CH615157A5
CH615157A5 - Process for the preparation of novel substituted phenylguanidines

Info

Publication number: CH615157A5
Application number: CH86479A
Authority: CH
Inventors: Heinrich Dr Koelling; Herbert Dr Thomas; Arno Dr Widdig; Hartmund Dr Wollweber
Original assignee: Bayer Ag
Priority date: 1974-05-15
Filing date: 1979-01-29
Publication date: 1980-01-15
Abstract

Novel substituted phenylguanidines of the formula <IMAGE> wherein X represents the sulphinyl group or the sulphonyl group and the substituents R, R<1>, R<2> and R<3> are defined in Claim 1, are obtained when, in corresponding substituted phenylguanidines having a thio group, the latter is oxidised. The oxidation is usually performed with H2O2 or with organic per-acids. The novel compounds mentioned possess an anthelmintic action and may be used as at least one active component in anthelmintics.
Description

       

  
 

**WARNUNG** Anfang DESC Feld konnte Ende CLMS uberlappen **.

 



   PATENTANSPRÜCHE
1. Verfahren zur Herstellung von neuen substituierten Phenylguanidinen der Formel
EMI1.1     
 in welcher
R und R1 voneinander verschieden sind und wechselseitig für jeweils einen der Reste
EMI1.2     
 stehen, in welchen
R4 für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Amino, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Aralkyl und
R5 für gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Alkenyl, gegebenenfalls substituiertes Alkinyl und
R6 für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Alkenyloxy, gegebenenfalls substituiertes Alkinyloxy, gegebenenfalls substituiertes Aryl,

   gegebenenfalls substituiertes Aralkyl, gegebenenfalls substituiertes Alkenyl, gegebenenfalls substituiertes Alkinyl steht, und worin R2 und R3 gleich oder verschieden sein können und für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Amino, Halogen, Cyano, gegebenenfalls substituiertes Alkylthio, gegebenenfalls substituiertes Acyl, gegebenenfalls substituiertes Carbalkoxy stehen, und worin X für die Sulfinylgruppe oder die Sulfonylgruppe steht und mit Stellung 4 oder 5 der substituierten Aminophenylgruppe verknüpft sein kann, dadurch gekennzeichnet, dass man Verbindungen der Formel
EMI1.3     
 in welcher R,   Rl,    R2 und R3 die oben angegebene Bedeutung besitzen, mit der entsprechenden Menge eines Oxydationsmittels oxydiert.



   2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass R2 und R3 substituiertes Alkyl, vorzugsweise Halogenalkyl, bedeuten.



   Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von neuen substituierten Phenylguanidinen, die als Arzneimittel, insbesondere als Anthelmintika, verwendet werden können.



   Es ist bereits bekannt geworden, dass Phenylguanidine der allgemeinen Formel
EMI1.4     
 in der
R niederes Alkyl und
R' sowohl niederes Alkyl als auch Wasserstoff bedeuten kann, anthelmintische Wirkungen aufweisen (siehe dazu deutsche Offenlegungsschrift 2 117 293).



   Sie zeigen jedoch den Nachteil, dass ihre anthelmintische Wirkung wesentlich schwächer ausgeprägt ist als bei den erfindungsgemässen substituierten Phenylguanidinen.



   Es wurde gefunden, dass die neuen, erfindungsgemäss herstellbaren substituierten Phenylguanidine der Formel
EMI1.5     
 in welcher
R und R' voneinander verschieden sind und wechselseitig für jeweils einen der Reste
EMI1.6     
 stehen, in welchen
R4 für Wasserstoff gegebenenfalls substituiertes Alkyl gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Amino, gegebenenfalls substituiertes Alkoxy und gegebenenfalls substituiertes Aralkyl,    R5    für gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Alkenyl und gegebenenfalls substituiertes Alkinyl,  



   R6 für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Alkenyloxy, gegebenenfalls substituiertes Alkinyloxy, gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Aralkyl, gegebenenfalls substituiertes Alkenyl, gegebenenfalls substituiertes Alkinyl steht, und worin
R2 und R3 gleich oder verschieden sein können und für Wasserstoff, gegebenenfalls substituiertes Alkyl, vorzugsweise Halogenalkyl, gegebenenfalls substituiertes Alkoxy, gegebenenfalls substituiertes Amino, Halogen, Cyano, gegebenenfalls substituiertes   Älkylthio,    gegebenenfalls substituiertes Acyl,

   gegebenenfalls substituiertes Carbalkoxy stehen und worin
X für die Sulfinylgruppe oder die Sulfonylgruppe steht und mit Stellung 4 oder 5 der substituierten Aminophenylgruppe verknüpft sein kann, sehr gute anthelmintische Wirkungen aufweisen.



   Die erfindungsgemäss herstellbaren Verbindungen der Formel (I) können in tautomeren Formen vorliegen, wie an folgendem Beispiel gezeigt werden soll:
EMI2.1     

Hier werden die jeweiligen Strukturformeln aus Gründen der Einheitlichkeit in allen Fällen gleichartig formuliert.



   Das erfindungsgemässe Verfahren zur Herstellung der vorgenannten Verbindungen der Formel (I), in denen X ein Sulfinyl- oder ein Sulfonylrest bedeutet, ist dadurch gekennzeichnet, dass man Verbindungen der Formel
EMI2.2     
 in welcher R,   Rl,    R2 und R3 die oben angegebene Bedeutung besitzen, mit der entsprechenden Menge eines Oxydationsmittels oxydiert.



   So können z. B. durch Oxydation der Verbindungen der Formel (I), in denen X ein Schwefelatom bedeutet, mit einem Äquivalent H202 Phenylsulfinylphenylguanidine und mit zwei Äquivalenten H202 Phenylsulfonylguanidin erhalten werden. Das folgende Beispiel erläutert diese   bevprzugte    Ausführungsform:
EMI2.3     
  
EMI3.1     

Anstelle von H202 kann man auch andere Oxydationsmittel verwenden, beispielsweise seien genannt:
Organische Persäuren, wie Peressigsäure, Perameisensäure.



  Perbenzoesäure, m-Chlorperbenzoesäure, Monoperphthalsäure, anorganische Peroxide, wie Wasserstoffperoxid, gelöst in Wasser oder verdünnten organischen Säuren, anorganische Oxydationsmittel, wie Chromsäure, Salpetersäure, Kaliumpermanganat, Chlor, Brom, Halogensauerstoffsäuren, wie Unterchlorige-, Chlorige-, Chlor- oder Überchlorsäure, tert. Butylhypochlorit Methylhypochlorit, tert.-Butylchromat, organische N-Halogenverbindungen, wie N-Chlorsuccinimid, N-Bromsuccinimid sowie N-Halogensulfonsäureamide oder N-Halogencarbonsäureamide.



   Durch entsprechende, literaturbekannte Wahl der Reaktionsbedingungen kann das Oxydationspotential entsprechend eingestellt und die Reaktion zur Herstellung der Sulfoxide bzw. Sulfone gelenkt werden.



     Überraschenderweise    zeigen die erfindungsgemäss erhaltenen, substituierten Phenylguanidine eine erheblich höhere anthelmintische Wirkung als die in der deutschen Offenlegungsschrift 2 117 293 genannten Phenylguanidine, welche die chemisch nächstliegenden Wirkstoffe gleicher Wirkungsart sind. Die erfindungsgemäss erhältlichen Wirkstoffe stellen somit eine wertvolle Bereicherung der Pharmazie dar.



   In den Formeln (I) und (II) steht als gegebenenfalls substituiertes Alkyl R2, R3, R4, R5 und R6 geradkettiges oder verzweigtes Alkyl mit vorzugsweise 1 bis 6, insbesondere 1 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Methyl, Äthyl, n- und i-Propyl, n-, i- und t-Butyl genannt.



   Als gegebenenfalls substituiertes Alkenyl R5 und R6 steht geradkettiges oder verzweigtes Alkenyl mit vorzugsweise 2 bis 6, insbesondere 2 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Äthenyl, Propenyl-(1), Propenyl-(2) und Butenyl-(3) genannt.



   Als gegebenenfalls substituiertes Alkinyl R5 und R6 steht geradkettiges oder verzweigtes Alkinyl mit vorzugsweise 2 bis 6. insbesondere 2 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Äthinyl,   Propinyl-(1),    Propinyl-(2) und Butinyl-(3) genannt.



   Als gegebenenfalls substituiertes Alkoxy R2, R3, R4, R6 steht geradkettiges oder verzweigtes Alkoxy mit vorzugsweise 1 bis   6.    insbesondere 1 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Methoxy, Äthoxy, n- und i-Propoxy und n-, i- und t-Butoxy genannt.



   Als gegebenenfalls substituiertes Alkylthio R2, R3 steht geradkettiges oder verzweigtes Alkylthio mit vorzugsweise 1 bis 6, insbesondere 1 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituierte Methylthio, Äthylthio, nund i-Propylthio, n-, i- und t-Butylthio genannt.



   Als gegebenenfalls substituiertes Acyl R2 und R3 steht insbesondere Acyl mit 1 bis 6, vorzugsweise 2 bis 4 Kohlenstoffatomen. Beispielhaft seien genannt: Formyl, Acetyl, Propionyl, n-Butyryl, i-Butyryl.



   Als gegebenenfalls substituiertes Carbalkoxy R2, R3 steht geradkettiges oder verzweigtes Carbalkoxy mit vorzugsweise 2 bis 7, insbesondere 2 bis 5 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Carbomethoxy, Carbo äthoxy, Carbo-n- und -i-propyloxy und Carbo-n-, -i- und -t-butyloxy genannt.



   Halogenalkyl R2 und R3 enthält vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatome und vorzugsweise 1 bis 5, insbesondere 1 bis 3 gleiche oder verschiedene Halogenatome, wobei als Halogenatome vorzugsweise Fluor, Chlor und Brom, insbesondere Fluor und Chlor stehen. Beispielhaft seien Trifluormethyl, Chlor-di-fluormethyl, Brommethyl, 2,2,2-Trifluoräthyl und Pentafluoräthyl genannt.



   Als Halogen R2, R3 steht vorzugsweise Fluor, Chlor, Brom und Jod, insbesondere Fluor, Chlor und Brom.



   Als gegebenenfalls substituiertes Aryl R4 und R6 steht Aryl mit vorzugsweise 6 oder vorzugsweise 6 bis 10 Kohlenstoffatomen im Arylteil. Beispielhaft seien gegebenenfalls substituiertes Phenyl oder Naphthyl genannt.



   Als gegebenenfalls substituiertes Aralkyl R4 und R6 steht gegebenenfalls im Arylteil und/oder Alkylteil substituiertes Aralkyl mit vorzugsweise 6 oder 10, insbesondere 6 Kohlenstoffatomen im Arylteil und vorzugsweise 1 bis 4, insbesondere 1 oder 2 Kohlenstoffatomen im Alkylteil, wobei der Alkylteil geradkettig oder verzweigt sein kann. Beispielhaft seien gegebenenfalls substituiertes Benzyl und Phenyläthyl genannt.



   Als gegebenenfalls substituiertes Cycloalkyl R4, R6 steht vor allem mono- bi- und tricyclisches Cycloalkyl mit vorzugsweise 3 bis 10, insbesondere 3, 5 oder 6 Kohlenstoffatomen.



  Beispielhaft seien gegebenenfalls substituiertes Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, Bicyclo   [2,2,11-heptyl,      Bicyclo-[2,2,21-octyl    und Adamantyl genannt.



   Als gegebenenfalls substituiertes Alkenyloxy R6 steht geradkettiges oder verzweigtes Alkenyloxy mit vorzugsweise 2 bis 6, insbesondere 2 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Äthenyloxy, Propenyl   (1 )-oxy,    Propenyl-(2)-oxy und Butenyl-(3)-oxy genannt.



   Als gegebenenfalls substituiertes Alkinyloxy R6 steht geradkettiges oder verzweigtes Alkinyl mit vorzugsweise 2 bis 6, insbesondere 2 bis 4 Kohlenstoffatomen. Beispielhaft seien gegebenenfalls substituiertes Äthinyloxy,   Propinyl oxy,    Propinyl-(2)-oxy und Butinyl-(3)-oxy genannt.

 

   Als Substituenten für die Reste R2, R3, R4,   R5    und R6 kommen in Frage: Acyl mit vorzugsweise 2 bis 4 Kohlenstoffatomen, Carboalkoxy mit 2 bis 4 Kohlenstoffatomen, Alkoxyalkyl mit jeweils 1 bis 4 Kohlenstoffatomen im Alkoxy und im Alkylteil, Aralkyl mit vorzugsweise 1 bis 4 Kohlenstoffatomen im Alkylteil und vorzugsweise 6 Kohlenstoffatomen im Arylteil.



   Besonders bevorzugt sind Verbindungen der Formel (I), in denen
R2 und R3 für Wasserstoff, Methyl, Äthyl, n-Butyl, Methoxy, Äthoxy, Fluor, Chlor, Brom, Cyan, Methylmercapto, Trifluormethyl, Acetyl, Propionyl, Acetylamino, Carbomethoxyamino stehen,
R4 für Methyl, Äthyl, Propyl, n-Butyl, i-Butyl, n-Pentyl.



     n- Hexyl,    Cyclopentyl, Cyclohexyl, Phenyl, Benzyl. Methoxy  methyl, Methoxy, Äthoxy, Phenoxymethyl, Methylamino, Äthylamino, n-Butylamino,   n-Cyanpentylamino,      ss-Methoxy-    äthylamino steht,
R5 für Methyl, Äthyl, i-Propyl, sec.-Butyl, Propenyl-(2) Propinyl steht,
R6 für Methyl, Äthyl, Propyl, Isopropyl, n-Amyl, Isoamyl, n-Butyl, Cyclohexyl, Benzyl, Methoxymethyl, Phenoxymethyl, Allyl, Crotyl, Methallyl, Methoxy, Äthoxy-i-Propoxy, sec.-Butyloxy, Propenyl-(2)-oxy, Propinyl-(2)-oxy, 2-Me   thyl-propenyl-(2)-oxy    steht.



   Bevorzugte, im erfindungsgemässen Verfahren eingesetzter Ausgangsverbindungen der Formel   (II)    sind die folgenden: N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl
N''-propionyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-äthoxycarbonyl
N''-propionyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-iso-propoxycarbo nyl-N''-propionyl-guanidin,   N-(2-Acetamido-4-phenylthio-phenyl)-N'-sec.-butoxycarbo-    nyl-N''-propionyl-guanidin,   N-(2-Propionamido-4-phenylthio-phenyl)-N'-methoxycarbo-    nyl-N''-propionyl-guanidin,   N-(2-Butyramido-4-phenylthio-phenyl)-N'-methoxyCarbo-    nyl-N''-propionyl-guanidin, N-(2-Valeramido-4-phenylthio-phenyl)-N'-n nyl-N''-propionyl-guanidin, N-(2-Cyclopentancarbonamido-4-phenylthio thoxycarbonyl-N"-propionyl-guanidin, N-(2-Cyclohexancarbonamido-4-phenylthio-ph   

     methoxycarbonyl-N"    -propionyl-guanidin,   N-(2-Benzamido-4-phenylthio-phenyl)-N'-methoxycarbo-    nyl-N''-propionyl-guanidin,   N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxyCarbonyl-   
N"-acetyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarb
N''-butyryl-guanidin,   N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-   
N''-cyclohexancarbonyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-m
N"-benzoyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl    N"    -phenylacetyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl
N''-phenoxyacetyl-guanidin, N-[2-(2'-Methylureido)-4-phenylthio-phenyl]-N'-methoxy carbonyl-N''-propionyl-guanidin, N-[2-(2'-Äthylureido)-4-phenylthio-phenyl]-N'-methoxy carbonyl-N''-propionyl-guanidin,  <RTI  

    ID=4.13> N-[2-(2'-Butylureido)-4-phenylthio-phenyll-N'-methoxy-       carbonyl-N"    -propionyl-guanidin,   N-[2-(2'-sv-Cyanpentylureido)-4-phenylthio-phenyll-N'        methoxycarbonyl-N"    -propionyl-guanidin, N-[2-(2'-ss-Methoxymethylureido)-4-phenylthio-phenyl]
N'-methoxycarbonyl-N''-propionyl-guanidin, N-[2-(2'-Benzylureido)-4-phenylthio-phenyl]-N'-methoxy carbonyl-N''-propionyl-guanidin, N-[2-(2'-Phenylureido)-4-phenylthio-phenyl]-N'-methoxy    carbonyl-N"    -propionyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N',N carbonyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-äthoxy carbonyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N'   ,N"-bis-iso-prop-    oxycarbonyl-guanidin, N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-sec.-but 

   oxycarbonyl-guanidin, N-(2-Propionamido-4-phenylthio-phenyl)-N oxycarbonyl-guanidin, N-(2-Butyramido-4-phenylthio-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-iso-Butyramido-4-phenylthio-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Valeramido-4-phenylthio-phenyl)-N', oxycarbonyl-guanidin, N-(2-iso-Valeramido-4-phenylthio-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Capronamido-4-phenylthio-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-iso-Capronamido-4-phenylthio-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Cyclopentancarbonamido-4-phenylthio-phenyl)
N',N''-bis-methoxycarbonyl-guanidin,   N-(2-Cyclohexancarbonamido-4-phenylthio-phenyl)-   
N',N''-bis-methoxycarbonyl-guanidin, N-   (2-Phenylacetamido-4-phenylthio-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-4-phenylthio-phenyl)-N',N''-bis 

   methoxycarbonyl-guanidin,    N-(2-Benzamido-4-phenylthio-phenyl)-N',N"-bis-methoxy-    carbonyl-guanidin, N-[2-(2'-Methylureido)-4-phenylthio-phenyl]-N',N''-bis methoxycarbonyl-guanidin, N-[2-(2'-Äthylureido)-4-phenylthio-phenyl]-N',N''-bis methoxycarbonyl-guanidin, N-[2-(2'-Butylureido)-4-phenylthio-phenyl]-N',N''-bis methoxycarbonyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-4-phenylthi    bis-methoxycarbonyl-guanidin,   N-[2-(2'-ss-Methoxyäthylureido)-4-phenylthio-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-(2'-Benzylureido)-4-phenylthio-phenyl]-N',N''-bis methoxycarbonyl-guanidin, N-[2-(2'-Phenylureido)-4-phenylthio-phenyl]-N methoxycarbonyl-guanidin,    N-[2-Propionamido-4-(4-methyl-phenylthio)-phenyll-
N',N"-bis-methoxycarbonyl-guanidin,   

    N-[2-Propionamido-4-(3-methyl-phenylthio)-phenyl
N',N''-bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-    (4-chlor-phenylthio)   -phenyll      -N'      ,N" -    bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-chlor-phenylthio)-phenyl bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(2-chlor-phenylthio)-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-methoxy-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-methoxy-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-methylthio-phenylthio)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-methylthio-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-cyan-phenylthio)-phenyl]-N',N''  

   bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-acetyl-phenylthio)-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-cyan-phenylthio) bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-propionyl-phenylthio)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-acetylamino-phenylthio)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-methoxycarbonyl-ph nyl]-N',N''-bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(3,4-dimethyl-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3,4-dichlor-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl
N''-propionyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N'-äthoxycarbonyl    N"    -propionyl-guanidin,  <RTI  

    ID=5.2>  N-(2-Acetamido-5-phenylthio-phenyl)-N'-iso-propoxycarbo-    nyl-N''-propionyl-guanidin,    N-(2-Acetamido-5-phenylthio-phenyl)-N'-sec.-butoxycarbo-    nyl-N''-propionyl-guanidin, N-(2-Propionamido-5-phenylthio-phenyl)-N'-methoxy nyl-N''-propionyl-guanidin,    N-(2-Butyramido-5-phenylthio-phenyl)-N'-methoxycarbo-    nyl-N''-propionyl-guanidin,    N-(2-Valeramido-5-phenylthio-phenyl)-N'-methoxycarbo-    nyl-N''-propionyl-guanidin, N-(2-Cyclopentancarbonamido-5-phenylthio-phenyl methoxycarbonyl-N''-propionyl-guanidin, N-(2-Cyclohexancarbonamido-5-phenylthio-phenyl) methoxycarbonyl-N"-propionyl-guanidin, N-(2-Benzamido-5-phenylthio-phenyl)-N'-methoxycarbo nyl-N''-propionyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl
N"-acetyl-guanidin,  <RTI  

    ID=5.6>  N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-   
N''-butyryl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl
N''-cyclohexancarbonyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl
N''-benzoyl-guanidin, N-   (2-Acetamido-5    -phenylthio-phenyl)-N' -methoxycarbonyl
N''-phenylacetyl-guanidin,   N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-   
N''-phenoxyacetyl-guanidin, N- [2-(2'   -Methylureido) -5      -phenylthio-phenyll-N'    -methoxy carbonyl-N''-propionyl-guanidin, N-[2-(2'-Äthylureido)-5-phenylthio-phenyl]-N'-methoxy carbonyl-N''-propionyl-guanidin,   N-[2-(2'-Butylureido)-S-phenylthio-phenyll-N'-methoxy-    carbonyl-N''-propionyl-guanidin,  <RTI  

    ID=5.12> N-[2-(2'-#-Cyanpentylureido)-5-phenylthio-phenyl]-N'-    methoxycarbonyl-N''-propionyl-guanidin, N-[2-(2'-ss-Methoxymethylureido)-5-phenylthio-phenyl]
N'-methoxycarbonyl-N''-propionyl-guanidin, N-[2-(2'-Benzylureido)-5-phenylthio-phenyl]-N'-methoxy carbonyl-N''-propionyl-guanidin, N-   [2-(2'-Phenylureido)-5-phenylthio-phenyll-N'-methoxy-       carbonyl-N"    -propionyl-guanidin, N- (2-Acetamido-5-phenylthio-phenyl)-N'   ,N"    -bis-methoxy carbonyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-äthoxy carbonyl-guanidin,    N-(2-Acetamido-5-phenylthio-phenyl)-N',N"-bis-iso-prop-    oxycarbonyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-sec.-bu oxycarbonyl-guanidin, N-(2-Propionamido-5-phenylthio-phenyl)-N',N''-bis-met 

   oxycarbonyl-guanidin, N-(2-Butyramido-5-phenylthio-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-iso-Butyramido-5-phenylthio-phenyl) methoxycarbonyl-guanidin, N- (2-Valeramido-5-phenylthio-phenyl)-N'   ,N" -bis-meth-    oxycarbonyl-guanidin, N- (2-iso-Valeramido-5 -phenylthio-phenyl)   -N'      ,N" -bis-    methoxycarbonyl-guanidin, N-(2-Capronamido-5-phenylthio-phenyl)-N' oxycarbonyl-guanidin,   N-(2-    iso-Capronamido-5-phenylthio-phenyl)-N'   ,N"-bis-    methoxycarbonyl-guanidin, N-(2-Cyclopentancarbonamido-5-phenylthio-phenyl)
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Cyclohexancarbonamido-5-phenylthio-phenyl)-N',N'' bis-methoxycarbonyl-guanidin, N-(2-Phenylacetamido-5-phenylthio-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-5-phenylthio-pheny 

   methoxycarbonyl-guanidin, N-(2-Benzamido-5-phenylthio-phenyl-N',N''-bis-methoxy carbonyl-guanidin, N-[2-(2'-Methylureido)-5-phenylthio-phenyl]-N',N''-bis methoxycarbonyl-guanidin, N-[2-(2'-Äthylureido)-5-phenylthio-pheny methoxycarbonyl-guanidin, N-[2-(2'-Butylureido)-5-phenylthio-pheny methoxycarbonyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-5-phenylt    bis-methoxycarbonyl-guanidin,   N-[2-(2'-ss-Methoxyäthylureido)-5-phenylth@   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-(2'-Benzylureido)-5-phenylthio-phenyl methoxycarbonyl-guanidin, N- [2- (2'-Phenyluriedo)-5-phenylthio-phenyl]-N'   ,N"-bis-    methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methyl-phenylthio-phenyl]-N',N'' 

   bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methyl-phenylthio)-phen
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-chlor-phenylthio)-phenyl bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-chlor-phenylthio)-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-chlor-phenylthio)-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methoxy-phenylthi
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methoxy-phenylthi
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methylthio-phenylt
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methylthio-phenylt
N'   ,N"-bis-methoxycarbonyl-guanidin.   



  N-[2-Propionamido-5-(4-cyan-phenylthio) bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-acetyl-phenylthio    bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(3-cyan-phenylthio)-phenyl bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-propionyl-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-acetylamino-phenylthio)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methoxycarbonyl-phenylthio)-phe    nyll-N' ,N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(3,4-dimethyl-phenylthio)-phenyl
N',N"-bis-methoxycarbonyl-guanidin und N-[2-Propionamido-5-(3,4-dichlor-phenylt
N',N''-bis-methoxycarbonyl-guanidin.



   Nach dem erfindungsgemässen Verfahren können folgende bevorzugte Verbindungen hergestellt werden:   N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxyCarbo-    nyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl) nyl-N''-propionyl-guanidin,   N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-iso-propoxy carbonyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-sec.-butoxy carbonyl-N''-propionyl-guanidin, N-(2-Propionamido-4-phenylsulfinyl-phenyl)-N'-methoxy carbonyl-N''-propionyl-guanidin, N-(2-Butyramido-4-phenylsulfinyl-phenyl)-N'-methoxycar bonyl-N''-propionyl-guanidin,   N-(2-Valeramido-4-phenylsulfinyl-phenyl)-N'-methoxycar-    bonyl-N" -propionyl-guanidin, N-   (2-Cyclopentancarbonamido-4-phenylsulfinyl-phenyl)-N'     

   methoxycarbonyl-N''-propionyl-guanidin, N-(2-Cyclohexancarbonamido-4-phenylsulfin    methoxycarbonyl-N"    -propionyl-guanidin, N-(2-Benzamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-acetyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-butyryl-guanidin,   N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbo-    nyl-N''-cyclohexancarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxy nyl-N''-benzoyl-guanidin,   N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbo-    nyl-N''-phenylacetyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl) nyl-N''-phenoxyacetyl-guanidin, N-[2-(2'-Methylureido)-4-phenylsulfinyl-p    oxycarbonyl-N" -propionyl-guanidin,   

    N-[2-(2'-Äthylureido)-4-phenylsulfinyl-phenyl]-N'-meth    oxycarbonyl-N"    -propionyl-guanidin,   N-[2-(2'-Butylureido)-4-phenylsulfinyl-phenyll-N'-meth-       oxycarbonyl-N"    -propionyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-4-phenylsulfinyl-phenyl]-   
N'-methoxycarbonyl-N''-propionyl-guanidin,   N-[2-(2'-#-Methoxymethylureido)-4-phenylsulfinyl-phenyl]-   
N'-methoxycarbonyl-N''-propionyl-guanidin,   N-[2-(2'-Benzylureido)-4-phenylsulfinyl-phenyll-N'-meth- oxycarbonyl-N" -propionyl-guanidin,    N-[2-(2'-Phenylureido)-4-phenylsulfinyl    oxycarbonyl-N"    -propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl) oxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N',N''-bis-äth 

   oxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl) propoxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N',N''-bis-sec. butoxycarbonyl-guanidin, N-(2-Propionamido-4-phenylsulfinyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Butyramido-4-phenylsulfinyl-phenyl) methoxycarbonyl-guanidin,   N-(2-iso-Butyramido-4-phenylsulfinyl-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin, N-(2-Valeramido-4-phenylsulfinyl-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-iso-Valeramido-4-phenylsulfinyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Capronamido-4-phenylsulfinyl-phenyl methoxycarbonyl-guanidin,   N-(2-iso-Capronamido-4-phenylsulfinyl-phenyl)-N' ,N"-bis-    methoxycarbonyl-guanidin, N-(2-Cyclopentancarbonamido-4-phenylsulfi
N',N''-bis-methoxycarbonyl-guanidin,   N- 

   (2-Cyclohexancarbonamido-4-phenylsulfiny enyl)-   
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Phenylacetamido-4-phenylsulfinyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-4-phenylsulfinyl-phenyl)-N',N'' bis-methoxycarbonyl-guanidin, N-(2-Benzamido-4-phenylsulfinyl-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-[2-(2'-Methylureido)-4-phenylsulfinyl-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N- [2-   (2' -Äthylureido)    -4-phenylsulfinyl-phenyl].   -N'      ,N" -bis-    methoxycarbonyl-guanidin, N-[2-(2'-Butylureido)-4-phenylsulfinyl-phenyl]-N',N''-bis methoxycarbonyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-4-phenylsulfinyl-phen   
N',N''-bis-methoxycarbonyl-guanidin,   N-[2-(2'-ss-Methoxyäthylureido)-4-phenylsulfinyl-ph@   
N'  <RTI  

    ID=6.22> ,N"-bis-methoxycarbonyl-guanidin,    N-[2-(2'-Benzylureido)-4-phenylsulfinyl-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-(2'-Phenylureido)-4-phenylsulfinyl bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-(4-methyl-phenylsulfinyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-methyl-phenylsulfinyl)-phenyl
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(2-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-methoxy-phenylsulfinyl)-phen
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-methoxy-phenylsulfinyl)-phen
N',N''-bis-methoxycarbonyl-guanidin,  <RTI  

    ID=6.24> N-[2-Propionamido-4-(4-methylthio-phenylsulfinyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-(3-methylthio-phenylsulfinyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-(4-cyan-phenylsulfinyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-(4-acetyl-phenylsulfinyl)-phenyll-   
N'   ,N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-4-(3-cyan-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-propionyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-acetylamino-phenylsulfinyl)-phe nyl]-N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-methoxycarbonyl-phenylsulfinyl) phenyl]-N',N''-bis-methoxycarbonyl-guanidin,  <RTI  

    ID=6.29> N-[2-Propionamino-4-(3 ,4-dimethyl-phenylsulfinyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3,4-dichlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin,   N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo-    nyl-N''-propionyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-äthoxycarbo nyl-N''-propionyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-iso-propoxy carbonyl-N''-propionyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-sec.-butoxy carbonyl-N''-propionyl-guanidin,   N-(2-Propionamido-5-phenylsulfinyl-phenyl)-N'-methoxy-    carbonyl-N''-propionyl-guanidin,   N-(2-Butyramido-5-phenylsulfinyl-phenyl)-N'-methoxycar-       bonyl -N"    -propionyl-guanidin,  <RTI   

    ID=6.34> N-(2-Valeramido-5-phenylsulfinyl-phenyl)-N'-methoxycar-    bonyl-N''-propionyl-guanidin,     N-(2-Cyclopentanearbonamido-5-phenylsulfinyl-phenyl)-N'-    methoxycarbonyl-N''-propionyl-guanidin, N-(2-Cyclohexancarbonamido-5-phenylsulfinyl    methoxycarbonyl-N"    -propionyl-guanidin, N-(2-Benzamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-propionyl-guanidin,   N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxyCarbo- nyl-N"-acetyl-guanidin,    N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo    nyl-N"-butyryl-guanidin,    N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-cyclohexancarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo    nyl-N"-benzoyl-guanidin,    N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo 

   nyl-N''-phenylacetyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbo nyl-N''-phenoxyacetyl-guanidin,   N-[2-(2'-Methylureido)-S-phenylsulfinyl-phenyll-N'-meth-    oxycarbonyl-N"-propionyl-guanidin,   N-[2- (2'-Äthylureido)-5-phenylsulfinyl-phenyl -meth-       oxycarbonyl-N"    -propionyl-guanidin,   N-[2-(2'-Butylureido)-5-phenylsulfinyl-phenyll-N'-meth-       oxyearbonyl-N"    -propionyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-5-phenylsulfinyl-phenyl]-N'-       methoxycarbonyl-N"    -propionyl-guanidin, N-[2-(2'-ss-Methoxymethylureido)-5-phenylsulfinyl-phenyl]
N'   -methoxyearbonyl-N"    -propionyl-guanidin, N-[2-(2'-Benzylureido)-5-phenylsulfinyl-phenyl]-N'-meth 

   oxycarbonyl-N"-propionyl-guanidin, N-[2-(2'-Phenylureido)-5-phenylsulfinyl-phenyl]-N'-meth    oxycarbonyl-N"    -propionyl-guanidin,   N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N"-bis-meth-    oxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl) oxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N''-bis-iso propoxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N''-bis-sec.

   butoxycarbonyl-guanidin, N-(2-Propionamido-5-phenylsulfinyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Butyramido-5-phenylsulfinyl-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin,   N-(2-iso-Butyramido-5-phenylsulfinyl-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin,
N-(2-Valeramido-5-phenylsulfinyl-phenyl) oxycarbonyl-guanidin, N-(2-iso-Valeramido-5-phenylsulfinyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Capronamido-5-phenylsulfinyl-phenyl)-N methoxycarbonyl-guanidin,   N-(2-iso-Capronamido-5-phenylsulfinyl-phenyl)-N' ,N"-bis-    methoxycarbonyl-guanidin,   N-(2-Cyelopentanearbonamido-5-phenylsulfinyl-phenyl)-   
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Cyclohexancarbonamido-5-phenylsulfinyl-phenyl)
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Phenylacetamido-5-phenylsulfinyl-phenyl)-N',N''-1 

   methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-5-phenylsulfinyl-phenyl)-N',N'' bis-methoxycarbonyl-guanidin, N-(2-Benzamido-5-phenylsulfinyl-phenyl)-N',N''-bis-met oxycarbonyl-guanidin,   N-[2-(2'-Methylureido)-5-phenylsulfinyl-phenyll-N' ,N"-    bis-methoxycarbonyl-guanidin,
N-[2-(2'-Äthylureido)-5-phenylsulfinyl-phenyl]-N',N''-bis methoxycarbonyl-guanidin, N-[2-(2'-Butylureido)-5-phenylsulfinyl-phenyl]-N',N''-bis methoxycarbonyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-5-phenylsulfinyl-phenyl]-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-(2'-ss-Methoxyäthylureido)-5-phenylsulfinyl-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-(2'-Benzylureido)-5-phenylsulfinyl-phenyl]-N',N'' bis-methoxycarbonyl-guanidin, N-[2-(2'-Phenylureido)-5-phenylsulfinyl-phenyl]-N',N'' 

   bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-chlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methoxy-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methoxy-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methylthio-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methylthio-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-cyan-phenylsulfinyl)

  )-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-acetyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-cyan-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-propionyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-acetylamino-phenylsulfinyl)-phe nyl]-N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-methoxycarbonyl-phenylsulfinyl) phenyl]-N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3,4-dimethyl-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3,4-dichlor-phenylsulfinyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-äthoxycarbo 

   nyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-iso-propoxy carbonyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-sec.-butoxy carbonyl-N''-propionyl-guanidin, N-(2-Propionamido-4-phenylsulfonyl-phenyl)-N'-methoxy carbonyl-N''-propionyl-guanidin, N-(2-Butyramido-4-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N''-propionyl-guanidin, N-(2-Valeramido-4-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N''-propionyl-guanidin, N-(2-Cyclopentancarbonamido-4-phenylsulfonyl-phenyl)
N'-methoxycarbonyl-N''-propionyl-guanidin, N-(2-Cyclohexancarbonamido-4-phenylsulfonyl-phenyl)-N' methoxycarbonyl-N''-propionyl-guanidin, N-(2-Benzamido-4-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N''-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N''-acetyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycar 

   bonyl-N''-butyryl-guanidin,     N- (2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxyCar-    bonyl-N"-cyclohexancarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N' -methoxycar    bonyl-N"-benzoyl-guanidin,    N- (2-Acetamido-4-phenylsulfonyl-phenyl)-N' -methoxycar    bonyl-N"-phenylacetyl-guanidin,    N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N' -methoxycar    bonyl-N"-phenoxyacetyl-guanidin,    N-[2-(2'-Methylureido)-4-phenylsulfonyl-phenyl]-N'-meth oxycarbonyl-N"-propionyl-guanidin, N-[2-(2'-Äthylureido)-4-phenylsulfonyl-phenyl]-N'-meth    oxycarbonyl-N' -propionyl-guanidin,    N-[2-(2'-Butylureido)-4-phenylsulfonyl-phenyll-N'-meth oxycarbonyl-N''-propionyl-guanidin,   N-[2- (2'-w    

   -Cyanpentylureido)-4-phenylsulfonyl-phenyll
N'-methoxycarbonyl-N''-propionyl-guanidin, N-[2-(2'-ss-Methoxymethylureido)-4-phenylsulfonyl-phenyl]
N'-methoxycarbonyl-N"-propionyl-guanidin, N-[2-(2'-Benzylureido)-4-phenylsulfonyl-phenyl]-N'-meth oxycarbonyl-N"-propionyl-guanidin, N-[2-(2'-Phenylureido)-4-phenylsulfonyl-phenyll-N' -meth oxycarbonyl-N"-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N' ,N" -bis-äth oxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N',N" -bis-iso propoxycarbonyl-guanidin, N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis-sec.

   butoxycarbonyl-guanidin, N-(2-Propionamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis methoxycarbonyl-guanidin,   N-(2-Butyramido-4-phenylsulfonyl-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin, N-(2-iso-Butyramido-4-phenylsulfonyl-phenyl)-N' ,N"-bis methoxycarbonyl-guanidin, N-(2-Valeramido-4-phenylsulfonyl-phenyl)-N'   ,N"-bis-    methoxycarbonyl-guanidin, N-(2-iso-Valeramido-4-phenylsulfonyl-phenyl)-N' ,N"-bis methoxycarbonyl-guanidin,   N-(2-Capronamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis-    methoxycarbonyl-guanidin, N-(2-iso-Capronamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis methoxycarbonyl-guanidin,   N-(2-Cyclopentancarbonamido-4-phenylsulfonyl-phenyl)-   
N',N''-bis-methoxycarbonyl-guanidin,    N-(2-Cyclohexancarbonamido-4-phenylsulfonyl-phenyl)-   
N'  <RTI  

    ID=8.12> ,N"-bis-methoxycarbonyl-guanidin,    N-(2-Phenylacetamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-4-phenylsulfonyl-phenyl)-N' ,N" bis-methoxycarbonyl-guanidin, N-(2-Benzamido-4-phenylsulfonyl-phenyl)-N' ,N"-bis-meth oxycarbonyl-guanidin,   N-[2-(2'-Methylureido)-4-phenylsulfonyl-phenyll-N',N"-    bis-methoxycarbonyl-guanidin,   N-[2-(2'-Äthylureido)-4-phenylsulfonyl-phenyll-N'    ,N" bis-methoxycarbonyl-guanidin,   N-[2-(2'-Butylureido)-4-phenylsulfonyl-phenyll-N'    ,N" bis-methoxycarbonyl-guanidin,    N-[2-(2'-#-Cyanpentylureido)-4-phenylsulfonyl-phenyl]-   
N'   ,N"-bis-methoxycarbonyl-guanidin,    N-[2-(2'-ss-Methoxyäthylureido)-4-phenylsulfonyl-phenyll    N',N"-bis-methoxycarbonyl-guanidin,   

    N-[2-(2'-Benzylureido)-4-phenylsulfonyl-phenyl]-N',N' bis-methoxycarbonyl-guanidin,    N-[2-(2'-Phenylureido)-4-phenylsulfonyl-phenyll-N',N"-    bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-methyl-phenylsulfonyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-methyl-phenylsulfonyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-chlor-phenylsulfonyl)-phenyl]
N',N"-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3-chlor-phenylsulfonyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N- [2-Propionamido-4-(2-chlor-phenylsulfonyl)-phenyll
N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-4- (4-methoxy-phenylsulfonyl) phenyl]-   
N'   ,N"-bis-methoxycarbonyl-guanidin,    N- [2-Propionamido-4-(3  <RTI  

    ID=8.23> -methoxy-phenylsulfonyl)-phenyll-       N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-4-(4-methylthio-phenylsulfonyl)-phe    nyll-N',N' -bis-methoxycarbonyl-guanidin, N [2-Propionamido-4-(3 -methylthio-phenylsulfonyl)-phe-    nyl]-N' ,N" -bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-cyan-phenylsulfonyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin,   N-[2-Propionamido-4-(4-acetyl-phenylsulfonyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-   [2-Propionamido-4-(3-cyan-phenylsulfonyl)-phenyll-   
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(4-propionyl-phenylsulfonyl)-phenyll    N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-4-(4-acetylamino-phenylsulfonyl)-phe    nyl]-N' 

   ,N"-bis-methoxycarbonyl-guanidin,    N- [2-Propionamido-4-(4-methoxycarbonyl-phenylsulfonyl) phenyl]-N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3 ,4-dimethyl-phenylsulfonyl)-phe nyl]-N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-4-(3   ,4-dichlor-phenylsulfonyl)-phenyl]-   
N' ,N" bis-methoxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N"-propionyl-guanidin, N-   (2-Acetamido-5-phenylsulfonyl-phenyl)-N'-äthoxycarbo    nyl-N"-propionyl-guanidin, N-   (2-Acetamido-5-phenylsulfonyl-phenyl)-N'-iso-propoxy-       carbonyl-N"-propionyl-guanidin, N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-sec.-butoxy-    carbonyl-N"-propionyl-guanidin, N-(2-Propionamido-5-phenylsulfonyl-phenyl)-N'-methoxy    carbonyl-N"-propionyl-guanidin,   

    N-(2-Butyramido-5-phenylsulfonyl-phenyl)-N'-methoxycar    bonyl-N"-propionyl-guanidin,    N-(2-Valeramido-5-phenylsulfonyl-phenyl)-N'-methoxycar    bonyl-N"-propionyl-guanidin, N-(2-Cyclopentancarbonamido-5-phenylsulfonyl-phenyl)-
N'-methoxycarbonyl-N' -propionyl-guanidin,      N-(2-Cyclohexancarbonamido-5-phenylsulfonyl-phenyl)-N'     methoxycarbonyl-N' -propionyl-guanidin,    N-(2-Benzamido-5-phenylsulfonyl-phenyl)-N'-methoxycar bonyl-N"-propionyl-guanidin, N- (2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar-    bonyl-N"-acetyl-guanidin,   N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar-    bonyl-N" -butyryl-guanidin,   N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar-    bonyl-N"  

   -cyclohexancarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar    bonyl-N"-benzoyl-guanidin,    N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycar    bonyl-N"-phenylacetyl-guanidin,    N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N' -methoxycar    bonyl-N"-phenoxyacetyl-guanidin,    N-[2-(2'-Methylureido)-5-phenylsulfonyl-phenyll-N' -meth    oxycarbonyl-N"-propionyl-guanidin,        N-[2-(2'-Äthylureido)-5-phenylsulfonyl-phenyll-N'    -meth oxycarbonyl-N"-propionyl-guanidin,   N-[2-(2'-Butylureido)-5-phenylsulfonyl-phenyll-N'    -meth    oxycarbonyl-N"    -propionyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-5-phenylsulfonyl-phenyl]-   

   
N'-methoxycarbonyl-N''-propionyl-guanidin, N-[2-(2'-ss-Methoxymethylureido)-5-phenylsulfonyl-phe nyl]-N'-methoxycarbonyl-N''-propionyl-guanidin,   N-[2-(2'-Benzylureido)-S-phenylsulfonyl-phenyll-N'-meth-       oxycarbonyl-N"    -propionyl-guanidin, N-[2-(2'-Phenylureido)-5-phenylsulfonyl    oxyearbonyl-N"-propionyl-guanidin,    N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N',N''-bis-meth oxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N',N''-bis-äth oxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N',N''-bis-iso propoxycarbonyl-guanidin, N-(2-Acetamido-5-phenyslulfonyl-phenyl)-N',N''-bis-sec.



   butoxycarbonyl-guanidin,   N-(2-Propionamido-5-phenylsulfonyl-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin, N-(2-Butyramido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-iso-Butyramido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Valeramido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-iso-Valeramido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Capronamido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-iso-Capronamido-5-phenylsulfonyl-phenyl)-N',N''-bis methoxycarbonyl-guanidin, N-(2-Cyclopentancarbonamido-5-phenylsulfonyl
N'   ,N"-bis-methoxycarbonyl-guanidin,    N-(2-Cyclohexancarbonamido-5-phenylsulfonyl-phenyl)    N' ,N"    -bis-methoxycarbonyl-guanidin, N-(2-Phenylacetamido-5-phenylsulfonyl-phenyl)-N',N''-bis 

   methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-5-phenylsulfonyl-phenyl)-N',N'' bis-methoxycarbonyl-guanidin,   N-(2-Benzamido-5-phenylsulfonyl-phenyl)-N',N"-bis-meth-    oxycarbonyl-guanidin, N-[2-(2'-Methylureido)-5-phenylsulfonyl bis-methoxycarbonyl-guanidin, N-[2-(2'-Äthylureido)-5-phenylsulfonyl-phenyl bis-methoxycarbonyl-guanidin, N-[2-(2'-Butylureido)-5-phenylsulfonyl-phenyl]-N',N''-bis methoxycarbonyl-guanidin,   N-[2-(2'-#-Cyanpentylureido)-5-phenylsulfonyl-phenyl]
N' ,N"-bis-methoxycarbonyl-guanidin,    N-[2-(2'-ss-Methoxyäthylureido)-5-phenylsulfonyl-phenyl    N' ,N"    -bis-methoxycarbonyl-guanidin, N-[2-(2'-Benzylureido)-5-phenylsulfonyl-phenyl bis-methoxycarbonyl-guanidin, N-[2-(2'-Phenylureido)-5-phenylsulfonyl-phenyl]-N',N'' bis-methoxycarbonyl-guanidin,  <RTI  

    ID=9.14> N-[2-Propionamido-5-(4-methyl-phenylsulfonyl)-phenyll-   
N',N''-Bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-methyl-phenylsulfonyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-chlor-phenylsulfonyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3-chlor-phenylsulfonyl)-phenyl]    N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(3-chlor-phenylsulfo    N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(4-methoxy-phenylsulfonyl
N',N''-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(3-methoxy-phenylsulfonyl)-phenyll-   
N'   ,N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(4-methylthio-phenylsulfo nyl]-N',N''-bis-methoxycarbonyl-guanidin, N-  <RTI  

    ID=9.19> [2-Propionamido-5-(3-methylthio-phenylsulfonyl)-phe-    nyll-N'   ,N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(4-cyan-phenylsulfonyl)-phenyl]
N',N''-bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(4-acetyl-phenylsulfonyl)-phenyl
N',N''-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(3-cyan-phenylsulfonyl)-phenyll-
N',N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(4-propionyl-phenylsulfo
N'   ,N"-bis-methoxycarbonyl-guanidin,    N-[2-Propionamido-5-(4-acetylamino-phenylsulfonyl)-p    nyll-N' ,N"-bis-methoxycarbonyl-guanidin,      N-[2-Propionamido-    5-(4-methoxycarbonyl-phenylsulfonyl) phenyll-N'   ,N"    -bis-methoxycarbonyl-guanidin, N-[2-Propionamido-5-(3,4-dimethyl-phenylsulfonyl)-phe 

   nyl]-N',N''-bis-methoxycarbonyl-guanidin sowie   N-[2-Propionamido-5-(3,4-dichlor-phenylsulfonyl)-phenyll-
N' ,N" -bis-methoxycarbonyl-guanidin.   



   Die erfindungsgemäss hergestellten Verbindungen, ebenso wie auch die Ausgangsverbindungen der Formel   (II),    die ebenfalls neu sind, zeigen eine überraschend gute und breite Wirkung gegen folgende Nematoden und Cestoden:
1. Hakenwürmer (z. B. Uncinaria stenocephala, Ancylos toma caninum, Bunostomum trigonocephalum),
2. Trichostrongyliden (z. B. Nippostrongylus muris,   Hae-    monchus contortus, Trichostrongylus   colubriformis,      Os-    tertagia circumcincta),
3. Strongyliden (z. B. Oesophagostomum columbianum),
4. Rhabditiden (z. B. Strongyloides ratti),
5. Spulwürmer (z. B. Ascaris suum, Toxocara canis, Toxas    caris leonina),   
6.   Madenwünmer (z.    B. Aspiculuris tetraptera),
7. Heterakiden (z. B.

  Heterakis spumosa),    8.      Peitschenwürmer (z.    B. Trichuris muris),
9. Filarien (z. B. Litomosoides carinii, Dipetalonema witei),
10. Cestoden (z. B. Hymenolepis nana, Taenia pisiformis,
Echinococcus multilocularis).



   Die Wirkung wurde im Tierversuch nach oraler und parenteraler Applikation bei stark mit Parasiten befallenen Versuchstieren geprüft. Die angewendeten Dosierungen wurden sehr gut von den Versuchstieren vertragen.



   Die neuen Wirkstoffe können als Anthelmintika sowohl in der Human- als auch in der Veterinärmedizin   verwendet    werden.



   Die neuen Wirkstoffe können in bekannter Weise in die üblichen Formulierungen übergeführt werden.



   Die neuen Verbindungen können entweder als solche oder aber in Kombination mit pharmazeutisch annehmbaren Trägern zur Anwendung gelangen. Als Darreichungsformen in Kombination mit verschiedenen inerten Trägern kommen Tabletten, Kapseln, Granulate, wässrige Suspensionen, injizierbare Lösungen, Emulsionen und Suspensionen, Elixiere, Sirup, Pasten und dergleichen in Betracht. Derartige Träger umfassen feste Verdünnungsmittel oder Füllstoffe, ein steriles, wässriges Medium sowie verschiedene nichttoxische organische Lösungsmittel und dergleichen. Selbstverständlich   kön-    nen die für eine orale Verabreichung in Betracht kommenden Tabletten und dergleichen mit   Süssstoffzusatz    und ähnlichem versehen werden. 

  Die therapeutisch wirksame Verbindung soll im vorgenannten Fall in einer Konzentration von etwa 0,5 bis 90 Gew. % der Gesamtmischung vorhanden sein. d. h.  



  in Mengen, die ausreichend sind, um den oben genannten Dosierungsspielraum zu erreichen.



   Die Formulierungen können in bekannter Weise hergestellt werden, z. B. durch Verstrecken der Wirkstoffe mit Lösungsmitteln und/oder Trägerstoffen, gegebenenfalls unter Verwendung von Emulgiermitteln und/oder Dispergiermitteln, wobei z. B. im Fall der Benutzung von Wasser als Verdünnungsmittel gegebenenfalls organische Lösungsmittel als Hilfslösungsmittel verwendet werden können.



   Als Hilfsstoffe seien beispielhaft aufgeführt: Wasser, nichttoxische organische Lösungsmittel, wie Paraffine (z. B. Erdölfraktionen), pflanzliche Öle (z. B. Erdnuss-/Sesamöl), Alkohole (z. B. Äthylalkohol, Glycerin), Glykole (z. B. Propylenglykol, Polyäthylenglykol) und Wasser; feste Trägerstoffe, wie z. B. natürliche Gesteinsmehle (z. B. Kaoline, Tonerden, Talkum, Kreide), synthetische Gesteinsmehle (z. B. hochdisperse Kieselsäure, Silikate), Zucker (z. B. Roh-, Milchund Traubenzucker); Emulgiermittel, wie nichtionogene und anionische Emulgatoren (z. B. Polyoxyäthylen-Fettsäure Ester, Polyoxyäthylen-Fettalkohol-Äther, Alkylsulfonate und Arylsulfonate), Dispergiermittel (z. B. Lignin, Sulfitablaugen, Methylcellulose, Stärke und Polyvinylpyrrolidon) und Gleitmittel (z. B. Magnesiumstearat, Talkum, Stearinsäure und Natriumlaurylsulfat).



   Im Falle der oralen Anwendung können Tabletten selbstverständlich ausser den genannten Trägerstoffen auch Zusätze, wie Natriumcitrat, Calciumcarbonat und Dicalciumphosphat, zusammen mit verschiedenen Zuschlagstoffen, wie Stärke, vorzugsweise Kartoffelstärke, Gelatine und dergleichen, enthalten. Weiterhin können Gleitmittel, wie Magnesiumstearat, Natriumlaurylsulfat und Talkum, zum Tablettieren mitverwendet werden.



   Im Falle wässriger Suspensionen und/oder Elixieren, die für orale Anwendungen gedacht sind, können die Wirkstoffe ausser mit den oben genannten Hilfsstoffen mit verschiedenen Geschmacksaufbesserern oder Farbstoffen versetzt werden.



   Für den Fall der parenteralen Anwendung können Lösungen der Wirkstoffe unter Verwendung geeigneter flüssiger Trägermaterialien eingesetzt werden.



   Die Wirkstoffe können in Kapseln, Tabletten, Pastillen, Dragees, Ampullen usw. auch in Form von Dosierungseinheiten enthalten sein, wobei jede Dosierungseinheit so angepasst ist, dass sie eine einzelne Dosis des aktiven Bestandteils liefert.



   Die neuen Verbindungen können in den Formulierungen auch in Mischungen mit anderen bekannten Wirkstoffen vorliegen.



   Die neuen Wirkstoffe können in üblicher Weise angewendet werden. Die Applikation erfolgt vorzugsweise oral, eine parenterale, insbesondere subkutane, aber auch eine dermale Applikation sind jedoch ebenfalls möglich.



   Im allgemeinen hat es sich als vorteilhaft erwiesen, Mengen von etwa 0,1 bis etwa 50 mg der neuen Verbindungen je kg Körpergewicht pro Tag zur Erzielung wirksamer Ergebnisse zu verabreichen.



   Trotzdem kann es gegebenenfalls erforderlich sein, von den genannten Mengen abzuweichen, und zwar in Abhängigkeit vom Körpergewicht des Versuchstieres bzw. der Art des Applikationsweges, aber auch aufgrund der Tierart und deren individuellem Verhalten gegenüber dem Medikament bzw.



  der Art von dessen Formulierung und dem Zeitpunkt bzw.



  Intervall, zu welchem die Verabreichung erfolgt. So kann es in einigen Fällen ausreichend sein, mit weniger als der vorgenannten Mindestmenge auszukommen, während in anderen Fällen die genannte obere Grenze überschritten werden muss.



  Im Fall der Applikation grösserer Mengen kann es empfehlenswert sein, diese in mehrere Einzelgaben über den Tag zu verteilen. Für die Applikation in der Human- und Veterinärmedizin ist der gleiche Dosierungsspielraum vorgesehen.



  Sinngemäss gelten auch die weiteren obigen Ausführungen.



   Die anthelmintische Wirkung der erfindungsgemäss erhaltenen Wirkstoffe sei anhand der folgenden Anwendungsbeispiele näher erläutert. Die Verbindungen der Formel (II) sind ebenfalls neu und zeigen die gleiche Wirksamkeit wie die Verbindungen der Formel (1).



   Die Herstellung der Ausgangsprodukte der Formel (II) ist in den nachstehenden Präparaten sowie auch im Schweizer Patent Nr. 612 925 beschrieben.



   Beispiel A
Magen- und Darmwurm-Test/Schaf
Experimentell mit Haemonchus contortus oder Trichostrongylus colubriformis infizierte Schafe wurden nach Ablauf der Präpatenzzeit der Parasiten behandelt. Die Wirkstoffmenge wurde als reiner Wirkstoff in Gelatinekapseln oral appliziert.



   Der Wirkungsgrad wird dadurch bestimmt, dass man die mit dem Kot ausgeschiedenen Wurmeier vor und nach der Behandlung quantitativ auszählt.



   Ein völliges Sistieren der Eiausscheidung nach der Behandlung bedeutet, dass die Würmer abgetrieben wurden oder so geschädigt sind, dass sie keine Eier mehr produzieren können (Dosis effectiva).



   Geprüfte Wirkstoffe und wirksame Dosierungen (Dosis effectiva minima) sind aus der nachfolgenden Tabelle ersichtlich.



  Tabelle zu Beispiel A neuer Wirkstoff Dosis effectiva minima  (Red.  > 90%) in mg/kg
EMI10.1     
 Haemonchus cont. 1 Trichostrong. col. 1  
Tabelle (Fortsetzung) neuer Wirkstoff Dosis effectiva minima  (Red.  > 90%) in mg/kg
EMI11.1     
   Haemonchus cont. 0,5 Trichostrong. col. 1   
Haemonchus cont. 1 Verwandte Präparate zum Vergleich (bekannt aus DOS 2 117 293)
Dosis effectiva minima  (Red.  > 90%) in mg/kg
EMI11.2     
 Haemonchus cont.  > 100 Trichostrong. col. 50
Haemonchus cont. 50
Trichostrong. col. 10 Präparat 1
EMI11.3     

14.3 g   (0,05    Mol) 2-Amino-5-phenylthio-butyranilid (Fp. 1520C) werden in 100 ml Methanol mit 10 g (0,05 Mol) N.N'   -bis-Methoxycarbonyl-isothioharnstoff-S    -methyläther unter Zusatz von 1 g p-Toluolsulfonsäure 3 Stunden erhitzt.



  Man erhält nach Aufarbeitung analog Beispiel 3 13,8 g N-(2   -Butyramido-4-phenylthio-phenyl)-N'    ,N" -bis-methoxycarbonyl-guanidin vom Fp.   155     C.



   In entsprechender Arbeitsweise erhält man aus N.N'-di substituierten   Isothioharnstoff-S-methvläthern    und 2-Amino
5-phenylthio-aniliden folgende Verbindungen:     Ausgangsmaterial: Hergestellte Stoffe der Formel (II)   
EMI12.1     

EMI12.2     

 R <SEP> R' <SEP> F( C) <SEP> R <SEP> R' <SEP> R'' <SEP> R''' <SEP> Fp.

  <SEP> ( C)
<tb> H <SEP> COCH3 <SEP> 119 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOCH3 <SEP> 160
<tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COC2H5 <SEP> 131-132
<tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOC2H5 <SEP> 145-146
<tb> H <SEP> COC2H5 <SEP> 145 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 176
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COC2H5 <SEP> 130
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOC2H5
<tb> H <SEP> COC3H7 <SEP> 152 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOC2H5 <SEP> 128
<tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COC2H5 <SEP> 127
<tb> H <SEP> COC4H9 <SEP> 117 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COOCH3 <SEP> 137
<tb> H <SEP> COC4H9-iso <SEP> H <SEP> COC4H9-iso <SEP> COOCH3 <SEP> COOCH3 <SEP> 145
<tb> H <SEP> COOCH3 <SEP> H <SEP> COOCH3 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> 

   COOC2H5 <SEP> 93-94 <SEP> H <SEP> COOC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 159
<tb> H <SEP> COC5H11 <SEP> 105 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COOCH3 <SEP> 127
<tb> H <SEP> COC6H13 <SEP> H <SEP> COC6H13 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-CH=CH2
<tb> H <SEP> COC5H11 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COC2H5 <SEP> 122
<tb> H <SEP> COC4H9 <SEP> 117 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COC2H5 <SEP> 160
<tb> H <SEP> CO-C=CH2 <SEP> 120 <SEP> H <SEP> CO-C=CH2 <SEP> COOCH3 <SEP> COOCH3 <SEP> 161
<tb> CH3 <SEP> CH3
<tb> H <SEP> CO-CH(CH3)2 <SEP> H <SEP> CO-CH(CH3)2 <SEP> COOCH3 <SEP> COOCH3 <SEP> 161
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C=CH
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C(CH3)=CH2
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH2-CH=CH2 <SEP>  

   COOCH2-CH=CH2
<tb> H <SEP> CO-# <SEP> H <SEP> CO-# <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> CO-# <SEP> H <SEP> CO-# <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COCH2OCH3 <SEP> 95 <SEP> H <SEP> COCH2OCH3 <SEP> COOCH3 <SEP> COOCH3 <SEP> 129-130
<tb> H <SEP> CO-CH2-OC2H5 <SEP> H <SEP> CO-CH2-OC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 119
<tb> H <SEP> CO-CH2OC6H5 <SEP> 109-110 <SEP> H <SEP> COCH2OC6H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 144-146
<tb>      Tabelle (Fortsetzung) Ausgangsmaterial:

  Hergestellte Stoffe der Formel (II) R R' F( C) R R' R'' R''' Fp.( C) 4-CH3 COC3H7 136 4-CH3 COC3H7 COOCH3 COOCH3 171 3-CH3 COC3H7 3-CH3 COC3H7 COOCH3 COOCH3 2-CH3 COC3H7 2-CH3 COC2H7 COOCH3 COOCH3 4-Cl COC2H5 4-Cl COC2H5 COOCH3 COOCH3 3-Cl COC2H5 3-Cl COC2H5 COOCH3 COOCH3 2-Cl COC2H5 126 2-Cl COC2H5 COOCH3 COOCH3 144 4-NHCOCH3 COC2H5 4-NHCOCH3 COC2H5 COOCH3 COOCH3 4-Br COC3H7 130 4-Br COC3H7 COOCH3 COOCH3 176 3,4-Cl2 COC3H7 3,4-Cl2 COC3H7 COOCH3 COOCH3 4-C4H9 COC3H7 4-C4H9 COC3H7 COOCH3 COOCH3 4-C2H5 COC3H7 98 4-C2H5 COC3H7 COOCH3 COOCH3 167 2,5-(OCH3)2 COC3H7 146 2,5-(OCH3)2 COC3H7 COOCH3 COOCH3 142 4-CH3 COC3H7 122 4-CH3 COC3H7 COOCH3 COC2H5 110 4-Cl CO-C3H7 126 4-Cl CO-C3H7 COOCH3 COOCH3 176 4-Cl CO-C3H7 4-Cl CO-C3H7 COOCH3 COC2H5 155 2-Cl COC3H7 155 2-Cl COC3H7 COOCH3 COOCH3 154 2-Cl COCH2OCH3 166 2-Cl COCH2OCH3 COOCH3 COOCH3 138 4-Br COC2H5 154 4-Br COC2H5 COOCH3 COOCH3 158 3-CH3,

   4-Br COC3H7 143 3-CH3, 4-Br COC3H7 COOCH3 COOCH3 170 3-CH3, 4-Br COC2H5 3-CH3, 4-Br COC2H5 COOCH3 COOCH3 3-CH3, 4-Br COCH2OCH3 119-120 3-CH2, 4-Br COCH2OCH3 COOCH3 COOCH3 141 4-C2H5 COC2H5 97 4-C2H5 COC2H5 COOCH3 COOCH3 155 4-C2H5 COCH2OCH3 94 4-C2H5 COCH2OCH3 COOCH3 COOCH3 126 3-CF3 COC3H7 3-CF3 COC3H7 COOCH3 COOCH3 3-CF3 COCH2OCH3 64 3-CF3 COCH2OCH3 COOCH3 COOCH3 120 4-C4H9 COCH2OCH3 4-C4H9 COCH2OCH3 COOCH3 COOCH3 3-OCH3 COCH2OCH3 3-OCH3 COCH2OCH3 COOCH3 COOCH3 4-OCH3 COCH2OCH3 63 4-OCH3 COCH2OCH3 COOCH3 COOCH3 131 2-OC2H5 COC3H7 2-OC2H5 COC3H7 COOCH3 COOCH3 128 2-OC2H5 COCH2OCH3 133 2-OC2H5 COCH2OCH3 COOCH3 COOCH3 110 2-COOCH3 COC3H7 2-COOCH3 COC3H7 COOCH3 COOCH3 2-COOCH3 COC2H5 2-COOCH3 COC2H5 COOCH3 COOCH3 2-COOCH3 COCH2OCH3 2-COOCH3 COCH2OCH3 COOCH3 COOCH3 H COCH2OCH3 95 H COCH2OCH3 COOCH3 COOC2H5 125-127 H COCH2OC6H5 109-110 H COCH2OC6H5 COOCH3 COC2H5 138-140 H COCH2-O-C2H5 86 H 

   COCH2-O-C2H5 COOCH3 CO-C2H5 111 2,4-(CH3)2 COC3H7 2,4-(CH3)2 COC3H7 COOCH3 COOCH3 3-OC2H5 COC3H7 3-OC2H5 COC3H7 COOCH3 COOCH3 4-OCH3 COC3H7 103 4-OCH3 COC3H7 COOCH3 COOCH3 185 3-OCH3 COC3H7 88 3-OCH3 COC3H7 COOCH3 COOCH3 160 4-SCH3 COC3H7 4-SCH3 COC3H7 COOCH3 COOCH3 2-OC2H5 COC2H5 2-OC2H5 COC2H5 COOCH3 COOCH3        Tabelle (Fortsetzung) Ausgangsmaterial:

  Hergestellte Stoffe der Formel (II) R R' F ( C) R R' R'' R''' Fp. ( C) 3-CH3, 4-Br COC2H5 3-CH3, 4-Br COC2H5 COOOCH3 COOCH3 3-CF3 COC2H5 3-CF3 COC2H5 COOCH3 COOCH3 4-F COCH2OCH3 89 4-F COCH2OCH3 COOCH3 COOCH3 127 4-CH3CO COC2H5 4-CH3CO COC2H5 COOCH3 COOCH3 3-CH3CO COC2H5 3-CH3CO COC2H5 COOCH3 COOCH3 4-C3H7CO COC2H5 4-C3H7CO COC2H5 COOCH3 COOCH3 4-NHCOOCH3 COC2H5 4-NHCOOCH3 COC2H5 COOCH3 COOCH3 4-CN COC2H5 4-CN COC2H5 COOCH3 COOCH3 3-CN COC2H5 3-CN COC2H5 COOCH3 COOCH3 4-F CO-C3H7 121 4-F CO-C3H7 COOCH3 COOCH3 155 4-F CO-C3H7 4-F CO-C3H7 COOCH3 COC2H5 136-137 4-Br CO-CH2-O-CH3 143 4-Br CO-CH2-O-CH3 COOCH3 COOCH3 114 3-Cl CO-C3H7 142 3-Cl CO-C3H7 COOCH3 COOCH3 129 3-Cl CO-CH2-O-CH3 113 3-Cl CO-CH2-O-CH3 COOCH3 COOCH3 124 4-C(CH3)3 CO-C3H7 4-C(CH3)3 CO-C3H7 COOCH3 COOCH3 169      Präparat 2
EMI15.1     

Aus 14,3 g (0,05 Mol)   2-Amino-4-phenylthio-butyranilid    

   und 10,3 g (0,05 Mol) N,N'-bis-Methoxycarbonyl-isothioharnstoff-S-methyläther erhält man 14,5 g N-(2-Butyramido   5-phenylthio-phenyl)-N',N"-bis-methoxycarbonyl-guanidin vomFp. 164 bis 166 C.   



   In entsprechender Arbeitsweise erhält man aus N,N'-disubstituierten   Isothioharnstoff-S-methyläthern    und 2-Amino4-phenylthio-aniliden folgende Verbindungen:     Ausgangsmaterial; Hergestellte Stoffe der Formel (II)   
EMI16.1     

EMI16.2     

 R <SEP> R' <SEP> F <SEP> ( C) <SEP> R <SEP> R' <SEP> R'' <SEP> R''' <SEP> Fp.

  <SEP> ( C)
<tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COC2H5
<tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOC2H5
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COC2H5
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2H5
<tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COOC2H5
<tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COC2H5
<tb> H <SEP> COC4H9 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COC4H9-iso <SEP> H <SEP> COC4H9-iso <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COOCH3 <SEP> H <SEP> COOCH3 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COOC2H5 <SEP> H <SEP> COOC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COC5H11 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COOCH3
<tb> H 

   <SEP> COC6H13 <SEP> H <SEP> COC6H13 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-CH=CH2
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C#CH
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH-C(CH3)=CH2
<tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH2-CH=CH2 <SEP> COOCH2-CH=CH2
<tb> H <SEP> CO-# <SEP> H <SEP> CO-# <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> CO-# <SEP> H <SEP> CO-# <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> COCH2OCH3 <SEP> H <SEP> COCH2OCH3 <SEP> COOCH3 <SEP> COOCH3
<tb> H <SEP> CO-CH2OC6H5 <SEP> H <SEP> COCH2OC6H5 <SEP> COOCH3 <SEP> COOCH3
<tb> 4-CH3 <SEP> COC3H7 <SEP> 4-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb> 3-CH3 <SEP> COC3H7 <SEP> 3-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb> 2-CH3 <SEP> COC3H7 <SEP> 2-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb> 4-Cl <SEP> COC2H5 <SEP> 

   4-Cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> 3-Cl <SEP> COC2H5 <SEP> 3-Cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> 2-Cl <SEP> COC2H5 <SEP> 2-Cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> 4-NHCOCH3 <SEP> COC2H5 <SEP> 4-NHCOCH3 <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
<tb> 4-Br <SEP> COC3H5 <SEP> 4-Br <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb> 3,4-Cl2 <SEP> COC3H7 <SEP> 3,4-Cl2 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb> 4-C4H9 <SEP> COC3H7 <SEP> 4-C4H9 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
<tb>      Tabelle (Fortsetzung) Ausgangsmaterial: 

  Hergestellte Stoffe der Formel (II) R R' F ( C) R R' R'' R''' Fp. ( C) 4-C2H5 COC3H7 4-C2H5 COC3H7 COOCH3 COOCH3 3,5-(CH3)2 COC3H7 3,5-(CH3)2 COC3H7 COOCH3 COOCH3 2,4-(CH3)2 COC3H7 2,4-(CH3)2 COC3H7 COOCH3 COOCH3 3-OC2H5 COC3H7 3-OC2H5 COC3H7 COOCH3 COOCH3 4-OCH3 COC3H7 4-OCH3 COC3H7 COOCH3 COOCH3 3-OCH3 COC3H7 3-OCH3 COC3H7 COOCH3 COOCH3 4-SCH3 COC3H7 4-SCH3 COC3H7 COOCH3 COOCH3 2-OC2H5 COC2H5 2-OC2H5 COC2H5 COOCH3 COOCH3 3-CH3, 4-Br COC2H5 3-CH3,

   4-Br COC2H5 COOCH3 COOCH3 3-CF3 COC2H5 3-CF3 COC2H5 COOCH3 COOCH3 4-F COC2H5 4-F COC2H5 COOCH3 COOCH3 4-CH3CO COC2H5 4-CH3CO COC2H5 COOCH3 COOCH3 3-CH3CO COC2H5 3-CH3CO COC2H5 COOCH3 COOCH3 4-C3H7CO COC2H5 4-C3H7CO COC2H5 COOCH3 COOCH3 4-NHCOOCH3 COC2H5 4-NHCOOCH3 COC2H5 COOCH3 COOCH3 4-CN COC2H5 4-CN COC2H5 COOCH3 COOCH3 3-CN COC2H5 3-CN COC2H5 COOCH3 COOCH3      Beispiel 1
EMI18.1     

Zu einer Lösung von 8,9 g   N- (2-Butyramido-4-phenyl-      thio-phenyl)-N',N"-bis-methoxycarbonyl-guanidin    [Fp.



     155       C,j    in   1,4 1    Essigsäureanhydrid tropft man 2,3 ml   H202    (30%ig). Nach 10 Stunden engt man den Ansatz im Vakuum ein, versetzt den Rückstand mit einem Gemisch von Essigester und Petroläther und filtriert ab.



   Man erhält 8,5 g   N-(2-Butyramido-4-phenylsulfinyl-phe-    nyl)-N,N'-bis-methoxycarbonyl-guanidin vom Fp. 186  C (Zers.), (umgelöst aus Methanol/Essigester). Das Massenspektrum zeigt ein Mol-Peak von 460.



   In entsprechender Arbeitsweise erhält man aus 31,2 g N-(2-Methoxyacetamido-4-phenylthio-phenyl)-N',N''-bis methoxycarbonyl-guanidin und 8,5 ml   H202    (30%ig) 30 g N-(2-Methoxyacetamido-4-phenylsulfinyl-phenyl)-N',N' bis-methoxycarbonyl-guanidin von Fp. 134  C.

 

  Beispiel 2
EMI18.2     

Nach der im Beispiel 1 beschriebenen Methode erhält man aus 13,3 g N-(2-Butyramido-4-phenylthio-phenyl) N',N"-bis-methoxycarbonyl-guanidin und 20 ml H202 (30%ig) 12,7 g N-(2-Butyramido-4-phenylsulfonyl-phenyl) N',N''-bis-methoxycarbonyl-guanidin vom Fp. 180  C. Das Massenspektrum zeigt einen Mol-Peak von 476.



   In entsprechender Arbeitsweise erhält man aus 8,9 g   N-(2--Methoxyacetamido-4-phenylthio-phenyl)-N',N"-bis-    methoxycarbonyl-guanidin und 14 g   H202    (30%ig) 8,0 g N-(2-Methoxyacetamido-4-phenylsulfonyl-phenyl)-N',N''bis-methoxycarbonyl-guanidin vom Fp. 142  C. 



  
 

** WARNING ** beginning of DESC field could overlap end of CLMS **.

 



   PATENT CLAIMS
1. Process for the preparation of new substituted phenylguanidines of the formula
EMI1.1
 in which
R and R1 are different from each other and mutually for one of the residues
EMI1.2
 stand in which
R4 for hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted amino, optionally substituted alkoxy, optionally substituted aralkyl and
R5 for optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl and
R6 for hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted aryl,

   optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, and in which R2 and R3 can be identical or different and represent hydrogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amino, halogen, cyano, optionally substituted alkylthio, optionally substituted acyl , optionally substituted carbalkoxy, and in which X represents the sulfinyl group or the sulfonyl group and can be linked to position 4 or 5 of the substituted aminophenyl group, characterized in that compounds of the formula
EMI1.3
 in which R, Rl, R2 and R3 have the meaning given above, oxidized with the appropriate amount of an oxidizing agent.



   2. The method according to claim 1, characterized in that R2 and R3 are substituted alkyl, preferably haloalkyl.



   The present invention relates to a process for the preparation of new substituted phenylguanidines which can be used as medicaments, in particular as anthelmintics.



   It has already become known that phenylguanidines have the general formula
EMI1.4
 in the
R lower alkyl and
R 'can mean both lower alkyl and hydrogen, have anthelmintic effects (see German Offenlegungsschrift 2 117 293).



   However, they show the disadvantage that their anthelmintic effect is much weaker than that of the substituted phenylguanidines according to the invention.



   It has been found that the new substituted phenylguanidines of the formula which can be prepared according to the invention
EMI1.5
 in which
R and R 'are different from each other and mutually for each of the residues
EMI1.6
 stand in which
R4 for hydrogen optionally substituted alkyl optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted amino, optionally substituted alkoxy and optionally substituted aralkyl, R5 for optionally substituted alkyl, optionally substituted alkenyl and optionally substituted alkynyl,



   R6 represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted aryl, optionally substituted aralkyl, optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, and in which
R2 and R3 may be the same or different and for hydrogen, optionally substituted alkyl, preferably haloalkyl, optionally substituted alkoxy, optionally substituted amino, halogen, cyano, optionally substituted alkylthio, optionally substituted acyl,

   optionally substituted carbalkoxy and where
X represents the sulfinyl group or the sulfonyl group and can be linked to position 4 or 5 of the substituted aminophenyl group, have very good anthelmintic effects.



   The compounds of the formula (I) which can be prepared according to the invention can be present in tautomeric forms, as will be shown in the following example:
EMI2.1

For reasons of uniformity, the respective structural formulas are formulated in the same way in all cases.



   The process according to the invention for the preparation of the abovementioned compounds of the formula (I) in which X denotes a sulfinyl or a sulfonyl radical is characterized in that compounds of the formula
EMI2.2
 in which R, Rl, R2 and R3 have the meaning given above, oxidized with the appropriate amount of an oxidizing agent.



   So z. B. by oxidation of the compounds of formula (I) in which X represents a sulfur atom, with one equivalent of H202 phenylsulfinylphenylguanidine and with two equivalents of H202 phenylsulfonylguanidine. The following example illustrates this preferred embodiment:
EMI2.3
  
EMI3.1

Instead of H202, other oxidizing agents can also be used, for example:
Organic peracids, such as peracetic acid, performic acid.



  Perbenzoic acid, m-chloroperbenzoic acid, monoperphthalic acid, inorganic peroxides, such as hydrogen peroxide, dissolved in water or dilute organic acids, inorganic oxidizing agents, such as chromic acid, nitric acid, potassium permanganate, chlorine, bromine, halogen oxygen acids, such as hypochlorous, chlorine, chlorine or superchloric acid tert. Butyl hypochlorite, methyl hypochlorite, tert-butyl chromate, organic N-halogen compounds, such as N-chlorosuccinimide, N-bromosuccinimide and N-halosulfonamides or N-halocarboxamides.



   The oxidation potential can be set accordingly by appropriate selection of the reaction conditions known from the literature and the reaction for the production of the sulfoxides or sulfones can be controlled.



     Surprisingly, the substituted phenylguanidines obtained according to the invention have a considerably higher anthelmintic effect than the phenylguanidines mentioned in German Offenlegungsschrift No. 2,117,293, which are the chemically closest active substances of the same type of action. The active ingredients obtainable according to the invention thus represent a valuable addition to the pharmaceutical industry.



   In formulas (I) and (II), the optionally substituted alkyl R2, R3, R4, R5 and R6 is straight-chain or branched alkyl having preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples of optionally substituted methyl, ethyl, n- and i-propyl, n-, i- and t-butyl may be mentioned.



   As optionally substituted alkenyl R5 and R6 there is straight-chain or branched alkenyl with preferably 2 to 6, in particular 2 to 4, carbon atoms. Examples include optionally substituted ethenyl, propenyl (1), propenyl (2) and butenyl (3).



   As optionally substituted alkynyl R5 and R6 there is straight-chain or branched alkynyl having preferably 2 to 6, in particular 2 to 4, carbon atoms. Substituted ethynyl, propynyl (1), propynyl (2) and butynyl (3) may be mentioned as examples.



   As optionally substituted alkoxy R2, R3, R4, R6 there is straight-chain or branched alkoxy with preferably 1 to 6. in particular 1 to 4 carbon atoms. Examples include optionally substituted methoxy, ethoxy, n- and i-propoxy and n-, i- and t-butoxy.



   The optionally substituted alkylthio R2, R3 is straight-chain or branched alkylthio having preferably 1 to 6, in particular 1 to 4, carbon atoms. Examples which may be substituted are methylthio, ethylthio, n and i-propylthio, n-, i- and t-butylthio.



   Acyl R2 and R3 which are optionally substituted are, in particular, acyl having 1 to 6, preferably 2 to 4, carbon atoms. Examples include: formyl, acetyl, propionyl, n-butyryl, i-butyryl.



   The optionally substituted carbalkoxy R2, R3 is straight-chain or branched carbalkoxy having preferably 2 to 7, in particular 2 to 5, carbon atoms. Examples include optionally substituted carbomethoxy, carbo-ethoxy, carbo-n- and -i-propyloxy and carbo-n-, -i and -t-butyloxy.



   Haloalkyl R2 and R3 preferably contain 1 to 4, in particular 1 or 2 carbon atoms and preferably 1 to 5, in particular 1 to 3 identical or different halogen atoms, the halogen atoms being preferably fluorine, chlorine and bromine, in particular fluorine and chlorine. Examples include trifluoromethyl, chlorodifluoromethyl, bromomethyl, 2,2,2-trifluoroethyl and pentafluoroethyl.



   Halogen R2, R3 is preferably fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.



   Aryl R4 and R6 which are optionally substituted are aryl having preferably 6 or preferably 6 to 10 carbon atoms in the aryl part. Substituted phenyl or naphthyl may be mentioned as examples.



   Aralkyl R4 and R6 which is optionally substituted is optionally substituted aralkyl in the aryl part and / or alkyl part, preferably having 6 or 10, in particular 6, carbon atoms in the aryl part and preferably 1 to 4, in particular 1 or 2, carbon atoms in the alkyl part, where the alkyl part can be straight-chain or branched . Substituted benzyl and phenylethyl may be mentioned as examples.



   The optionally substituted cycloalkyl R4, R6 is especially mono- and tricyclic cycloalkyl, preferably having 3 to 10, in particular 3, 5 or 6, carbon atoms.



  Examples of optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, bicyclo [2,2,11-heptyl, bicyclo- [2,2,21-octyl and adamantyl.



   As optionally substituted alkenyloxy R6 there is straight-chain or branched alkenyloxy with preferably 2 to 6, in particular 2 to 4, carbon atoms. Examples include substituted ethenyloxy, propenyl (1) -oxy, propenyl- (2) -oxy and butenyl- (3) -oxy.



   Optionally substituted alkynyloxy R6 is straight-chain or branched alkynyl having preferably 2 to 6, in particular 2 to 4, carbon atoms. Examples of optionally substituted ethynyloxy, propynyloxy, propynyl- (2) -oxy and butynyl- (3) -oxy are mentioned.

 

   Possible substituents for the radicals R2, R3, R4, R5 and R6 are: acyl with preferably 2 to 4 carbon atoms, carboalkoxy with 2 to 4 carbon atoms, alkoxyalkyl each with 1 to 4 carbon atoms in the alkoxy and in the alkyl part, aralkyl with preferably 1 up to 4 carbon atoms in the alkyl part and preferably 6 carbon atoms in the aryl part.



   Compounds of the formula (I) in which
R2 and R3 represent hydrogen, methyl, ethyl, n-butyl, methoxy, ethoxy, fluorine, chlorine, bromine, cyano, methylmercapto, trifluoromethyl, acetyl, propionyl, acetylamino, carbomethoxyamino,
R4 for methyl, ethyl, propyl, n-butyl, i-butyl, n-pentyl.



     n-hexyl, cyclopentyl, cyclohexyl, phenyl, benzyl. Methoxy methyl, methoxy, ethoxy, phenoxymethyl, methylamino, ethylamino, n-butylamino, n-cyanpentylamino, ss-methoxy-ethylamino,
R5 represents methyl, ethyl, i-propyl, sec-butyl, propenyl- (2) propynyl,
R6 for methyl, ethyl, propyl, isopropyl, n-amyl, isoamyl, n-butyl, cyclohexyl, benzyl, methoxymethyl, phenoxymethyl, allyl, crotyl, methallyl, methoxy, ethoxy-i-propoxy, sec.-butyloxy, propenyl- ( 2) -oxy, propynyl- (2) -oxy, 2-methyl-propenyl- (2) -oxy.



   Preferred starting compounds of the formula (II) used in the process according to the invention are the following: N- (2-acetamido-4-phenylthio-phenyl) -N'-methoxycarbonyl
N '' - propionyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-ethoxycarbonyl
N '' - propionyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-iso-propoxycarbonyl-N '' - propionyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl ) -N'-sec.-butoxycarbonyl-N "propionyl guanidine, N- (2-propionamido-4-phenylthio-phenyl) -N'-methoxycarbonyl-N" propionyl guanidine, N - (2-butyramido-4-phenylthio-phenyl) -N'-methoxycarbonyl-N '' - propionyl-guanidine, N- (2-valeramido-4-phenylthio-phenyl) -N'-n nyl-N ' '-propionyl-guanidine, N- (2-cyclopentanecarbonamido-4-phenylthio thoxycarbonyl-N "-propionyl-guanidine, N- (2-cyclohexanecarbonamido-4-phenylthio-ph

     methoxycarbonyl-N "-propionyl-guanidine, N- (2-benzamido-4-phenylthio-phenyl) -N'-methoxycarbonyl-N" -propionyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl ) -N'-methoxycarbonyl-
N "-acetyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-methoxycarb
N '' - butyryl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-methoxycarbonyl-
N '' - cyclohexane carbonyl guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-m
N "-benzoyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-methoxycarbonyl N" -phenylacetyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N'-methoxycarbonyl
N '' - phenoxyacetyl-guanidine, N- [2- (2'-methylureido) -4-phenylthio-phenyl] -N'-methoxy carbonyl-N '' - propionyl-guanidine, N- [2- (2'- Ethylureido) -4-phenylthio-phenyl] -N'-methoxy carbonyl-N '' - propionyl-guanidine, <RTI

    ID = 4.13> N- [2- (2'-butylureido) -4-phenylthio-phenyll-N'-methoxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-sv-cyanopentylureido) - 4-phenylthio-phenyll-N 'methoxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-ss-methoxymethylureido) -4-phenylthio-phenyl]
N'-methoxycarbonyl-N "propionyl guanidine, N- [2- (2'-benzylureido) -4-phenylthio-phenyl] -N'-methoxy carbonyl-N" propionyl guanidine, N- [2 - (2'-Phenylureido) -4-phenylthio-phenyl] -N'-methoxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N ', N carbonyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N ', N' '- bis-ethoxy carbonyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N', N "-bis- iso-prop-oxycarbonyl-guanidine, N- (2-acetamido-4-phenylthio-phenyl) -N ', N' '- bis-sec.-but

   oxycarbonyl-guanidine, N- (2-propionamido-4-phenylthio-phenyl) -N oxycarbonyl-guanidine, N- (2-butyramido-4-phenylthio-phenyl) -N ', N' '- bis-meth oxycarbonyl-guanidine , N- (2-iso-butyramido-4-phenylthio-phenyl) -N ', N' '- to methoxycarbonyl-guanidine, N- (2-valeramido-4-phenylthio-phenyl) -N', oxycarbonyl-guanidine, N- (2-iso-valeramido-4-phenylthio-phenyl) -N ', N' '- to methoxycarbonyl-guanidine, N- (2-capronamido-4-phenylthio-phenyl) -N', N '' - bis -meth oxycarbonyl-guanidine, N- (2-iso-capronamido-4-phenylthio-phenyl) -N ', N' '- bis methoxycarbonyl-guanidine, N- (2-cyclopentane carbonamido-4-phenylthio-phenyl)
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-cyclohexanecarbonamido-4-phenylthio-phenyl) -
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-4-phenylthio-phenyl) -N', N "-bis-methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-4-phenylthio- phenyl) -N ', N' '- bis

   methoxycarbonyl-guanidine, N- (2-benzamido-4-phenylthio-phenyl) -N ', N "-bis-methoxy-carbonyl-guanidine, N- [2- (2'-methylureido) -4-phenylthio-phenyl] -N ', N' '- bis methoxycarbonyl-guanidine, N- [2- (2'-ethylureido) -4-phenylthio-phenyl] -N', N '' - bis methoxycarbonyl-guanidine, N- [2- ( 2'-butylureido) -4-phenylthio-phenyl] -N ', N' '- to methoxycarbonyl-guanidine, N- [2- (2' - # - cyanopentylureido) -4-phenylthi bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -4-phenylthio-phenyll-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2- (2'-benzylureido) -4-phenylthio-phenyl] -N', N '' - bis-methoxycarbonyl-guanidine, N- [2- ( 2'-phenylureido) -4-phenylthio-phenyl] -N methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methyl-phenylthio) phenyl-
N ', N "-bis-methoxycarbonyl-guanidine,

    N- [2-Propionamido-4- (3-methylphenylthio) phenyl
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-chlorophenylthio) phenyl -N', N "- bis-methoxycarbonyl-guanidine, N- [2-propionamido -4- (3-chlorophenylthio) phenyl bis-methoxycarbonyl guanidine, N- [2-propionamido-4- (2-chlorophenylthio) phenyl] -N ', N' 'bis-methoxycarbonyl guanidine, N- [2-propionamido-4- (4-methoxyphenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methoxy-phenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methylthio-phenylthio) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methylthio-phenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-cyanophenylthio) phenyl] -N', N ''

   bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-acetyl-phenylthio) phenyl] -N ', N' 'bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3- cyanophenylthio) bis-methoxycarbonylguanidine, N- [2-propionamido-4- (4-propionylphenylthio) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-acetylamino-phenylthio) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methoxycarbonyl-ph nyl] -N', N '' - bis-methoxycarbonyl-guanidine, N- [2-propionamido -4- (3,4-dimethylphenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3,4-dichlorophenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl
N "propionyl guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-ethoxycarbonyl N" -propionyl guanidine, <RTI

    ID = 5.2> N- (2-acetamido-5-phenylthio-phenyl) -N'-iso-propoxycarbonyl-N '' - propionyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N '-sec.-butoxycarbonyl-N' '- propionyl-guanidine, N- (2-propionamido-5-phenylthio-phenyl) -N'-methoxy-nyl-N' '- propionyl-guanidine, N- (2- Butyramido-5-phenylthio-phenyl) -N'-methoxycarbonyl-N "propionyl guanidine, N- (2-valeramido-5-phenylthio-phenyl) -N'-methoxycarbonyl-N" propionyl -guanidine, N- (2-cyclopentanecarbonamido-5-phenylthio-phenyl methoxycarbonyl-N '' - propionyl-guanidine, N- (2-cyclohexanecarbonamido-5-phenylthio-phenyl) methoxycarbonyl-N "-propionyl-guanidine, N- ( 2-Benzamido-5-phenylthio-phenyl) -N'-methoxycarbonyl-N '' - propionyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl
N "acetyl guanidine, <RTI

    ID = 5.6> N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl-
N '' - butyryl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl
N '' - cyclohexane carbonyl guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl
N '' - benzoyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N '-methoxycarbonyl
N '' - phenylacetyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N'-methoxycarbonyl-
N '' - phenoxyacetyl-guanidine, N- [2- (2 '-methylureido) -5 -phenylthio-phenyl-N' -methoxycarbonyl-N '' - propionyl-guanidine, N- [2- (2'-ethylureido ) -5-phenylthio-phenyl] -N'-methoxy carbonyl-N '' - propionyl-guanidine, N- [2- (2'-butylureido) -S-phenylthio-phenyl-N'-methoxy-carbonyl-N ' '-propionyl-guanidine, <RTI

    ID = 5.12> N- [2- (2 '- # - Cyanpentylureido) -5-phenylthio-phenyl] -N'- methoxycarbonyl-N' 'propionyl-guanidine, N- [2- (2'-ss-methoxymethylureido ) -5-phenylthio-phenyl]
N'-methoxycarbonyl-N "propionyl guanidine, N- [2- (2'-benzylureido) -5-phenylthio-phenyl] -N'-methoxy carbonyl-N" propionyl guanidine, N- [2 - (2'-Phenylureido) -5-phenylthio-phenyll-N'-methoxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N ', N" -bis- methoxy carbonyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N ', N' '- bis-ethoxy carbonyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N', N "-bis-iso-prop-oxycarbonyl-guanidine, N- (2-acetamido-5-phenylthio-phenyl) -N ', N" - bis-sec.-bu oxycarbonyl-guanidine, N- (2-propionamido -5-phenylthio-phenyl) -N ', N' '- bis-met

   oxycarbonyl-guanidine, N- (2-butyramido-5-phenylthio-phenyl) -N ', N' '- bis-meth oxycarbonyl-guanidine, N- (2-iso-butyramido-5-phenylthio-phenyl) methoxycarbonyl-guanidine , N- (2-valeramido-5-phenylthio-phenyl) -N ', N "-bis-meth-oxycarbonyl-guanidine, N- (2-iso-valeramido-5-phenylthio-phenyl) -N', N" -bis- methoxycarbonyl-guanidine, N- (2-capronamido-5-phenylthio-phenyl) -N 'oxycarbonyl-guanidine, N- (2-iso-capronamido-5-phenylthio-phenyl) -N', N "-bis - methoxycarbonyl-guanidine, N- (2-cyclopentane carbonamido-5-phenylthio-phenyl)
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-cyclohexanecarbonamido-5-phenylthio-phenyl) -N', N '' bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-5-phenylthio- phenyl) -N ', N "- bis methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-5-phenylthio-pheny

   methoxycarbonyl-guanidine, N- (2-benzamido-5-phenylthio-phenyl-N ', N' '- bis-methoxy carbonyl-guanidine, N- [2- (2'-methylureido) -5-phenylthio-phenyl] - N ', N "- bis methoxycarbonyl-guanidine, N- [2- (2'-ethylureido) -5-phenylthio-pheny methoxycarbonyl-guanidine, N- [2- (2'-butylureido) -5-phenylthio-pheny methoxycarbonyl-guanidine, N- [2- (2 '- # - cyanopentylureido) -5-phenylt bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -5-phenylth @
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2- (2'-benzylureido) -5-phenylthio-phenyl methoxycarbonyl-guanidine, N- [2- (2'-phenyluriedo) -5-phenylthio- phenyl] -N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methylphenylthio-phenyl] -N', N" "

   bis-methoxycarbonyl guanidine, N- [2-propionamido-5- (3-methylphenylthio) phen
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-chlorophenylthio) phenyl bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-chloro -phenylthio) -phenyl] -N ', N' 'bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-chlorophenylthio) -phenyl] -N', N '' bis-methoxycarbonyl-guanidine , N- [2-propionamido-5- (4-methoxyphenylthi
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methoxy-phenylthi
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methylthio-phenylt
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methylthio-phenylt
N ', N "-bis-methoxycarbonyl-guanidine.



  N- [2-propionamido-5- (4-cyano-phenylthio) bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetyl-phenylthio bis-methoxycarbonyl-guanidine, N- [2-propionamido 5- (3-cyanophenylthio) phenyl bis-methoxycarbonyl guanidine, N- [2-propionamido-5- (4-propionylphenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetylamino-phenylthio) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methoxycarbonyl-phenylthio) -phenyl-N', N "-bis-methoxycarbonyl-guanidine, N- [2- Propionamido-5- (3,4-dimethylphenylthio) phenyl
N ', N "-bis-methoxycarbonyl-guanidine and N- [2-propionamido-5- (3,4-dichlorophenylt
N ', N "- bis-methoxycarbonyl guanidine.



   The following preferred compounds can be prepared by the process according to the invention: N- (2-acetamido-4-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N '' -propionyl-guanidine, N- (2-acetamido-4-phenylsulfinyl) -phenyl) nyl-N '' - propionyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N'-iso-propoxy carbonyl-N '' - propionyl-guanidine, N- (2-acetamido 4-phenylsulfinyl-phenyl) -N'-sec.-butoxy carbonyl-N '' - propionyl-guanidine, N- (2-propionamido-4-phenylsulfinyl-phenyl) -N'-methoxy carbonyl-N '' - propionyl- guanidine, N- (2-butyramido-4-phenylsulfinyl-phenyl) -N'-methoxycar bonyl-N '' propionyl-guanidine, N- (2-valeramido-4-phenylsulfinyl-phenyl) -N'-methoxycarbonyl -N "-propionyl-guanidine, N- (2-cyclopentanecarbonamido-4-phenylsulfinyl-phenyl) -N '

   methoxycarbonyl-N '' - propionyl-guanidine, N- (2-cyclohexanecarbonamido-4-phenylsulfine methoxycarbonyl-N "-propionyl-guanidine, N- (2-benzamido-4-phenylsulfinyl-phenyl) -N'-methoxycarbononyl-N '' -propionyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N '' - acetyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N '-methoxycarbonyl-N' '- butyryl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N' '- cyclohexanecarbonyl-guanidine, N- (2-acetamido-4 -phenylsulfinyl-phenyl) -N'-methoxy nyl-N '' - benzoyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N '' - phenylacetyl-guanidine, N - (2-acetamido-4-phenylsulfinyl-phenyl) nyl-N '' - phenoxyacetyl-guanidine, N- [2- (2'-methylureido) -4-phenylsulfinyl-p oxycarbonyl-N "-propionyl-guanidine,

    N- [2- (2'-ethylureido) -4-phenylsulfinyl-phenyl] -N'-meth oxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-butylureido) -4-phenylsulfinyl-phenyl- N'-methoxycarbonyl-N "-propionyl-guanidine, N- [2- (2 '- # - cyanopentylureido) -4-phenylsulfinyl-phenyl] -
N'-methoxycarbonyl-N '' - propionyl-guanidine, N- [2- (2 '- # - methoxymethylureido) -4-phenylsulfinyl-phenyl] -
N'-methoxycarbonyl-N "propionyl guanidine, N- [2- (2'-benzylureido) -4-phenylsulfinylphenyl-N'-methoxycarbonyl-N" -propionyl guanidine, N- [2- (2'-Phenylureido) -4-phenylsulfinyl oxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) oxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) - N ', N' '- bis-äth

   oxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) propoxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfinyl-phenyl) -N ', N' '- bis-sec. butoxycarbonyl-guanidine, N- (2-propionamido-4-phenylsulfinyl-phenyl) -N ', N' 'bis methoxycarbonyl-guanidine, N- (2-butyramido-4-phenylsulfinyl-phenyl) methoxycarbonyl-guanidine, N- ( 2-iso-butyramido-4-phenylsulfinyl-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine, N- (2-valeramido-4-phenylsulfinyl-phenyl) -N', N" - bis-meth oxycarbonyl -guanidine, N- (2-iso-valeramido-4-phenylsulfinyl-phenyl) -N ', N' '- bis methoxycarbonyl-guanidine, N- (2-capronamido-4-phenylsulfinyl-phenyl methoxycarbonyl-guanidine, N- ( 2-iso-capronamido-4-phenylsulfinyl-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine, N- (2-cyclopentane carbonamido-4-phenylsulfi
N ', N' '- bis-methoxycarbonyl-guanidine, N-

   (2-cyclohexanecarbonamido-4-phenylsulfinyenyl) -
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-4-phenylsulfinyl-phenyl) -N', N '' - bis-methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-4-phenylsulfinyl- phenyl) -N ', N' 'bis-methoxycarbonyl-guanidine, N- (2-benzamido-4-phenylsulfinyl-phenyl) -N', N '' - bis-meth oxycarbonyl-guanidine, N- [2- (2nd '-Methylureido) -4-phenylsulfinyl-phenyl] -N', N '' bis-methoxycarbonyl-guanidine, N- [2- (2 '-ethylureido) -4-phenylsulfinyl-phenyl]. -N ', N "-bis-methoxycarbonyl-guanidine, N- [2- (2'-butylureido) -4-phenylsulfinyl-phenyl] -N', N" - bis methoxycarbonyl-guanidine, N- [2- ( 2 '- # - Cyanpentylureido) -4-phenylsulfinyl-phen
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -4-phenylsulfinyl-ph @
N ' <RTI

    ID = 6.22>, N "-bis-methoxycarbonyl-guanidine, N- [2- (2'-benzylureido) -4-phenylsulfinyl-phenyl] -N ', N"' bis-methoxycarbonyl-guanidine, N- [2- (2'-phenylureido) -4-phenylsulfinyl bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methyl-phenylsulfinyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methylphenylsulfinyl) phenyl
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (2-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methoxy-phenylsulfinyl) -phen
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methoxy-phenylsulfinyl) -phen
N ', N' '- bis-methoxycarbonyl-guanidine, <RTI

    ID = 6.24> N- [2-propionamido-4- (4-methylthio-phenylsulfinyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methylthio-phenylsulfinyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-cyanophenylsulfinyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-acetyl-phenylsulfinyl) -phenyll-
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-cyanophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-propionylphenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-acetylamino-phenylsulfinyl) -phenyl] -N', N '' - bis-methoxycarbonyl-guanidine, N- [ 2-propionamido-4- (4-methoxycarbonyl-phenylsulfinyl) phenyl] -N ', N' '- bis-methoxycarbonyl-guanidine, <RTI

    ID = 6.29> N- [2-propionamino-4- (3, 4-dimethylphenylsulfinyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3,4-dichlorophenylsulfinyl) phenyl]
N ', N "- bis-methoxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N" -propionyl-guanidine, N- (2-acetamido-5 -phenylsulfinyl-phenyl) -N'-ethoxycarbonyl-N '' - propionyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-iso-propoxy carbonyl-N '' - propionyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-sec.-butoxy carbonyl-N '' - propionyl-guanidine, N- (2-propionamido-5-phenylsulfinyl-phenyl) -N'-methoxy- carbonyl-N '' - propionyl-guanidine, N- (2-butyramido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonyl -N "-propionyl-guanidine, <RTI

    ID = 6.34> N- (2-valeramido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N '' - propionyl-guanidine, N- (2-cyclopentanearbonamido-5-phenylsulfinyl-phenyl) -N'- methoxycarbonyl-N '' - propionyl-guanidine, N- (2-cyclohexanecarbonamido-5-phenylsulfinyl methoxycarbonyl-N "-propionyl-guanidine, N- (2-benzamido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N '' -propionyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonyl-N "-acetyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N '-methoxy-carbonyl-N "-butyryl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-methoxy-carbonyl-N" - cyclohexanecarbonyl-guanidine, N- (2-acetamido-5-phenylsulfinyl -phenyl) -N'-methoxycarbonyl-N "-benzoyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-methoxycarbo

   nyl-N '' - phenylacetyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N'-methoxycarbonon-N '' - phenoxyacetyl-guanidine, N- [2- (2'-methylureido) - S-phenylsulfinyl-phenyl-N'-meth-oxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-ethylureido) -5-phenylsulfinyl-phenyl-meth-oxycarbonyl-N" -propionyl-guanidine, N - [2- (2'-Butylureido) -5-phenylsulfinylphenyl-N'-meth-oxyearbonyl-N "-propionyl-guanidine, N- [2- (2 '- # - cyanopentylureido) -5-phenylsulfinyl-phenyl ] -N'- methoxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-ss-methoxymethylureido) -5-phenylsulfinyl-phenyl]
N'-methoxyearbonyl-N "-propionyl-guanidine, N- [2- (2'-benzylureido) -5-phenylsulfinyl-phenyl] -N'-meth

   oxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-phenylureido) -5-phenylsulfinyl-phenyl] -N'-meth oxycarbonyl-N" -propionyl-guanidine, N- (2-acetamido-5- phenylsulfinyl-phenyl) -N ', N "-bis-meth-oxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) oxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) - N ', N' '- bis-iso propoxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfinyl-phenyl) -N', N '' - bis-sec.

   butoxycarbonyl-guanidine, N- (2-propionamido-5-phenylsulfinyl-phenyl) -N ', N' '- to methoxycarbonyl-guanidine, N- (2-butyramido-5-phenylsulfinyl-phenyl) -N', N '' bis-meth oxycarbonyl guanidine, N- (2-iso-butyramido-5-phenylsulfinylphenyl) -N ', N "-bis methoxycarbonyl guanidine,
N- (2-valeramido-5-phenylsulfinyl-phenyl) oxycarbonyl-guanidine, N- (2-iso-valeramido-5-phenylsulfinyl-phenyl) -N ', N' '- to methoxycarbonyl-guanidine, N- (2- Capronamido-5-phenylsulfinyl-phenyl) -N methoxycarbonyl-guanidine, N- (2-iso-capronamido-5-phenylsulfinyl-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine, N- (2-cyelopentanearbonamido-5 -phenylsulfinyl-phenyl) -
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-cyclohexanecarbonamido-5-phenylsulfinyl-phenyl)
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-5-phenylsulfinyl-phenyl) -N', N '' - 1

   methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-5-phenylsulfinyl-phenyl) -N ', N' 'bis-methoxycarbonyl-guanidine, N- (2-benzamido-5-phenylsulfinyl-phenyl) -N', N '' bis-met oxycarbonyl-guanidine, N- [2- (2'-methylureido) -5-phenylsulfinyl-phenyll-N ', N "- bis-methoxycarbonyl-guanidine,
N- [2- (2'-ethylureido) -5-phenylsulfinyl-phenyl] -N ', N' '- to methoxycarbonyl-guanidine, N- [2- (2'-butylureido) -5-phenylsulfinyl-phenyl] - N ', N' '- bis methoxycarbonyl-guanidine, N- [2- (2' - # - cyanpentylureido) -5-phenylsulfinyl-phenyl] -
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -5-phenylsulfinyl-phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2- (2'-benzylureido) -5-phenylsulfinyl-phenyl] -N', N '' bis-methoxycarbonyl-guanidine, N- [2- ( 2'-phenylureido) -5-phenylsulfinyl-phenyl] -N ', N' '

   bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methylphenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methylphenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-chlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methoxy-phenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methoxy-phenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methylthio-phenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methylthio-phenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-cyanophenylsulfinyl)

  -phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetylphenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-cyanophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-propionylphenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetylamino-phenylsulfinyl) -phenyl] -N', N '' - bis-methoxycarbonyl-guanidine, N- [ 2-propionamido-5- (4-methoxycarbonyl-phenylsulfinyl) phenyl] -N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3,4-dimethyl-phenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3,4-dichlorophenylsulfinyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N' '- propionyl-guanidine, N- (2-acetamido-4- phenylsulfonyl-phenyl) -N'-ethoxycarbo

   nyl-N '' - propionyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N'-iso-propoxy carbonyl-N '' - propionyl-guanidine, N- (2-acetamido-4-phenylsulfonyl -phenyl) -N'-sec.-butoxy carbonyl-N '' - propionyl-guanidine, N- (2-propionamido-4-phenylsulfonyl-phenyl) -N'-methoxy carbonyl-N '' - propionyl-guanidine, N - (2-Butyramido-4-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N '' - propionyl-guanidine, N- (2-valeramido-4-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N '' -propionyl-guanidine, N- (2-cyclopentane carbonamido-4-phenylsulfonylphenyl)
N'-methoxycarbonyl-N '' - propionyl-guanidine, N- (2-cyclohexane carbonamido-4-phenylsulfonyl-phenyl) -N 'methoxycarbonyl-N' '- propionyl-guanidine, N- (2-benzamido-4-phenylsulfonyl- phenyl) -N'-methoxycar bonyl-N '' - propionyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N '' - acetyl-guanidine, N- (2- Acetamido-4-phenylsulfonyl-phenyl) -N'-methoxycar

   bonyl-N "-butyryl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N" -cyclohexanecarbonyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl ) -N '-methoxycar bonyl-N "-benzoyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N' -methoxycar bonyl-N" -phenylacetyl-guanidine, N- (2-acetamido-4 -phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N "-phenoxyacetyl-guanidine, N- [2- (2'-methylureido) -4-phenylsulfonyl-phenyl] -N'-meth oxycarbonyl-N" -propionyl-guanidine , N- [2- (2'-Ethylureido) -4-phenylsulfonylphenyl] -N'-meth oxycarbonyl-N '-propionyl-guanidine, N- [2- (2'-Butylureido) -4-phenylsulfonylphenyl -N'-meth oxycarbonyl-N "propionyl guanidine, N- [2- (2'-w

   -Cyanpentylureido) -4-phenylsulfonylphenyll
N'-methoxycarbonyl-N '' propionyl guanidine, N- [2- (2'-ss-methoxymethylureido) -4-phenylsulfonylphenyl]
N'-methoxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-benzylureido) -4-phenylsulfonyl-phenyl] -N'-methoxycarbonyl-N" -propionyl-guanidine, N- [2- ( 2'-phenylureido) -4-phenylsulfonylphenyl-N'-meth oxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N ', N" - bis-meth oxycarbonyl -guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N ', N "-bis-ethoxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N', N" - bis-iso propoxycarbonyl-guanidine, N- (2-acetamido-4-phenylsulfonyl-phenyl) -N ', N "-bis-sec.

   butoxycarbonyl-guanidine, N- (2-propionamido-4-phenylsulfonyl-phenyl) -N ', N "-bis methoxycarbonyl-guanidine, N- (2-butyramido-4-phenylsulfonyl-phenyl) -N', N" -bis - methoxycarbonyl-guanidine, N- (2-iso-butyramido-4-phenylsulfonyl-phenyl) -N ', N "-bis methoxycarbonyl-guanidine, N- (2-valeramido-4-phenylsulfonyl-phenyl) -N', N "-bis-methoxycarbonyl-guanidine, N- (2-iso-valeramido-4-phenylsulfonyl-phenyl) -N ', N" -bis methoxycarbonyl-guanidine, N- (2-capronamido-4-phenylsulfonyl-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine, N- (2-iso-capronamido-4-phenylsulfonyl-phenyl) -N', N" -bis-methoxycarbonyl-guanidine, N- (2-cyclopentane-carbonamido-4-phenylsulfonyl-phenyl ) -
N ', N' '- bis-methoxycarbonyl-guanidine, N- (2-cyclohexanecarbonamido-4-phenylsulfonyl-phenyl) -
N ' <RTI

    ID = 8.12>, N "-bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-4-phenylsulfonyl-phenyl) -N ', N" -bis methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-4-phenylsulfonyl- phenyl) -N ', N "bis-methoxycarbonyl-guanidine, N- (2-benzamido-4-phenylsulfonyl-phenyl) -N', N" -bis-meth oxycarbonyl-guanidine, N- [2- (2'- Methylureido) -4-phenylsulfonylphenyl-N ', N "- bis-methoxycarbonyl-guanidine, N- [2- (2'-ethylureido) -4-phenylsulfonyl-phenyll-N', N" bis-methoxycarbonyl-guanidine, N- [2- (2'-butylureido) -4-phenylsulfonylphenyl-N ', N "bis-methoxycarbonylguanidine, N- [2- (2' - # - cyanopentylureido) -4-phenylsulfonylphenyl] -
N ', N "-bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -4-phenylsulfonyl-phenyl N', N" -bis-methoxycarbonyl-guanidine,

    N- [2- (2'-benzylureido) -4-phenylsulfonylphenyl] -N ', N' bis-methoxycarbonyl-guanidine, N- [2- (2'-phenylureido) -4-phenylsulfonylphenyl-N ' , N "- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methylphenylsulfonyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-methylphenylsulfonyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-chlorophenylsulfonyl) phenyl]
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-chlorophenylsulfonyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (2-chlorophenylsulfonyl) phenyl
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methoxy-phenylsulfonyl) phenyl] -
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3rd <RTI

    ID = 8.23> -methoxy-phenylsulfonyl) -phenyll- N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methylthio-phenylsulfonyl) -phenyl-N', N '- bis-methoxycarbonyl-guanidine, N [2-propionamido-4- (3-methylthiophenylsulfonyl) phenyl] -N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4th -cyan-phenylsulfonyl) -phenyll-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-acetylphenylsulfonyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3-cyanophenylsulfonyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-propionyl-phenylsulfonyl) phenyl N', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido 4- (4-acetylamino-phenylsulfonyl) -phenyl] -N '

   , N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (4-methoxycarbonyl-phenylsulfonyl) phenyl] -N ', N" - bis-methoxycarbonyl-guanidine, N- [2-propionamido-4 - (3, 4-dimethyl-phenylsulfonyl) -phenyl] -N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-4- (3, 4-dichlorophenylsulfonyl) phenyl] -
N ', N "bis-methoxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N" -propionyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl ) -N'-ethoxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-iso-propoxy-carbonyl-N" -propionyl-guanidine, N- (2- Acetamido-5-phenylsulfonyl-phenyl) -N'-sec.-butoxy-carbonyl-N "-propionyl-guanidine, N- (2-propionamido-5-phenylsulfonyl-phenyl) -N'-methoxy carbonyl-N" -propionyl -guanidine,

    N- (2-butyramido-5-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N "-propionyl-guanidine, N- (2-valeramido-5-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N" - propionyl guanidine, N- (2-cyclopentanecarbonamido-5-phenylsulfonylphenyl) -
N'-methoxycarbonyl-N '-propionyl-guanidine, N- (2-cyclohexane-carbonamido-5-phenylsulfonyl-phenyl) -N' methoxycarbonyl-N '-propionyl-guanidine, N- (2-benzamido-5-phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N "-propionyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-methoxycarbonyl-N" -acetyl-guanidine, N- (2-acetamido-5 -phenylsulfonyl-phenyl) -N'-methoxycarbononyl-N "-butyryl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-methoxycarbononyl-N"

   -cyclohexanecarbonyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N "-benzoyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N'-methoxycar bonyl-N "-phenylacetyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N '-methoxycar bonyl-N" -phenoxyacetyl-guanidine, N- [2- (2'-methylureido) -5- phenylsulfonylphenyl-N'-meth oxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-ethylureido) -5-phenylsulfonyl-phenyll-N '-meth oxycarbonyl-N" -propionyl-guanidine, N- [2- (2'-butylureido) -5-phenylsulfonylphenyl-N'-meth oxycarbonyl-N "-propionyl-guanidine, N- [2- (2 '- # - cyanopentylureido) -5-phenylsulfonyl-phenyl] -

   
N'-methoxycarbonyl-N "propionyl guanidine, N- [2- (2'-ss-methoxymethylureido) -5-phenylsulfonylphenyl] -N'-methoxycarbonyl-N" propionyl guanidine, N- [2- (2'-benzylureido) -S-phenylsulfonylphenyl-N'-meth-oxycarbonyl-N "-propionyl-guanidine, N- [2- (2'-phenylureido) -5-phenylsulfonyl oxyearbonyl-N" - propionyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N ', N' '- bis-meth oxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N', N '' -bis-eth oxycarbonyl-guanidine, N- (2-acetamido-5-phenylsulfonyl-phenyl) -N ', N' '- bis-iso propoxycarbonyl-guanidine, N- (2-acetamido-5-phenyslulfonyl-phenyl ) -N ', N' '- bis-sec.



   butoxycarbonyl-guanidine, N- (2-propionamido-5-phenylsulfonyl-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine, N- (2-butyramido-5-phenylsulfonyl-phenyl) -N', N '' -bis methoxycarbonyl-guanidine, N- (2-iso-butyramido-5-phenylsulfonyl-phenyl) -N ', N' '- bis methoxycarbonyl-guanidine, N- (2-valeramido-5-phenylsulfonyl-phenyl) -N' , N '' - to methoxycarbonyl-guanidine, N- (2-iso-valeramido-5-phenylsulfonyl-phenyl) -N ', N' '- to methoxycarbonyl-guanidine, N- (2-capronamido-5-phenylsulfonyl-phenyl ) -N ', N' '- to methoxycarbonyl-guanidine, N- (2-iso-capronamido-5-phenylsulfonyl-phenyl) -N', N '' - to methoxycarbonyl-guanidine, N- (2-cyclopentane carbonamido-5 -phenylsulfonyl
N ', N "-bis-methoxycarbonyl-guanidine, N- (2-cyclohexanecarbonamido-5-phenylsulfonyl-phenyl) N', N" -bis-methoxycarbonyl-guanidine, N- (2-phenylacetamido-5-phenylsulfonyl-phenyl) -N ', N' '- bis

   methoxycarbonyl-guanidine, N- (2-phenoxyacetamido-5-phenylsulfonyl-phenyl) -N ', N' 'bis-methoxycarbonyl-guanidine, N- (2-benzamido-5-phenylsulfonyl-phenyl) -N', N "- bis-methoxycarbonyl guanidine, N- [2- (2'-methylureido) -5-phenylsulfonyl bis-methoxycarbonyl guanidine, N- [2- (2'-ethylureido) -5-phenylsulfonylphenyl bis-methoxycarbonyl- guanidine, N- [2- (2'-butylureido) -5-phenylsulfonylphenyl] -N ', N' 'to methoxycarbonylguanidine, N- [2- (2' - # - cyanopentylureido) -5-phenylsulfonyl -phenyl]
N ', N "-bis-methoxycarbonyl-guanidine, N- [2- (2'-ss-methoxyethylureido) -5-phenylsulfonyl-phenyl N', N" -bis-methoxycarbonyl-guanidine, N- [2- (2nd '-Benzylureido) -5-phenylsulfonylphenyl bis-methoxycarbonyl-guanidine, N- [2- (2'-phenylureido) -5-phenylsulfonyl-phenyl] -N', N '' bis-methoxycarbonyl-guanidine, <RTI

    ID = 9.14> N- [2-propionamido-5- (4-methylphenylsulfonyl) phenyl-
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methylphenylsulfonyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-chlorophenylsulfonyl) phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-chlorophenylsulfonyl) phenyl] N', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido -5- (3-chlorophenylsulfo N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methoxy-phenylsulfonyl
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-methoxy-phenylsulfonyl) phenyl-
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-methylthio-phenylsulfonyl] -N', N" - bis-methoxycarbonyl-guanidine, N- <RTI

    ID = 9.19> [2-propionamido-5- (3-methylthio-phenylsulfonyl) phenyl-N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-cyanophenylsulfonyl -phenyl]
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetylphenylsulfonyl) phenyl
N ', N' '- bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3-cyanophenylsulfonyl) phenyl-
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-propionyl-phenylsulfo
N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (4-acetylamino-phenylsulfonyl) -p nyll-N', N" -bis-methoxycarbonyl-guanidine, N- [2-propionamido - 5- (4-methoxycarbonyl-phenylsulfonyl) phenyl-N ', N "-bis-methoxycarbonyl-guanidine, N- [2-propionamido-5- (3,4-dimethyl-phenylsulfonyl) -phe

   nyl] -N ', N' '- bis-methoxycarbonyl-guanidine and N- [2-propionamido-5- (3,4-dichlorophenylsulfonyl) phenyl-
N ', N "-bis-methoxycarbonyl-guanidine.



   The compounds prepared according to the invention, as well as the starting compounds of the formula (II), which are also new, show a surprisingly good and broad activity against the following nematodes and cestodes:
1. hookworms (e.g. Uncinaria stenocephala, Ancylos toma caninum, Bunostomum trigonocephalum),
2. Trichostrongyliden (eg Nippostrongylus muris, Haemonchus contortus, Trichostrongylus colubriformis, Ostertagia circumcincta),
3. Strongyles (e.g. Oesophagostomum columbianum),
4. rhabditides (e.g. Strongyloides ratti),
5. roundworms (e.g. Ascaris suum, Toxocara canis, Toxas caris leonina),
6. maggot worm (e.g. Aspiculuris tetraptera),
7. heteracids (e.g.

  Heterakis spumosa), 8.Whipworms (e.g. Trichuris muris),
9. filariae (e.g. Litomosoides carinii, Dipetalonema witei),
10.Cestodes (e.g. Hymenolepis nana, Taenia pisiformis,
Echinococcus multilocularis).



   The effect was tested in animal experiments after oral and parenteral administration in experimental animals heavily infested with parasites. The doses used were very well tolerated by the experimental animals.



   The new active ingredients can be used as anthelmintics in both human and veterinary medicine.



   The new active ingredients can be converted into the customary formulations in a known manner.



   The new compounds can be used either as such or in combination with pharmaceutically acceptable carriers. Dosage forms in combination with various inert carriers are tablets, capsules, granules, aqueous suspensions, injectable solutions, emulsions and suspensions, elixirs, syrups, pastes and the like. Such carriers include solid diluents or fillers, a sterile aqueous medium, and various non-toxic organic solvents and the like. Of course, the tablets and the like which are suitable for oral administration can be provided with added sweeteners and the like.

  In the aforementioned case, the therapeutically active compound should be present in a concentration of approximately 0.5 to 90% by weight of the total mixture. d. H.



  in amounts sufficient to achieve the dosage range mentioned above.



   The formulations can be prepared in a known manner, e.g. B. by stretching the active ingredients with solvents and / or carriers, optionally using emulsifiers and / or dispersants, z. B. in the case of the use of water as a diluent, organic solvents can optionally be used as auxiliary solvents.



   Examples of auxiliary substances are: water, non-toxic organic solvents, such as paraffins (e.g. petroleum fractions), vegetable oils (e.g. peanut / sesame oil), alcohols (e.g. ethyl alcohol, glycerol), glycols (e.g. B. propylene glycol, polyethylene glycol) and water; solid carriers, such as. B. natural rock flours (e.g. kaolins, clays, talc, chalk), synthetic rock flours (e.g. highly disperse silica, silicates), sugar (e.g. raw, milk and glucose); Emulsifiers, such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates), dispersants (e.g. lignin, sulfite liquors, methyl cellulose, starch and polyvinylpyrrolidone B) and lubricants (e.g. Magnesium stearate, talc, stearic acid and sodium lauryl sulfate).



   In the case of oral use, tablets can of course also contain additives, such as sodium citrate, calcium carbonate and dicalcium phosphate, in addition to the carrier substances mentioned, together with various additives, such as starch, preferably potato starch, gelatin and the like. Lubricants such as magnesium stearate, sodium lauryl sulfate and talc can also be used for tableting.



   In the case of aqueous suspensions and / or elixirs which are intended for oral applications, the active ingredients can be mixed with various flavor enhancers or colorants in addition to the abovementioned auxiliaries.



   In the case of parenteral use, solutions of the active ingredients can be used using suitable liquid carrier materials.



   The active ingredients can also be contained in capsules, tablets, lozenges, dragees, ampoules, etc. in the form of dosage units, each dosage unit being adapted to deliver a single dose of the active ingredient.



   The new compounds can also be present in the formulations in mixtures with other known active compounds.



   The new active ingredients can be used in the usual way. The application is preferably oral, but parenteral, in particular subcutaneous, but also dermal application is also possible.



   In general, it has been found to be advantageous to administer amounts of about 0.1 to about 50 mg of the new compounds per kg of body weight per day for effective results.



   Nevertheless, it may be necessary to deviate from the amounts mentioned, depending on the body weight of the test animal or the type of application route, but also on the basis of the animal type and its individual behavior towards the medication or



  the type of its formulation and the time or



  Interval at which the administration takes place. In some cases it may be sufficient to make do with less than the aforementioned minimum quantity, while in other cases the above upper limit must be exceeded.



  In the case of application of larger quantities, it may be advisable to distribute them in several single doses throughout the day. The same dosage range is provided for application in human and veterinary medicine.



  The other statements above also apply accordingly.



   The anthelmintic effect of the active compounds obtained according to the invention will be explained in more detail using the following application examples. The compounds of formula (II) are also new and show the same activity as the compounds of formula (1).



   The preparation of the starting products of the formula (II) is described in the preparations below and also in Swiss Patent No. 612 925.



   Example A
Stomach and intestinal worm test / sheep
Sheep experimentally infected with Haemonchus contortus or Trichostrongylus colubriformis were treated after the parasites had reached the prepatent time. The amount of active ingredient was administered orally as a pure active ingredient in gelatin capsules.



   The efficiency is determined by quantitatively counting the worm eggs excreted in the faeces before and after the treatment.



   A complete suspension of egg excretion after treatment means that the worms have been aborted or damaged so that they can no longer produce eggs (effective dose).



   Tested active substances and effective doses (dose effectiva minima) are shown in the table below.



  Table for example A new active ingredient dose effectiva minima (Red.> 90%) in mg / kg
EMI10.1
 Haemonchus cont. 1 Trichostrong. col. 1
Table (continued) new active substance dose effectiva minima (Red.> 90%) in mg / kg
EMI11.1
   Haemonchus cont. 0.5 Trichostrong. col. 1
Haemonchus cont. 1 Related preparations for comparison (known from DOS 2 117 293)
Effective dose minimum (Red.> 90%) in mg / kg
EMI11.2
 Haemonchus cont. > 100 Trichostrong. col. 50
Haemonchus cont. 50
Trichostrong. col. 10 preparation 1
EMI11.3

14.3 g (0.05 mol) of 2-amino-5-phenylthio-butyranilide (mp. 1520C) are added in 100 ml of methanol with 10 g (0.05 mol) of NN'-bis-methoxycarbonyl-isothiourea-S-methyl ether heated by 1 g of p-toluenesulfonic acid for 3 hours.



  After working up analogously to Example 3, 13.8 g of N- (2-butamido-4-phenylthio-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine of mp 155 C.



   In a corresponding procedure, isothiourea-S-methylene ether and 2-amino are obtained from N.N'-di
5-phenylthio-anilides the following compounds: Starting material: Manufactured substances of the formula (II)
EMI12.1

EMI12.2

 R <SEP> R ' <SEP> F (C) <SEP> R <SEP> R ' <SEP> R '' <SEP> R '' ' <SEP> Fp.

   <SEP> (C)
 <tb> H <SEP> COCH3 <SEP> 119 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOCH3 <SEP> 160
 <tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COC2H5 <SEP> 131-132
 <tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOC2H5 <SEP> 145-146
 <tb> H <SEP> COC2H5 <SEP> 145 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 176
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COC2H5 <SEP> 130
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOC2H5
 <tb> H <SEP> COC3H7 <SEP> 152 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOC2H5 <SEP> 128
 <tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COC2H5 <SEP> 127
 <tb> H <SEP> COC4H9 <SEP> 117 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COOCH3 <SEP> 137
 <tb> H <SEP> COC4H9-iso <SEP> H <SEP> COC4H9-iso <SEP> COOCH3 <SEP> COOCH3 <SEP> 145
 <tb> H <SEP> COOCH3 <SEP> H <SEP> COOCH3 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP>

   COOC2H5 <SEP> 93-94 <SEP> H <SEP> COOC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 159
 <tb> H <SEP> COC5H11 <SEP> 105 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COOCH3 <SEP> 127
 <tb> H <SEP> COC6H13 <SEP> H <SEP> COC6H13 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-CH = CH2
 <tb> H <SEP> COC5H11 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COC2H5 <SEP> 122
 <tb> H <SEP> COC4H9 <SEP> 117 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COC2H5 <SEP> 160
 <tb> H <SEP> CO-C = CH2 <SEP> 120 <SEP> H <SEP> CO-C = CH2 <SEP> COOCH3 <SEP> COOCH3 <SEP> 161
 <tb> CH3 <SEP> CH3
 <tb> H <SEP> CO-CH (CH3) 2 <SEP> H <SEP> CO-CH (CH3) 2 <SEP> COOCH3 <SEP> COOCH3 <SEP> 161
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C = CH
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C (CH3) = CH2
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH2-CH = CH2 <SEP>

   COOCH2-CH = CH2
 <tb> H <SEP> CO- # <SEP> H <SEP> CO- # <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> CO- # <SEP> H <SEP> CO- # <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COCH2OCH3 <SEP> 95 <SEP> H <SEP> COCH2OCH3 <SEP> COOCH3 <SEP> COOCH3 <SEP> 129-130
 <tb> H <SEP> CO-CH2-OC2H5 <SEP> H <SEP> CO-CH2-OC2H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 119
 <tb> H <SEP> CO-CH2OC6H5 <SEP> 109-110 <SEP> H <SEP> COCH2OC6H5 <SEP> COOCH3 <SEP> COOCH3 <SEP> 144-146
 <tb> table (continued) Starting material:

  Manufactured substances of formula (II) RR 'F (C) RR' R '' R '' 'Mp. (C) 4-CH3 COC3H7 136 4-CH3 COC3H7 COOCH3 COOCH3 171 3-CH3 COC3H7 3-CH3 COC3H7 COOCH3 COOCH3 2 -CH3 COC3H7 2-CH3 COC2H7 COOCH3 COOCH3 4-Cl COC2H5 4-Cl COC2H5 COOCH3 COOCH3 3-Cl COC2H5 3-Cl COC2H5 COOCH3 COOCH3 2-Cl COC2H5 126 2-Cl COC2H5 COOCH3 COOCH3 COOCH3 COOCH3 COOCH3 4-Br COC3H7 130 4-Br COC3H7 COOCH3 COOCH3 176 3,4-Cl2 COC3H7 3,4-Cl2 COC3H7 COOCH3 COOCH3 4-C4H9 COC3H7 4-C4H9 COC3H7 COOCH3 COOCH3 4-C2H3 COC3CH3 CO7CH3 CO7CH3 , 5- (OCH3) 2 COC3H7 146 2.5- (OCH3) 2 COC3H7 COOCH3 COOCH3 142 4-CH3 COC3H7 122 4-CH3 COC3H7 COOCH3 COC2H5 110 4-Cl CO-C3H7 126 4-Cl CO-C3H7 COOCH3 COOCH3 176 4 -Cl CO-C3H7 4-Cl CO-C3H7 COOCH3 COC2H5 155 2-Cl COC3H7 155 2-Cl COC3H7 COOCH3 COOCH3 154 2-Cl COCH2OCH3 166 2-Cl COCH2OCH3 COOCH3 COOCH3 138 4-Br COC2H5 154 4-Br COC3OCH3 3-CH3,

   4-Br COC3H7 143 3-CH3, 4-Br COC3H7 COOCH3 COOCH3 170 3-CH3, 4-Br COC2H5 3-CH3, 4-Br COC2H5 COOCH3 COOCH3 3-CH3, 4-Br COCH2OCH3 119-120 3-CH2, 4 -Br COCH2OCH3 COOCH3 COOCH3 141 4-C2H5 COC2H5 97 4-C2H5 COC2H5 COOCH3 COOCH3 155 4-C2H5 COCH2OCH3 94 4-C2H5 COCH2OCH3 COOCH3 COOCH3 126 3-CF3 COC3H7 3-CF3 CFCCH3CH3CH3CH3CH3 COOCH3 120 4-C4H9 COCH2OCH3 4-C4H9 COCH2OCH3 COOCH3 COOCH3 3-OCH3 COCH2OCH3 3-OCH3 COCH2OCH3 COOCH3 COOCH3 4-OCH3 COCH2OCH3 634-OCH3 COCH2OCH3 COOCH3 COOH3 COOH3 2-OC2H5 COCH2OCH3 COOCH3 COOCH3 COOCH3 2-110 COC3H7 COC3H7 2-COOCH3 COOCH3 COOCH3 COOCH3 2 COC2H5 COC2H5 2-COOCH3 COOCH3 COOCH3 COOCH3 2-COCH2OCH3 2-COOCH3 COOCH3 COOCH3 H COCH2OCH3 COCH2OCH3 95 H COOCH3 COCH2OCH3 COOC2H5 H 125-127 109 COCH2OC6H5 -110 H COCH2OC6H5 COOCH3 COC2H5 138-140 H COCH2-O-C2H5 86 H

   COCH2-O-C2H5 COOCH3 CO-C2H5 111 2,4- (CH3) 2 COC3H7 2,4- (CH3) 2 COC3H7 COOCH3 COOCH3 3-OC2H5 COC3H7 3-OC2H5 COC3H7 COOCH3 COOCH3 4-OCH3 COC3H7 CO3CH3C3CH7 COOCH3 185 3-OCH3 COC3H7 88 3-OCH3 COC3H7 COOCH3 COOCH3 160 4-SCH3 COC3H7 4-SCH3 COC3H7 COOCH3 COOCH3 2-OC2H5 COC2H5 2-OC2H5 COC2H5 COOCH3 COOCH3 Table (continued)

  Manufactured substances of formula (II) RR 'F (C) RR' R '' R '' 'Mp. (C) 3-CH3, 4-Br COC2H5 3-CH3, 4-Br COC2H5 COOOCH3 COOCH3 3-CF3 COC2H5 3 -CF3 COC2H5 COOCH3 COOCH3 4-F COCH2OCH3 89 4-F COCH2OCH3 COOCH3 COOCH3 127 4-CH3CO COC2H5 4-CH3CO COC2H5 COOCH3 COOCH3 3-CH3CO COC2H3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3CH3 CO3 COC2H5 4-NHCOOCH3 COC2H5 COOCH3 COOCH3 4-CN COC2H5 4-CN COC2H5 COOCH3 COOCH3 3-CN COC2H5 3-CN COC2H5 COOCH3 COOCH3 4-F CO-C3H7 121 4-F CO-C3H7 COOCH3 COOCH3 COOCH3 COOCH3 -F CO-C3H7 COOCH3 COC2H5 136-137 4-Br CO-CH2-O-CH3 143 4-Br CO-CH2-O-CH3 COOCH3 COOCH3 114 3-Cl CO-C3H7 142 3-Cl CO-C3H7 COOCH3 COOCH3 129 3-Cl CO-CH2-O-CH3 113 3-Cl CO-CH2-O-CH3 COOCH3 COOCH3 124 4-C (CH3) 3 CO-C3H7 4-C (CH3) 3 CO-C3H7 COOCH3 COOCH3 169 Preparation 2
EMI15.1

From 14.3 g (0.05 mol) of 2-amino-4-phenylthio-butyranilide

   and 10.3 g (0.05 mol) of N, N'-bis-methoxycarbonyl-isothiourea-S-methyl ether gives 14.5 g of N- (2-butyramido 5-phenylthio-phenyl) -N ', N "- bis-methoxycarbonyl-guanidine, mp 164-166 C.



   In a corresponding procedure, the following compounds are obtained from N, N'-disubstituted isothiourea-S-methyl ethers and 2-amino4-phenylthio-anilides: starting material; Manufactured substances of formula (II)
EMI16.1

EMI16.2

 R <SEP> R ' <SEP> F <SEP> (C) <SEP> R <SEP> R ' <SEP> R '' <SEP> R '' ' <SEP> Fp.

   <SEP> (C)
 <tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COC2H5
 <tb> H <SEP> COCH3 <SEP> H <SEP> COCH3 <SEP> COOCH3 <SEP> COOC2H5
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COC2H5
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2H5
 <tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COOC2H5
 <tb> H <SEP> COC3H7 <SEP> H <SEP> COC3H7 <SEP> COOCH3 <SEP> COC2H5
 <tb> H <SEP> COC4H9 <SEP> H <SEP> COC4H9 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COC4H9-iso <SEP> H <SEP> COC4H9-iso <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COOCH3 <SEP> H <SEP> COOCH3 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COOC2H5 <SEP> H <SEP> COOC2H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COC5H11 <SEP> H <SEP> COC5H11 <SEP> COOCH3 <SEP> COOCH3
 <tb> H

    <SEP> COC6H13 <SEP> H <SEP> COC6H13 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-CH = CH2
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH2-C # CH
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH-C (CH3) = CH2
 <tb> H <SEP> COC2H5 <SEP> H <SEP> COC2H5 <SEP> COOCH2-CH = CH2 <SEP> COOCH2-CH = CH2
 <tb> H <SEP> CO- # <SEP> H <SEP> CO- # <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> CO- # <SEP> H <SEP> CO- # <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> COCH2OCH3 <SEP> H <SEP> COCH2OCH3 <SEP> COOCH3 <SEP> COOCH3
 <tb> H <SEP> CO-CH2OC6H5 <SEP> H <SEP> COCH2OC6H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> 4-CH3 <SEP> COC3H7 <SEP> 4-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> 3-CH3 <SEP> COC3H7 <SEP> 3-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> 2-CH3 <SEP> COC3H7 <SEP> 2-CH3 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> 4-cl <SEP> COC2H5 <SEP>

   4-cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> 3-cl <SEP> COC2H5 <SEP> 3-Cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> 2-cl <SEP> COC2H5 <SEP> 2-Cl <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
 <tb> 4-NHCOCH3 <SEP> COC2H5 <SEP> 4-NHCOCH3 <SEP> COC2H5 <SEP> COOCH3 <SEP> COOCH3
 4-Br <SEP> COC3H5 <SEP> 4-Br <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> 3,4-Cl2 <SEP> COC3H7 <SEP> 3,4-Cl2 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> 4-C4H9 <SEP> COC3H7 <SEP> 4-C4H9 <SEP> COC3H7 <SEP> COOCH3 <SEP> COOCH3
 <tb> table (continued) Starting material:

  Manufactured substances of formula (II) RR 'F (C) RR' R '' R '' 'Mp. (C) 4-C2H5 COC3H7 4-C2H5 COC3H7 COOCH3 COOCH3 3,5- (CH3) 2 COC3H7 3,5- (CH3) 2 COC3H7 COOCH3 COOCH3 2,4- (CH3) 2 COC3H7 2,4- (CH3) 2 COC3H7 COOCH3 COOCH3 3-OC2H5 COC3H7 3-OC2H5 COC3H7 COOCH3 COOCH3 4-OCH3 COC3H3 OCH3 CO3CHOCH3 COC3H7 3-OCH3 COC3H7 COOCH3 COOCH3 4-SCH3 COC3H7 4-SCH3 COC3H7 COOCH3 COOCH3 2-OC2H5 COC2H5 2-OC2H5 COC2H5 COOCH3 COOCH3 3-CH3, 4-Br COC2H5 3-CH3,

   4-Br COC2H5 COOCH3 COOCH3 3-CF3 COC2H5 3-CF3 COC2H5 COOCH3 COOCH3 4-F COC2H5 4-F COC2H5 COOCH3 COOCH3 4-CH3CO COC2H5 4-CH3CO3 CO3 CH3 CO3 CH3 CO3 CH3 CO3 CH3 CO3 CH3 CO3 4-C3H7CO COC2H5 COOCH3 COOCH3 4-NHCOOCH3 COC2H5 4-NHCOOCH3 COC2H5 COOCH3 COOCH3 4-CN COC2H5 4-CN COC2H5 COOCH3 COOCH3 3-CN COC2H5 3-CN COC2H3 COOCH3OCH3
EMI18.1

To a solution of 8.9 g of N- (2-butyramido-4-phenylthio-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine [mp.



     155 C, j in 1.4 1 acetic anhydride, drop 2.3 ml H202 (30%). After 10 hours, the mixture is concentrated in vacuo, the residue is mixed with a mixture of ethyl acetate and petroleum ether and filtered off.



   8.5 g of N- (2-butyramido-4-phenylsulfinyl-phenyl) -N, N'-bis-methoxycarbonyl-guanidine of mp. 186 C (dec.), (Redissolved from methanol / ethyl acetate) are obtained. The mass spectrum shows a mol peak of 460.



   In a corresponding procedure, 31 g of N- (2-methoxyacetamido-4-phenylthio-phenyl) -N ', N "- bis methoxycarbonyl-guanidine and 8.5 ml of H202 (30%) give 30 g of N- (2-methoxyacetamido-4-phenylsulfinylphenyl) -N ', N' bis-methoxycarbonyl-guanidine of mp 134 C.

 

  Example 2
EMI18.2

According to the method described in Example 1, 13.7 g of N- (2-butyramido-4-phenylthio-phenyl) N ', N "-bis-methoxycarbonyl-guanidine and 20 ml of H202 (30%) give 12.7 g N- (2-butyramido-4-phenylsulfonylphenyl) N ', N' '- bis-methoxycarbonyl-guanidine, mp 180 ° C. The mass spectrum shows a mol peak of 476.



   In a corresponding procedure, 8.9 g of N- (2-methoxyacetamido-4-phenylthio-phenyl) -N ', N "-bis-methoxycarbonyl-guanidine and 14 g of H202 (30%) give 8.0 g of N - (2-methoxyacetamido-4-phenylsulfonylphenyl) -N ', N' 'bis-methoxycarbonyl-guanidine, mp 142 C.
Claims

PATENT CLAIMS 1. Process for the preparation of new substituted phenylguanidines of the formula EMI1.1 in which R and R1 are different from each other and mutually for one of the residues EMI1.2 stand in which R4 for hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted amino, optionally substituted alkoxy, optionally substituted aralkyl and R5 for optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl and R6 for hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted aryl,
optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, and in which R2 and R3 can be identical or different and represent hydrogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted amino, halogen, cyano, optionally substituted alkylthio, optionally substituted acyl , optionally substituted carbalkoxy, and in which X represents the sulfinyl group or the sulfonyl group and can be linked to position 4 or 5 of the substituted aminophenyl group, characterized in that compounds of the formula EMI1.3 in which R, Rl, R2 and R3 have the meaning given above, oxidized with the appropriate amount of an oxidizing agent.
2. The method according to claim 1, characterized in that R2 and R3 are substituted alkyl, preferably haloalkyl.
The present invention relates to a process for the preparation of new substituted phenylguanidines which can be used as medicaments, in particular as anthelmintics.
It has already become known that phenylguanidines have the general formula EMI1.4 in the R lower alkyl and R 'can mean both lower alkyl and hydrogen, have anthelmintic effects (see German Offenlegungsschrift 2 117 293).
However, they show the disadvantage that their anthelmintic effect is much weaker than that of the substituted phenylguanidines according to the invention.
It has been found that the new substituted phenylguanidines of the formula which can be prepared according to the invention EMI1.5 in which R and R 'are different from each other and mutually for each of the residues EMI1.6 stand in which R4 for hydrogen optionally substituted alkyl optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted amino, optionally substituted alkoxy and optionally substituted aralkyl, R5 for optionally substituted alkyl, optionally substituted alkenyl and optionally substituted alkynyl, ** WARNING ** End of CLMS field could overlap beginning of DESC **.