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DE1156085B - Process for the preparation of 5-nitrofurfurol-N '- (ª ‰ -chloraethyl) -semicarbazone - Google Patents

Process for the preparation of 5-nitrofurfurol-N '- (ª ‰ -chloraethyl) -semicarbazone

Info

Publication number
DE1156085B
DE1156085B DEN19440A DEN0019440A DE1156085B DE 1156085 B DE1156085 B DE 1156085B DE N19440 A DEN19440 A DE N19440A DE N0019440 A DEN0019440 A DE N0019440A DE 1156085 B DE1156085 B DE 1156085B
Authority
DE
Germany
Prior art keywords
nitrofurfurol
semicarbazone
preparation
chloroethyl
chloraethyl
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
Application number
DEN19440A
Other languages
German (de)
Inventor
Frank F Ebetino
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.)
Warner Chilcott Pharmaceuticals Inc
Original Assignee
Norwich Pharmacal 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 Pharmacal Co filed Critical Norwich Pharmacal Co
Publication of DE1156085B publication Critical patent/DE1156085B/en
Pending legal-status Critical Current

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
    • 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Verfahren zur Herstellung von 5-Nitrofurfurol-N'-(ß-chloräthyl)-semicarbazon Die Erfindung betrifft ein Verfahren zur Herstellung von 5-Nitrofurfurol-N'-(B-chloräthyl)-semi carbazon der Formel Diese Verbindung besitzt eine hervorragende Wirkung gegenüber Eimeria tenella, dem Erreger der Coccidiose. In der Tabelle sind die Ergebnisse zusammengestellt, die bei der Verabreichung eines mit dem neuen Nitrofuranderivat sowie eines mit bekannten Nitrofuranderivaten vermischten Futters an Küken, die mit Eimeria tenella infiziert waren, erhalten wurden. Sterblichkeit Ver- Konzentration der der bin- im Futter (°/0) behandelten unbehandelten dung Tierel Tierel Gesamtzahl Gesamtzahl A 0,011 7/20 (= 350/0) 16/20 (= 800/0) B 0,022 14/20 (= 700/0) 14/21 (= 670/0) C 0,022 16/20 (= 800/0) 16/20 (= 800/0) A=5 5-Nitrofurfurol-N'-(ß-chloräthyl)-semicarbazon.Process for the preparation of 5-nitrofurfurol-N '- (β-chloroethyl) -semicarbazone The invention relates to a process for the preparation of 5-nitrofurfurol-N' - (B-chloroethyl) -semicarbazone of the formula This compound has an excellent effect on Eimeria tenella, the causative agent of coccidiosis. The table summarizes the results obtained when chicks infected with Eimeria tenella were given a feed mixed with the new nitrofuran derivative and a feed mixed with known nitrofuran derivatives. mortality Ver concentration of the bin- in the feed (° / 0) treated untreated dung Tierel Tierel Total number total number A 0.011 7/20 (= 350/0) 16/20 (= 800/0) B 0.022 14/20 (= 700/0) 14/21 (= 670/0) C 0.022 16/20 (= 800/0) 16/20 (= 800/0) A = 5 5-nitrofurfurol-N '- (β-chloroethyl) semicarbazone.

B = 5-Nitrofurfurol-N'-(B-hydroxyäthyl)-semi carbazon.B = 5-nitrofurfurol-N '- (B-hydroxyethyl) -semi carbazon.

C = 5-Nitrofurfurol-N'-(,B-dimethylaminoäthyl)-semicarbazonhydrochlorid.C = 5-nitrofurfurol-N '- (, B-dimethylaminoethyl) semicarbazone hydrochloride.

Hieraus ergibt sich, daß das 5-Nitrofurfurol-N'-(p-chloräthyl)-semicarbazon bereits bei einer Konzentration von 0,011 Gewichtsprozent im Futter einen erheblichen Rückgang in der Sterblichkeit der Küken bewirkt, während die bekannten Verbindungen die Coccidiose nicht beeinflussen. Außerdem ist das neue Nitrofuranderivat auch gegen Staphylococcus aureus wirksam. Bei Mäusen, die mit tödlichen Mengen an Staphylococcus aureus infiziert waren, beträgt bereits bei Verabreichung einer Einzeldosis von 210 mg/kg die Überlebensrate der Tiere 600/0. It follows from this that the 5-nitrofurfurol-N '- (p-chloroethyl) -semicarbazone even at a concentration of 0.011 percent by weight in the feed a considerable amount Decrease in chick mortality causes while the known compounds do not affect coccidiosis. Plus, the new nitrofuran derivative is also effective against Staphylococcus aureus. In mice exposed to fatal amounts of Staphylococcus aureus was infected with a single dose of 210 mg / kg the survival rate of the animals 600/0.

Das 5-Nitrofurfurol-N'-(/3-chloräthyl)-semicarbazon ist gut verträglich, und es konnten bei seiner Verabreichung keine schädlichen Nebenwirkungen beobachtet werden. Zur Behandlung von Tieren wird die Substanz in üblicher Weise mit dem Futter oder Trinkwasser vermischt. 5-Nitrofurfurol-N '- (/ 3-chloroethyl) -semicarbazone is well tolerated, and no harmful side effects were observed in its administration will. For the treatment of animals, the substance is added to the feed in the usual way or mixed drinking water.

Die Herstellung des 5-Nitrofurfurol-N'-(B-chlor äthyl)-semicarbazons erfolgt dadurch, daß man N-(5-Nitrofurfuryliden)-3-amino-2-imino-oxazolidinhydrochlorid der Formel in Xylol unter Rückfluß erhitzt. Das als Ausgangsmaterial verwendete N-(5-Nitrofurfuryliden)-3-amino-2-imino-oxazolidinhydrochlorid kann aus 5 Nitrofurfurol - N' - - hydroxyäthyl) - semicarbazon und Thionylchlorid nach dem in den österreichischen Patentschriften 192 407 und 197 816 im Beispiel 1 beschriebenen Verfahren erhalten werden.5-Nitrofurfurol-N '- (B-chloroethyl) -semicarbazone is prepared by adding N- (5-nitrofurfurylidene) -3-amino-2-imino-oxazolidine hydrochloride of the formula heated under reflux in xylene. The N- (5-nitrofurfurylidene) -3-amino-2-imino-oxazolidine hydrochloride used as starting material can be prepared from 5 nitrofurfurol - N '- - hydroxyethyl) - semicarbazone and thionyl chloride according to the method described in Austrian patents 192 407 and 197 816 in example 1 described method can be obtained.

Beispiel 186 g N-(5-Nitrofurfuryliden)-3-amino-2-iminooxazolidinhydrochlorid werden in 2 1 Xylol aufgenommen, und das Gemisch wird 30 Minuten unter Rückfluß erhitzt. Man filtriert den gebildeten orangefarbenen Niederschlag ab und wäscht diesen mit Äther, Wasser und Äthanol. Man erhält 178 g 5-Nitrofurfurol-N'-(p-chloräthyl)-semicarbazon vom F. 194 bis 196"C. Example 186 g of N- (5-nitrofurfurylidene) -3-amino-2-iminooxazolidine hydrochloride are taken up in 2 l of xylene, and the mixture is refluxed for 30 minutes heated. The orange-colored precipitate formed is filtered off and washed this with ether, water and ethanol. 178 g of 5-nitrofurfurol-N '- (p-chloroethyl) semicarbazone are obtained from F. 194 to 196 "C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 5-Nitrofurfurol-N'-(B-chloräthyl)-semicarbazon der Formel dadurch gekennzeichnet, daß man N-(iNitrofurfuryliden)- 3-amino -2-imino-oxazolidinhydro- chlorid der Formel in Xylol unter Rückfluß erhitzt.PATENT CLAIM: Process for the production of 5-nitrofurfurol-N '- (B-chloroethyl) -semicarbazone of the formula characterized in that N- (nitrofurfurylidene) -3-amino -2-imino-oxazolidine hydrochloride of the formula heated under reflux in xylene. In Betracht gezogene Druckschriften: Österreichische Patentschriften Nr. 192 407, 197816, 198261; USA.-Patentschrift Nr. 2 726 241. Publications considered: Austrian patent specifications No. 192 407, 197816, 198261; U.S. Patent No. 2,726,241.
DEN19440A 1960-02-23 1961-01-17 Process for the preparation of 5-nitrofurfurol-N '- (ª ‰ -chloraethyl) -semicarbazone Pending DE1156085B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US1156085XA 1960-02-23 1960-02-23

Publications (1)

Publication Number Publication Date
DE1156085B true DE1156085B (en) 1963-10-24

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEN19440A Pending DE1156085B (en) 1960-02-23 1961-01-17 Process for the preparation of 5-nitrofurfurol-N '- (ª ‰ -chloraethyl) -semicarbazone

Country Status (1)

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DE (1) DE1156085B (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726241A (en) * 1954-01-15 1955-12-06 Norwich Pharma Co New series of nitrofurans
AT192407B (en) * 1954-03-11 1957-10-25 Norwich Pharma Co Process for the preparation of new N- (5-nitro-2-furylacylidene) -3'-amino-oxazolidonen- (2 ')
AT197816B (en) * 1953-08-10 1958-05-27 Norwich Pharma Co Process for the preparation of new hydrazino compounds of the 5-nitrofuran series
AT198261B (en) * 1945-08-28 1958-06-25 Norwich Pharma Co Process for the preparation of new nitrofuran compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT198261B (en) * 1945-08-28 1958-06-25 Norwich Pharma Co Process for the preparation of new nitrofuran compounds
AT197816B (en) * 1953-08-10 1958-05-27 Norwich Pharma Co Process for the preparation of new hydrazino compounds of the 5-nitrofuran series
US2726241A (en) * 1954-01-15 1955-12-06 Norwich Pharma Co New series of nitrofurans
AT192407B (en) * 1954-03-11 1957-10-25 Norwich Pharma Co Process for the preparation of new N- (5-nitro-2-furylacylidene) -3'-amino-oxazolidonen- (2 ')

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