2-Carbalkoxyamino-5-benzimidazolyl aminophenyl ethers - prepd e.g. by reacting 1,2-phenylenediamines with alkyl S-methyl-isothiourea-carboxylates

Ethers of formula (I) (where R1 is 1-4C alkyl, R2 and R3 are 1-4C alkyl or NR2R3 is a 5- or 6-membered ring which may be interrupted by -O- or -NCH3-, each R4 (same or different) is H, 1-4C alkyl, OH, 1-4C alkoxy, halogen or CF3, n is 0, 1 or 2, and X is O or S), e.g. methyl 5-(3-dimethyl-aminopheno...

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Hauptverfasser: LOEWE,HEINZ,DR, DUEWEL,DIETER,DR, KIRSCH,REINHARD,DR, URBANIETZ,JOSEF
Format: Patent
Sprache:eng ; ger
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Zusammenfassung:Ethers of formula (I) (where R1 is 1-4C alkyl, R2 and R3 are 1-4C alkyl or NR2R3 is a 5- or 6-membered ring which may be interrupted by -O- or -NCH3-, each R4 (same or different) is H, 1-4C alkyl, OH, 1-4C alkoxy, halogen or CF3, n is 0, 1 or 2, and X is O or S), e.g. methyl 5-(3-dimethyl-aminophenoxy)-2-benzimidazolyl-carbamate, are new cpds. which may be prepd. by condensing a 1,2-phenylenediamine of formula (VII) with an alkyl S-methyl-isothiourea-carboxylate of the formula CH3-S-C(=NH)-NH-COOR1 (IV) or a cyanamide-carboxylate of the formula NC-NH-COOR1 (VI) at pH 1-6. (I) are useful as chemotherapeutic agents against parasitic diseases in humans and animals. They are partic. useful as anthelmintics against Ancylostoma, although they also show good activity against other helminths.