Bayer Aktiengesellschaft

Heinrich Kolling

Herbert Thomas

Hartmund Wollweber

Arno Widdig

Axel Haberkorn

Eckart Kranz

Peter Andrews

Josef H Reisdorff

Gerd Aichinger

Toyohiko Kume

Ekkehard Niemers

Hans Peter Schulz

Manfred Federmann

Shinpei Kuyama

Jurgen Kurz

Horst Boshagen

Jurgen Schramm

1-[-(Benzothia- or -oxazol-2-ylthio- or -2-yloxy)phenyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-triones of the formula ##STR1## in which R is lower alkyl,

Intermediate(1,3-benzothiazol-2H-yl or 1,3-benzoxazol-2H-yl)4-oxy-or

1-[4-(Benzothia- or -oxazol-2-ylthio- or -2-yloxy)phenyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-triones of the formula ##STR1## in which R is lower alkyl,

Anti-coccidal agents 1-[4-(benzothia- or -oxazol-2-ylthio- or

Anthelmintically active novel substituted salicylic acid amides of the formula ##STR1## in which X and Y each independently is halogen, and,

Substituted salicylic acid amide anthelmintics

The invention relates to 2-benzimidazolylcarbamic acid esters, substituted on the benzenoid nucleus by an aminoalkoxy, aminoalkylthio, an aminoalkylsulphinyl or an aminoalkylsulphonyl grouping. The invention also includes methods for making the compounds of the invention, compositions containing said compounds and the use of said compounds and compositions as anthelmintic agents.

Benzimidazolylcarbamic acid ester compounds, their production, and their

The invention relates to 2-benzimidazolylcarbamic acid esters, substituted on the benzenoid nucleus by an aminoalkoxy, aminoalkylthio, an aminoalkylsulphinyl or an aminoalkylsulphonyl grouping. The invention also includes methods for making the compounds of the invention, compositions containing said compounds and the use of said compounds and compositions as anthelminitic agents.

Benzimidazolylcarbamic acid esters substituted on the benzenoid nucleus

The invention relates to new substituted o-phenylenediamine derivatives of the general formula ##STR1## in which R represents optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkinyl,

Substituted omicron-phenylenediamine derivatives, process for their

Novel substituted benzenesulphonic acid esters, particularly useful as anthelmintics are provided. The novel compounds are those of the general formula ##STR1## in which R represents hydrogen, optionally substituted alkyl, cyano, alkoxy, halogen, trifluoromethyl, amino, acylamino or nitro,

Substituted benzenesulphonic acid esters, processes for their

N-(2-formamidophenyl)-N',N'-bis-carbonylguanidines bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(formamido)-phenyl group are anthelminetic agents. The compounds, of which N-(2-formamido-4-phenylthiophenyl)-N',N'-bis-carbomethoxyguanidine is a typical example, are prepared through the reaction of isothiourea-S-alkyl ether and an appropriately substituted 2-aminoformanilide.

2-Formamido phenylguanidines and processes for their preparation and use

N-[2-(Substituted amido)phenyl]-N',N'-bis-carbonylguanidines bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(substituted amido)-phenyl group are anthelmintic agents. The compounds, of which N-(2-acetamido-4-phenylthiophenyl)-N',N'-bis-carbomethoxyguanidine is a typical example, are prepared through the reaction of isothiourea-S-alkyl ether and an appropriately substituted 2-aminoanilide.

Substituted phenylguanidines and processes for their preparation and use

N-[2-(Substituted amido)phenyl]-N',N'-bis-carbonylguanidines bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(substituted amido)phenyl group are anthelmintic agents. The compounds, of which N-(2-acetamido-4-phenylthiophenyl)-N',N'-bis-carbomethoxyguanidine is a typical example, are prepared through the reaction of isothiourea-S-alkyl ether and an appropriately substituted 2-aminoanilide.

Phenylguanidines useful as anthelmintic agents

N-[2-(Substituted amido)phenyl]-N'-carbonyl-S-substituted isothioureas bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(substituted amido)-phenyl group are anthelmintic agents. The compounds, of which N-(2-acetamido-4-phenoxyphenyl)-N'-carbomethoxy-S-methylthiourea is a typical example, are prepared through the reaction of S-substituted N-(mercaptohalomethylene)carbamic acid ester and an appropriately substituted 2-aminoanilide, or through alkylation of the corresponding S-unsubstituted thiourea.

Substituted phenylisothioureas and processes for their preparation and

N-[2-(Substituted amido)phenyl]-N'-carbonyl-S-substituted isothioureas bearing an optionally substituted phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl group in the 4- or 5-position of the 2-(substituted amido)-phenyl group are anthelmintic agents. The compounds, of which N-(2-acetamido-4-phenoxyphenyl)-N'-carbomethoxy-S-methylthiourea is a typical example, are prepared through the reaction of S-substituted N-(mercaptohalomethylene)carbamic acid ester and an apropriately substituted 2-aminoanilide, or through alkylation of the corresponding S-unsubstituted thiourea.

New thionosalicylic acid anilides and salts with bases are provided which have parasiticidal activity in sheep and cattle particularly against adult liver flukes in sheep and cattle and other domestic animals, especially against juvenile liver flukes. The new compounds are produced by the reaction of poly-substituted phenols with substituted aromatic isothiocyanates, the hydrolysis products of oxo-thiono- or dithiono-dihydrobenzoxazines or by the reaction of N-phenyl-salicyl-imide chlorides with thio-compounds. Typical compounds are 3,5-dichloro-4'-bromo-thionosalicylic acid anilide and 2-acetoxy-3,5-dichloro-N-(2'-methyl-4'-chlorophenyl)-thionobenzamide. Novel benzoxazines obtainable from the above anilides are also provided and have similar properties. Typical compounds are 3-(3',5'-bis-trifluoromethyl-phenyl)-6,8-dibromo-2-oxo-4-thionodihydrobenz oxazine-(1,3), 3-(3',4'-dichlorophenyl)-6,8-dichloro-2,4-dithiono-dihydrobenzoxazine-(1,3 ) and 3-(4'-bromophenyl)-6-chloro-8-bromo-2,4-dithiono-dihydrobenzoxazine-(1,3). Methods for preparing a large number of both types of compounds are described. The compounds are administered orally or subcutaneously in doses of 2.5 to 100 mg/kg, preferably 5 to 15 mg/kg, of body weight.

Growing community of inventors

Haan, Germany

Heinrich Kolling