CS196281B2 - Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles - Google Patents

Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles Download PDF

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Publication number
CS196281B2
CS196281B2 CS786322A CS632278A CS196281B2 CS 196281 B2 CS196281 B2 CS 196281B2 CS 786322 A CS786322 A CS 786322A CS 632278 A CS632278 A CS 632278A CS 196281 B2 CS196281 B2 CS 196281B2
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CS
Czechoslovakia
Prior art keywords
formula
producing
oxibenzimidazoles
phenylsulphonyl
alkoxycarbonyl
Prior art date
Application number
CS786322A
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Czech (cs)
Inventor
Heinz Loewe
Josef Urbanietz
Dieter Duewel
Reinhard Kirsch
Original Assignee
Hoechst Ag
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Publication date
Priority claimed from DE2441201A external-priority patent/DE2441201C2/en
Application filed by Hoechst Ag filed Critical Hoechst Ag
Priority to CS786322A priority Critical patent/CS196281B2/en
Publication of CS196281B2 publication Critical patent/CS196281B2/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

2-alkoxykarbonylaminobénzintidazolyloVé deriváty s alkylovými zbytky, acyiovýmí zbytky, fenoxyskupinami a fenylthioskupinami v poloze 5(6) jsou již jako anthelmintika známy (P. Actor a další, Nátuře 2Ϊ5, 321 .(1967); DOS 2 029 637; DOS 2 164 690; DOS 2 363 348).2-alkoxycarbonylaminobenzenesulfazolyl derivatives with alkyl radicals, acyl radicals, phenoxy and phenylthio groups in the 5-position (6) are already known as anthelmintics (P. Actor et al., Nature 2-5, 321 (1967); DOS 2 029 637; DOS 2 164 690); ; DOS 2,363,348).

Předmětem vynálezu jsou anthelminticky účinné 2-alkoxykarbonylamino-5:(-6)-fenylsulfonyloxybenzimidazoly obecného vzorce 1, The present invention provides anthelmintically active 2-alkoxycarbonylamino-5 : (-6) -phenylsulfonyloxybenzimidazoles of formula 1,

(1) v němž(1) in which:

Ri znamená alkylový zbytek s 1 až 4 atomy'uhlíku,R 1 represents an alkyl radical having 1 to 4 carbon atoms,

R2 a Rj znamenají vždy nezávisle na sobě vodík, alkoxyskupinu s 1 až 4 atomy uhlíku, halogen, trifluormethylovou skupinu, alkylo196281 vou skupinu s 1 až 4 atomy uhlíku nebo kyanoskupinu.R 2 and R 1 are each independently hydrogen, C 1 -C 4 alkoxy, halogen, trifluoromethyl, C 1 -C 4 alkyl or cyano.

Jako· alkylové zbytky v substituentech Ri, Rž a R3 přicházejí v úvahu: methyl, ethyl, propyl, isopropyl, butyl, sek.butyl, terc.butyl. Jako alkoxyskupiny v substituentech R2 a Ř3 přicházejí v úvahu: methoxyškupína, ethoxyskupina,.propoxyskupina, isopropoxyskupina a butoxyskupina. Jako atomy halogenu v substituentech R2 a R3 přicházejí v úvahu: fluor, chlor, brom a jod.Suitable alkyl radicals in the substituents R1, R2 and R3 are: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl. Suitable alkoxy groups in substituents R 2 and R 3 are: methoxy, ethoxy, propoxy, isopropoxy and butoxy. Suitable halogen atoms in the substituents R 2 and R 3 are: fluorine, chlorine, bromine and iodine.

Zvláště výhodné jsou sloučeniny vzorce 1, v němž znamená Ri methyl, ethyl, propyl nebo butylí Rž vodík nebo chlor a R3 vodík, chlor nebo trifluormethylovou skupinu.Particularly preferred are compounds of formula 1 wherein R 1 is methyl, ethyl, propyl or butyl R 2 is hydrogen or chlorine and R 3 is hydrogen, chlorine or trifluoromethyl.

Předmětem vynálezu je způsob výroby 2-The object of the invention is a process for producing 2-

Claims (1)

alkoxykarbonylamino-5 (6 j -fenylsulf onyloxybenzimidazolů vzorce 1, v němž Ri, R2 a R3 mají shora uvedený význam, který se vyznačuje tím, že se..derivát o-fenylendiminu obecného vzorce 2 v němžalkoxycarbonylamino-5- (6'-phenylsulphonyloxybenzimidazoles of formula 1 wherein R 1, R 2 and R 3 are as defined above, characterized in that the o-phenylenedimine derivative of formula 2 wherein: Rz a R3 mají stejný význám jako ve vzorci i,' · - ;R 2 and R 3 have the same meanings as in formula 1, -; nechá reagovat s esterem kyseliny bis-alkylneho his-arylthiomethylenaminomravenčí obecného vzorce 6, ;reacting a bis-alkyl ester of his-arylthiomethyleneamine formic acid of formula 6; 'R4S'R4S XX C = N—C—ORiC = N - C - OR 1 RsS ORsS O ..,(6) v němž.., (6) in which Ri má význam uvedený ve vzorci 1 a R4 a Rs jsou buď stejné, nebo rozdílné a znamenají aíkylový zbytek s 1 až 4 atomy uhlíku, alkylenový zbytek se 3 až 5 atomy uhlíku, cyklohexylový zbytek nebo popřípadě substituovaný fenylový, popřípadě benízylový zbytek obecných vzorců 7, popřípadě 8 (8.1 přičemž znamenáR 1 is as defined in formula 1, and R 4 and R 5 are either the same or different and are C 1 -C 4 alkyl, C 3 -C 5 alkylene, cyclohexyl or an optionally substituted phenyl or benzyl radical of formulas 7 or 8 (8.1 wherein X nezávisle na sobě atom halogenu, methylovou skupinu' nebo nitroskupinu a n číslo 0, 1 nebo 2, nebo v němž R4 a Rs mohou být také spojeny do kruhu, který, obsahuje 2 nebo 3 methylenové skupiny.X independently of one another is a halogen atom, a methyl group or a nitro group and n is 0, 1 or 2, or wherein R 4 and R 5 may also be joined to a ring containing 2 or 3 methylene groups.
CS786322A 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles CS196281B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS786322A CS196281B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE2441201A DE2441201C2 (en) 1974-08-28 1974-08-28 2-Carbalkoxyamino-5 (6) -phenyl-sulfonyloxy-benzimidazoles and process for their preparation
CS755619A CS196278B2 (en) 1974-08-28 1975-08-15 Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles
CS786322A CS196281B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles

Publications (1)

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CS196281B2 true CS196281B2 (en) 1980-03-31

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CS786320A CS196279B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles
CS786321A CS196280B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl- oxybenzimidazoles
CS786322A CS196281B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl-oxibenzimidazoles

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CS786320A CS196279B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles
CS786321A CS196280B2 (en) 1974-08-28 1978-08-29 Method of producing 2-alkoxycarbonyl-amino-5/6/-phenylsulphonyl- oxybenzimidazoles

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CS196280B2 (en) 1980-03-31

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