (de) 1960-02-23 1961-02-21 Verfahren zur Herstellung von 1-Acetyl-1-(B-hydroxy-äthyl)-2-(5'-nitrofurfuryliden)-hydrazin

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH205161A CH382760A (de) 1960-02-23 1961-02-21 Verfahren zur Herstellung von 1-Acetyl-1-(B-hydroxy-äthyl)-2-(5'-nitrofurfuryliden)-hydrazin

Country Status (4)

Country Link
US (1) US3108122A (de)
CH (2) CH382759A (de)
ES (1) ES264402A1 (de)
GB (1) GB952097A (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416234A (en) * 1945-08-28 1947-02-18 Eaton Lab Inc Series of nitrofuran compounds
US2416236A (en) * 1945-08-28 1947-02-18 Eaton Lab Inc Series of nitrofuran compounds

Also Published As

Publication number Publication date
US3108122A (en) 1963-10-22
GB952097A (en) 1964-03-11
CH382760A (de) 1964-10-15
ES264402A1 (es) 1961-06-16

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