NO751618L - - Google Patents

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Publication number
NO751618L
NO751618L NO75751618A NO751618A NO751618L NO 751618 L NO751618 L NO 751618L NO 75751618 A NO75751618 A NO 75751618A NO 751618 A NO751618 A NO 751618A NO 751618 L NO751618 L NO 751618L
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NO
Norway
Prior art keywords
amino
guanidine
methoxycarbonyl
phenyl
phenoxy
Prior art date
Application number
NO75751618A
Other languages
English (en)
Inventor
H Koelling
H Thomas
A Widdig
H Wollweber
Original Assignee
Bayer Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19742423679 external-priority patent/DE2423679C3/de
Application filed by Bayer Ag filed Critical Bayer Ag
Publication of NO751618L publication Critical patent/NO751618L/no

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D45/00—Separating dispersed particles from gases or vapours by gravity, inertia, or centrifugal forces
    • B01D45/04—Separating dispersed particles from gases or vapours by gravity, inertia, or centrifugal forces by utilising inertia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D47/00—Separating dispersed particles from gases, air or vapours by liquid as separating agent
    • B01D47/06—Spray cleaning

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Substituerte fenylguanidiner, en
fremgangsmåte for deres frem-
stilling og deres bruk som
legemidler.
Foreliggende oppfinnelse angår nye substituerte fenylguanidiner, en fremgangsmåte for deres fremstilling og benyttelse av forbindelsene som legemidler, særlig som Anthelmintika.(ormdrepende midler).
Det er allerede kjent at fenylguanidiner med gene-rell formel
hvor
R betegner lav-alkyl og
R' betegner lav-alkyl eller hydrogen,
har antelmintiske virkninger (se tysk utlegningsskrift nr. 2.117.293).
Disse forbindelser har imidlertid den ulempe at den antelmintiske virkning er vesentlig svakere enn hos substituerte fenylguanidiner i henhold til oppfinnelsen.
•Man fant at de nye substituerte'f enylguanidiner med formel
hvor
R og R"*" er forskjellige fra hverandre og vekselvis betegner en av gruppene
hvor
R betegner hydrogen, eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert aryl, eventuelt substituert amino, eventuelt substituert alkoksy og- ....
eventuelt substituert aralkyl,-
R betegner eventuelt substituert alkyl, eventuelt substituert alkenyl og eventuelt substituert alkinyl,
R^betegner hydrogen,
eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert alkoksy., eventuelt substituert alkenyl-
oksy, eventuelt substituert alkinyloksy, eventuelt substituert aryl, eventuelt substituert aralkyl, eventuelt substituert al-
kenyl,. eventuelt substituert alkinyl,
2 ^ • ..
og hvor R og RJ kan være like eller forskjellige
og betegner hydrogen, eventuelt substituert alkyl, eventuelt substituert,alkoksy,.eventuelt substituert amino, halogen, halogenalky1, cyano, eventuelt substituert alkyltio, eventuelt substituert acyl, eventuelt substituert karbalkoksy, og hvor
X betegner et oksygenatom, et svovelatom, en sulfinylgruppe eller en sulfonylgruppe,
har meget gode antelmintiske virkninger.
Videre fant man at de substituerte fenylguani-
diner med formel I kan fremstilles ved å omsette substituerte anilinderivater med formel
hvor
2 "5 *J
R , R , R og X har den ovenfor angitte betydning og hvor X kan være bundet til 4- eller 5-stilling på den substituerte 1-amino-fenylgruppe i formel II, med isotioureaforbindelser med formel
hvor
S "f) . ■
R^ og R har de tidligere angitte betydninger og
Ry1betegner alkyl med 1-4 C-atomer,
i nærvær av et fortynningsmiddel og eventuelt i nærvær av en _ syre.
Forbindelsene- med■formel I i henhold til oppfinnel-
sen kan foreligge i tautomere former, hvilket skal fremgå av følgende eksempel:
For enkelhets skyld er de angitte strukturformler i foreliggende beskrivelse formulert likeartet.
Overraskende viser substituerte fenylguanidiner ifølge oppfinnelsen en betraktelig høyere antelmintisk virkning enn de fenylguanidiner som er nevnt i tysk utlegningsskrift 2.117.293j som betegner de kjemisk nærmest liggende aktive stoffer med samme virkningsområde. De virksomme stoffer ifølge oppfinnelsen betyr således en verdifull berikelse av farmasien.
Benytter man N,N'-bis-metoksykarbonyl-S-mety1-isotiourea og 2-amino-5_fenoksy-n-butyranilid som utgangsstoffer, kan reaksjonsforløpet gjengis ved følgende formelskjerna: anvender man N-metoksykarbonyl-N'-propionyl-S-metyl-isotiourea og 2-amino-5-fenyltio-acetanilid som utgangsstoffer, kan prosessen gjengis med følgende skjema:
I formlene II og III står eventuelt substituert alkyl R<2>, R-5, r\R<5>og R<6>for rettkjedet eller forgrenet alkyl med fortrinnsvis 1 - 6 og helst 1-4 C-atomer. For eksempel nevnes eventuelt substituert metyl, etyl, n- og i-propyl, n-, i- og t-butyl.
Andre veier til overnevnte forbindelser med formel I, hvori X betyr en sulfinyl- og/eller en sulfonylrest, er likeledes mulig. Således fåes ved oksydasjon av forbindelser med formel I, hvori X betyr et svovelatom, med et ekvivalent R^C^fenylsulfinylfenylguanidiner og med to ekvi-valenter ^ 2^ 2 ^enylsul^ony1Suanidin. Følgende eksempel for-klarer metoden:
Istedenfor H^C^kan man også anvende andre oksydasjonsmidlerjeksempelvis skal det nevnes: Organiske persyrer, som pereddiksyre, permaursyre, perbenzosyre, m-klorperbenzosyre, monoperftalsyre, uorganiske peroksyder, som hydrogenperoksyd, oppløst i vann eller fortynnede organiske syrer, uorganiske oksydasjonsmidler som kromsyre, salpetersyre, kaliumpermanganat, klor, brom, halogenoksygen-syrer, som underklorsyrling, klorsyrling, klorsyre eller over-klorsyre, tert.-butylhypoklorit metylhypoklorit, tert.-butyl-kromat, organiske N-halogenforbindelser som N-klorsukksinimid, N-bromsukksinimid samt N-halogensulfonsyreamider eller N-halo-genkarboksylsyreamider.
Ved tilsvarende, litteraturkjente valg av reak-sjonsbetingelser kan oksydasjonspotensialet innstilles tilsvarende og reaksjonen styres for fremstilling av sulfoksyder resp. sulfoner.
c 5 Eksempler på eventuelt substituert, alkenyl R- 3 og R i formel II er rettkjedet og forgrenet alkenyl med fortrinnsvis 2 - 6 og helst 2-4 C-atomer. Eksempler er eventuelt substituert etenyl, propeny1-(1), propenyl-(2) og butenyl-(3)•
Eksempler på eventuelt substituert alkenyl R-^ og R med formel III er .rettkjedet eller forgrenet alkinyl med 2-6 eller helst 2-4 C-atomer. Særlige eksempler er eventuelt substituert etinyl, propinyl-(1), propinyl-(2) og butinyl-(3).
Eventuelt substituert alkoksy R<2>, R^3 R^, R^ i - —" formel II og III kan være rettkjedet eller forgrenet alkoksy med fortrinnsvis 1 - 6 og helst 1-4 C-atomer. Eksempler er eventuelt substituert metoksy, etoksy, n- og i-propoksy og n-3i- og t-butoksy.
Eksempler på eventuelt substituert alkyltio R 2 , R<3>
i formel II kan være rettkjedet eller forgrenet alkyltio med 1 - .6'og helst 1-4 C-atomer. Eksempler er eventuelt substituert metyltio, etyltio, n- og i-propyltio3n-3i- og t-butyltio.
Eksempler på'eventuelt substituert acyl R 2 og R^3
1 formel II er acyl med 1 - 63og særlig 2 - 43 C-atomer3som formyljacetyl, propionyl, n-butyryl, -i-butyryl. Eksempler på eventuelt substituert karbalkoksy R 2, R^ i formel II er rettkjedet eller forgrenet karbalkoksy med 2 - 7 og helst 2-5 C-atomer, som eventuelt substituert karbometoksy, karboetoksy, karbo-n- og -i-propyloksy og karbo-n-3-i- og -t-butyloksy.
Halogenalkyl R 2 og ~ Ry 3 med formel II inneholder fortrinnsvis 1 - 43og særlig 1 eller 2 C-atomer, og fortrinnsvis 1-5, særlig 1-3, like eller forskjellige halogenatomer, idet man som halogenatomer fortrinnsvis bruker fluor, klor og brom, særlig fluor og klor. Eksempler er trifluormetyl, klor-di-fluormety1, brommetyl, 2,2,2-trifluoretyl og pentafluoretyl.
Som halogen R 2 , R^ 3i formel II står fortrinnsvis fluor, klor, brom eller jod, særlig fluor, klor og brom. 4 6 Eksempler på eventuelt substituert aryl R og R i formel II og III er aryl med fortrinnsvis 6 eller fortrinnsvis 6-10 C-atomer i aryldelen. Eksempler er eventuelt substituert fenyl eller naftyl. Eksempler på eventuelt substituert aralkyl R 4 og R^ i formel.III er aralkyl med fortrinnsvis 6 - 10 og særlig 6 C-atomer i aryldelen, hvor aryldelen og/eller alkyldelen eventuelt er substituert, og med fortrinnsvis 1 - 4 og særlig I eller 2 C-atomer i alkyldelen, hvor alkyldelen kan være rettkjedet eller forgrenet.
Eksempler er eventuelt substituert benzyl og fenyl-etyl.
Som eventuelt substituert cykloalkyl R 4 , R 6i - formel II og III står mono-, bi- og tri-cyklisk cykloalkyl med fortrinnsvis 3 - 10 og særlig 3, 5 eller 6 C-atomer. Eksempler er eventuelt substituert cyklopropyl, cyklobutyl, cyklopentyl., cykloheksyl, cykloheptyl, bicyklo-[.2 , 2 ,1] -heptyl,' bicyklo-[2,2,2]-okty1 og adamantyl.
Eksempler på eventuelt substituert alkenyloksy R^ i formel III er rettkjedet eller forgrenet alkenyloksy med 2-6 eller helst 2-4 C-atomer, som eventuelt substituert etenyl-oksy, propenyl-(1)-oksy, propeny1-(2)-oksy og butenyl-(3)-oksy.
Eksempler på eventuelt substituert alkinyloksy R^ i formel III er rettkjedet eller forgrenet alkinyl med fortrinnsvis 2 - 6, og særlig 2-4 C-atomer, som eventuelt substituert etinyloksy, propinyl-(1 )-oksy, propinyl-(2)-oksy og butinyl-(3)_oksy.
Som alkyl R' i formel III står fortrinnsvis metyl eller etyl. 2 3 4 5 6 Som substituenter for restene R" , R , R,, R^ og R kommer særlig følgende i betraktning: acyl med fortrinnsvis 2-4 C-atomer, karboalkoksy med 2-4 C-atomer, alkoksyalkyl med 1-4 C-atomer i alkoksy- og i alkyl-delen, aralkyl med fortrinnsvis 1-4 C-atomer i alkyldelen og fortrinnsvis 6 C-atomer i aryldelen.
Særlig foretrekkes forbindelser med formel I hvor
R og R^ betegner hydrogen, metyl, etyl, n-butyl, metoksy, etoksy, fluor, klor, brom, cyan, metylmerkapto, trifluormetyl, acetyl,•propionyl, acetylamino, karbometoksy-amino,
R ii betegner metyl, etyl, propyl, n-butyl, i-butyl, n-pentyl, n-heksyl, cyklopentyl, cykloheksyl, fenyl, benzyl,
metoksymetyljmetoksy, etoksy, fenoksymety1, metylamino,
etylamino, n-butylamino, n-cyanpentylamino, B-metoksyetyl-
amino,
R-^ betegner metyl, etyl, i-propyl, sek.-butyl, propeny1-(2), propinyl,
R^ betegner metyl, etyl, propyl, isopropyl, n-amyl, isoamyl, h-butyl, cykloheksyl, benzyl, metoksymetyl, fenoksy-
metyl, allyl, krotyl, metallyl, metoksy, etoksy-i-propoksy, sek. -butyloksy , propenyl-( 2 )-oksy , propinyl-( 2 )-oksy , 2-metyl— propenyl-(2)-oksy.
Tioureaforbindelsene som brukes som utgangsstoffer
er definert med formel III. De er delvis kjent (se Olin og Dains,. J. Amer. chem. Soc. 52, 3326 (1930) samt U.S. patent
2.993.502) og kan forøvrig lett fremstilles i analogi med kjente metoder. For deres, fremstilling går man i alminnelig-
het ut fra kjente N-acyltioureaforbindelser (se f.eks. Berichte der deutschen Chemischen Gesellschaft, 6, 755 (1873), Ann.
chim. (5) 11, 313 (1877 ), J. Amer. Chem. Soc. 62_, 3274 (1940))
som man på' likeledes kjent måte omsetter med alkyleringsmidler som alkylhalogenider, -sulfater og -sulfonater til de tilsva-
rende S-alkyl-N-acyl-iso-tiourea-produkter (se f.eks. J. org.
Chem. 30, 560, (1965), Chem. Pharm. Bull (Tokio), 9, 245,
(1961) ). Disse S-alkyl-N-acyl-isotiourea-forbindelser kan
derpå omsettes med halogenmaursyreestere eller med pyrokull-syre-dialkylestere (se Ber. dtsch. chem. Ges. 71, 1797 (1938))
til S-alkyl-N-acyl-N'-alkoksykarbony1-isotiourea-forbindelser.
Denne siste reaksjon tilsvarer prinsippet til den
kjente substitusjon av S-alkyl-isotiourea-forbindelser med klormaursyrealkylestere (se J. Amer. chem. Soc. 5_2 3 3326
(1930)).
Som eksempler på isotiourea-forbindelser som kan
benyttes ifølge oppfinnelsen nevnes: N,N'-bis-metoksykarbonyl-S-metyl-isotiourea (sm.p. 99-100°C), N,N'-bis-etoksykarbonyl-S-metyl-isotiourea (sm.p. 50-51°C), N-etoksykarbonyl-N'-propionyl-S-metyl-isotiourea (sm.p. 92-
94°C),
N-metoksykarbonyl-N'-propionyl-S-metyl-isotiourea (sm.p. 97
99°C),
N-metoksykarbonyl-N'-etoksyacetyl-S-metyl-isotiourea (sm.p.
69-70°C)
N-metoksykarb ony1-N'-cykloheksylkarbony1-S-mety1-isotiourinstoff
(sm.p. 67-68°C),
N-metoksykarbonyl-N1 -fenylacety1-S-mety1-isotiourinstoff (sm.p.
55-56°C)3
N-etoksykarbonyl-N^-benzoyl-S-metyl-isotiourinstoff (sm.p. 79~
80°C)3
N-etoksykarbonyl-N'-metoksykarbonyl-S-metyl-isotiourinstoff (sm.p. 69°C).. N-allyloksykarbonyl-N'-metoksykarbony1-S-mety1-isotiourinstoff. N-propinyloksykarb ony1-N'-metoksykarbony1-S-mety1-isotiourin-
stoff.
N,N'-bis-allyloksykarbony1-S-mety1-isotiourinstoff.
Nj N'-bis-propinyloksykarbony1-S-mety1-isotiourinstoff.
De 2-aminoanilider som brukes som utgangsstoffer
er delvis ukjente. De kan lett fremstilles i analogi med litteraturkjente metoder.
Således kan man f.eks. fremstille 2-amino-5-fenoksy-butyranilid ut fra det kjente 2-nitro-5~fenoksy-anilin ved acy-
lering med butyrylklorid til 2-nitro-5-fenoksy-butyranilid og derpå ved følgende katalytiske hydrogenering:
Penylsulfinylanilider kan på forøvrig kjent måte fremstilles ved oksydasjon av fenyltio-anilider med H^C^ i acetanhydrid eller med benzopersyre i dioksan eller kloroform, f.eks.
Ved oksydasjon med H^C^i iseddik ved forhøyet temperatur får man fenylsulfonylanilider, f.eks.
Enkelte fenylsulfonylaniliner lar seg fremstille ved omsetning av benzensulfinsurt natrium med 2-nitro-5_klor-anilin i henhold til følgende ligning:
Som eksempler på utgangsstoffer av typen 2-aminoanilider nevnes: 2-amino-5-fenoksy-acetanilid
2-amino-5~fenoksy-propionanilid
2-amino-5-fenoksy-butyranilid
2-amino~5-fenoksy-iso-butyrani lid
2-amino-5_fenoksy-valeranilid 2-amin0-5-fenoksy-iso-valeranilid
2-amino-5-fenoksy-kapronanilid
2-amino-5-fenoksy-iso-kaproanilid
2-amino-5-fenoksy-cyklopentankarbonanilid
2-Amino-5-phenoxy-cyclohexancarbonanilid 2-Amino-5-phenoxy-phenylacetanilid 2-Amino-5-phenoxy-phenoxyacetanilid 2-Amino-5-phenoxy-benzanilid
N-(2-Amino-5-phenoxy-phenyl)-N'-methyl-harnstoff N-(2-Amino-5-phenoxy-phenyl)-N'-åthyl-harnstoif N-(2-Amino-5-phenoxy-phenyl)-N'-butyl-harnstoff N-(2-Amino-5-phenoxy-phenyl)-N'- CO -cyanpentyl-harnstoff N-(2-Amino-5-phenoxy-phenyl)-N'-B-methoxyåthyl-harnstof f N-(2-Amino-5-phenoxy-phenyl)-N'-benzyl-harnstoff N-(2-Amino-5-pheno.<y-phenyl) -N ' -phenyl-harnstoff 2-Amino-5-(4-methyl-phenoxy)-propionanilid
2-Amino-5-(4-methyl-phenoxy)-butyranilid 2-Amino-5-(4-methyl-phenoxy)-acetanilid 2-Amino-5-(3-methyl-phenoxy)-propionanilid 2-Amino-5-(3-methyl-phenoxy)-butyranilid 2-Araino-5-(3-methyl-phenoxy)-acetanilid 2-Amino-5-(2-methyl-phenoxy)-propionanilid 2-Amino-5-(2-methyl-phenoxy)-butyranilid 2-Amino-5-(2-methyl-phenoxy)-acetanilid 2-Amino-5-(4-chlor-phenoxy)-propionanilid 2-Amino-5-(4-chlor-phenoxy)-butyranilid 2-Amino-5-(4-chlor-phenoxy)-acetanilid 2-Amino-5-(3-chlor-phenoxy)-propionanilid
2-;\mino-5-(3-chlor-phenoxy) -butyranilid 2-Amino-5-(3-chlor-phenoxy)-acetanilid 2-Amino-5-(2-chlor-phenoxy)-propionanilid 2-Amino-5-(2-chlor-phenoxy)-butyranilid 2-Amino-5-(2-chlor-phenoxy)-acetanilid 2-Amino-5-(4-methoxy-phenoxy)-propionanilid 2-Amino-5-(4-methoxy-phenoxy)-butyranilid 2-Amino-5- (A--me thoxy-phenoxy) -acetanilid 2-Amino-5-(3-methoxy-phenoxy)-propionanilid 2-Amino-5-(3-methoxy-phenoxy)-butyranilid 2-Amino-5-(3-methoxy-phenoxy)-acetanilid
2-Amino-5 -(4-methylthio-phenoxy)-propionanilid 2-Amino-5-(4-methylthio-phenoxy)-butyranilid 2-Amino-5-(4-methylthio-phenoxy)-acetanilid 2-vmino-5- (3-m.ethylthio-phenoxy) -propionanilid 2-Amino-5-(3-methylthio -phenoxy)-butyranilid 2-Amino-5-(3-methylthio-phenoxy)-acetanilid 2-Amino-5-(4-cyan-phenoxy)-propionanilid 2-Amino-5-(4-cyan-phenoxy)-butyranilid 2-Amino-5-(4-cyan-phenoxy)-acetanilid
2-Amino-5-(3-cyan-phenoxy)-propionanilid 2-Amino-5-(3-cyan-phenoxy)-butyranilid 2-Amino-5-(3-cyan-phenoxy)-acetanilid 2-Amino-5- ('4-acetyl-phenoxy) -propionanilid
.2-Amino-5-(4-acetyl-phenoxy)-butyranilid 2-Amino-5-(4-acetyl-phenoxy)-acetanilid 2-Amino-5-(4-propionyl-phenoxy)-propionanilid 2-Amino-5-(4-propionyl-phenoxy)-butyranilid 2-Amino-5-(4-propionyl-phenoxy)-acetanilid 2-Amino-5-(4-acetylamino-phenoxy)-propionanilid 2-Amino-5-(4-acetylamino-phenoxy)-butyranilid 2-Amino-5-(4-acetylamino-phenoxy)-acetanilid 2-Amino-5- (4-methoxycarbonylamino-phenoy.y) -propionanilid 2-Amino-5-(4-methoxycarbonylamino-phenoxy)-butyranilid 2-Amino-5-(4-methoxycarbonylamino-phenoxy)-acetanilid 2-Amino-5-(4-arethoxycarbonyl-phenoxy)-propionanilid
2-Amino-5-(4-methoxycarbonyl-phenoxy)-butyranilid 2-Amino-5-(4-methoxycarbonyl-phenoxy)-acetanilid 2-Amino-5-(3,4-dimethyl-phenoxy)-propionanilid 2-Amino-5-(3,4-dimethyl-phenoxy)-butyranilid 2-Aminc-5-(3,4-dimethyl-phenoxy)-acetanilid 2-Amino-5-(2-methyl-4-chlor-phenoxy)-propionanilid 2-Amino-5-(2-methyl-4-chlor-phenoxy)-butyranilid 2-Amino-5-(2-methy1-4-chlor-phenoxy)-acetanilid 2-Amino-5-(4-athyl-phenoxy)-propionanilid 2-Amino-5-(4-åthyl-phenoxy)-butyranilid
2-Amino-5 - (4-athyl-phenoxy)-acetanilid 2-Amino-5-(3,4-dichlor-phenoxy)-propionanilid 2-Amino-5-(3,4-dichlor-phenoxy)-butyranilid 2 -Amino-5 -(3., 4-dichlor-phenoxy)-acetanilid
2-Amino-5-(A-brom-phenoxy)-propionanilid 2-Amino-5-(4-brom-phenoxy)-butyranilid 2-Amino-5-(4-brom-phenoxy)-acetanilid 2-Amino-5-(3,5-dimethyl-phenoxy)-propionanilid 2-Amino-5-(3,5-dimethyl-phenoxy)-butyranilid 2-Amino-5-(3,5-dimethyl-phenoxy)-acetanilid 2-AminoT5-(4-butyl-phenoxy)-propionanilid 2-Amino-5-(4-butyl-phenpxy)-butyranilid 2-Amino-5-(4-butyl-phenoxy)-acetanilid 2-Amino-5-(3-butyl-phenoxy)-propionanilid 2-Amino-5-(3-butyl-phenoxy)-butyranilid 2-Amino-5-(3-butyl-phenoxy)-acetanilid 2-Amino-4-phenoxy-acetanilid
2-Amino-4-phenoxy-propionanilid
2-Amino-4-phenoxy-butyranilid
2-Amino-4-phenoxy-iso-butyranilid 2-Amino-4-phenoxy-valeranilid
2-Amino-4-phenoxy-iso-valeranilid
2-Amino-4-phenoxy-capronanilid
2-Amino-4-phenoxy-iso-capronanilid 2-Amino-4-phenoxy-cyclopentancarbonanilid 2-Amino-4-phenoxy-cyclohexancarbonanilid 2-Amino-4-phenoxy-phenylacetanilid 2-Amino-4-phenoxy-phenoxyacetanilid 2-Amino-4-phenoxy-benzanilid
N-(2-Amino-4-phenoxy-phenyl)-N<1->methyl-harnstoff N-(2-Amino-4-phenoxy-phenyl)-N'-athyl-harastof f N-(2-Amino-4-phenoxy-phenyl)-N'-butyl-harnstoff N-(2-Amino-4-phenoxy-phenyl)-N1 - Co -cyanpentyl-harnstoff N-(2-Araino-4-phenoxy-phenyl)-N'-fl-methoxyåthyl-harnstoff N-(2-Amino-4-phenoxy-phenyl)-N'-benzyl-harnstoff
N-(2-Amino-4-phenoxy-phenyl)-N'-phenyl-harnstoff
2-Amino-4-(4-methyl-phenoxy)-propionanilid 2-Amino-4-(4-methyl-phenoxy)-butyranilid 2-Amino-4-(4-'methyl-phenoxy) -acetanilid 2-Amino-4-(3-methyl-phenoxy)-propionanilid 2-Amino-4-(3-methyl-phenoxy)-butyranilid 2-Amino-4-(3-methyl-phenox'y) -acetanilid 2-Amino-4-(2-methyl-phenoxy)-propionanilid 2-Amino-4-(2-methyl-phenoxy)-butyranilid 2-Amino-4-(2-methyl-phenoxy)-acetanilid 2-Amino-4-(4-chlor-phenoxy)-propionanilid 2-Amino-4-(4-chlor-phenoxy)-butyranilid 2-Amino-4-(4-chlor-phenoxy)-acetanilid 2-Amino-4-(3-chlor-phenoxy)-propionanilid 2-Amino-4-(3-chlor-phenoxy)-butyranilid 2-Amino-4-(3-chlor-phenoxy)-acetanilid 2-Amino-4-(2-chlor-phenoxy)-propionanilid 2-Amino-4-(2-chlor-phenoxy)-butyranilid 2-Amino-4-(2-chlor-phenoxy)-acetanilid 2-Amino-4-(4-methoxy-phenoxy)-propionanilid 2-Amino-4-(4-methoxy-phenoxy)-butyranilid 2-Amino-4-(4-methoxy-phenoxy)-acetanilid 2-Amino-4-(3-methoxy-phenoxy)-propionanilid 2-Amino-4-(3-methoxy-phenoxy)-butyranilid 2-Amino-4-(3-methoxy-phenoxy)-acetanilid 2-Amino-4-(4-methylthio-phenoxy)-propionanilid 2-Amino-4-(4-methylthio-phenoxy)-butyranilid 2-Amino-4-(4-methylthio-phenoxy)-acetanilid 2-Amino-4-(3-methylthio-phenoxy)-propionanilid
2-Amino-4-(3-methylthio-phenoxy)-butyranilid 2-Amino-4-(3-methylthio-phenoxy)-acetanilid 2-Amino-4-(4-cyan-phenoxy)-propionanilid
2-Amino-4-(4-cyan-phenoxy)-butyranilid 2-Amino-4-(4-cyan-phenoxy)-acetanilid
. 2-Amino-4-(3-cyan-phenoxy)-propionanilid 2-Amino-4-(3-cyan-phenoxy)-butyranilid 2-Amino-4-(3-cyan-phenoxy)-acetanilid 2-Amino-4-(4-acetyl-phenoxy)-propionanilid 2-Amino-4-(4-acetyl-phenoxy)-butyranilid 2-Amino-4-(4-acetyl-phenoxy)-acetanilid 2-Amino-4-(4-propionyl-phencxy)-propionanilid 2-Amino-4-(4-propionyl-phenoxy)-butyranilid 2-Amino-4-(4-propionyl-phenoxy)-acetanilid 2-Amino-4- ( 4-acetylarnino-phenoxy) -propionanilid 2-Amino-4-(4-acetylamino-phenoxy)-butyranilid 2-Amino-4-(4-acetylamino-phenoxy)-acetanilid 2-Amino-4-(4-methoxycarbonylamino-phenoxy)-propionanilid 2-Amino-4-(4-methoxycarbonylamino-phenoxy)-butyranilid '2-Amino-4-(4-methoxycarbonylamino-phenoxy)-acetanilid 2-Amino-4-(4-methoxycarbonyl-phenoxy)-propionanilid
2-Amino-4-(4-methoxycarbonyl-phenoxy)-butyranilid 2-Amino-4-(4-methoxycarbonyl-phenoxy)-acetanilid 2-Amino-4-(3,4-dimethyl-phenoxy)-propionanilid 2-Amino-4-(3,4-dimethyl-phenoxy)-butyranilid 2-Amino-4-(3,4-dimethyl-phenoxy)-acetanilid 2-Amino-4-(2-methyl-4-chlor-phenoxy)-propionanilid 2-Araino-4-(2-methyl-4-chlor-phenoxy)-butyranilid 2-Amino-4-(2-raethyl-4-chlor-phenoxy)-acetanilid 2-Amino-4-(4-athyl-phenoxy)-propionanilid 2-Amino-4-(4-åthyl-phenoxy)-butyranilid 2-Amino-4-(4-athyl-phenoxy)-acetanilid 2-Amino-4-(3,4-dichlor-phenoxy)-propionanilid 2-Amino-4-(3,4-dichlor-phenoxy)-butyranilid 2-Amino-4-(3,4-dichlor-phenoxy)-acetanilid 2-Amino-4-(4-brom-phenoxy)-propionanilid, 2-Amino-4-(4-brora-phenoxy)-butyranilid 2-Amino-4-(4-brom-phenoxy)-acetanilid 2-Amino-4-(3,5-dimethyl-phenoxy)-propionanilid 2-Amino-4-(3,5-dimethyl-phenoxy)-butyranilid 2-Amino-4-(3,5-dimethyl-phenoxy)-acetanilid
2-Amino-A-( U-butyl-phenoxy)-propionanilid 2-Amino-4-(4-buty1-phenoxy)-butyranilid 2-Amino-4-(A-butyl-phenoxy)-acetanilid 2-Amino-A-(3-butyl-phenoxy)-propionanilid 2-Amino-A -(3-buty1-phenoxy)-butyranilid 2-Amino-A-(3-butyl-phenoxy)-acetanilid 2-Amino-5-phenylthio-acetanilid 2-Amino-5-phenylthio-propionanilid
2-Amino-5-phenylthio-butyranilid
2-Amino-5-phenylthio-iso-butyranilid 2-Amino-5-phenylthio-valeranilid
2-Amino-5-phenylthio-iso-valeranilid 2-Aminb-5-phenylthio-capronanilid
2-Amino-5-phenylthio-iso-capronanilid 2-Amino-5-phenylthio-cyclopentancarbonanilid 2-Amino-5-phenylthio-cyclohexancarbonanilid 2-Amino-5-phenylthio-phenylacetanilid 2-Amino-5-phenylthio-phenoxyacetanilid 2-Amino-5-phenylthio-benzanilid
N-(2-Amino-5-phenylthio-phenyl)-N'-methyl-harnstoff N-(2-Amino-5-phenylthio-pheny1)-N<1->athyl-harnstoff N-(2-Amino-5-phenylthio-phenyl)-N'-butyl-harnstoff N-(2-Amino-5-phenylthio-phenyl)-N'- CJ -cyanpentyl-harnstoff M-(2-Amino-5-phenylthio-phenyl)-N'-3-methoxyathyl-harnstoff N-(2-Amino-5-phenylthio-phenyl)-N'-benzyl-harnstoff N-(2-Amino-5-phenylthio-phenyl)-N'-phenyl-harnstoff 2-Amino-5-(A-methyl-phenylthio)-propionanilid
2-Amino-5-(A-methyl-phenylthio)-butyranilid 2-Amino-5-(A-methyl-phenylthio)-acetanilid 2-Amino-5-(3-methyl-phenylthio)-propionanilid 2-Amino-5-(3-methyl-phenylthio)-butyranilid 2-Amino-5-(3-methyl-phenylthio)-acetanilid 2-Amino-5-(2-methyl-phenylthio)-propionanilid 2-Amino-5-(2-methyl-phenylthio)-butyranilid 2-Amino-5 -(2-methyl-phenylthio)-acetanilid
2-Amino-5-(4-chlor-phenylthio)-propionanilid 2-Amino-5-(4-chlor-phenylthiq)-butyranilid 2-Amino-5-(4-chlor-phenylthio)-acetanilid 2-Amino-5-(3-chlor-phenylthio)-propionanilid 2-Amino-5-(3-chlor-phenylthio)-butyranilid 2-Amino-5-(3-chlor-phenylthio)-acetanilid 2-Amino-5-(2-chlor-phenylthio)-propionanilid 2-Amino-5-(2-chlor-phenylthio)-butyranilid 2-Amino-5-(2-chlor-phenylthio)-acetanilid 2-Amino-5-(4-methoxy-phenylthio)-propionanilid 2-Amino-5-(4-methoxy-phenylthio)-butyranilid 2-Amino-5-(4-methoxy-phenylthio)-acetanilid 2-Amino-5-(3-methoxy-phenylthio)-propionanilid 2-Amino-5-(3-methoxy-phenylthio)-butyranilid 2-Amino-5-(3-methoxy-phenylthio)-acetanilid 2-Amino-5-(4-methylthio-phenylthio)-propionanilid 2-Amino-5-(4-methylthio-phenylthio)-butyranilid 2-Amino-5-(4-methylthio-phenylthio)-acetanilid 2-Amino-5-(3-methylthio-phenylthio)-propionanilid 2-Amino-5-(3-methylthio-phenylthio)-butyranilid 2-Amino-5-(3-methylthio-phenylthio)-acetanilid 2-Amino-5-(4-cyan-phenylthio)-propionanilid 2-Amino-5-(4-cyan-phenylthio)-butyranilid 2-Amino-5-(4-cyan-phenylthio)-acetanilid 2-Amino-5-(3-cyan-phenylthio)-propionanilid 2-Amino-5-(3-cyan-phenylthio)-butyranilid 2-Amino-5-(3-cyan-phenylthio)-acetanilid 2-Amino-5-(4-acetyl-phenylthio)-propionanilid 2-Amino-5-(4-acetyl-phenylthio)-butyranilid 2-Amino-5-(4-acetyl-pheny1thio)-acetanilid 2-Amino-5-(4-propionyl-phenylthio)-propionanilid 2-Amino-5-(4-propiohyl-phenylthio)-butyranilid 2-Amino-5-: (4-pr. opi onyl-phe ny lthio) -acetanilid 2-Amino-5-(4-acetylamino-phenylthio)-propionanilid 2-Amino-5-(4-acetylamino-phenylthio)-butyranilid 2-Amino-5-(4-acetylamino-phenylthio)-acetanilid 2-Amino-5-(4-methoxycarbonylamino-phenylthio)-propionanilid 2-Amino-5-(4-methoxycarbonylamino-phenylthio)-butyranilid 2-Amino-5-(4rmethoxycarbonalamino-phenylthio)-acetanilid 2-Amino-5-(4-methoxycarbonyl-phenyIthio)-propionanilid
2-Amino-5-(4-metho^ycarbonyl-phenylthio)-butyranilid 2-Amino-5-(4-metho^ycarbonyl-phenylthio)-acetanilid 2-Amino-5-(3,4-dimethyl-phenylthio)-propionanilid
,2-Amino-5-(3,4-dimethyl-phenylthio)-butyranilid 2-Amino-5-(3,4-dimethyl-phenylthio)-acetanilid 2-Amino-5-(2-methyl-4-chlor-phenylthio)-propionanilid 2-Amino-5-(2-methyl-4-chlor-phenylthio)-butyranilid 2-Amino-5-(2-methyl-4-chlor-phenylthio)-acetanilid 2-Amino-5-(4-athyl-phenylthio)-propionanilid 2-Amino-5-(4-åthyl-phenylthio)-butyranilid 2-Arnino-5- (4-athyl-phenylthio) -acetanilid 2-Amino-5-(3,4-dichlor-phenylthio)-propionanilid 2-Amino-5-(3,4-dichlor-phenylthio)-butyranilid 2-Amino-5-(3,4-dichlor-phenylthio)-acetanilid 2-Amino-5-(4-brom-phenylthio)-propionanilid 2-Amino-5-(4-brom-phenylthio)-butyranilid 2-Amino-5-(4-brom-phenylthio)-acetanilid 2-Amino-5-(3,5-dimethyl-phenylthio)-propionanilid 2-Amino-5-(3,5-dimethyl-phenylthio)-butyranilid 2-Amino-5-(3,5-dimethyl-phenylthio)-acetanilid 2-Amino-5-(4-butyl-pheny1thio)-propionanilid 2-Amino-5-(4-butyl-phenylthio)-butyranilid 2-Amino-5-(4-butyl-phenylthio)-acetanilid 2-Amino-5-(3-butyl-phenylthio)-propionanilid 2-Amino-5-(3-butyl-phenylthio)^butyranilid 2-Amino-5-(3-butyl-phenylthio)-acetanilid 2-Amino-4-phenylthio-acetanilid
2-Amino-4-phenylthio-propionanilid
2-Amino-4-phenylthio-butyranilid
2-Amino-4-phenylthio-iso-butyranilid
2-Amino-4-phenylthio-valeranilid
2-Amino-4-phenylthio-iso-valeranilid 2-Amino-4-phenylthio-capronanilid
2-Amino-4-pheny1thio-iso-capronanilid 2-Amino-4-phenylthio-cyclopentancarbonanilid 2-Amino-4-phenylthio-cyclohexancarbonanilid 2-Amino-4-phenylthio-phenylacetanilid 2-Amino-4-phenylthio-phenoxyacetanilid ,2-Amino-4-phenylthio-benzanilid
N-(2-Amino-4-phenylthio-phenyl)-N'-methyl-harnstolf N-(2-Amino-4-phenylthio-phenyl) -N'' -athyl-harnstof f N-(2-Amino-4-phenylthio-phenyl)-N'-butyl-harnstoff N-(2-Amino-4-phenylthio-phenyl) -N ' - Cc7-cyanpentyl-harnstof f N-(2-Amino-4-phenylthio-phenyl)-N'-fi-methoxyåthyl-harnstoff
■N-(2-Araino-4-phenylthio-phenyl)-N'-benzyl-harnstoff N-(2-Amino-4-phenylthio-phenyl)-N'-phenyl-harnstoff 2-Amino-4-(4-methyl-phenylthio)-propionanilid
2-Amino-4-(4-methyl-phenylthio)-butyranilid 2-Amino-4-(4-methyl-phenylthio)-acetanilid 2-Amino-4-(3-methyl-phenylthio)-propionanilid 2-Amino-4-(3-methyl-phenylthio)-butyranilid 2-Amino-4-(3-methyl-phenylthio)-acetanilid 2-Amino-4-(2-methyl-phenylthio)-propionanilid 2-Amino-4-(2-methyl-phenylthio)-butyranilid 2-Amino-4-(2-methyl-phenylthio)-acetanilid 2-Amino-4-(4-chlor-phenylthio)-propionanilid 2-Amino-4-(4-chlor-phenylthio)-butyranilid 2-Amino-4-(4-chlor-phenylthio)-acetanilid 2-Amino-4-(3-chlor-phenylthio)-propionanilid 2-Amino-4-(3-chlor-phenylthio)-butyranilid 2-Amino-4-(3-chlor-phenylthio)-acetanilid 2-Amino-4-(2-chlor-phenylthio)-propionanilid 2-Amino-4-(2-chlor-phenylthio)-butyranilid 2-Amino-4-(2-chlor-phenylthio)-acetanilid 2-Amino-4-(4-methoxy-phenylthio)-propionanilid
2-Amino-4-(4-methoxy-phenylthio)-butyranilid 2-Amino-4-(4-methoxy-phenylthio)-acetanilid 2-Amino-4-(3-methoxy-phenylthio)-propionanilid 2-Amino-4-(3-methoxy-phenylthio)-butyranilid 2-Amino-4-(3-methoxy-phenylthio)-acetanilid 2-Amino-4-(4-methylthio-phenylthio)-propionanilid
2-Amino-4-(4-methylthio-phenylthio)-butyranilid 2-Amino-4-(4-methylthio-phenylthio)-acetanilid 2-Amino-4-(3-methylthio-phenylthio)-propionanilid 2-Amino-4-(3-methylthio-phenylthio)-butyranilid 2-Amino-4-(3-methylthio-phenylthio)-acetanilid'2-Amino-4-(4-cyan-phenylthio)-propionanilid 2-Amino-4-(4-cyan-phenylthio)-butyranilid 2-Amino-4-(4-cyan-phenylthio)-acetanilid 2-Amino-4-(3-cyan-phenylthio)-propionanilid 2-Amino-4-(3-cyan-phenylthio)-butyranilid 2-Amino-4-(3-cyan-phenylthio)-acetanilid 2-Amino-4-(4-acetyl-phenylthio)-propionanilid 2-Amino-4-(4-acety1-phenylthio)-butyranilid 2-Amino-4-(4-acety1-phenylthio)-acetanilid 2-Amino-4-(4-propionyl-phenylthio)-propionanilid - 2-Amino-4-(4-propiony1-phenylthio)-butyranilid 2-Amino-4-(4-propionyl-phenylthio)-acetanilid 2-Amino-4-(4-acetylamino-phenylthio)-propionanilid 2-Amino-4-(4-acetylamino-phenylthio)-butyranilid 2-Amino-4-(4-acetylamino-phenylthio)-acetanilid 2-Amino-4-(4-methoxycarbonylamino-phenylthio)-propionanilid 2-Amino-4-(4-methoxycarbonylamino-phenylthio)-butyranilid 2-Amino-4-(4-methoxycarbonylamino-phenylthio)-acetanilid 2-Amino-4-(4-methoxycarbonyl-phenylthio)-propionanilid 2-Amino-4-(4-methoxycarbonyl-phenylthio)-butyranilid
2-Amino-4-(4-methoxycarbony1-phenylthio)-acetanilid 2-Amino-4-(3,4-dimethyl-phenylthio)-propionanilid 2-Amino-4-(3,4-dimethyl-phenylthio)-butyranilid 2-Amino-4~(3,4-dimethyl-phenylthio)-acetanilid
2-Amino-4-(2-arethyl-4-chlor-phenylthio)-propionanilid 2-Amino-4-(2-methyl-4-chlor-phenylthio)-butyranilid 2-Amino-4-(2-methyl-4-chlor-phenylthio)-acetanilid 2-Amino-4-(4-athyl-phenylthio)-propionanilid 2-Amino-4-(4-athyl-phenylthio)-butyranilid 2-Amino-4-(4-åthy1-phenylthio)-acetanilid 2-Amino-4-(3,4-dichlor-phenylthio)-propionanilid 2-Amino-4-(3,4-dichlor-phenylthio)-butyranilid 2-Amino-4-(3,4-dichlor-phenylthio)-acetanilid 2-Amino-4-(4-brom-phenylthio)-propionanilid 2-Amino-4-(4-brom-phenylthio)-butyranilid 2-Amino-4-(4-brom-phenylthio)-acetanilid 2-Amino-4-(3,5-dimethyi-phenylthio)-propionanilid 2-Amino-4-(3,5-dimethyl-phenylthio)-butyranilid 2-Amino-4-(3,5-dimethyl-phenylthio)-acetanilid 2-Amino-4-(4-butyl-phenylthio)-propionanilid 2-Amino-4-(4-buty1-phenylthio)-butyranilid 2-Amino-4-(4-butyl-phenylthio)-acetanilid 2-Amino-4-(3-butyl-phenylthio)-propionanilid 2-Amino-4-(3-butyl-phenylthio)-butyranilid ■ 2-Amino-4-(3-butyl-phenylthio)-acetanilid 2-Amino-5-phenylsulfinyl-acetanilid
2 -Amino-5-phenylsulfinyl-propionanilid 2-Amino-5-phenylsulfinyl-butyranilid 2-Amino-5-pheny1sulfinyl-iso-butyranilid
.2-Amino-5-phenylsulfinyl-valeranilid 2-Amino-5-phenylsulfinyl-iso-valeranilid 2-Amino-5-phenylsulfinyl-capronanilid 2-Amino-5-phenylsulfinyl-iso-capronanilid 2-Amino-5-phenylsulfinyl-cyclopentancarbonanilid 2-Amino-5-phenylsulfinyl-cyclohexancarbonanilid 2-Amino-5-phenylsulfinyl-phenylacetanilid 2-Amino-5-phenylsulfinyl-phenoxyacetanilid 2-Amino-5-phenylsulfinyl-benzanilid
N-(2-Amino-5-phenylsulfinyl-phenyl)-N'-methyl-harnstoff
N-(2-Amino-5-phenylsulfinyl-phenyl)-N'-athyl-harnstoff IJ- (2-Amino-5-phenylsulfinyl-phenyl) -N ' -butyl-harnstof f
.N-(2-Amino-5-phenylsulfinyl-phenyl)-N'- -cyanpentyl-harnstoff N-(2-Amino-5-phenylsulfinyl-phenyl)-N'-3-methoxyåthyl-harnstoff N-(2-Amino-5-phenylsulfinyl-phenyl)-N'-benzyl-harnstoff N-(2-Amino-5-phenylsulfinyl-phenyl)-N'-phenyl-harnstoff 2-Amino-5~(4-methyl-phenylsulfinyl)-propionanilid 2-Amino-5-^(4-me thyl-phenylsulf inyl) -butyranilid 2-Amino-5-(4-methyl-phenylsulfinyl)-acetanilid 2-Amino-5-(3-methyl-phenylsulfinyl)-propionanilid 2-Amino-5-(3-methyl-phenylsulfinyl)-butyranilid 2-Amino-5-(3-methyl-phenylsulfinyl)-acetanilid 2-Amino-5-(2-methyl-phenylsulfinyl)-propionanilid 2 T-Amino-5-(2-methy 1-phenyl sulf inyl) -butyranilid
2-Amino-5-(2-methyl-phenylsulfinyl)-acetanilid 2-Amino-5-(4-chlor-phenylsulfinyl)-propionanilid 2-Amino-5-(4-chlor-phenylsulfinyl)-butyranilid 2-Amino-5-(4-chlor-phenylsulfinyl)-acetanilid 2-Amino-5-(3-chlor-phenylsulfinyl)-propionanilid 2-Amino-5-(3-chlor-phenylsulfinyl)-butyranilid 2-Amino-5-(3-chlor-phenylsulfinyl)-acetanilid 2-Amino-5-(2-chlor-phenylsulfinyl)-propionanilid 2-Amino-5-(2-chlor-phenylsulfinyl)-butyranilid 2-Amino-5-(2-chlor-phenylsulfinyl)-acetanilid 2-Amino-5-(4-methoxy-phenylsulfinyl)-propionanilid 2-Amino-5-(4-methoxy-phenylsulfinyl)-butyranilid 2-Amino-5-(4-methoxy-phenylsulfinyl)-acetanilid 2-Amino-5-(3-methoxy-phenylsulfinyl)-propionanilid 2-Amino-5-(3-methoxy-phehylsulfinyl)-butyranilid 2-Amino-5 -(3-methoxy-phenylsulfinyl)-acetanilid 2-Amino-5-(4-methylthio-phenylsulfinyl)-propionanilid 2-Amino-5-(4-methylthio-phenylsulfinyl)-butyranilid 2-Amino-5-(4-methylthio-phenylsulfinyl)-acetanilid 2-Amino-5-(3-methylthio-phenylsulfinyl)-propionanilid 2-Amino-5-(3-arethylthio-phenylsulfinyl)-butyranilid
2-Amino-5-(3-methylthio-phenylsulfinyl)-acetanilid 2-Amino-5-(A-cyan-phenylsulfinyl)-propionanilid
2-Arnino-5-( A-c.yan-pheny lsulf inyl) -butyranilid
2-Amino-5-(A-cyan-phenylsulfinyl)-acetanilid
2-Amino-5 - (3-cyan-pheny lsulf inyl") -propionanilid
2-Amino-5-(3-cyan-phenylsulfinyl)-butyranilid 2-Amino-5-(3-cyan-phenylsulfinyl)-acetanilid
2-Amino-5-(A-acetyl-phenylsulfinyl)-propionanilid
2-Amino-5-(A-acety1-phenylsulfinyl)-butyranilid
2-Amino-5-(A-acetyl-phenylsulfinyl)-acetanilid
2-Amino-5-(A-propionyl-phenylsulfinyl)-propionanilid 2-Amino-5-(A-propiony1-phenylsulfinyl)-butyranilid 2-Amino-5-(A-propionyl-phenylsulfinyl)-acetanilid
2-Amino-5-(A-acetylamino-phenylsulfinyl)-propionanilid 2-Amino-5-(A-acetylamino-phenylsulfinyl)-butyranilid
2-Amino-5-(A-acetylamino-phenylsulfinyl)-acetanilid 2-Amino-5-(A-methoxycarbonylamino-phenylsulfinyl)-propionanilid 2-Amino-5-(A-methoxycarbonylamino-phenylsulfinyl)-butyranilid 2-Amino-5 -(A-methoxycarbonylamino-phenylsulfinyl)-acetanilid 2-Amino-5-(A-methoxycarbonyl-phenylsulfinyl)-propionanilid 2-Amino-5-(A-methoxycarbonyl-phenylsulfinyl)-butyranilid 2-Amino-5-(A-methoxycarbonyl-phenylsulfinyl)-acetanilid 2-Amino-5-(3,A-dimethy>phenylsulfinyl)-propionanilid 2-Amino-5-(3 , A-diraethyl-phenylsulf inyl)-butyranilid 2-Amino-5-(3,A-dimethytphenylsulfinyl)-acetanilid
2-Amino-5-(2-methyl-A-chlor-phenylsulfinyl)-propionanilid 2-Amino-5-(2-methyl-A-chlor-phenylsulfinyl)-butyranilid 2-Amino-5-(2-methyl-A-chlor-phenylsulfinyl)-acetanilid 2-Amino-5-(A-athyl-phenylsulfinyl)-propionanilid
2-Amino-5-(A-athyl-phenylsulfinyl)-butyranilid
2-Amino-5-(A-athyl-phenylsulfinyl)-acetanilid
2-Amino-5-(3,A-dichlor-phenylsulfinyl)-propionanilid 2-Amino-5-(3,A-dichlor-phenylsulfinyl)-butyranilid 2-Araino-5-(3,A-dichlor-phenylsulfinyl)-acetanilid
2-Amino-5-(4-brom-phenylsulfinyl)-propionanilid 2-Amino-5-(4-brom-phenylsulfinyl)-butyranilid 2-Amino-5-(4-brom-phenylsulfinyl)-acetanilid 2-Amino-5-(3,5-dimethyl-phenylsulfinyl)-propionanilid 2-Amino-5-(3,5-dimethy1-phenylsulfinyl)-butyranilid 2-Amino-5-(3,5-dimethyl-phenylsulfinyl)-acetanilid 2-Amino-5-(4-butyl-phenylsulfinyl)-propionanilid 2-Amino-5-(4-butyl-phenylsulfinyl)-butyranilid 2-Amino-5-(4-butyl-phenylsulfinyl)-acetanilid 2-Amino-5-(3-butyl-phenylsulfinyl)-propionanilid 2-Amino-5-(3-butyl-phenylsulfinyl)-butyranilid 2-Amino-5-(3-butyl-phenylsulfinyl)-acetanilid 2-Amino-4-phenylsulfinyl-acetanilid
2-Amino-4-phenylsulfinyl-propionanilid
2-Amino-4-phenylsulfinyl-butyranilid
2-Amino-4-phenylsulfinyl-iso-butyranilid
2-Amino-4-phenylsulfinyl-valeranilid
2-Amino-4-phenylsull'inyl-iso-valeranilid
2-Amino-4-phenylsulfinyl-capronanilid
2-Amino-4-phenylsulfinyl-iso-capronanilid
2-Amino-4-phenylsulfinyl-cyclopentancarbonanilid 2-Amino-4-phenylsulfinyl-cyclohexancarbonanilid 2-Amino-4-phenylsulfinyl-phenylacetanilid
2-Amino-4-phenylsulfinyl-phenoxyacetanilid
2-Amino-4-phenylsulfinyl-benzanilid
N-(2-Amino-4-phenylsulfinyl-phenyl)-N<1->methyl-harnstoff N-(2-Amino-4-phenylsulfinyl-phenyl)-N<1->åthyl-harnstpff N-(2-Amino-4-phenylsulfinyl-phenyl)-N'-butyl-harnstoff N-(2-Amino-4-phenylsulfinyl-phenyl)-N'- 6c? -cyanpentyl-harn-s-toff N-(2-Amino-4-phenylsulfinyl-phenyl)-N *-3-methoxyathyl-harnstoff N-(2-Amino-4-phenylsulfinyl-phenyl)-N<1->benzyl-harnstoff N-(2-Amino-4-phenylsulfinyl-phenyl)-N<1->phenyl-harnstoff 2-Amino-4-(4-methyl-phenylsulfinyl)-propionanilid 2-Amino-4-(4-methyl-phenylsulfinyl)-butyranilid 2-Amino-4-(4-methyl-phenylsulfinyl)-acetanilid 2-;imino-4-(3-methyl-phenylsulf inyl) -propionanilid 2-Amino-4-(3-methyl-phenylsulfinyl)-butyranilid 2-Amino-4-(3-methyl-phenylsulfinyl)-acetanilid 2-Amino-4-(2-methyl-phenyisulfinyl)-propionanilid 2-Amino-4-(2-methyl-phenylsulfinyl)-butyranilid 2-Amino-4-(2-methyI-phenylsulfinyl)-acetanilid 2-Amino-4-(4-chlor-phenylsulfinyl)-propionanilid 2-Amino-4-(4-chlor-phenylsulfinyl)-butyranilid 2-Amino-4-(4-chlor-phenylsulfinyl)-acetanilid 2-Amino-4-(3-chlor-phenylsulfinyl)-propionanilid 2-Amino-4-(3-chlor-phenylsulfinyl)-butyranilid 2-Amino-4-(3-chlor-phenylsulfinyl)-acetanilid 2-Amino-4-(2-chlor-phenylsulfinyl)-propionanilid 2-Amino-4-(2-chlor-phenylsulfinyl)-butyranilid 2-Amino-4-(2-chlor-phenylsulfinyl)-acetanilid 2-Amino-4-(4-methoxy-phenylsulfinyl)-propionanilid 2-Amino-4-(4-methoxy-phenylsulfinyl)-butyranilid 2-Amino-4-(4-methoxy-phenylsulfinyl)-acetanilid 2-Amino-4-(3-methoxy-phenylsulfinyl)-propionanilid 2-Amino-4-(3-methoxy-phenylsulfinyl)-butyranilid 2-Amino-4-(3-methoxy-phenylsulfinyl)-acetanilid 2-Amino-4-(4-methylthio-phenylsulfinyl)-propionanilid 2-Amino-4-(4-methylthio-phenylsulfinyl)-butyranilid 2-Amino-4-(4-methylthio-phenylsulfinyl)-acetanilid 2-Amino-4-(3-methylthio-phenylsulfinyl)-propionanilid 2-Amino-4-(3-methylthio-phenylsulfinyl)-butyranilid 2-Amino-4-(3-methylthio-phenylsulfinyl)-acetanilid 2-Amino-4-(4-cyan-phenylsulfinyl)-propionanilid 2-Amino-4-(4-cyan-phenylsulfinyl)-butyranilid 2-Amino-4-(4-cyan-phenylsulfinyl)-acetanilid 2-Amino-4-(3-cyan-phenylsulfinyl)-propionanilid 2-Amino-4-(3-cyan-phenylsulfinyl)-butyranilid 2-Amino-4-(3-cyan-phenylsulfinyl)-acetanilid 2-Amino-4-(4-acetyl-phenylsulfinyl)-propionanilid 2-Amino-4-(4-acetyi-phenylsulfinyl)-butyranilid 2-Amino-4-(4-acetyl-phenylsulfinyl)-acetanilid 2-Ami.no-4-(4-propionyl-phenylsulf inyl) -propionanilid 2-Amino-4-(4-propionyl-phenylsulfinyl)-butyranilid 2-Amino-4-(4-propiony1-phenylsulfinyl)-acetanilid 2-Amino-4-(4-acetylamino-phenylsulfinyl)-propionanilid-2-Amino-4-(4-acetylamino-phenylsulfinyl)-butyranilid 2-Amino-4-(4-acetylamino-phenylsulfinyl)-acetanilid 2-Amino-4-(4-methoxycarbonylamino-phenylsulfinyl)-propionanilid 2-Amino-4-(4-methoxycarbonylamino-phenylsulfinyl)-butyranilid 2-Amino-4-(4-methoxycarbonylamino-phenylsulfinyl)-acetanilid 2-Amino-4-(4-methoxycarbonyl-phenylsulfinyl)-propionanilid
2-Amino-4-(4-methoxycarbonyl-phenylsulfinyl)-butyranilid 2-Amino-4-(4-methoxycarbonyl-phenylsulfinyl)-acetanilid 2-Amino-4-(3,4-dimethyl-phenylsulfinyl)-propionanilid 2-Amino-4-(3,4-dimethyl-phenylsulfinyl)-butyranilid 2-Amino-4-(3,4-dimethyl-phenylsulfinyl)-acetanilid 2-Amino-4-(2-methyl-4-chlor-phenylsulfinyl)-propionanilid 2-Amino-4-(2-methy1-4-chlor-phenylsulfinyl)-butyranilid 2-Amino-4-(2-methyl-4-chlor-phenylsulfinyl)-acetanilid 2-Amino-4-(4-athyl-phenylsulfinyl)-propionanilid 2-Amino-4-(4-athy1-phenylsulfinyl)-butyranilid 2-Amino-4-(4-athyl-phenylsulfinyl)-acetanilid 2-Amino-4-(3,4-dichlor-phenylsulfinyl)-propionanilid 2-Amino-4-(3,4-dichlor-phenylsulfinyl)-butyranilid 2-Amino-4-(3,4-dichlor-phenylsulfinyl)-acetanilid 2-Amino-4-(4-brom-phenylsulfinyl)-propionanilid 2-Amino-4-(4-brom-phenylsulfinyl)-butyranilid 2-Amino-4-(4-brom-phenylsulfinyl)-acetanilid' 2-Amino-4-(3,5-dimethyl-phenylsulfinyl)-propionanilid 2-Amino-4-(3,5-dimethy1-phenylsulfinyl)-butyranilid 2-Amino-4-(3,5-dimethy1-phenylsulfinyl)-acetanilid 2-Amino-4-(4-butyl-phenylsulfinyl)-propionanilid 2-Amino-4-(4-butyl-phenylsulfinyl)-butyranilid 2-Amino-4-(4-butyl-phenylsulfinyl)-acetanilid 2-Amino-4-(3-butyl-phenylsulfinyl)-propionanilid
2-Amino-4r(3-butyI-phenylsulfinyl)-butyranilid
2-Amino-4-(3-butyl-phenylsulfinyl)-acetanilid
2-Amino-5-phenylsulfony1-acetanilid
2-Amino-5-phenylsulfony1-propionanilid
2-Amino-5-phenylsulfony1-butyranilid
2-Amino-5-phenylsulfonyl-iso-butyranilid 2-Amino-5-phenylsulfony1-valeranilid
2-Amino-5-phenylsulfony1-iso-valeranilid
2-Amino-5-phenylsulfonyl-capronanilid
2-Amino-5-phenylsulfonyl-iso-capronanilid
2-Amino-5-phenylsulfonyl-cyclopentancarbonanilid 2-Amino-5-phenylsulfonyl-caclohexancarbonanilid
2-Amino-5-phenylsulfonyl-phenylacetanilid
2-Amino-5-phenylsulfony1-phenoxyacetanilid
2-Amino-5-phenylsulfonyl-benzanilid
N-(2-Amino-5-phenylsulfonyl-phenyl)-N'-methyl-harnstoff N-(2-Amino-5-phenylsulfonyl-phenyl)-N'-athyl-harnstoff N-(2-Amino-5-phenylsulfonyl-phenyl)-N'-butyl-harnstoff N- (2-Amino-5-phenylsulf onyl-phenyl) -IM 1 - LO -cyanpentyl-harnstof f N-(2-Amino-5-phenylsulfonyl-phenyl)-N'-fl-methoxyåthyl-harnstoff N-(2-Amino-5-phenylsulfony1-phenyl-N'-benzyl-harnstoff N-(2-Amino-5-phenylsulfonyl-phenyl)-N'-phenyl-harnstoff 2-Amino-5-(4-methyl-phenylsulfony1)-propionanilid 2-Amino-5-(4-methyl-phenylsulfonyl)-butyranilid
2-Amino-5-(4-methyl-phenylsulfony1)-acetanilid
2-Amino-5-(3-methy1-phenylsulfonyl)-propionanilid 2-Amino-5-(3-methyl-phenylsulfonyl)-butyranilid 2-Amino-5 - (3-methy'l-phenylsulf onyl) -acetanilid
2-Amino-5-(2-methyl-phenylsulfonyl)-propionanilid 2-Amino-5-(2-methyl-phenylsulfonyl)-butyranilid
2-Amino-5-(2-methyl-phenylsulfonyl)-acetanilid
2-Amino-5-(4-chlor-phenylsulfonyl)-propionanilid 2-Amino-5-(4-chlor-phenylsulfonyl)-butyranilid
2-Amino-5-(4-chlor-phenylsulfonyl)-acetanilid
2-Amino-5-(3-chlor-phenylsulfonyl)-propionanilid 2-Amino-5-(3-chlor-phenylsulfonyl)-butyranilid 2-Amino-5-(3-chlor-phenylsulfonyl)-acetanilid 2-Amino-5-(2-chlor-phenylsulfonyl)-propionanilid 2-Amino-5-(2-chlor-phenylsulfonyl)-butyranilid 2-Amino-5-(2-chlor-phenylsulfonyl)-acetanilid 2-Amino-5-(4-methoxy-phenylsulfonyl)-propionanilid 2-Amino-5-(4-methoxy-phenylsulfonyl)-butyranilid 2-Amino-5-(4-methoxy-phenylsulfonyl)-acetanilid 2-Amino-5-(3-methoxy-phenylsulfonyl)-propionanilid 2-Amino-5-(3-methoxy-phenylsulfonyl)-butyranilid 2-Amino-5-(3-metho.:y-phenylsulf onyl) -acetanilid 2-Amino-5-(4-methylthio-phenylsulfonyl)-propionanilid '2-Amino-5-(4-methylthio-phenylsulfonyl)-butyranilid 2-Amino-5-(4-methylthio-phenylsulfonyl)-acetanilid 2-Amino-5-(3-methylthio-phenylsulfonyl)-propionanilid 2-Amino-5-(3-methylthio-phenylsulfonyl)-butyranilid 2-Amino-5-(3-methylthio-phenylsulfonyl)-acetanilid 2-Amino-5-(4-cyan-phenylsulfonyl)-propionanilid 2-Amino-5-(4-cyan-phenylsulfonyl)-butyranilid 2-Amino-5 - (4-cyan-phenylsulf'onyl) -acetanilid 2-Amino-5-(3-cyan-phenylsulfonyl)-propionanilid 2-Amino-5-(3-cyan-phenylsulfonyl)-butyranilid 2-Amino-5-(3-cyan-phenylsulfonyl)-acetanilid 2-Amino-5-(4-acetyl-phenylsulfonyl)-propionanilid 2-Amino-5-(4-acetyl-phenylsulfonyl)-butyranilid 2-Amino-5- (4-acetyl-phenylsulf onyl) -acetanilid 2-Amino-5-(4-propionyl-phenylsulfonyl)-propionanilid 2-Amino-5-(4-propionyl-phenylsulfonyl)-butyranilid 2-Amino-5 -(4-propionyl-phenylsulfonyl)-acetanilid 2-Amino-5-(4-acetylamino-phenylsulfonyl)-propionani lid 2-Amino-5-(4-acetylamino-phenylsulfonyl)-butyranilid 2-Amino-5-(4-acetylamino-phenylsulfonyl)-acetanilid 2-Amino-5-(4-methoxycarbonylamino-phenylsulfonyl)-propionanilid 2-Amino-5-(4-methoxycarbonylamino-phenylsulfonyl)-butyranilid 2-Amj no-5-(A-methoxycarbonylamino-phenylsulfonyl)-acetanilid 2-Amino-5-(A-methoxycarbonyl-phenylsulfonyl)-pråpionanilid 2-Amino-5-(A-methoxycarbonyl-phenylsulfonyl)-butyranilid 2-Amino-5-(4-methoxycarbonyl-phenylsulfonyl)-acetanilid 2-Amino-5-(3 , A-dimethyl-phenylsulf onyl)-propionanilid 2-Amino-5-(3 , A-dimethyt-phenylsulf onyl)-butyranilid 2-Amino-5-(3 ,A-dime thyl-phenylsulf onyl)-acetanilid 2-Amino-5-(2-methyl-A-chlor-phenylsulfonyl)-propionanilid 2-Amino-5-(2-arethyl-A-chlor-phenylsulfonyl)-butyranilid 2-Amino-5-(2-methyl-A-chlor-phenylsulfonyl)-acetanilid 2-Amino-5-(A-athyl-phenylsulfonyl)-propionanilid
2-Amino-5-(A-athyl-phenylsulfonyl)-butyranilid
2-Amino-5-(A-athyl-phenylsulfonyl)-acetanilid
2-Amino-5-(3,A-dichlor-phenylsulfonyl) -propionanilid 2-Amino-5-(3,A-dichlor-phenylsulfonyl)-butyranilid 2-Amino-5-(3,A-dichlor-phenylsulfonyl)-acetanilid 2-Amino-5-(A-brom-phenylsulfonyl)-propionanilid 2-Amino-5-(A-brom-phenylsulfonyl)-butyranilid
2-Amino-5-(A-brom-phenylsulfonyl)-acetanilid
2-Amino-5-(3,5-dimethyl-phenylsulfonyl)-propionanilid 2-Amino-5-(3,5-dimethyl-phenylsulfonyl)-butyranilid 2-Amino-5-(3,5-dimethyl-phenylsulfonyl)-acetanilid 2-Amino-5-(A-butyl-phenylsulfonyl)-propionanilid 2-Amino-5-(A-butyl-phenylsulfonyl)-butyranilid
2-Amino-5-(A-butyl-phenylsulfonyl)-acetanilid
2-Amino-5-(3-butyl-phenylsulfonyl)-propionanilid 2-Amino-5-(3-butyl-phenylsulfonyl)-butyranilid
2-Amino-5-(3-butyl-phenylsulfonyl)-acetanilid
2-Amino-A-phenylsulfonyl-acetanilid
2-Amino-A-phenylsulfonyl-propionanilid
2-Amino-A-phenylsulfony1-butyranilid
2-Amino-A-phenylsulfonyl-iso-butyranilid
2-Amino-A-phenylsulfonyl-valeranilid
2-Amino-A-phenylsulf onyi-i so-valer ani lid
2-Amino-A-phenylsulfonyl-capronanilid
2-Amino-A-phenylsulfonyl-iso-capronanilid 2-Amino-A-phenylsulfonyl-cyclopentancarbonanilid 2-Amino-A-phenylsulfonyl-cyclohexancarbonanilid 2-Amino-A-phenylsulfonyl-phenylacetanilid 2-Amino-A-phenylsulfony1-phenoxyacetanilid 2-Amino-A-phenylsulfonyl-benzanilid N-(2-Amino-A-phenylsulfonyl-phenyl)-N'-methyl-harnstoff N-(2-Amino-A-phenylsulfonyl-phenyl)-M<1->athyl-harnstoff N-(2-Amino-A-phenylsulfonyl-phenyl) -N'-butyl-harnstoff N-(2-Amino-A-phenylsulfonyl-phenyl)-N1 - CJ -cyanpentyl-harnstoi N-(2-Amino-A-phenylsulfonyl-phenyl)-N'-fi-methoxyathyl-harnstof N-(2-Amino-A-phenylsulfonyl-phenyl)-N'-benzyl-harnstoff N-(2-Amino-A-phenylsulfonyl-phenyl)-N'-phenyl-harnstoff 2-Amino-A-(A-methyl-phenylsulfonyl)-propionanilid
2-Aniino-A-(A-methyl-phenylsulf onyl)-butyranilid 2-Amino-A-(A-methyl-phenylsulfonyl)-acetanilid 2-Amino-A-(3-methyl-phenylsulfonyl)-propionanilid 2-Amino-A-(3-methyl-phenylsulfonyl)-butyranilid 2-Amino-A-(3-methyl-phenylsulfonyl)-acetanilid 2-Amino-A'- (2-methyl-phenylsulf onyl) -propionanilid 2-Amino-A-(2-methyl-phenylsulfonyl)-butyranilid ' 2-Amino-A-(2-methyl-phenylsulfonyl)-acetanilid 2-Amino-A-(A-chlor-phenylsulfonyl)-propionanilid 2-Amino-A-(A-chlor-phenylsulfonyl)-butyranilid 2-Amino-A-(A-chlor-phenylsulfonyl)-acetanilid 2-Amino-A-(3-chlor-phenylsulfonyl)-propionanilid 2-Amino-A-(3-chlor-phenylsulfonyl)-butyranilid 2-Amino-A-(3-chlor-phenylsulfonyl)-acetanilid 2-Amino-A-(2-chlor-phenylsulfonyl)-propionanilid 2-Amino-A-(2-chlor-phenylsulfonyl)-butyranilid 2-Amino-A-(2-chlor-phenylsulfonyl)-acetanilid 2-Amino-A-(A-methoxy-phenylsulfonyl)-propionanilid 2-Amino-A-(A-methoxy-phenylsulfonyl)-butyranilid 2-Amino-A-( A-methoxy-phenylsulf onyl )-acetanil id
2-Amino-4-(3-methoxy-phenylsulfonyl)-propionanilid 2-Amino-4-(3-methoxy-phenylsulfonyl)-butyranilid 2-Amino-4-(3-methoxy-phenylsulfonyl)-acetanilid 2-Amino-4-(4-methylthio-phenylsulfonyl)-propionanilid 2-Amino-4-(4-methylthio-phenylsulfonyl)-butyranilid 2-Amino-4-(4-methyl.thio-phenylsulf onyl)-acetanilid 2-Amino-4-(3-methylthio-phenylsulfonyl)-propionanilid 2-Amino-4-(3-methylthio-phenylsulfonyl)-butyranilid 2-Amino-4-(3-methylthio-phenylsulfonyl)-acetanilid. 2-Amino-4-(4-cyan-phenylsulfonyl)-propionanilid 2-Amino-4-(4-cyan-phenylsulfonyl)-butyranilid
2-Amino-4-(4-cyan-phenylsulfonyl)-acetanilid
2-Amino-4-(3-cyan-phenylsulfonyl)-propionanilid 2-Amino-4-(3-cyan-phenylsulfonyl)-butyranilid
2-Amino-4-(3-cyan-phenylsulfonyl)-acetanilid
2-Amino-4-(4-acetyl-phenylsulfonyl)-propionanilid 2-Amino-4-(4-acetyl-phenylsulfonyl)-butyranilid . 2-Amino-4-(4-acetyl-phenylsulfonyl)-acetanilid 2-Amino-4-(4-propionyl-phenylsulfonyl)-propionanilid 2-Amino-4-(4-propionyl-phenylsulfonyl)-butyranilid 2-Amino-4-(4-propionyl-phenylsulfonyl)-acetanilid 2-Amino-4-('4-ace ty lamino-phenyl sulf onyl) -propionanilid 2-Amino-4-(4-acetylamino-phenylsulfonyl)-butyranilid 2-Amino-4-(4-acetylamino-phenylsulfonyl)-acetanilid 2-Amino-4-(4-methoxycarbonylamino-phenylsulfonyl)-propionanilid 2-Amino-4-(4-methoxycarbonylamino-phenylsulfonyl)-butyranilid
.2-Amino-4-(4-methoxycarbonylamino-phenylsulfonyl)-acetanilid 2-Amino-4-(4-methoxycarbonyl-phenylsulfonyl)-propionanilid 2-Amino-4-(4-methoxycarbonyl-phenylsulfonyl)-butyranilid 2-Amino-4-(4-methoxycarbonyl-phenylsulfonyl)-acetanilid 2-Amino-4-(3,4-dimethyl-phenylsulfonyl)-propionanilid 2-Amino-4-(3,4-dimethyl-phenylsulfonyl)-butyranilid 2-Amino-4-(3,4-dimethyl-phenylsulfonyl)-acetanilid
2-amino-4-(2-mety1-4-klor-fenylsulfony1)-propionanilid 2-amino-4-(2-mety1-4-klor-fenylsulfony1)-butyranilid
2-amino-4-(2-metyl-4-klor-fenylsulfonyl)-acetanilid
2-amino-4-(4-etyl-fenylsulfony1)-propionanilid
2-amino-4- (4-ety.l-f enylsulf ony 1)-butyranilid
2-amino-4-(4-etyl-fenylsulfonyl)-acetanilid
2-amino-4- (3, 4-diklor-f enylsulf onyl) -propionanilid
2-amino-4-(3,4-diklor-fenylsulfony1)-butyranilid 2-amino-4-(3,4-diklor-fenylsulfonyl)-acetanilid
2-amino-4-(4-brom-fenylsulfony1)-propionanilid
2-amino-4-(4-brom-fenylsulfonyl)-butyranilid
2-amino-4-(4-brom-fenylsulfonyl)-acetanilid
2-amino-4-(3,5-dimety 1-fenylsulfonyl)-propionanilid
2-amino-4-(3,5-dimety 1-fenylsulfony1)-butyranilid
2-amino-4-(3,5-dimety 1-fenylsulfony1)-acetanilid
2-amino-4-(4-butyl-fenylsulfony1)-propionanilid
2-amino-4-(4-buty1-fenylsulfonyl)-butyranilid
2-amino-4-(4-buty1-fenylsulfonyl)-acetanilid
2-amino-4-(3-buty1-fenylsulfonyl)-propionanilid
2-amino-4-(3-butyl-fenylsulfonyl)-butyranilid
2-amino-4-(3-butyl-fenylsulfonyl)-acetanilid.
Som fortynningsmiddel kan man benytte alle polare organiske oppløsningsmidler for utførelse av fremgangsmåten ifølge oppfinnelsen. Hertil hører fortrinnsvis alkoholer som metanol, etanol, isopropanol og deres blandinger med vann,
ketoner som aceton (også blandet med vann), eddiksyre (eventuelt blandet med vann) og etere som dioksan eller tetrahydrofuran.
De syrer som tilsettes som katalysatorer til pro-
sessen kan i prinsippet velges fra rekken av kjente organiske eller uorganiske syrer som ønsket. Fortrinnsvis brukes imidler-
tid vanlige syrer med teknisk betydning, som f.eks.: Saltsyre, svovelsyre, salpetersyre, maursyre, eddiksyre, p-toluensulfonsyre.
Reaksjonstemperaturene kan varieres innenfor et stort område. I alminnelighet arbeides mellom 0 og 120°C og fortrinnsvis mellom 30 og 100°C. Omsetningen gjennomføres vanligvis ved normaltrykk.
Ved utførelse av prosessen ifølge oppfinnelsen tilsettes pr. 1 mol substituert 2-amino-anilid 1 mol. isotiourea-
eter. Hvis man går over eller under denne mengde kan mari f.eks.
øke eller minske med ca. 20% uten vesentlige utbyttereduksjoner. Reaksjonen gjennomføres fortrinnsvis i kokende oppløsningsmiddel s hvorved alkylmerkaptan fåes som biprodukt. Sluttproduktet felles ut krystallinsk ved avkjøling av reaksjonsblandingen og kan fra-filtreres og eventuelt renses ved omkrystallisasjon.
Som nye virksomme stoffer nevnes eksempelvis: N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-åthoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-iso-propoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-sec.-butoxycarbonyl-N''-propionyl-guanidin,
N-(2-Propionamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Butyramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N'' -
propionyl-guanidin,
N-(2-Valeramido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Cyclopentancarbonamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Cyclohexancarbonamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N ''-propi onyl-guanidin,
N-(2-Benzamido-4>phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin, -
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-acetyl-guanidin,
Le A 15 666
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-butyryl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-cyclohexancarbonyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-•
benzoyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-phenylacetyl-guanidin,
N-(2-Acetamido-4-phenoxy-phenyl)-N'-methoxycarbonyl-N''-phenoxyacetyl-guanidin,
N-( 2-(2'-Methylurei do)-4-phenoxy-phenyl7-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-[ 2-(<2>'-Aeth<y>lureido)-4-<p>henoxy-<p>heny<l>/-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-/^2(<2>'-But<y>lureido)-4-<p>henoxy-<p>heny<l>7-N'-methoxycarbonyl-N''-propionyl-guanidin,
N- { 2-{2'-LU-Cyanpentylureido)-4-phenoxy-phenyl/-N'-methoxycarbonyl-N ''-propionyl-guanidin,
N-/J-(2'-B-Methoxymethylureido)-4-phenoxy-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-/2- (2' -Benzylureido) -4-phenoxy-phenyl/-N' -methoxycarbonyl-N''-propionyl-guanidin,
N-/J- (2' -Phenylureido) -4-phenoxy-phenyl"/-N' -methoxycarbonyl-N''-propionyl-guanidin,
Le A 15 666
N-(2-Acetamido-4-phenoxy-phenyl)-N', N''-bis-methoxycarbonyl-guanidin,
N-(2-Acétamido-4-phenoxy-phenyl)~N',N''-bis-athoxycarbonyl-guanidin,
N-(2-Acetamido~4-phenoxy-phenyl)-N',N''-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-4-phenoxy~phenyl)-N' ,N' '-bis-sec. ^-butoxy-carbonyl-guanidin,
N-(2-Propionaarido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Butyramido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-iso-Butyramido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Valeramido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-iso-Valeramido-4-phenoxy-phenyl)-N'-N<*>'-bis-methoxycarbonyl-guanidin,,
N-(2-Capronamido-4-phenoxy-phenyl)-N'-N''-bis-methoxycarbonyl-guanidin,
N-(2-iso-Capronamido-4-phenoxy-phenyl)-N'-N''-bis-methoxycarbonyl-guanidin,
N-(2-Cyclopentancarbonamido-4-phenoxy-phenyl)-N,N''-bis-methoxycarbonyl-guanidin,
N-(2-Cyclohexancarbonamido-4-phenoxy-phenyl)-N',N''-bis methoxycarbonyl-guanidin,
Lfi A 15 666
N-(2-Phenylacetamido-A-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guani.din,
N-(2-Phenoxyacetamido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Benzamido-4-phenoxy-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-/2-(2-Methylureido)-4-phenoxy-phenyl7-N' -N''-bis-methoxycarbonyl-guanidin,
N-/^-(2'-Aethylureido)-4-phenoxy-phenyl7-N' ,N' '-bis-methoxycarbonyl-guanidin,
N-/2-(2'-Butylureido)-4-phenoxy-phenyl7-N',N''-bis-methoxycarbonyl-guanidin,
N-/2-(2'-lo -Cyanpentylureido)-4-phenoxy-phenyl/-N',N''-bis-methoxycarbonyl-guanidin ,
N-/j2-(2'-B-Methoxyathyl-ureido)-4-phenoxy-phenyl/-N' ,N' '-bis-methoxycarbonyl-guanidin,
N-//_2-(2'-Benzylureido)-4-phenoxy-phenyl/-N' , N' '-bis-methoxycarbonyl-guanidin,
N-/_2-(2'-Phenylureido)-4-phenoxy-phenyl/-N' ,N' '-bis-methoxy- '
carbonyl-guanidin.
N-/2-Propionami do-4-( 4-me thyl-phenoxy )-pheny^-N' ,N' '-bis-methoxycarbonyl-guanidin,
N-/T-Propionamido-4-(3-methyl-phenoxy)-phenyl7-N' ,N' '-bis-methoxycarbonyl-guanidin,
Le A 13 666
N-/~2-Propionamido-4-(4-chlor-phenoxy)-phenyl_7-N'^"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4-(3-chlor-phenoxy)-pheny 1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(2-chlor-phenoxy)-pheny1_7-N' ,iv"-bis-methoxycarbonyl-guanidin,
N-i/~2-Propionamido-4-(4-methoxy-phenoxy)-pheny 1_7-N1 ,N".-t>is-methoxycarbonyl-guanidin, .N-/_~2-Propionamido-4-(3-methoxy-phenoxy) -phenyl_7-N' , N"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4-(4-methylthio-phenoxy) - phenyl_7-W 1 , N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(3-methylthio-phenoxy)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-J/~2-Pr opionamido-4-(4-cyan-phenoxy) -pheny 1_7-N1 ,N" -bis-methoxycarbonyl-guanidin,
N-/_ 2-Propionamido-4-(4-acetyl-phenoxy)-phenyl_7-iM 1 ^"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4 - (3-cyan-phenoxy) -phenyl_7-N' , N"-bis-methoxycarbonyl-guanidin,
N-/_ 2-Propionamido-4-(4-propionyl-phenoxy)-pheny 1_7-N1 ,W"-bis-methoxycarbonyl-guanidin,
N-/_ 2-Propionamido-4-(4-acetylamino-phenoxy)-pheny1_7-N', W"-bis-methoxycarbonyl-guanidin,
N-/__2-Propionamido-4- (4-methoxycarbonyl-phenoxy) -phenyl_7~ N' ,IM"-bis-methoxycarbonyl-guanidin, N-/_~2-Propionamido-4- (3 ,4-dimethyl-phenoxy) -pheny 1_7-M ' , N"-bis-methoxycarbonyl-guanidin, N-/_ 2-Propionamido-4-(3,4-dichlor-phenoxy)-pheny1_7-N1, N" - bis-methoxycarbonyl-guanidin,
Le A 13 666
N-(2-Acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-athoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-iso-propoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-sec.-butoxycarbonyl-N''-propionyl-guanidin,
N-(2-Propionamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Butyramido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Valeramido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Cyclopentancarbonamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Cyclohexancarbonamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
Le a 15 666
N-( 2-Benzamido-5-phenoxy-phenyl) -N' -ra-:thoxycarbonyl-N' ' -
propionyl-guanidin,
N-(2-Acetami.do-5-phenoxy-phényl)-N'-methoxycarbonyl-N''-acetyl-guanidin,
N-(2-Acetamido-5-phenoxy-phanyl)-N'-methoxycarbonyl-N''<->
butyryl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-cyclohexancarbonyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-benzoyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-phenylacetyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N'-methoxycarbonyl-N''-phenoxyacetyl-guanidin,
N-[ 2-(2'-Methylureido)-5-phenoxy-phenyl/-N'-methoxycarbonyl-N''-propionyl-guanidin, . N-/_2-(2' -Aethylureido)~5-phenoxy-pheny_l/-N' -methoxyca^bonyl-N,'-propionyl-guanidin, ■
N-/2-(2'-Butylureido)-5-phenoxy-phenyl7-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-/2-(2'- uJ-Cyanpentylureido)-5-phenoxy-phenyl7-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-/ 2-( 2' -S-Methoxymethylureido)-5-phenoxy-pheny_l7-N' -methoxycarbonyl-N' '-propionyl-guanidin,
Le A 15 666
N-/_~2-(2 '-Benzylureido)-5-phenoxy-phenyl_7-N'-methoxycarbonyl-N" -propionyl-guanidin,
N-/~2-(2 ' -Phenylureido)-5-phenoxy-phenyl__7-N> -methoxycarbonyl-M"-propionyl-guanidin,
N-(2-Acetarnido-5-phenoxy-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
N- (2-Acetamido-5-phenoxy-phenyl)-N',N"-bis-athoxycarbonyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N',N"-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-5-phenoxy-phenyl)-N',N"-bis-sec.-butoxy-carbonyl-guanidin,
N-(2- Pr opionamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-Butyramido-5-phenoxy-phenyl)-N'^"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Butyramido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-Valeramido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Valeramido-5-phenoxy-phenyl)-N'^"-bis-methoxycarbonyl-guanidin,
N-(2-Capronamido-5-phenoxy-phenyl)-N',N"-bis-methoxy-.carbonyl-guanidin,
N-(2-iso-Capronamido-5-phenoxy-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-Cyclopentancarbonamido-5-phenoxy-phenyl)-N1, N"-bis-methoxycarbonyl-guanidin,
N-(2-Cyclohexancarbonamido-5-phenoxy-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-(2-Phenylacetamido-5-phenoxy-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-(2-Phenoxyacetamido-5-phenoxy-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-(2-Benzamido-5-phenoxy-phenyl)-N1, N"-bis-methoxycarbonyl-guanidin, N-/~2-(2*' -Methylureido)-5-phenoxy-phenyl_7-N' , N" -bis-methoxycarbonyl-guanidin, N-/"2-(2 ' -/vthy lure ido )-5-phenoxy-phenyl_7-N' ,N" -bis-methoxycarbonyl-guanidin,. N-/_~2-(2 '-Butylureido)-5-phenoxy-phenyl_7~N' , N"-bis-methoxycarbonyl- guanidin,
N-/~2-(2'- CO -Cyanpentylureido)-5-phenoxy-phenyl_7-N',N"- ■ bis-methoxycarbonyl-guanidin,
N-/~2-(2'-O-Methoxyaethyl-ureido)-5-phenoxy-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-(2•-Benzylureido)-5-phenoxy-pheny1_7-N'^"-bis-methoxycarbonyl-guanidin,
'N-/"2-(2'-Phenylureido)-5-phenoxy-phenyl_7-W,N"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-5-(4-methyl-phenoxy)-phenyl_7-N' ^"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-5-(3-methyi-phenoxy)-pheny 1_7-N ' ,N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-chlor-phenoxy)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-J/~2-Propionamido-5- (3-chlor-phenoxy) -pheny 1_7~N1 »N"-bis-methoxycarbonyl-guanidin,
N-J/~2-Propionamido-5-(2-chlor-phenoxy) -phenyl_7-N1 , N"-bis-methoxycarbonyl-guanidin,
N-/r2-Propionamido-5-(4-methoxy-phenoxy)-phenyl_7-N1, IM"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-5-(4-methoxy-phenoxy)-phenyl_7-N ' ,N"-bis-methoxycarbonyl-guanidin,
N-w(/~2-Propionamido-5 - (4-methylthio-phenoxy) -pheny 1_7-N 1 , N" -bis-methoxycarbonyl-guanidin,.
Le A 15 666
N-Z^-Propionamido-S-O-methylthio-phenoxyKphenyl^-N' ,N"-bis-methoxycarbonyl-guanidin,
W-/~2-Propion-amldo-5-(4-cyan-phenoxy)-pheny 1_7-N' ^"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-acetyi-phenoxy)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/<_>~2-Pro<p>ionamido-5-(3-c<y>an-<p>henoxy)-<p>hen<y>l_7-<i>'^',<W>"-bis-methoxycarbonyl-guanidin,
W-/_~2-Propionamido-5-(4-propionyl-phenoxy)-pheny 1_7~N' ,W"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-acetylamino-phenoxy)-pheny1_7~N<1>,N"-bis-methoxycarbonyl-guanidin,
N-/~2-Pr opionamido-5-(4-methoxycarbony1-phenoxy)-phenyl_7-1M1 , IM" -bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(3,4-dimethyl-phenoxy)-pheny1_7-N', I^-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(3,4-dichlor-phenoxy)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N- (2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylthio-pheny1)-N'-åthoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidin,
N-(2-Propionamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Butyramido-4-phenylthio-phenyl)-N<1->methoxycarbonyl-N"-propionyl-guanidin,
Le A 13 666
N-(2-Valeramido-A-phenylthio-phenyl)-N'-methoxycarbonyl-N''-%propionyl-guanidin,
N-(2-Cyclopentancarbonamido-A-phenylthio-phenyl)-Ni-methoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Cyclohexancarbonamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin
N-(2-Benzamido-4~phenylthio-phenyl)-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N'-methoxycarbonyl-N''-acetyl-guanidin,
N-(2-Acetamido-A-phenylthio-phenyl)-N'-methoxycarbonyl-N''-butyryl-guanidin,
N-(2-Acetamido-A-phenylthi o-phenyl)-N'-methoxycarbonyl-N''-cyclohexancarbonyl-guanidin,
N-(2-Acetamido-A-phenylthio-phenyl)-N'-methoxycarbonyl-N''-benzoyl-guanidin,
N-(2-Acetamido-A-phenylthio-phenyl)-N'-methoxycarbonyl-N''-phenylacetyl-guanidin,
N-(2-Acetamido-A-phenylthio-phenyl)-N'-methoxycarb-onyl-N' '-phenoxyacetyl-guanidin,
N-/_2-( 2' -Methylureido)-4-phenylthio-phenyl7-N' -methoxycarbonyl-N' '-propionyl-guanidin,
N-/j2-(2' -Aethylure ido )-4-phenylthio-phenyl7-N' -methoxycarbonyl-N' '-propionyl-guanidin,
Le A 15 666
N-/ 2-(2'-Butylureido)-4-phenylthio-phenyl7-N'-methoxycarbonyl-N* '-propionyl-guanidin,
N-/2- (2iw-Cyanpentylureido) -4.-phenylthio-phenyl/-N' -methoxycarbonyl-N''-propionyl-guanidin,
N-/2-(2'-B-Methoxymethylureido)-4-phenylthio-pheny_l/-N'-
raethoxycarbonyl-N''-propionyl-guanidin,
N-/2-(2'-Benzylureido)-4-phenylthio-phenyl/-N'-methoxycarbonyl-N' '-propionyl-guanidin,
(2' -Phenylureido)-4-phenylthio-phenyl_/-N' -methoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-aethoxycar-bonyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-4-phenylthio-phenyl)-N',N''-bis-sec.-butoxy-carbonyl-guanidin,
N-(2-Propionamido-4-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Butyramido-4-phenylthio-phe.nyl)-N' ,N' '-bis methoxycarbonyl-guanidin ,
N-(2-iso-Butyramido-4-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-(2-Valeramido-4~phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-iso-Valeramido-4-phenylthio-phenyl)-N',N' ' -bis-methoxycarbonyl-guanidin,
N-(2-Capronamido-4-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-iso-Ca<p>ronamido-4-phen<y>lthio-phen<y>l)-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-methoxycarbonyl-guanidin,
N-/2-(2'-Methylureido)-4-phenylthio-phenyl7-N'-N"-bis-methoxycarbonyl-guanidin ,
N-/2"-(2'-Aethylureido)-4-phenylthio-phenyl7-N' ,N' '-bis-methoxycarbonyl-guanidin,
N-/2-(2'-Butylureido)-4-phenylthio-phenyl/-N',N''-bis-methoxy-carbonyl-guanidin,
N-/j-(2'-uj-Cyanpentylureido)-4-phenylthio-phenyl7-N',N''-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/~2-(2'-fi-Methoxyathyl-ureido)-4-phenylthio-phenyl_7-N', N"-bis-methoxycarbonyl-guanidin,
N-/_~2-(2 ' -Benzylureido)-4-phenylthio-phenyl_7-N' , W" -bis-methoxycarbonyl-guanidin,
N-/~2-(2'-Phenylureido)-4-phenylthio-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/_~2-Propionamido-4-(4-methyl-phenylthio) -pheny 1_7-N '-, N" - bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(3-methyl-phenylthio)-pheny1_7-N', N"-bis-methoxycarbonyl-guanidin, N-/_5-Propionamido-4- (4-chlor-phenylthio) -phenyl_7~N' , N"-bis-methoxycarbonyl-guanidin,
N.-/~2-Propionamido-4- (3-chlor-phenylthio)-pheny 1_7-N 1 , N"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4-(2-chlor-phenylthio)-pheny 1_7-W' ,N"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4-(4-methoxy-phenylthio)-pheny 1_7-N' ,{^"-bis-methoxycarbonyl-guanidin,
N-/_~2-Propionamido-4-(3-methoxy-phenylthio)-pheny 1_7-N,' ,^'-bis-methoxycarbonyl-guanidin,
N-/_ 2-Propionamido-4-(4-methylthio-phenylthio)-phenyl_7-N', N"-bis-methoxycarbonyl-guanidin,
N-/_ 2-Propionamido-4-(3-methylthio-phenylthio)-phenyl_7-. N',N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/~2-Propionamido-4-(4-cyan-phenylthio)-pheny1_7-N',N"-bis-methoxycarponyl-guanidin,
N-/_~2-Propionamido-4- (4-acetyl-phenylthio)-pheny1_7~N',N"-bis-methoxycarbonyl-guanidin,
N-_//"2-Propionamido-4-(3-cyan-phenylthio)-phenyl_7-N' ,w"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(4-propionyl-phenylthio)-phenyl_7-N1, N "-bi s-methoxycarbonyl-guanidin, N-J/"2-Propionamido-4-(4-acetylamino-phenylthio) -pheny 1_7-N',N"-bis-methoxycarbonyl-guanidin, N-_i/~2-Propionamido-4- (4-methoxycarbonyl-phenylthio) -pheny 1_7_ N ' , M" -bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(3,4-dimethyl-phenylthio)-pheny1_7~M' , N" -bis-methoxycarbonyl-guanidin, N-/_~2-Propionamido-4 - (3,4-dichlor-phenylthio) -pheny 1_7~U',N"-bis-methoxycarbonyl-guanidin, N- (2-.\cetamido-5-phenylthio-phenyl) -N ' -methoxycarbonyl-N" - propionyl-guanidin, N-(2-Acetamido-5-phenylthio-phenyl)-N<1->aethoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N'-iso-propoxycarbonyl-M"-propionyl-guanidin, ■
N-(2-A"etamido-5-phenylthio-phenyl)-N<1->sec.-butoxycarbonyl-N"-propionyl-guanidin, N-(2-Propionamido-5-phenylthio-phenyl)-N'-methoxycarponyl-N''-propionyl-guanidin, N-( 2-Butyramido"-5-phenylthiO-phenyl) -N' -methoxycarbonyl-N' '-propionyl-guanidin,
N- (2-Valeramido-5-phenylthio-phenyl) -N' -methoxycarbonyl-N''' -
propionyl-guanidin,
N-(2 Cyclopentancarbonamido-5-phenylthio-phenyl)-N'-methoxy-.
carb.onyl-N' '-propionyl-guanidin,
N-(2-Cyclohexancarbonamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-( 2TBenzamido-5-phenylthi:o-phenyl)-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N'-methoxycarbonyl-N''-acetyl-guanidin,
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,
Le A 15 666
N-/2-(2' Methylureido)-5-phenylthio-phenyl7--N'-methoxycarbonyl-N' '-propionyl-guanidin,
(2'-Aethylureido)-5-phenylthi o-phenyl/-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-/2"-(2' -Butylureido)-5-phenylthio-phenyl/-N' -methoxycarbonyl-N' '-propionyl-guanidin,
N- l2-(2'-OJ-Cyanpentylureido)-5-phenylthio-phenyl/-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N- J2-(2'-8-Methoxymethylureido)-5-phenylthio-phenyl7-N'-methoxycarbonyl-N''-propionyl-guanidin,
N-/2-(2'-Benzylureido)-5-phenylthio-phenyl/-N'-methoxycarbonyl-N' '-propionyl-guanidin,
N-,/2-( 2'-Phenylureido)-5-phenylthio-phenyl/-N'-methoxycarbonyl-N' '-prooionyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-aethoxycarbonyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-5-phenylthio-phenyl)-N',N''-bis-sec.butoxy-carbonyl-guanidin,
N-(2-Propionamido-5-phenylthio-phenyl)-N',N''-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-(?-lliit.yrninulo-,>-phGnylthlo-phfinyl)-N' ,N' '-bis-rnct;hoxy-
i
c.arhony 1-/';uan.i din,
N-Cr-ir.n-Uiityi-amido-O-phonylthio-phony] )-N' ,N' '-bir>-methoxy-rarbony1-ifunnidin,
N-C^-Valcramido^-phenylthio-phonyl)-!^,N' '-bin-methoxycarbonyl-^unnidin,
N-C.^-i .".o-Valcramido-r)-phonylthio-phonyl)-N' ,M' *-bin-methoxycarbonyl -f:uanir].i
N-(.'"-Capronanudo-r?-p}renylthio-pheny.l)-N', N' ' -bir.;-methoxycarbonyl-Ruanidin,
N-(r-iso-Capronnmido-5-phenylthio-phenyl)-N',N*'-bis-methoxycarbonyl-fjuanidin,
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-phenyl) -N.' , N '■' -bis-methbxy-carbonyl-guanidin,
N-(2-Benzamido-5—phenylthio-phenyl-N' ,N"-bis-methoxycar-r bonyl-guanidin,
N-/J-C2• -Methylureido)-5-p'henylthio-phenyl7-N' -N'»-bis-methoxycarbonyl-guanidin,
N-/2-(2'-Aethylureido)-5-phenylthio.-phenyl7-N' ,N» '-bis-methoxycarbonyl-guanidin,
Le A' 15 666
N-/"2-(2'-Butylureido)-5-phenylthio-phenyl_7-N'^"-bis-methoxycarbonyl-guanidin,
N-/~2-(2'- Gj .-Cyanpentylureido)-5-phenylthio-phenyl_7-N* ,N"-bis-methoxycafbonyl-guanidin,
N-/~2-(2'-B-Methoxyaethyl-ureido)-5-phenylthio-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-(2<1->Benzylureido)-5-phénylthio-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin , N-/"2- (2 ' - Pheny lureido") -5-phenylthio-phenyl_7-N ' , N" -bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-methyl-phenylthio-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methyl-phenylthio)-pheny1_7-N1^"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-chlor-phenylthio)-pheny1_7~N1 , N" -bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-chlor-phenylthio)-phenyl_7~N1,N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-( 3-chlor-phenylthio) -pheny 1__7~N1 , N" -bis-methoxycarbonyl-guanidin , N-/ 2-Propionamido-5-(4-methoxy-phenylthio)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methoxy-phenylthio)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, 2-Propionamido-5-(4-methylthio-phenylthio)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methylthio-phenylthio)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/ 2-Propionamido-5-(4-cyan-phenylthio)-phenyl_7-N1^"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-('4-acetyl-phenylthio)-pheny 1_7-N' ,N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/~2-Propionamido-5-(3-cyan-phenylthio)-phenyl_7-N<1>,N"^bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-5-(4-propionyl-phenylthio)-pheny1_7-N',N<M->. bis-methoxycarbonyl-guanidin<,>N-/~2-Propionåmido-5-(4-acetylamino-phenylthio)-pheny 1__7~ N1 ,N" -bis-methoxycarbonyl-guanidin, N'-/~2-Propionamido-5-(4-methoxycarbonyl-phenylthio)-pheny 1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3,4-dimethyl-phenylthio)-pheny 1_7-N1,N"-bis-methoxycarbonyl-guanidin, . N-/~2-Propionamido-5-(3,4-dichlor-phenylthio)-pheny1_7-N',NM-bis-methoxycarbonyl-guanidin, N-(2-\cetamido-4-phenylsulfinyl-phenyl)-N<1->metho^ycarbonyl-N"'-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-athoxycarbonyl-N"-propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-iso-propoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N<1->sec.-butoxy-carbonyl-N"-propionyl-guanidin,
N-(2-Propionamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Butyramido-4-phenylsulf inyl-phenyl )-N' -methoxycarbonyl-i W"-propionyl-guanidin,
N-(2-Valeramido-4-phenylsulfinyl-phenyl)-w<1->methoxycarbonyl-J\i"-propionyl-guanidin, ■
N-(2-Cyclopentancarbonamido-4-phenyls.ulf inyl-phenyl )-N'-methoxycarbonyl-N"-propionyl-guanidin, N-(2-Cyclohexancarbonamido-4-phenylsulfinyl-phenyl)-M<1->methoxycarbonyl-N" -propionyl-guanidin, N-(2-Benzamido-4-phenylsulfinyl-phenyl)-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-méthoxycarbonyl-N"-acetyl-guanidin,
Le A 15 666 .N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidin,
N-(2-Acetamido-4-pheriylsulfinyl-phenyl)-W-methoxycarbonyl-N"-cyclohexancå'rbonyl-guanidin,
N-(2-Acetamido-4-phenylsuirinyl-phenyl )-N'-metho.iycarbonyl-N"-benzoyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidin,
N- (2-Acetamido-4-phenylsulf inyl-phenyl ).-N' -me thoxycarbonyl-N"-phenoxyacetyl-guanidin,
N-/~2-(21-Methylureido)-4-phenylsulfinyl-pheny1_7-N '-methoxycarbonyl-N"-propionyl-guanidin,
N-/~2 - (2 ! -Ae thy lure ido )-4-phenylsulfinyl-phenyl_7-N1 -methoxy-• carbonyl-N"-propionyl-guanidin,
N-/~2-(2<1->Butylureido)-4-phenylsulfinyl-phenyl_7-N<*->methoxycarbonyl-N" -propionyl-guanidin,
N-/~2-(21 - CU -Cyanpentylureido)-4-phenylsulfinyl-phenyl_7-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-/~2-(2 1 -fl-Methoxymethylureido)-4-phenylsulf inyl-pheny1_7-N'-methoxycarbonyl-N"-propionyl-guanidin, N-/~2-(2'-Benzylureido)-4-phenylsulfinyl-phenyl_7-N'-methoxycarbonyl-N" -propionyl-guanidin, N-/~2-(2<1->Phenylureido)-4-phenylsulfinyl-pheny1_7-N'-methoxycarbonyl-N" -propionyl-guanidin, N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin , N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N<1>,N"-bis-aethoxy-carbonyl-guanidin,
N-(2-Acetamido-4-phenylsulfinyl-phenyl)-N<1>,N"-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-4-phenylsulfinyl-phenyl) -N ', N"-bis-sec. -butoxy- • carbonyl-guanidin,
N-(2-Propionamido-4-phenylsulfinyl-phenyl)-II<1>,N"-bis-methoxycarbonyl-guanidin,
Le A 15 666 - N-(2-Butyramidq-4-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin, N-(2-iso-Butyramido-4-phenylsulfinyl-phenyl)-N<1>^"-bis-methoxycarbonyl-guanidin,
N-(2-Valeramido-A-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin, N-(2-iso-Valeramido-4-phenyls.ulf inyl-phenyl)-N ' , W"-bis-methoxycarbonyl-guanidin, N- (2-Capronami do-4-phenyl sulf inyl-phenyl) - N ',,N" -bis-methoxycarbonyl-guanidin, N-(2-lso-Capronamido-4-phenylsulfinyl-phenyl)-N',w"-bis-. methoxycarbonyl-guanidin, lM- (2-Cy cl opent ane ar bonami do-4-phe ny lsulf inyl-phenyl) -N ' , N"-bis-methoxycarbonyl-guanidin, N-(2-Cyclohexancarbonamido-4-phenylsulfinyl-phenyl)-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)-W',W"-bis-methoxycarbonyl-guanidin, N-/~2-(2'-Methylureido)-4-phenylsulfinyl-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-(2'-Aethylureido)-4-phenylsulfinyl-phenyl_7-W',N"-bis-methoxycarbonyl-guanidin, N-/"2-(2<1->Butylureido)-4-phenylsulfinyl-phenyl_7-N'^"-bis-methoxycarbonyl-guanidin,
N-/_ 2-(2'- Co -Cyanpentylureido)-4-phenylsulfinyl-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/ 2-(2'-B-Methoxyåthyl-uréido)-4-phenylsulfinyl-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-(2'-Benzylureido)-4-phenylsulfinyl-phenyl_7-N'^"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/"2-(2'-Phenylureido)-4-phenylsulfinyl-pheny 1__7-N* ,N"- . bis-methoxycarbonyl-guanidin, N-/"2-Fropionamido-4-(4-m'ethyi-pheny lsulf inyl)-phenyl_7-N1,N"-bis-methoxycarbonyl-guanidin, N-/ 2-Propionamido-4-(3-methyl-phenylsulfinyl)-pheny 1__7-NN"-bis-methoxycarbonyl-guanidin, N-/"2-Propionamido-4-(4-chlor-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(3-chl6r-phenylsulf inyl)-pheny 1__7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(2-chlor-phenylsulfinyl)-pheny1_7~N<*>,N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(4-methoxy-phenylsulf inyl)-phenyl__7-.N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(3-methoxy-phenylsulfinyl)-phenyl __7-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(4-methylthio-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(3-methylthio-phenylsulfinyl)-pheny 1__7-N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(4-cyan-phenylsulfinyl)-phenyl _7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(4-acetyl-phenylsulfinyl)-pheny1_7-N•,N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(3-cyan-phenylsulf inyl)-pheny 1__7-N' ,N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(4-propionyl-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(4-acetylamino-phenylsulfinyl)-phenyl _ J-N<1>,N"-bis-methoxycarbonyl-guanidin, N-/"2-Propionamido-4-(4-methoxycarbonyl-phenylsulfinyl)-phenyl7-N',N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/~2-Propionamino-4-(3,4-dimethyl-phenyisulfinyl)-pheny 1_ J-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-4-(3.4-dlchlor-phenylsulfinyl)-pheny1_7-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-(2-/cetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-aethoxycarbonyl-N"-propionyl-guanidin,
N-(2rAcetamido-5-phenylsulfinyl-phenyl)-N<1->iso-propoxy-carbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsuf linyl-phenyl)-lM1 -sec. -butoxycarbonyl-N"-propionyl-guanidin,
N-(2-Propionamido-5-phenylsulfinyl-phenyl)-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Butyramido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N- (2-Valeram'ido-5-phenylsulf inyl-phenyl) -N1 -methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Cyclopentancarbonamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Cyclohexancarbonåmido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Benzamido-5-phenylsulfinyl-phenyl)-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N<1->methoxycarbonyl-N"-acetyl-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-butyryl-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbpnyl-N"-cyclohexancarbony1-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-benzoyl-guanidin,
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-phenylac.etyl-guanidin,
Le 15 666
N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidin,
N-/~2-(2'-Methylureido)-5-phenylsulfinyl-phenyl_7-N'-methoxycarbonyl-M"-propionyl-guanidin,
N-/~2-(2 1 -.aethylureido)-5-phenylsulfinyl-phenyl_7-W ' -methoxycarbonyl-N" -propionyl-guanidin, N-/~2-(2' -liutylureido)-5-phe-nylsulf inyl-pheny 1__7-N 1 -methoxycarbonyl-N" -propionyl-guanidin,
N-/~2-(2'- OJ -Cyanpentylureido)-5-phenylsulfinyl-phenyl_7-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-/_~2-(2 ' - fi-Methoxymethylureido)-5-phenylsulf inyl-phenyl_7-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-/~2-(2'-Benzylureido)-5-phenylsulfinyl-phenyl_7-N'-methoxycarbonyl-N" -propionyl-guanidin,
N-/_~2-(2 ' -Phenylureido)-5-phenylsulf inyl-phenyl_7-N1 -methoxycarbonyl-N" -propionyl-guanidin,
N- (2-Acetamido-5-phenylsulf inyl-phenyl) - N ' ,.N" -bis-methoxycarbonyl-guanidin, •N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N"-bis-aethoxy-car bonyl -guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N"-bis-iso-propoxycarbonyl-guanidin, N-(2-Acetamido-5-phenylsulfinyl-phenyl)-N',N"-bis-sec.-butoxy-carbonyl-guanidin, N-(2-Propionamido-5-phenylsulfinyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin, N-(2-Butyramido-5-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin, N-(2-iso-Butyramido-5-phenylsulfinyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin, N-(2-Valeramido-5-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin, N-(2-iso-Valeramido-5-phenylsulfinyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin ,
Le A 15 666
I
N-(2-Capron«imido-5-phenylsulf inyl-phenyl)-N" ,N"-bis-methoxy- j! carbonyl-guanidin, N-(2-iso-Cap^onåmido-5-phenylsulfinylrphenyl)-N, ^^"-bis-methoxycarbonyl-guanidin, N-(2-Cyclopentancarbonamido-5-phenylsulfinyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin, N-(2-Cyclohexancarbonamido-5-phenylsulfinyl-phenyl)-N<1>,w"-bis-methoxycarbonyl-guanidin, 'j (2-Phenylaceta'mido-5-phenylsulf inyl-phenyl )-N 1, W"-bis- i methoxycarbonyl-guanidin, N-(2-Phenoxyacetamido-5-phenylsulfinyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin, N-(2-Benzamido-5-phenylsulfinyl-phenyl)-N',W"-bis-methoxycarbonyl-guanidin,
■N-/"2-(2'-Methylureido)-5-phenylsulfinyl-phenyl_7-N<1>^"-bis-methoxycarbonyl-guanidin,
N-/"2-(2 '-Aethylureido)-5-phenylsulf inyl-pheny 1__7-N1,N"-bis-methoxycarbonyl-guanidin ,
N-/~2-(2'-Butylureido)-5-phenylsulfinyl-phenyl_7-N',W"-bis-methoxycarbonyl-guanidin, W-/~2-(2'- CO -Cyanpentylureido)-5-phenylsulfinyl-phenyl_7-N', - NH<->bis-methoxycarbonyl-guanidin, N-/~2-(2'-B-Methoxyaethyl-ureido)-5-phenylsulfinyl-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, ..N-/"2-(2'-Benzylureido^-5-phenylsulfinyl-phenyl_7-N<1>,M"-bis-methoxycarbonyl-guanidin, N-/~2-(2 1 -Phenylureido)-'5-phenylsulf inyl-phenyl_7-N' ^"-bis-methoxycarbonyl-guanidin, N-/"~2-Propionamido-5-(4-methyl-phenylsulf inyl)-phenyl__7-N' , N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methyl-phenylsulfinyl)-pheny1_7-N<1>,N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-chlor-phenylsulf inyl)-pheny 1__7-N<1>,N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/ 2-Propionaraido-5-(3-chlor-phenylsulfinyl)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-5-(3-chlor-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-_//~2-Propicnamido-5-( 4-methoxy-phenylsulfinyl)-phenyi_7~N',-N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methoxy-phenylsulfinyl)-phenyl_7~N',N"-bis-methoxycarbonyl-guanidin, N-^~2-Fropionamido-5-(4-methylthio-phenylsulfinyl)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methylthio-phenylsulfinyl)-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-cyan-phenylsulfinyl)-pheny1_7-N', N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-acetyl-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-cyan-phenylsulfinyl)-pheny1_7-N', N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-propionyl-phenylsulfinyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-acetylamino-phenylsulfinyl)-pheny1_7_
N1,N" -bis-methoxycarbonyl-guanidin,
N-J/"2-Propionamido-5-(4-me thoxycarbonyl-phenylsulf inyl )-phenyl7-N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(3,4-dimethyl-phenylsulfinyl)-phenyl_7~N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(3,4-dichlor-phenylsulfinyl)-pheny1_7~N<1>,N"-bis-methoxycarbonyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-aethoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N<1->iso-propoxy-carbony1-N"-propionyl-guanidin,
Le A 15 666
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-sec.-butoxy-carbony1-N"-propionyl-guanidin,
N-(2-Propionamido-4-phenylsulfonyl-phenyl) -N-' -methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Butyramido-4-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,'
N - (2-Valeramido-4-phenylsulf onyl-phenyl) - N' -methoxycarbony-l-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<1->raethoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N<1->methoxycarbonyl-N"-acetyl-guanidin,
N-(2 - '■■ cetamido-4-phenylsulf onyl-phenyl) -N' -methoxycarbonyl-N"-butyryl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-cyclohexancarbonyl-guanidin,.
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N' -methoxycarbonyl-N"-benzoyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-phenoxyacetyl-guanidin, N-/ 2-(2'-Methylureido)-4-phenylsulfonyl-phenyl_7~N'-methoxycarbonyl-N" -propionyl-guanidin, N- £ 2-(21-Aethylureido)-4-phenylsulfonyl-phenyl_7-N'-methoxycarbonyl-N" -propionyl-guanidin, 2-(2 1 -Butylureido)-4-phenylsulfonyl-phenyl_7-N 1 -methoxycarbonyl-N "-propionyl-guanidin,
N-/~2-(2l<->CJ -Cyanpentylureido)-4-phenylsulfonyl-phenyl_7-N'-methoxycarbonyl-N"-propionyl-guanidin,
Le A 15666
N-/~2-(2'-B-Methoxymethylureido)-4-phenylsulfonyl-phenyl_7-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-/~2- (2 ' -Benzylureido) -4-rphenylsulf onyl-phehyl_7-N' -methoxycarbonyl-N"-propionyl-guanidin,
N-/~2-(2'-Phenylureido)-4-phenylsulfonyl-phenyl_7-N<1->methoxycarbonyl-N" -propionyl-guanidin ,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N',N"-bis-methoxy-~carbonyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N',N"-bis-aethoxy-carbonyl -guanidin,
N-(2-Acetamido-4-phenylsulfony1-phenyl)-N',N"-bis-iso-propoxy-carbonyl-guanidin,
N-(2-Acetamido-4-phenylsulfonyl-phenyl)-N',N"-bis-sec.-butoxy-carbonyl-guanidin,
N-(2-Propionamido-4-phenylsulfonyl-phenyl)-N<1>,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-pheny lsulf onyl-phenyl) -N' , N" -bis-methoxycarbonyl-guanidin,
W-(2-iso-Valeramido-4-phenylsulfonyl-phenyl)-N1 , N"-bis-methoxycarbonyl-guanidin,
N-(2-Capronamido-4-phenylsulfonyl-phenyl)-N', {^"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Capronamido-4-phenylsulfonyl-phenyl)-N',N"-bis-methoxy-. carbonyl-guanidin,
N-(2-Cyclopentancarbonamido-4-phenylsulfonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-Cyclohexancarbonamido-4-phenylsulfony1-phenyl)-N<1>,N"-bis-methoxy car bonyl -guanidin,
N-(2-Phenylacetamido-4-phenylsulfonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-(2-Phenoxyacetamido-4-phenylsulfonyl-phenyl)-W',N"-bis-methoxycarbonyl-guanidin,
W-(2-Benzamido-4-phenylsu'lf onyl-phenyl )-N' , iV-bis-methoxycarbonyl-guanidin,
iM-/"2-(2 '-Hethylureido)-4-phenylsulf onyl-phenyl_7-N ' ,N"r bis-methoxycarbonyl-guanidin,
N-/~2-(2 '-Aethylureido)-4-phe.nylsulfonyl-phenyl_7-N' , N" — bis-methoxycarbonyl-guanidin,
N-/~2-(2'-Butylureido)-4-phenylsulfonyl-phenyl_7-N',N"-bis-methoxy-carbonyl-guanidin, M-/~2-(2'- CJ -Cyanpentylureido)-4-phenylsulfonyl-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin, W-/~2-(2'-B-Methoxyathyl-ureido)-4-phenylsulfonyl-phenyl_7-N'-N"-bis-methoxycarbonyl-guanidin, N-i/~2-(2<1->Benzylureido)-4-phenylsulfonyl-phenyl_7-N'^"-bis-methoxycarbonyl-guanidin, N-J/~2-(2'-Phenylureido)-4-phenylsulfonyl-phenyl_7-N'^"-bis-methoxy -carbonyl-guanidin, N-/~2-Pr opi onamido-4- (4-me thy 1-phenyl sulf ony l)-phenyl_7-N' , N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(3-methyl-phenylsulfonyl)-pheny1_7-N<1>,N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(4-chlor-phenylsulfonyl)-pheny1_7~N<1>,N"-bis-methoxycarbonyl-guanidin, N-i/~2-Propionamido-4-(3-chlor-phenylsulfonyl)-pheny 1_7-N' ,N"-bis-me thoxycarbonyl- guanidin, N-i/~2-Propionamido-4- (2-chlor-phenylsulf onyl) -pheny 1_7~N1 , N" - bis-methoxycarbonyl-guanidin, N-/_ 2-Propionamido-4-(4-methoxy-phenylsulfonyl)-pheny1_7-N1,N"-bis-methoxycarbonyl-guanidin, N-/ 2-Propionamido-4-(3-methoxy-phenylsulfonyl)-pheny1_7-N1,N"-bis-methoxycarbonyl-guanidin, N-/_~2-Propionamido-4- (4-methylthio-phenylsulf onyl) -pheny 1_7~ N',N"-bis-methoxycarbonyl-guanidin,
Le A 15 666
N-/"2-Propionamido-4-(3-methylthio-phenylsulfonyl)-pheny1_7-N1, N"-bis-methoxycarboriyl-guanidin,
N-/"2-Propionamldo-4-(4-cyån-phenylsulfonyl)-phenyl^-N<1>,N"-bis-methoxycarbonyl-guanidin j'
N-/"2-Propionamido-4-(4-acetyl-phenylsulf onyl)-pheny 1__7-N<1>,N"-bis-methoxycarbonyl-guanidin, N-y^"2-Propionamido-4- (3-cyan-^phenylsulf onyl) -pheny 1_7-N1, N"-bis-methoxycarbonyl-guanidin, N-/"2-Propionamido-4-(4-propionyl-phenylsuli'onyl)-pheny 1_7-N1, N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-4-(4-acetylamino-phenylsulfonyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/_~2-Propionamido-4-(4-me thoxycarbonyl-phenylsulf onyl) - phenyl__7-N',N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-4-(3,4-dimethyl-phenylsulfonyl)-pheny1_7-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionåmido-4-(3,4-dichlor-phenylsulfonyl)-pheny1_7-N1, N"-bis-methoxycarbonyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N<1->aethoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N<1->iso-propoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-sec.-butoxycarbonyl-N"-propionyl-guanidin, N-(2-Propionamido-5-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-propionyl-guanidin, N-(2-Butyramido-5-phenylsulfonyl-phényl)-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Valeramido-5-phenylsulfonyl-phenyl)-N'-arethoxycarbonyl-N"-propionyl-guanidin
N-(2-Cyclopehtancarbonamido-5-phenylsulfonyl-phenyl)-N<1->me thoxycarbony1-N"-propiony1-guani din,
Le A 15 666
N-(2-Cyclohexancarbonamido-5-phenylsulfonylrphényl)-N1 - methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Benzamido-5-phenylsulfonyl-phenyl)-N'-méthoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-acetyl-guanidin,
N- (2-/\ cetamido-5-phenylsulf onyl-phenyl) -N' -methoxycarbonyl-N"-butyrylrguanidin,
N-(2-Acetamido-5-phenylsuli'onyl-phenyl)-w 1 -methoxycarbonyl-N"-cyclohexancarbonyl-guanidin,
N-(2-Acetamido-5-phenylsul±'onyl-phenyl)-N' -methoxycarbonyl-N"-benzoyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'-methoxycarbonyl-N"-phenylacetyl-guanidln,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N<1->methoxycarbonyl-N"-phenoxyacetyl-guanidin,
N-/~2-(2'-Hethylureido)-5-phenylsulfonyl-phenyl_7-N'-methoxycarbonyl-N" -propionyl-guanidin,
N-/~2-(2•-Aethylureido)-5-phenylsulfonyl-phenyl_7-N<1->methoxycarbonyl-N"-propionyl-guanidin,
N-/"2-(2'-Butylureido)-5-phenylsulfonyl-pheny1_7-N'-methoxycarbonyl-N" -propionyl-guanidin,
N-/_~2-(2'- CJ -C/anpentylureido)-5-phenylsulfonyl-pheny1_7-N'-methoxycarbonyl-N"-propionyl-guanidin, N-/~2-(2'-fl-Methoxymethylureido)-5-phenylsulfonyl-phenyl_7-N'-methOAycarbonyl-N"-propionyl-guanidin,
N-/~2-(2 *-Benzylureido)-5-phenylsulfonyl-phenyl_7-N1-methoxycarbonyl-N"-propionyl-guanidin,
N-/~2-(21 -Phenylureido)-5-phenylsulf onyl-phenyl_7-N' -methoxycarbonyl-N"-propionyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N'^"-bis-methoxycarbonyl-guanidin,
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N',N"-bis-aethoxy-carbonyl-guanidin,
Le A 15 666
N-(2-Acetamido-5-phenylsulfonyl-phenyl)-N',N"-bis-iso-propoxy-carbonyl-guanidin,
H-(2-Acetamido-5-phenylsulfonyl-phenyl)-N",N"-bis-sec.-butoxy-carbonyl-guanidin,
N-(2-Propionamido-5-phenylsulfonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin, N-(2-Butyramido-5-phenylsulfonyl-phenyl)-N'^"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Butyramido-5-phenylsulfonyl-phenyl)-N',N"-bis-me thoxycar bonyl-guanidin,'
N-(2-Valeramido-5-phenylsulfony1-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Valeramido-5-phenylsulfonyl-phenyl)-N',M"-bis-methoxycarbonyl-guanidin,
N-(2-Capronamido-5-phenylsulfonyl-phenyl)-W',N"-bis-methoxycarbonyl-guanidin,
N-(2-iso-Capronamido-5-phenylsulfonyl-phenyl)-N',M"-bis-methoxycarbonyl-guanidin ,
N-(2-Cyclopentancarbonamido-5-phenylsulfonyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-(2-Cyclohexancarbonamido-5-phenylsulfonyl-phenyl)-N',N"-bis-methoxycarbonyl-guanidin,
N-(2-Phenylacetamido-5-phenylsulfonyl-phenyl)-N'^"-bis-methoxycarbonyl-guanidin,
N-(2-Phenoxyacetamido-5-phenylsulfonyl-pheny1)-N *,N"-bis-methoxycarbonyl-guanidin,
N-(2-Benzamido-5-phenylsulfonyl-phenyl)-N<1>,N"-bis-methoxycarbonyl-guanidin,
N-/~2- (2 ' -Methylureido) -5-phenylsulf onyl-phenyl_7-N ' , {^"-bis-methoxy carbonyl-guanidin,
N-/~2-(2 ' -Aethylureido)-5-phenylsulf onyl-phenyl_7-N' , 1M"-bis-methoxycarbonyl-guanidin,
N-/~2-(2'-Butylureido)-5-phenylsulfonyl-phenyl_7-N',N"-bis-methoxycarbonyl-guanidin ,
N- J_~ 2-( 2'- CJ -Cyanpentylureido)-5-phenylsulfonyl-pheny1_7-N'^"-bis-methoxycarbonyl-guanidin,
n-/~2-(2 ' -fl-Met-hoxyaethyl--ureido)-5-phenylsuifonyl-phenyl__7-N',N"-bis-methoxycarbonyl-guanidin,
W-/~2-(2'-Benzylureido)-5-phenylsulfonyl-phenyl_7-w',N"-bis-methoxy-carbonyl-guanidin,
N-/~2-(2 "-Phenylureldo)-5-phenylsulfonyl-phenyl^-N1 ,l\l"-biTs-methoxy carbonyl-guanidin,
M-/~2-Propionamido-5-(4-methyl-phenylsulfonyi-phenyl_7-W',N"-bis-methoxycarbonyl-guanidin, N-/"2-fTopionamido-5-(3-methyl-phenylsulfony ]>-phenyl_7-N1,N"-bis-methoxycarbonyl-guanidin, i\!-/~2-Propionamido-5-(4-chlor-phenylsulf onyl)-pheny1_7-N ' ,N"- bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-5-(3-chlor-phenylsulfonyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin,
N-/"2-Propionamido-5-(3-chlor-phenylsulfonyl)-pheny1_7-N',N"-bis-rnethoxycarbonyl-guanidin,
N-/"2 -Pr opionamido-5 - (4-methoxy-phenylsulf onyl) -pheny 1__7-N', N " - bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(3-methoxy-phenylsulfonyl)-pheny1_7~N1 ,N" -bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-methylthio-phenylsulfonyl)-pheny1_7~N<1>,N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3-methylthio-phenylsulfonyl)-pheny1_7-N' , N"-bis~methox.ycarbonyl-guanidin, N-/~2-Propionamido-5-(4-cyan-phenylsulfonyl)-pheny1_7-N',N"-. bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-acetyl-phenylsulfonyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propi onamido-5-(3-cyan-phenylsulfony1)-pheny1_7-N1,N"-bis-methoxycarbonyl-guanidin,
N-/~2-Propionamido-5-(4-propionyl-phenylsulfonyl)-phenyl_]-N1,N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-acetylamino-phenylsulfonyl)-pheny1_7~ N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(4-methoxycarbonyl-phenylsulionyl)-phenyl7-N',N"-bis-methoxycarbonyl-guanidin, N-/~2-Propionamido-5-(3,4-dimethy^-phenylsulfonyl)-phenyl_7-N 1 , N" -bis-methoxycarbonyl-guanidin, N-/ 2-Propionaarido-5-(3,4-dichlor-phenylsulfonyl)-pheny1_7-N',N"-bis-methoxycarbonyl-guanidin.
r
Forbindelsene som fremstilles ifølge oppfinnelsen
har en overraskende god og bredspektret virkning mot følgende nematoder og cestoder: 1. Hakeormer (f.eks. Uncinaria stenocephala, Ancylostoma cani-nura, Bunostomum trigonocéphalum). 2. Trikostrongylider (f.eks. Nippostrongylus muris, Haemonchus contortus, Trichostrongylus colubriformis, Ostertagia circum-cincta) ....... 3- Strongylider (f.eks. Oesophagostomum columbianum).
4. Rhabditide (f.eks. Strongyloides ratti).
5. Spoleormer (f.eks. Ascaris suum, Toxocara canis, Toxacaris leonina).
6. Markormer (f.eks. Aspiculuris tetraptera).
7- Heterakide (f.eks. Heterakis spumosa).
8. Piskeormer (f.eks. Trichuris muris).
9. Filarier (f.eks. Litomosoides carinii, Dipetalonema witei).
10. Cestoder (f.eks. Hymenolepis nana, Taenia pisiformis, Echinococcus multilocularis).
Virkningen er påvist ved dyreforsøk etter oral og parenteral administrasjon, på forsøksdyr som er sterkt angrepet med parasitter. De anvendte doser tåles meget godt av forsøks-dyrene .
De nye.aktive stoffer kan brukes som anthelmintika
både i humanmedisin og veterinærmedisin.
Stoffene kan på kjent måte sammensettes i vanlige
preparater.
De nye forbindelser kan enten brukes som .sådanne eller i kombinasjon med farmasøytiske bærestoffer. Som preparat-former nevnes tabletter, kapsler, granulater, vandige suspensjoner, injiserbare oppløsninger, emulsjoner og suspensjoner, eliksirer-, • siruper, pastaer og lignende. Bærestoffene eller drøyningsmidlene omfatter fortynningsmidler eller fyllstoffer, sterile, vandige media eller ugiftige organiske oppløsningsmidler og lignende. Naturligvis kan tabletter og lignende som brukes oralt blandes
med søtningsstoffer og lignende.' 'De terapeutisk aktive stoffer bør i overnevnte tilfellet ha en konsentrasjon på ca. 0,5 til 90 vekt% av totalblandingen, dvs. finnes i mengder som er tilstrek-kelige til å gi nevnte doseringsspillerom.
Preparatene fremstilles på kjent måte, f.eks. ved
å blande de virksomme stoffer med oppløsningsmidler og/eller bærestoffer, eventuelt sammen med emulgeringsmldlet og/eller dispergeringsmidlet, hvorved man, når man f.eks. benytter vann som fortynningsmiddel, også kan benytte organiske oppløsnings-
midler som hjelpestoffer.
Blant andre hjelpestoffer nevnes: Vann, ugiftige organiske oppløsningsmidler som parafiner (f. eks. j ordol j ef rak--sjoner), planteolje (f.eks. jordnøttolje/sesamolje), alkoholer (f.eks. etylalkohol, glycerol), glykoler (f.eks. propylenglykol, polyetylenglykol) og vann; faste bærestoffer som naturlig steinmel (f.eks. kaolin, leirer, talkum, kritt), syntetisk stein-
mel (f.eks. høydispergert kieselsyre, silikater), sukker (f.eks. råsukker, melkesukker og druesukker); emulgeringsmidler som ikke-ionogene og anioniske emulgatorer (f.eks. polyoksyetylen-fettsyreestere, polyoksyetylen-fettalkoholetere, alkylsulfonater
og arylsulfonater), dispergeringsmidler (f.eks. lignin, sulfit-avluter, metylcellulose, stivelse og polyvinylpyrrolidon) samt glidemidler (f.eks. magnesiumstearat, talkum, stearinsyre og natriumlaurylsulfat).
Ved oral anvendelse kan tablettene naturligvis også
i tillegg til nevnte bærestoffer inneholde stoffer som natrium-
citrat, kalsiumkarbonat og dikalsiumfosfat sammen med forskjel-
lige tilsetninger som stivelse, fortrinnsvis potetstivelse,
gelatin og lignende. Videre kan man benytte glidemidler som magnesiumstearat, natriumlaurylsulfat og talkum, til tabletter-
ingen.
Når det fremstilles vandige suspensjoner og/eller eliksirer, som er beregnet for oral bruk kan de virksomme stof-
fer i tillegg til overnevnte hjelpestoffer tilsettes forskjel-
lige smaksforbedrere og fargestoffer.
Ved parenteral bruk kan oppløsningene av de virksomme stoffer blandes med egnede flytende bærestoffer.
De virksomme stoffene kan utformes som doseringsen-
heter i form av kapsler, tabletter, pastiller, drasjeer, ampul-
ler osv., hvor hver doseringsenhet er tilpasset slik at den gir en enkeltdose av aktivt stoff.
De nye forbindelser kan også i preparatene blandes
med andre kjente virksomme stoffer.
De nye forbindelser kan brukes på kjent måte. Så-
ledes oralt, parenteralt, særlig subkutant, men også eventuelt dermalt.
Generelt har det vist seg fordelaktig å benytte
mengder på ca. 0,1 til 50 mg aktivt stoff pr. kg kroppsvekt pr.
dag, for å oppnå gode resultater.
Det kan likevel være nødvendig å avvike fra de
nevnte mengder, nemlig avhengig av kroppsvekt, administrasjons.-vei samt dyreart og det individuelle forhold overfor medika-
mentet eller medikamentets art, tidspunkt, administrasjon-
intervall etc. Det kan i enkelte tilfeller være tilstrekkelig å bruke mindre enn nevnte minstemengde, mens man i andre tilfeller må overskride nevnte øvre grense. Ved bruk av større mengder enn nevnt kan det være en fordel å fordele denne over flere enkelt-porsjoner pr. dag. Det er brukt samme doseringsspillerom for mennesker og dyr. Således gjelder også overnevnte anførsler for humanmedis inen.
Den anthelmintiske virkning av de aktive stoffer
ifølge oppfinnelsen belyses ved hjelp av de følgende eksempler. Eksempel A.
Hakeorm- forsøk/ sau, hund.
Sauer som er infisert eksperimentelt med Bunostomum trigonocephalum behandles etter prepatens-tiden med forsøksfor-bindelser. Disse ble gitt som rent stoff i gelatinkapsler,
oralt.
Hunder eksperimentelt infisert med Uncinaria stenocephala henholdsvis Ancylostoma caninum ble behandlet etter for-
løpet av parasittenes- prepatens-tid. Mengden virksomt stoff ble gitt som ren forbindelse i gelatinkapsler, oralt.
Virkningsgraden ble bestemt ved at man tellet de overlevende ormer hos forsøksdyrene og de ormer som ble drevet ut ved behandlingen, etter tverrsnittsmetoden, og utregnet de utdrevne ormer i prosent.
Utprøvede virksomme stoffer, de anvendte doser og virkningen fremgår av den følgende tabell. I tabellen er det oppført de aktive stoffer og dens laveste dose i mg aktivt stoff pr. kg kroppsvekt for forsøksdyrene, som reduserer ormangrepet på forsøksdyrene med mer enn 90%.
Eksempel B.
Nippostrongylus muris- rotte.
Rotte infisert eksperimentelt med Nippostrongylus muris ble behandlet etter forløpet prepatens-tid. Den aktive stoffmengde ble gitt oralt som vandig suspensjon.
Preparatenes virkningsgrad ble bestemt ved at man tellet gjenværende ormer i forsøksdyret etter snittmetoden til sammenligning med antall ormer hos ubehandlede kontrolldyr, og deretter utregnet virkningsgraden i prosent.
I den følgende tabell finnes de aktive stoffer og laveste dosering som reduserer ormangrepet hos forsøksdyrene med mer enn 90%, sammenlignet med kjente, lignende preparater. Tillegg til tabell 1 (til eksempel A).
Eksempel C.
Mage- og tarmorm- forsøk/ sau.
Sauer som ble eksperimentelt infisert med Haemonchus contortus og Trichostrongylus colubriformis ble behandlet etter avsluttet prepatens-tid. Mengden virksomt stoff ble gitt oralt i gelatinkapsler.
Virkningsgraden ble bestemt ved at man tellet ormeggene som ble utskilt i sauelorten, før og etter behandlingen .
Fullstendig uteblivelse av eggutskillingen etter behandlingen betyr at ormene er drevet ut eller er så sterkt skadet at de ikke lenger kan produsere egg (Dosis effectiva).
De utprøvede stoffer og de virksomme doser (Dosis effectiva minima) fremgår av følgende tabell.
Eksempel E.
Spoleormforsøk/ hund, rotte.
Hunder eksperimentelt eller naturlig infisert med Toxascaris leonina ble gitt det aktive stoff som ren forbindelse i gelatinkapsler, oralt.
Rotter infisert eksperimentelt med Ascaris suum ble behandlet 2 til 4 dager etter infeksjon. De aktive stoffer ble gitt oralt som vandig suspensjon..
Preparatenes virkningsgrad ble bestemt ved at man etter snitt tellet gjenværende ormer i forsøksdyret sammenlignet med antallet hos ubehandlede kontrolldyr, og utregnet prosentsatsen.
I den følgende tabellen er det oppført de aktive stoffer og laveste doser, som reduserer ormangrepet hos for-søksdyrene med over 90%, sammenlignet med kjente og lignende preparater.
Eksempel F.
Aspiculuris tetraptera/ mus.
Mus som er infisert naturlig med Aspiculuris tetraptera ble behandlet etter prepatens-tidens forløp,
med parasitter. •
Mengden aktivt stoff ble gitt oralt som vandig suspensj on.
Preparatenes virkningsgrad ble bestemt ved at man tellet gjenværende ormer etter snittmetoden hos forsøks-dyret, sammenlignet med antall ubehandlede kontrolldyr, og utregnet virkningsgraden.
Eksempel G.
Hymenolepis nana/ mus.
Forsøksdyr infisert eksperimentelt med H.nana ble behandlet etter forløpet av parasittenes prepatens-tid. Den aktive stoffmengde ble gitt oralt som vandig suspensjon.
Preparatenes virkningsgrad ble bestemt som tidligere beskrevet»
Frems tillingseksempler.
Eksempel 1.
24,2 g (0,1 mol) 2-amino-5~fenoksy-acetanilid, smeltepunkt 120°C, ble kokt med 20,6 g (0,1 mol) N,N'-bis-metoksykarbonylisotiourea-S-metyleter og 2,6 g (0,015 mol)
p-toluensulfonsyre i 200 ml absolutt metanol 3 timer under røring og tilbakeløp. Man filtrerte varmt og etter avkjøling fikk man det utkrystalliserte N-(2-acetamido-4-fenoksyfenyl)-N',N"-bis-metoksykarbonyl-guanidin, som ble vasket med eter pg tørket i høyvakuum, smeltepunkt.l68°C, utbytte 27 g = 67,5% av teoretisk.
Ved opparbeidelse av moderluten kan utbyttet økes.
I analogi med eksempel 1 fikk man ut fra: 2-amino-5-fenoksy-acetanilid og N,N'-bis-etoksy-karbony1-isotiourea-S-metyleter: N-(2-acetamido-4-fenoksy-fenyl)-N',N"-bis-etoksykarbony1-guanidin, smeltepunkt 159°C.
2-amino-5-fenoksy-acetanilid og N,N'-bis-iso-propoksykarbonyl-isotiourinstoff-S-metyleter: N-(2-acetamido-4-fenoksy-fenyl)-N',N"-bis-iso-propoksykarbonyl-guanidin, smeltepunkt 165°C.
2-amino-5-fenoksy-propionanilid av smeltepunkt 122°C og NjN'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-(2-propionamido-4-fenoksy-fenyl)-N'3N"-bis-metoksy-karbonylguanidin, smeltepunkt 143°C.
2-amino-5~fenoksy-propionanilid og N5N'-bis-et oksykarbonyl-isotiourinstoff-S-metyleter: N-(2-propion-amido-4-fenoksy-fenyl)-N'3N"-bis-etoksykarbonyl-guanidin av smeltepunkt l67°C.
2-amino-5-fenoksy-propionanilid og N,N'-bis-iso-propoksy-karbonyl-isotiourinstoff-S-metyleter: N-(2-pro-pionamido-4-fenoksy-fenyl)-N',N"-bi s-iso-propoksykarbonyl-guanidin av smeltepunkt l6l°C.
2-amino-5~fenoksy-butyranilid av smeltepunkt ll8°C og N,N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter : N-(2-butyramido-4-fenoksy-fenyl)-N',N"-bis-metoksy-karbonyl-guanidin av smeltepunkt 136°C.
2-amino-5-fenoksy-butyranilid og N5N'-bis-et oksykarb ony 1-isot iourinstof f -S-metyleter : N-(2-butyramido-4-fenoksy-fenyl)-N'5N"-bis-etoksykarbonyl-guanidin av smeltepunkt 142°C.
2-amino-5-fenoksy-butyranilid og N,N'-bis-iso-propoksykarbony1-isotiourinstoff-S-metyleter: N-(2-butyramido-4-fenoksy-fenyl)-N',N"-bis-iso-propoksykarboriyl-guanidin av
smeltepunkt l63°C.
2-amino-5-fenoksy-benzanilid av smeltepunkt 140°C .og N3N' -bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-(2-benzamido-4-fenoksy-fenyl)-N',N"-bis-metoksykarbonyl-guanidin av smeltepunkt 157°C.
2-amino-5~fenoksy-benzanilid og N3N'-bis-etoksy-karbonyl-isotiourinstoff-S-metyleter: N-(2-benzamido-4-fenoksy-fenyl)-N'3N"-bis-etoksykarbonyl-guanidin av smeltepunkt.. l4l°C.
2-amino-5-fenoksy-benzanilid og N,N'-bis-iso-propoksykarbonyl-isotiourinstoff-S-metyleter: N-(2-benzamido-4- fenoksy-fenyl)-N'3N"-bis-iso-propoksykarbonyl-guanidin av smeltepunkt l88°C.
2-amino-5-fenoksy-cykloheksankarbonanilid av smeltepunkt 142 C og N3N'-bis-metoksykarbonyl-isotiourinstoff-5- metyleter: N-(2-cykloheksankarbonamido-4-fenoksy-fenyl)-N', N"-bis-metoksykarbonyl-guanidin av smeltepunkt 155°C.
2-amino~5-fenoksy-cykloheksankarbonanilid.og N j N'-bis-etoksykarbony1-isotiourinstoff-S-metyleter: N- (2-cykloheksankarbonamido-4-fenoksy-fenyl)-N'3N"-bis-etoksy-karbonyl-guanidin av smeltepunkt 132°C.
2-amino-5~fenoksy-metoksyacetanilid av smeltepunkt 93°C og N3N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-(2-metoksyacetamido-4-fenoksy-fenyl)-N'3N"-bis-metoksykarbo-nylguanidin av smeltepunkt l45°C.
2-amino-5~(3-klor-fenoksy)-acetanilid og N3N'-bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-/_ 2-acetamido-4-(3-klor-fenoksy)-fenyl/-N'3N"-bis-metoksykarbonyl-guanidin av smeltepunkt l60-l6l°C.
2-amino-5~(3-klor-fenoksy)-butyranilid og N3N'-bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-/_ 2-butyr amid o-4 - (3-klor-fenoksy) -f eny_l/ - N ' 3N"-bis-metoksykarbonyl-guanidin av smeltepunkt l63°C.
2-amino~5-(4-klor-fenoksy)-acetanilid av smeltepunkt 150-151°C og N3N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter : N-/~2-acetamido-4-( 4-klor-f enoksy )-f enyl/-N,?> 3N"-bis-metoksy-karbonyl-guanidin av smeltepunkt 170°C.
2-amino-5-(4-klor-fenoksy)-butyranilid av smeltepunkt 101°C og N3N'-bis-metoksykarbonyl-isotiourinstoff-S-
metyleter: N-/~2-butyramido-4-( 4-klor-f enoksy )-f enyl7-N' ,N"-bis-metoksykarbonyl-guanidin av smeltepunkt 201°C.
2-amino-5-(3-fluor-fenoksy)-butyranilid av smeltepunkt 121°C og N,N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-/<_>2-butyramido-4-(3-fluor-fenoksy)-fenyl7-N',N"-bis-metoksykarbonyl-guanidin av smeltepunkt 138°C.
2-amino-5-(3-fluor-fenoksy)-metoksyacetanilid
av smeltepunkt 106°fl og N^N^bis-metoksykarbonyl-isotiourin-.. st of f-S -me ty let er : N-/_~2-met oksyacetamido-4 - ( 3-fluor f enoksy ) - fenyl7-N'3N"-bis-metoksykarbonyl-guanidin av smeltepunkt l48°C.
2-amino-5-(3-metoksy-fenoksy)-acetanilid av smeltepunkt 107-108°C og N,N'-bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-/_—2-acetamido-4- ( 3-me tok sy-f enoksy) - feny<_>l/-N,<N>"-bis-m<é>toksykarbonyl-guanidin av smeltepunkt l64°C.
2-amino-5-(3-metoksy-fenoksy)-propionanilid av smeltepunkt 129-130°C og NSN'-bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-/_ 2-propionamido-4-(3-metoksy-fenoksy)-fenyl/-N',N"-bis-metoksykarbonyl-guanidin av smeltepunkt 133-134°C.
2-amino-5-(4-metyl-fenoksy)-propionanilid av smeltepunkt 125°C og N3N'-bis-metoksykarbonyl-isotiourinstoff-S-met ylet er : N-/_~2 -pr opionamido-4- (4-metyl-f enoksy) - f enyl / - N'3N"-bis-metoksykarbonyl-guanidin av smeltepunkt l65-l66°C.
2-amino-5-(4-metyl-fenoksy)-butyranilid av smeltepunkt 122°C og N5N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-/_—2-but yramido-4-( 4-metyl-f enoksy )-f enyl/-N' , N"-bis-metoksykarbonyl-guanidin av smeltepunkt l6l-l62°C.
2-amino-5-(4-acetamino-fenoksy)-propionanilid av • smeltepunkt 200°C og N ,N' -bis-met oksykarb ony 1-isotiour in.sbof f-S-metyleter : N-/_ 2 -pr opionamido-4- (4-acetamido- f enoksy) -f eny_l/- N'jN"-bis-metoksykarbonyl-guanidin av smeltepunkt 197-199°C.
2-amino-5-(4-acetamino-fenoksy)-butyranilid av smeltepunkt 150°C og N,N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-/_ 2-butyr amido-4-( 4-acetamido-f enoksy ) -f enyl/- N'JN"-bis-metoksykarbonyl-guanidin av smeltepunkt 190°C.
2-amino-5-(4-cyan-fenoksy)-butyranilid og N,N'-bis-metoksy-karbonyl-isotiourinstof f-S-metyleter : N-/_ 2-b ut yramido-4 - ( 4-cyan-f enoksy) - f enyl^Z-N ' ,N"-bis-met oksykarb onyl-guanidin.
2-amino-5-(4-fluor-fenoksy)-butyranilid og N,N'-bis-met oksy-karbony 1-isotiourinstof f-S-metyleter : N-/_ 2-butyramido-4-(4-cyan-fenoksy)-fenyl7-N',N"-bis-metoksykarbonyl-guanidin.
2-amino-5-(4-acetyl-fenoksy)-butyranilid og N ,N 1 - bis-metoksy-karbonyl-isotiourinstof f-S-metyleter : N-/_ 2-butyramido-4-(4-acetyl-fenoksy)-fenyl7-N',N"-bis-metoksykarbonyl-guanidin.
2-amino-5-(3-acetyl-fenoksy)-butyranilid og N,N' - bis-metoksy-karbonyl-isotiourinstoff-S-metyleter: N-/_ 2-butyramido-4-(3-acetyl-fenoksy)-fenyl7-N'3N"-bis-metoksykarbonyl-guanidin.-
2-amino-5-(4-metyltio-fenoksy)-butyranilid og N3N'-bis-metoksykarbonyl-isotiourinstof f-S-metyleter : N-/_ 2-butyr-amido-4-(4-metyltio-fenoksy)-fenyl7-N'3N"-bis-metoksy-karbony1-guanidin.
2-amino-5-(3-trifluormetyl-fenoksy)-butyranilid
og N3N'-bis-metoksykarbonyl-isotiourinstoff-S-metyleter: N-_/_2-butyramido-4-( 3-trif luormetyl-f enoksy ) - f enyl7-N ' 3N"-bis-metoksy-karbonyl-guanidin.
Eksempel 2.
24,2 g (0,1 mol) 2-amino-5-fenoksy-acetanilid
ble kokt under røring og tilbakeløp med 22 g (0,1 mol) N-metoksykarbonyl-N'-propiony1-isotiourea-S-metyleter og 2,6 g (0,015 mol) p-toluensulfonsyre i 200 ml absolutt metanol, i 3 timer. Man filtrerte varmt og fikk N-(2-acetamido-4-fenoksy-feriyl)-N'-metoksy-karbony1-N"-propionyl-guanidin etter avkj øl-ing av moderluten, som krystaller, disse ble vasket godt med eter og tørket i høyvakuum, smeltepunkt 134°C, utbytte 20 g = 50% av teoretisk. Utbyttet kan økes ved opparbeidelse av moderluten.
Analogt eksempel 2 fikk man ut fra:
2-amirio-5-fenoksy-propionanilid og N-metoksy-karbonyl-N' -propionyl-isotiourinstoff-S-metyleter: N- (2-propionamido-4-fenoksy-fenyl)-N'-metoksykarbony1-N"-propionyl-guanidin av smeltepunkt 132°C. 2-amino-5-fenoksy-butyranilid og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-(2-butyramido-4-fenoksy-fenyl)-N'-metoksykarb ony1-N"-propionyl-guanidin av smeltepunkt 125°C. 2-amino-5-fenoksy-benzanilid.og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-(2-benzamido-4-fenoksy-fenyl)-N'-metoksykarbony1-N"-propionyl-guanidin av smeltepunkt 151°C. 2-amino-5-fenoksy-cykloheksankarbonanilid og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-(2-cykloheksankarbonamido-4-fenoksy-fenyl)-N'-metoksykarbonyl-N"-propionyl-guanidin av smeltepunkt 139°C. 2-amino-5-fenoksy-acetanilid og N-etoksykarbony1-N'-benzoyl-isotiourinstoff-S-metyleter: N-(2-acetamido-4 - fenoksy-fenyl)-N'-etoksykarbony1-N"-benzoyl-guanidin av smeltepunkt 179°C. 2-amino-5-fenoksy-butyranilid og N-metoksykarbonyl-N' -cykloheksylkarbony1-isotiourinstoff-S-metyleter: N-(2-butyramido-4-fenoksy-fenyl)-N'-metoksykarbony1-N"-cyklo-heksy 1-karbonyl-guanidin av smeltepunkt l46°C. 2-amino-5-fenoksy-butyranilid og N-metoksykarbonyl-N' -etoksy-metylkarbonyl-isotiourinstoff-S-metyleter: N-(2-butyramido-4-fenoksy-fenyl)-N'-metoksykarbony1-N"-etoksy-metyl-karbony1-guanidin av smeltepunkt 137°C. 2-amino-5-(3-klor-fenoksy)-acetanilid og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-r~ 2-acetamido-4-(3-klor-fenoksy)-fenyl/-N'-metoksykarbonyl-N"-propiony1-guanidin av smeltepunkt 163°C. 2-amino-5-(3-klor-fenoksy)-butyranilid og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-/__2-butyramido-4- (3-klor-f enoksy )-f enyl7-N '-metoksykarbonyl-N"-propiony1-guanidin av smeltepunkt l63°C. 2-amino-5-(4-acetamido-fenoksy)-propionanilid og N-metoksykarb ony1-N'-propiony1-is otiourinstoff-S-met yleter: N-/_ 2- (propionamido-4- ( 4-acetamido-fenoksy )-fenyl/-N' -metoksy-karbonyl-N"-propionylguanidin av smeltepunkt 190°C. 2-amino-5_(4-acetamido-fenoksy)-butyranilid og N-metoksykarbonyl-N'-propionyl-isotiourinstoff-S-metyleter: N-_/ 2-but yr ami do- H'- ( 4-acetamido-f enoksy) - f enyl/-N' -me t oksykarb o-nyl-N"-propionylguanidin av smeltepunkt 178-l80°C.. 2-amino-5~(4-metyl-fenoksy)-butyranilid og N-metoksykarbonyl-N<*->propionyl-isotiourinstoff-S-metyleter: N- - "" l_ 2-butyramido-4- (4-metyl-f enoksy) - f eny_l/-N ' -me t oksykarb ony 1-N"-propionyl-guanidin av smeltepunkt 135°C. Eksempel 3-
12,8 g (0,05 mol) 2-amino-4-fenoksy-propionanilid (smeltepunkt 110-111°C) ble kokt under tilbakeløp i 100 ml metanol med 10,3 g (0,05 mol) N,N'-bis-metoksykarbonyl-isotiourea-S-metyleter under tilsetning av 1 g p-toluensulfonsyre, i 3 timer. Etter frafiltrering av bunnfallet ble dette vasket med eter og man fikk etter tørking 11,1 g N-(2-propionamido-5-fenoksy-fenyl)-N',N"-bis-metoksykarbonyl-guanidin med smeltepunkt 148-149°C
På tilsvarende måte får man ut fra N,N'-disubsti-tuerte isotiourea-S-metyletere og 2-amino-4-fenoksy-anilider følgende forbindelser:
Eksempel 4.
14,3 g (0,05 mol) 2-amino-5-fenyltio-butyranilid (smeltepunkt 152°C) ble oppvarmet i 100 ml metanol med 10 g (0,05 mol) N,N'-bis-metoksykarbonyl-isotiourea-S-metyleter under tilsetning av 1 g p-toluensulfonsyre i 3 timer. Man får etter opparbeidelse i analogi med eksempel 3 13}8 g N-(2-butyr-amido-4-fenyltio-fenyl)-N',N"-bis-metoksykarbonyl-guanidin med smeltepunkt 155°C.
I to tilsvarende måter får man ut.fra N,N'-disub-stituerte isotiourea-S-metyletere og 2-amino-5_fenyltio-anilider følgende forbindelser:
Eksempel 5-
På samme måten som beskrevet i eksempel 3 får man ut fra 14,3 g (0,05 mol) 2-amino-4-fenyltio-butyranilid og 10*3g (0,05 mol) N,N'-bis-metoksykarbony1-isotiourea-S-metyleter 14,5 g N-(2-butyramido-5-fenyltio-feny1)-N',N"-bis-metoksykarbonyl-guanidin med smeltepunkt l64-l66°C.
På tilsvarende måte får man ut fra N,N'-disubsti-tuerte isotiourea-S-metyletere og 2-amino-4-fenyltio-anilider følgende forbindelser:
Eksempel 6.
På samme måten som i eksempel 3 får man ut fra 14,2 g (0,05 mol) 2-amino-5-f.enylsulfiny 1-propionanilid og 10,3 g (0,05 mol) N,N'-bis-metoksykarbony1-isotiourea-S-metyleter 12,7 g N-( 2-propionamido-14-fenylsulf inyl-f enyl) -N ' ,N"-bis-metoksy karbonyl-guanidin med smeltepunkt 193-195°C.
På lignende måte får man ut fra N,N'-disubstituerte isotiourea-S-metyletere og 2-amino-5_fenylsulfiny1-anilider følgende forbindelser:
Eksempel 7-
På samme måten som beskrevet i eksempel 3 går man ut fra 14,2 g (0,05 mol) 2-amino-4-fenylsulfiny1-propionanilid og 10,3 g (0,05 mol) N,N'-bis-metoksykarbony1-isotiourea-S-mety leter 12,7 g N-(2-propionamido-5-fenylsulfinyl-fenyl)-N',N"-bis-metoksykarbonyl-guanidin.
På lignende måte får man ut fra N,N'-disubstituerte isotiourea-S-metyletere og 2-amino-4-fenylsulfiny1-anilider følgende forbindelser:
Eksempel 8.
Som beskrevet i eksempel 3 går man ut i fra 14,4 g (0,05 mol) 2-amino-5-fenylsulfony1-propionanilid med smeltepunkt 137°C og 10,3 g (0,05 mol) N,N'-bis-metoksykarbony1-isotiourea-S-metyleter, 12,7 g N-(2-propionamido-4-fenylsulfony1-fenyl)-N', N"-bis-metoksykarbony1-guanidin med smeltepunkt .197°C.
På analog måte får man ut fra N,N'-disubstituerte isotiourea-S-metyletere og 2-amino-5-fenylsulfony1-anilider følg-ende forbindelser:
Eksempel 9-
'14,4 g (0,05 mol) 2-amino-4-fenylsulfonyl-butyranilid (smeltepunkt 143-145°) ble oppvarmet i 100 ml metanol med 10,3 g (0,05 mol) N,N'-bis-metoksykarbonyl-isotiourea-S-metyleter under tilsetning av 1 g p-toluensulfonsyre, i 3 timer. Etter opparbeidelse som i eksempel 3 får man 15,8 g N-(2-butyr-amido-5-fenylsulfony1-fenyl)-N<1>,N"-bis-metoksy-karbony1-guanidin med smeltepunkt 173°C.
På lignende måte får man ut fra N,N'-disubstituerte isotiourea-S-metyletere og 2-amino-5~fenylsulfony1-anilider følgende forbindelser:
Eksempel 10.
Til en oppløsning av 8,9 g N-(2-butyramido-4-fenyltio~-fenyl)-N' ,N"-bis-metoksykarbonyl-guanidin [_ smeltepunkt 155°C, eksempel (4_)_/ i 1,4 liter eddiksyreanhydrid drypper man 2,3 ml<H>2<0>2(30%-ig).Etter 10 timer inndamper man blandingen i vakuum, blander, residuet med en blanding av eddikester og petroleter og filtrerer.
Man får 8,5 g N-(2-butyramido-4-fenylsulfinylfeny1)-N,N'-bis-metoksykarbonyl-guanidin med smeltepunkt 186°C under spaltning, (gjenoppløst fra metanol/eddikester). Massespektrum viser en mol-topp på 460.
På tilsvarende arbeidsmåte vil man av 3152 g N-(2-metoksyacetamido-4-fenyltio-fenyl)-N',N"-bis-metoksykarbonyl-guanidin og-8,5 ml H2<0>2(30%-ig) få 30g N-(2-metoksyacetamido-4-fenylsulfinyl-fenyl)-N',N"-bis-metoksykarbonyl-guanidin av smeltepunkt 134°C.
Eksempel 11.
Ifølge den i eksempel 10 omtalte metode vil man av 13,3 g N-(2-butyramido-4-fenyltio-feny1)-N',N"-bis-metoksy-karbonylguanidin og 20 ml H2<32 (30%-ig) få 12,7 g N-(2-butyramido-4-fenyl-sulfonyl-fenyl)-N',N"-bis-metoksykarbonyl-guanidin med smeltepunkt l80°C. Massespektrum viser en mol-topp på 476.
På tilsvarende måte vil man av 8,9 g N-(2-metoksy-acetamido-4-fenyltio-fenyl)-N',N"-bis-metoksykarbony1-guanidin og 14 g H202(30%-ig) få 8,0 g N-(2-metoksyacetamido-4-fenyl-sulf onyl- f enyl ) -N',N"-bis-metoksykarbonyl-guanidin av smeltepunkt 142°C.

Claims (4)

1. Substituerte fenylguanidiner med formel
hvori R og R <1> forskjellig fra hverandre og vekselsidig betyr for hver gang en av restene
hvori R betyr hydrogen, eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert aryl, eventuelt substituert amino, eventuelt substituert alkoksy, eventuelt substituert aralkyl og R betyr eventuelt substituert alkyl, eventuelt substituert alkenyl, eventuelt substituert alkinyl og R^ betyr hydrogen, eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert alkoksy, eventuelt substituert alkenyloksy, eventuelt substituert alkinyloksy, eventuelt substituert aryl, eventuelt substituert aralkyl, eventuelt substituert alkenyl, eventuelt substituert alkinyl, 2 ' 3 og hvori R og R kan være like eller forskjellige og bety hydrogen, eventuelt substituert alkyl, eventuelt .substituert alkoksy, eventuelt substituert amino, halogen, halogenalkyl, cyano, eventuelt substituert alkyltio, eventuelt substituert acyl, eventuelt substituert karbalkoksy, og hvori X kan bety et oksygenatom, et svovelatom, sulfinylgruppen eller sulfonylgruppen.
2. Fremgangsmåte til fremstilling av substituerte fenylguanidiner med formel
hvori R og R <1> er forskjellige fra hverandre og vekselsidig står for hver gang en av restene
hvori R betyr hydrogen, eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert aryl, eventuelt substituert amino, eventuelt substituert alkoksy, eventuelt substituert aralkyl og R^ betyr eventuelt substituert alkyl, eventuelt substituert alkenyl, eventuelt substituert alkinyl og R" betyr hydrogen, eventuelt substituert alkyl, eventuelt substituert cykloalkyl, eventuelt substituert alkoksy, eventuelt substituert alkenyloksy, eventuelt substituert alkinyloksy, eventuelt substituert aryl, eventuelt substituert aralkyl, eventuelt substituert alkenyl, eventuelt substituert alkinyl, og hvori R og R kan være like eller forskjellige og bety hydrogen, eventuelt substituert alkyl, eventuelt substi- .tuert alkoksy, eventuelt substituert amino, halogen, halogenalkyl, cyano, eventuelt substituert alkyltio, eventuelt substituert acyl, eventuelt substituert karbalkoksy, og hvori X kan bety et oksygenatom, et svovelatom, sulf iny lgruppen og- sulf ony lgruppen , karakterisert ved ata) substituerte anilinderivater med formel
2 3 4 hvori R , R , R og X har overnevnte betydning og hvori X kan være sammenknyttet med stilling 4 eller stilling 5 av den substituerte amino-fenylgruppe med formel II, omsettes med isotiourinstoffer med formel
5 6 7 hvori R og R har overnevnte betydning og R betyr alkyl med 1 til 4 karbonatomer, i nærvær av et fortynningsmiddel og eventuelt i nærvær av en syre eller b) at for fremstilling av forbindelser med formel I, 12 3 hvori restene R, R , R og R^ har overnevnte betydning og X betyr SO eller SC^ omsettes forbindelser med formel
12 3 hvori R, R , R og R har overnevnte betydning, med den tilsvarende mengde av et oksydas.i onsmiddel til forbindelser med formel
12 3 hvori restene R, R , R og R^ har overnevnte betydning og Z betyr SO eller S02 -
3. Legemiddel, karakterisert ved et innhold av minst et substituert fenylguanidin ifølge krav 1.
4. Fremgangsmåte til fremstilling av anthelmintiske midler, karakterisert ved at man blander substituerte f enylguanidiner' ifølge krav 1 med inerte, ikke-toksiske, farmasøytisk egnede bærestoffer.
5- Fremgangsmåte til behandling av he 1mintiaser, ■ karakterisert ved at inan appliserer substitu- - erte fenylguanidiner ifølge krav 1 til mennesker eller dyr, som er syke av helmintiaser.
NO75751618A 1974-05-15 1975-05-06 NO751618L (no)

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DE2651467A1 (de) * 1976-11-11 1978-05-18 Bayer Ag Substituierte o-phenylendiaminderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
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CH612925A5 (no) 1979-08-31
DK134282B (da) 1976-10-11
IE41058B1 (en) 1979-10-10
JPS5833842B2 (ja) 1983-07-22
IL47269A0 (en) 1975-07-28
ES437692A1 (es) 1977-01-16
JPS50157534A (no) 1975-12-19
JPS58131966A (ja) 1983-08-06
NL186811C (nl) 1991-03-01
AR208696A1 (es) 1977-02-28
NL7505603A (nl) 1975-11-18
HU174257B (hu) 1979-12-28
SE430887B (sv) 1983-12-19
LU72462A1 (no) 1976-03-17
ZA753122B (en) 1976-04-28
BE829052A (fr) 1975-11-14
NL186811B (nl) 1990-10-01
DE2423679A1 (de) 1975-11-20
IT1047751B (it) 1980-10-20
AR210116A1 (es) 1977-06-30
MY8000187A (en) 1980-12-31
IE41058L (en) 1975-11-15
CA1071649A (en) 1980-02-12
JPS5915904B2 (ja) 1984-04-12
EG11983A (en) 1978-06-30
FI63020C (fi) 1983-04-11
BR7503008A (pt) 1976-03-23
PL99857B1 (pl) 1978-08-31
DE2423679B2 (de) 1977-02-03
FR2270861B1 (no) 1978-11-10
JPS5945672B2 (ja) 1984-11-07
AU8115975A (en) 1976-11-18
FI751399A (no) 1975-11-16
ATA462777A (de) 1981-06-15
PL98595B1 (pl) 1978-05-31
DK134282C (da) 1977-03-14
IN142490B (no) 1977-07-16
DK211775A (da) 1975-11-16
AT365475B (de) 1978-07-15
US3993682A (en) 1976-11-23
FI63020B (fi) 1982-12-31
IL47269A (en) 1980-09-16
AT348540B (de) 1979-02-26
JPS50154223A (no) 1975-12-12
SU662006A3 (ru) 1979-05-05
GB1466839A (en) 1977-03-09
DD119224A5 (no) 1976-04-12
PH17307A (en) 1984-07-18
SE7505527L (sv) 1975-11-17
HK1680A (en) 1980-01-18
KE2773A (en) 1977-10-21
ATA365475A (de) 1978-07-15
FR2270861A1 (no) 1975-12-12

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