Gruppo Lepetit

Leonard J Lerner

Giulio Galliani

Pietro Consonni

Amedeo Omodei-Sale

Giorgio Winters

Emilio Toia

Amedeo Omodei Sale

Gianfranco Odasso

Amedeo Omodie Sale

New 3,5-disubstituted 1H-1,2,4-triazoles of formula I ##STR1## wherein: R is selected from hydrogen, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, allyloxy, propargyloxy, trifluoromethyl, phenyl, fluoro, chloro and dimethylamino;

3,5-Disubstituted-1H-1,2,4-triazole derivatives

New 3,5-disubstituted-1H-1,2,4-triazoles of formula ##STR1## wherein: R is selected from hydrogen, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, allyloxy, propargyloxy, trifluoromethyl, phenyl, fluoro, chloro and dimethylamino;

3,5-Disubstituted-1H-1,2,4-triazole derivatives as antifertility agents

A new process for preparing s-triazolo[5,1-a]-isoquinoline derivatives of the formula ##STR1## wherein A represents the group --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--; R is selected from hydrogen, amino, lower alkylamino, di-lower alkylamino, acylamino, diacylamino, ureido, thioureido, carbethoxythioureido, benzoylthioureido, sulfhydryl, lower alkyl, trifluoromethyl, phenyl, substituted phenyl, pyridyl, methylpyridyl and dimethylpyridyl; and R.sub.1 and R.sub.2 each independently represents hydrogen or lower alkoxy; by condensation of a 2-amino-3,4-dihydro-1(2H)-isoquinolinone with an imidolyl, cyanamide, cyanic or thiocyanic derivative. New compounds of the formula I wherein A represents the group --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, R has the same meaning as above with the exclusion of hydrogen, methyl, phenyl, and trifluoromethyl, R.sub.1 and R.sub.2 have the same meaning as above, with the proviso that when A represents the group --CH.dbd.CH--, R cannot be tolyl or pyridyl. The new compounds and some of the intermediates of the process are active as antiinflammatories, CNS depressants and anti-fertility agents.

2-Substituted phenyl-5-triazols [5,1-a] isoquinoline compounds

Novel tricyclic compounds containing two ring notrogen atoms and represented by the following formula I ##STR1## wherein: A is one of the groups --CH.sub.2 --; --CH.dbd.CH--; and --CH.sub.2 --CH.sub.2 --; R is hydrogen, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, cyclo(C.sub.3-6 alkyl)oxy, hydroxy, benzyloxy, halo, sulfamoyl, cyano, trifluoromethyl or nitro; R.sub.1 is hydrogen, lower alkoxy or halo; or R and R.sub.1 taken together are methylenedioxy; the sequence ##STR2## is one of the following moieties: ##STR3## WHEREIN R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen, methyl, carboxy, carbo(lower alkoxy), carbamyl, mono- or di-(lower alkyl) carbamyl or hydroxymethyl; provided that when the sequence ##STR4## is one of the moieties a) and b) wherein R.sub.2 is hydrogen or lower alkyl, A is not --CH.dbd.CH--; when the sequence ##STR5## is one of the moieties (a) and (b) wherein R.sub.2 is hydrogen, A is not --CH.sub.2 --; and when the sequence ##STR6## is one of the moieties (c) and (d) wherein R.sub.3 is hydrogen and when both R and R.sub.1 are hydrogen, A is not --CH.dbd.CH--; and the salts thereof with a non-toxic pharmaceutically-acceptable acid. The compounds of the invention have antireproductive activity.

Antireproductive imidazo[2,1-a]isoquinoline compounds

New heterocyclic compounds represented by the following formula: ##STR1## wherein: R and R.sub.1 are independently selected from hydrogen, hydroxy, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, (C.sub.3-5)alkenyloxy, (C.sub.3-5)alkynyloxy, (C.sub.3-6)cycloalkyloxy, or halo or taken together represent a methylenedioxy group; the symbols W and A are defined as follows: 1. W is the nitrogen atom and A is the group ##STR2## in which the carbon atom bearing the radical R.sub.2 is linked to the benzene ring and R.sub.2 is hydrogen, hydroxy, (C.sub.1-4)alkoxy or (C.sub.2-4)aliphatic acyloxy; 2. W is the group =CH-- and A is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 -- or --CH=CH--. The compounds have antireproductive utility.

2-Phenyl-pyrazolo-[1,5-a]quinoline compounds

New s-triazolo[5,1-a]isoindole derivatives of following formula I ##STR1## wherein R is selected from hydrogen, amino, lower alkyl amino, di-lower alkyl amino, acylamino, diacylamino, benzoylamino, ureido, thioureido, carbethoxythioureido, benzoylthioureido, sulfhydryl, lower alkyl, trifluoromethyl, phenyl, substituted phenyl, pyridyl, methylpyridyl and dimethylpyridyl; and R.sub.1 and R.sub.2 each independently represents hydrogen, chloro or lower alkoxy. A process for their manufacture which comprises the reaction of 2-aminophthalimidine with a reagent R-Z wherein R has the same meaning as above, and Z represents one of the following groups: ##STR2## wherein R.sub.3 is C.sub.1 -C.sub.4 alkyl. The compounds and some of the intermediates of the process are useful as antiinflammatories, analgesics, CNS depressants, antimicrobials and anti-fertility agents.

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Milan, Italy

Leonard J Lerner