Schering Aktiengesellschaft

Hans-Joachim Kessler

Clemens Rufer

Peter Strehlke

Eberhard Schroder

Ulrich Redmann

Helmut Biere

Katica Schwarz

Eberhard Schroeder

Hermann Ulbrich

2-(5-Nitro-2-imidazolyl)-benzimidazoles of the formula ##STR1## wherein R.sub.1 and R.sub.2 are H, halo, alkyl, alkoxy, nitro, trifluoromethyl or carboxy; A is H, alkyl, hydroxyalkyl or an ester thereof, haloalkyl, phenyl or a tertiary aminoalkyl group; and X is alkyl, hydroxyalkyl or an ester thereof, are antimicrobials, especially against Trichomonas vaginalis.

2-(5-Nitro-2-imidazolyl)-benzimidazoles

Nitroimidazoles of the formula ##STR1## wherein R is dialkylaminoacryloyl; 3-, 4-, or 5-pyrazolyl or a mixture thereof which is unsubstituted or substituted by alkyl or, at the 1-position, by hydroxyalkyl or a nitro ester thereof, acyloxyalkyl, nitro, phenyl or phenyl p-substituted by halo, alkoxy or nitro, or, in the 3- or 5-position or a mixture thereof by nitro; 3- or 5-alkyl-4-isooxazolyl or a mixture thereof; or 4-alkyl-5-pyrimidinyl, unsubstituted or substituted by alkyl, amino, 2-furyl or 5-nitro-2-furyl, and the physiologically acceptable acid addition salts thereof, possess anti-protozoal activity, e.g., against trichomonas vaginalis and Entamoeba histolytica.

Nitroimidazole derivatives and process for the preparation thereof

Compounds of the formula ##STR1## wherein Z is a direct bond or alkylene of 1 - 3 carbon atoms which is unsubstituted or substituted on the carbon atom alpha to the phenyl group by alkyl or unsubstituted or substituted phenyl, R.sub.2 and R.sub.3 singly are H, alkyl, alkoxy, alkylmercapto, halo, nitro or, collectively, C.sub.4 H.sub.4, and R.sub.4 is alkenyl, alkinyl, unsubstituted or substituted phenyl or phenylalkyl, or, when Z is substituted methylene, also alkyl, are useful in combating Germatophyte infections, especially Trichophyton rubrum and mentagrophytes, and yeast infections, especially Candida albicans, as well as bacterial and fungal infections.

Amino-, mercapto- and -oxy-substituted-phenyl and -phenalkyl imidazoles

2-ACYL-5-NITROTHIAZOLES OF THE FORMULA ##STR1## wherein A' is furyl, thienyl or pyrrolyl substituted by halo, or phenyl substituted by 3 to 5 of halo, hydroxy, alkyl or alkoxy of 1-4 carbon atoms, possess antifungal activity, e.g., against Candida albicans, Trichophyton metagrophytes and Trichophyton rubrum.

Certain halothien-2-yl 5-nitrothiazol-2-yl ketones and fungicidal

Amino-substituted nitroimidazolyl-methyleneaminoimidazolidinones of the formula ##SPC1## Wherein --NR.sub.2 R.sub.3 is dialkylamino or heterocyclic amino, and the physiologically acceptable salts thereof, possess antitrichomonial activity.

Amino-substituted nitroimidazolyl-methyleneaminoimidazolidinones

Nitroimidazolyl pyrimidines of the formula ##SPC1## And physiologically acceptable acid addition salts thereon wherein X is alkyl of 1-4 carbon atoms, R.sub.1 and R.sub.2 each are a hydrogen atom, alkyl of 1-4 carbon atoms, phenyl triflouromethyl or a monocyclic heterocyclic ring and R.sub.3 is a hydrogen atoms, alkyl of 1-4 carbon atoms, hydroxyalkoxy of 2-4 carbon atoms or an ester thereof of an alkanocarboxylic acid of 1-4 carbon atoms, oxoalkyl of 8-6 carbon atoms, or, when R.sub.1 or R.sub.2 is phenyl, alkylene having 1-2 carbon atoms in the chain joined to the 2-position of the phenyl ring possess trichomonicidal activity.

Nitroimidazolyl pyrimidines

Compounds of the formula v,2/12 Wherein R.sub.1 is H, lower-alkyl, hydroxyalkyl, phenyl, aralkyl, or --(CH.sub.2) .sub.n --X wherein n is 0-4 and X is --COO-lower-alkyl, C.tbd.N or --COOH and R.sub.2 is H, lower-alkyl or aralkyl, produced by condensing a diamine of the formula ##SPC1## With a nitro compound of the formula R.sub.1 --CH.sub.2 --NO.sub.2 in the presence of formalin or paraformaldehyde, or with the R.sub.1 -- C(CH.sub.2 OH).sub.2 NO.sub.2 reaction product of the above nitro compound and formalin or paraformaldehyde, or with formalin or paraformaldehyde followed by reaction with the above nitro compound, and their acid addition salts, possess antimicrobial activity against both gram-positive and gram-negative bacteria and also against dermatophytes, yeasts and other fungi.

Growing community of inventors

Berlin, Germany

Hans-Joachim Kessler