AT217461B - Process for the preparation of the new 1- [3- (5'-nitro-2'-furyl) -propen- (2) -ylidene- (1) -amino] -imidazolidin-thione- (2) - Google Patents

Process for the preparation of the new 1- [3- (5'-nitro-2'-furyl) -propen- (2) -ylidene- (1) -amino] -imidazolidin-thione- (2)

Info

Publication number: AT217461B
Authority: AT; Austria
Prior art keywords: sep; new; propen; thione; ylidene
Prior art date: 1959-10-23

Application number

AT656760A

Other languages

German (de)

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.)

1959-10-23

Filing date

1960-08-29

Publication date

1961-10-10

1960-08-29 Application filed by Norwich Pharma Co filed Critical Norwich Pharma Co

1961-10-10 Application granted granted Critical

1961-10-10 Publication of AT217461B publication Critical patent/AT217461B/en

Links

238000000034 method Methods 0.000 title description 3
241001465754 Metazoa Species 0.000 description 6
241000204725 Ascaridia galli Species 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
241000975692 Syphacia obvelata Species 0.000 description 2
IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 2
241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
241000282414 Homo sapiens Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000193985 Streptococcus agalactiae Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
230000000507 anthelmentic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
210000002257 embryonic structure Anatomy 0.000 description 1
235000013305 food Nutrition 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000011164 ossification Effects 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001228 spectrum Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

   <Desc/Clms Page number 1> 
 



   Verfahren zur Herstellung des neuen   l- [3- (5'-Nitro-. 2'-furyl)-    -propen-(2)-yliden-(1)-amino]-imidazolidin-thions- (2) 
Die Erfindung betrifft ein Verfahren zur Herstellung des neuen 1-[3-(5'-Nitro-2'-futyl)-propen-(2)-   -yliden- (1)-amino]-imidazolidin-thions- (2)   der Formel : 
 EMI1.1 
 
Es wurde gefunden, dass diese Verbindung ein breites antibakterielles Spektrum hat; sie ist z. B. ge-   gentiber Escherichia coli, Salmonella typhosa, Streptococcus pyogenes, Streptococcus agalactiae, Staphylo-    coccus aureus und Erysipelothrix rhusiopathiae wirksam. Ein besonderes Merkmal des neuen Nitrofuran-
Derivates ist seine überraschend hohe anthelmintische Wirksamkeit.

   So werden erstaunlich gute Erfolge erzielt, wenn man mit Syphacia obvelata oder mit Ascaridia galli infizierten Tieren relativ geringe Men- 
 EMI1.2 
 verursacht, dieserparasitAscaridose bei Kücken, welche das Wachstum beeinträchtigt, die   Knochenbildung   verhindert und oft zum
Tode der Tiere führt. 



   In der folgenden Tabelle sind die Ergebnisse zusammengestellt, welche nach 4-tägiger Behandlung (2x täglich oral) von mit Syphacia obvelata infizierten Mäusen erzielt wurden. 



   Tabelle 1 
 EMI1.3 
 
<tb> 
<tb> Dosis <SEP> Zahl <SEP> der <SEP> infizierten <SEP> 0/0 <SEP> 
<tb> (mg/kg) <SEP> Tiere/Gesamtzahl
<tb> 300 <SEP> 0/10 <SEP> 0
<tb> 100 <SEP> 0/10 <SEP> 0
<tb> 50 <SEP> 0/10 <SEP> 0
<tb> Kontrolle <SEP> 10/10 <SEP> 100
<tb> 
 
Die hervorragende prophylaktische Wirkung der neuen Verbindung gegenüber Ascaridia galli wird durch den folgenden Versuch näher   erläutert : Man   mischt das Nitrofuran-Derivat in einer Konzentration von 0, 01 bis   0, 02 Gew.. Jo dem KUckenfutterbei.   Dieses Futter wird den Tieren schon 2 Tage vor der In- 

 <Desc/Clms Page number 2> 

 fektion (Einführung von Embryonen enthaltenden Ascaridia galli-Eiern mittels einer Magensonde) verabreicht; nach der Infektion wird die Behandlung zirka 41 Tage weitergeführt. Dann werden die Tiere getötet, seziert und auf Würmer untersucht.

   Wie aus der nachstehenden Tabelle 2 hervorgeht, wird durch die Behandlung mit der neuen Verbindung eine beträchtliche Verminderung der Wurmanzahl   und-grosse   erzielt. 



   Tabelle 2 
 EMI2.1 
 
<tb> 
<tb> Konzentration <SEP> im <SEP> Zahl <SEP> der <SEP> Behandlungs-Tag <SEP> der <SEP> Zahl <SEP> der <SEP> Zahl <SEP> der <SEP> Durchschnittliche
<tb> Futter <SEP> (Gew. <SEP> -'10) <SEP> Kücken <SEP> dauer <SEP> (Tage) <SEP> Autopsie <SEP> infizierten <SEP> gefnde- <SEP> Grösse <SEP> der
<tb> Tiere/Ge- <SEP> nen <SEP> Wür- <SEP> Würmer <SEP> (cm)
<tb> samtzahl <SEP> mer <SEP> männl. <SEP> weibl. <SEP> 
<tb> 



  0, <SEP> 02 <SEP> 11-2 <SEP> bis <SEP> 41 <SEP> 43 <SEP> 1/11 <SEP> 1-2, <SEP> 5 <SEP> 
<tb> 0, <SEP> 01 <SEP> 10-2 <SEP> bis <SEP> 41 <SEP> 43 <SEP> 5/10 <SEP> 10 <SEP> 3, <SEP> 6 <SEP> 4, <SEP> 5 <SEP> 
<tb> Kontrolle <SEP> 10-40 <SEP> 10/10 <SEP> 98 <SEP> 5,1 <SEP> 6,7
<tb> Kontrolle <SEP> 10 <SEP> - <SEP> 42 <SEP> 10/10 <SEP> 92 <SEP> 5,7 <SEP> 7,1
<tb> 
 
 EMI2.2 




   <Desc / Clms Page number 1>
 



   Process for the preparation of the new l- [3- (5'-nitro-. 2'-furyl) -propen- (2) -ylidene- (1) -amino] -imidazolidine-thione- (2)
The invention relates to a process for the preparation of the new 1- [3- (5'-nitro-2'-futyl) -propen- (2) -ylidene- (1) -amino] -imidazolidin-thione- (2) Formula:
 EMI1.1
 
It has been found that this compound has a broad antibacterial spectrum; she is z. B. against Escherichia coli, Salmonella typhosa, Streptococcus pyogenes, Streptococcus agalactiae, Staphylococcus aureus and Erysipelothrix rhusiopathiae. A special feature of the new nitrofuran
Derivative is its surprisingly high anthelmintic effectiveness.

   Astonishingly good results are achieved if relatively low human beings are used in animals infected with Syphacia obvelata or Ascaridia galli.
 EMI1.2
 causes this parasite ascaridosis in chicks, which impairs growth, prevents bone formation and often causes
Animal deaths.



   The following table summarizes the results which were obtained after 4 days of treatment (twice daily orally) of mice infected with Syphacia obvelata.



   Table 1
 EMI1.3
 
<tb>
<tb> Dose <SEP> Number <SEP> of the <SEP> infected <SEP> 0/0 <SEP>
<tb> (mg / kg) <SEP> animals / total number
<tb> 300 <SEP> 0/10 <SEP> 0
<tb> 100 <SEP> 0/10 <SEP> 0
<tb> 50 <SEP> 0/10 <SEP> 0
<tb> Control <SEP> 10/10 <SEP> 100
<tb>
 
The excellent prophylactic effect of the new compound against Ascaridia galli is explained in more detail by the following experiment: The nitrofuran derivative is mixed with the chick feed in a concentration of 0.01 to 0.02 wt. This feed is given to the animals 2 days before

 <Desc / Clms Page number 2>

 fection (introduction of Ascaridia galli eggs containing embryos by means of a nasogastric tube); after the infection, the treatment is continued for about 41 days. The animals are then killed, dissected and examined for worms.

   As can be seen from Table 2 below, treatment with the new compound results in a considerable reduction in the number and size of worms.



   Table 2
 EMI2.1
 
<tb>
<tb> concentration <SEP> in the <SEP> number <SEP> the <SEP> treatment tag <SEP> the <SEP> number <SEP> the <SEP> number <SEP> the <SEP> average
<tb> food <SEP> (weight <SEP> -'10) <SEP> chickens <SEP> duration <SEP> (days) <SEP> autopsy <SEP> infected <SEP> found- <SEP> size <SEP > the
<tb> animals / genes <SEP> n <SEP> worms <SEP> worms <SEP> (cm)
<tb> total number <SEP> mer <SEP> male <SEP> female <SEP>
<tb>



  0, <SEP> 02 <SEP> 11-2 <SEP> to <SEP> 41 <SEP> 43 <SEP> 1/11 <SEP> 1-2, <SEP> 5 <SEP>
<tb> 0, <SEP> 01 <SEP> 10-2 <SEP> to <SEP> 41 <SEP> 43 <SEP> 5/10 <SEP> 10 <SEP> 3, <SEP> 6 <SEP> 4 , <SEP> 5 <SEP>
<tb> Control <SEP> 10-40 <SEP> 10/10 <SEP> 98 <SEP> 5.1 <SEP> 6.7
<tb> Control <SEP> 10 <SEP> - <SEP> 42 <SEP> 10/10 <SEP> 92 <SEP> 5.7 <SEP> 7.1
<tb>
 
 EMI2.2

AT656760A 1959-10-23 1960-08-29 Process for the preparation of the new 1- [3- (5'-nitro-2'-furyl) -propen- (2) -ylidene- (1) -amino] -imidazolidin-thione- (2) AT217461B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US217461XA	1959-10-23	1959-10-23

Publications (1)

Publication Number	Publication Date
AT217461B true AT217461B (en)	1961-10-10

Family

ID=21805903

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT656760A AT217461B (en)	1959-10-23	1960-08-29	Process for the preparation of the new 1- [3- (5'-nitro-2'-furyl) -propen- (2) -ylidene- (1) -amino] -imidazolidin-thione- (2)

Country Status (1)

Country	Link
AT (1)	AT217461B (en)

1960
- 1960-08-29 AT AT656760A patent/AT217461B/en active

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