Ciba-geigy Corporation

Ernst Aufderhaar

Walter Traber

Alfred Meyer

Manfred Kuhne

Jean J Gallay

Max Schellenbaum

Ernst Schweizer

Denis V Varsanyi

Jean-Jacques Gallay

Janos Zergenyi

Oswald Rechsteiner

Peter Labuhn

Georg Acklin

Ulrich Vogel

Jean-Paul Fumeaux

Klemenz Sprecher

Bernhard Raz

Gunter Kaupp

N,N-(dibenzohexatrienylene)urea medicaments can be manufactured in a smooth one-step reaction by reacting a corresponding N,N-(dibenzohexatrienylene)amine with cyanic acid.

Process for the manufacture of N,N-(Dibenzohexatrienylene)ureas

The invention relates to a process for the manufacture of the known 5-carbamoyl-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine of the formula III which is characterized in that, for example, 5-cyano-5H-dibenz[b,f]azepine of the formula I is nitrated to form 5-cyano-10-nitro-5H-dibenz[b,f]azepine of the formula II, this is subjected to hydrolysis, then reduction, then the reduction product contained in the reaction mixture is subjected to hydrolysis and the end product of the formula III is isolated in pure form. The process is illustrated by the following reaction scheme: ##STR1## The invention relates also to new intermediates produced in these reactions.

5-Cyano-10-isonitroso-10,11-dihydro-5H-dibenz[b,f]azepine

Process for the manufacture of

5-Cyano- and 5-carbamoyl-10-nitro-5H-dibenz[b,f]azepine

The invention relates to a novel and technically advanced process for producing 5-cyano-5H-dibenz[b,f]azepine by reacting 5H-dibenz[b,f]azepine with a halocyanogen in the presence of strongly polar substances. 5-Cyano-5H-dibenz[b,f]azepine can be used as starting material for producing 5-carbamyl-10(11)-oxo-10,11-dihydro-5H-dibenz[b,f]azepine, which is known to have central-depressant, anticonvulsive and central-muscle-relaxing activity.

Process for the production of 5-cyano-and

Benzimidazole derivatives of the formula ##STR1## in which R and R.sub.1 independently of one another are each hydrogen, an alkanoyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, an alkylsulphonyl group having 1 to 4 carbon atoms, a benzoyl group, a phenylsulphonyl group or a p-methylphenylsulphonyl group; R.sub.2 and R.sub.4 independently of one another are each hydrogen, halogen or a methyl group, R.sub.3 is hydrogen, halogen, a methyl group or a methoxy group; X is oxygen or sulphur; Y is halogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a methylthio group, a methylsulphinyl group, a methylsulphonyl group, a trifluoromethyl group, a nitro group, a hydroxyl group, a cyano group or an acetyl group; and m is 0, 1, 2 or 3; and if one of the two radicals R or R.sub.1 is hydrogen, the position of the other of these radicals on the N atoms cannot be clearly established, including, when at least one of the two radicals R or R.sub.1 is hydrogen, the possible tautomeric compounds of the formula I; and the disulphides obtainable by oxidation of compounds of the formula I. The compounds are useful for combating helminths in domestic animals and productive animals.

Benzimidazole sulphides as anthelmintic agents

The present invention relates to new dithiocarbamic acid esters having the formula ##STR1## wherein R.sub.1 represents a phenyloxyphenyl or phenylaminophenyl radical which is unsubstituted or substituted by lower alkyl, halogen, trifluoromethyl, nitro or cyano, R.sub.2 represents hydrogen or lower alkyl, and alk represents lower alkylidene or lower alkylene, and also to salts of compounds of the formula (I), wherein R.sub.2 represents hydrogen, with pharmaceutically acceptable bases. These new compounds possess a strong anthelminthic activity and are useful for the treatment of warm-blooded animals infected with parasitic helminths. A specific embodiment is the N-[4-(4-nitroanilino)-phenyl]-dithiocarbamic acid-(2-carboxyethyl)-ester.

Dithiocarbamic acid esters

A new process for the production of 3,4-dialkoxyanilines in which the two alkyl groups are different from each other is disclosed. The process comprises the stepwise introduction of the alkyl groups in different stages of the process by converting pyrocatechol into its monoalkyl ether, coupling said monoalkyl ether with a phenyldiazonium salt, alkylating the 3-alkoxy-4-hydroxy-azobenzene obtained to form 3,4-dialkoxyazobenzene and reductively cleaving the latter to the corresponding 3,4-dialkoxyaniline. The 3,4-dialkoxyanilines obtainable by the new process are valuable intermediates for the preparation of 4-hydroxy-6,7-dialkoxy-3-quinoline carboxylic acid esters which are excellent coccidiostats.

Process for the preparation of 3,4-dialkoxyanilines

Process for the control of parasitic helminths by the use of 2-trifluoromethyl-benzimidazole derivatives of formula I ##SPC1## wherein

Certain 2-trifluoromethylbenzimidazoles as anthelmintics

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Kaiseraugst, Switzerland

Ernst Aufderhaar