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Merck Patent Gesellschaft MIT Beschrankter Haftung

Merck Patent Gesellschaft MIT Beschraenkter Haftung

E. Merck

Herbert Thomas

Hartmund Wollweber

Peter Andrews

Heinrich Kolling

Arno Widdig

Jurgen Seubert

Hans Peter Schulz

Ekkehard Niemers

Rolf Pohlke

Friedrich Loebich

Ingeborg Hammann

Hans-Jochem Riebel

Bernhard Homeyer

Fritz Maurer

Engelbert Kuhle

Wilhelm Sirrenberg

Rolf Schroder

Jurgen Thyssen

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 includes phosphonylureidobenzene compounds of the general formula ##STR1## or pharmaceutically acceptable salts in which

Phosphonylureidobenzene derivatives and their medicinal use

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

2-Acyl-4-oxo-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives of the formula ##STR1## wherein COR is the acyl radical of an up to 26 carbon atom acid and their physiologically acceptable acid addition and quaternary ammonium salts, are anthelmintics and can be produced by reacting 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline with an acid or a reactive functional derivative thereof. This is a division, or application Ser. No. 742,133, filed on Nov. 15, 1976, which in turn is a divisional of Ser. No. 533,467, filed on Dec. 16, 1974, now U.S. Pat. No. 4,001,411.

2-Acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the

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

Isoquinolines of the formula ##STR1## wherein R.sup.1 is H, OH, alkyl; R.sup.2 is H, or an unsubstituted or substituted carbonyl, carbonyloxy or thiocarbonyl group; R.sup.3 is H, alkyl or hydroxy alkyl; R.sup.4 is H, alkyl or phenyl; R.sup.5 is O, H,H or H and alkyl, phenyl, halo or hydroxy; R.sup.6 and R.sup.7 are optional substituents; and R.sup.8 is H or alkyl, R.sup.2 being a thiocarbonyl or carbonyloxy group when R.sup.1 and R.sup.3 to R.sup.8 are H and X is O; and their physiologically acceptable salts, are antihelmintics, especially against cestodes and trematodes; some also possessing CNS activity, e.g., psychotropic and blood pressure regulating activity.

Ring substituted pyrazino-isoquinoline derivatives and their preparation

2-Acyl-4-oxo-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives of the formula ##STR1## wherein COR is the acyl radical of an up to 26 carbon atom acid and their physiologically acceptable acid addition and quaternary ammonium salts, are anthelmintics and can be produced by reacting 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino-[2,1-a]isoquinoline with an acid or a reactive functional derivative thereof.

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

2-Acyl-4-oxo-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives of the formula ##STR1## wherein COR is the acyl radical of an up to 26 carbon atom acid and their physiologically acceptable acid addition and quaternary ammonium salts, are anthelmintics and can be produced by reacting 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline with an acid or a reactive functional derivative thereof.

O-Alkyl-O-chloromethylsulfonylphenyl-thionophosphonic acid esters of the formula ##STR1## in which R represents alkyl with 1 to 6 carbon atoms,

O-alkyl-O-chloromethylsulfonylphenyl-thionophosphonic acid esters and

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

A new class of N'-(aminoacylaminophenyl) acetamidines: ##STR1## in which R.sup.1 and R.sup.2 are the same or different and represent hydrogen, alkyl, aryl or the substituted derivatives thereof or, together with the nitrogen atom to which they are attached, an heterocyclic ring; and R.sup.3 is hydrogen, alkyl, aryl, aralkyl, or a heterocyclic moiety including the substituted derivatives thereof. The products have utility as anthelmintics. The products are obtained by treating a suitable amino-acid or a carbonyl-activated amino-acid, with the appropriate N'-(4-aminophenyl)-N,N-dimethylacetamidine. In addition, the products are obtained by treating a suitable N'-(haloacylaminophenylacetamidine with an appropriate amine.

N'-(Aminoacylaminophenyl) acetamidines

Isoquinolines of the formula ##STR1## wherein R.sup.1 is H, OH, alkyl; R.sup.2 is H, or an unsubstituted or substituted carbonyl, carbonyloxy or thiocarbonyl group; R.sup.3 is H, alkyl or hydroxy alkyl; R.sup.4 is H, alkyl or phenyl; R.sup.5 is O, H,H or H and alkyl, phenyl, halo or hydroxy; R.sup.6 and R.sup.7 are optional substituents; and R.sup.8 is H or alkyl, R.sup.2 being a thiocarbonyl or carbonyloxy group when R.sup.1 and R.sup.3 to R.sup.8 are H and X is 0; and their physiologically acceptable salts, are antihelmintics, especially against cestodes and trematodes; some also possessing CNS activity, e.g., psychotropic and blood pressure regulating activity.

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Wuppertal, Germany

Herbert Thomas