Gruppo Lepetit S.p.a.

Luigi Fontanella

Luigi Mariani

Giorgio Tarzia

Emilio Occelli

Alessandro Assandri

Giangiacomo Nathansohn

Guilio Maffii

Edoardo Martinelli

New 3-azetidinylethyl-1-phenyl-2-imidazolidinones with neuroleptic activity, their use and methods for their preparation. The azetidinyl group bears alkyl substituents in position 3 and the phenyl group bears halogenated substituents in position 3 and hydroxy group or acylated hydroxy groups in position 4 and/or 6.

Neuroleptic 3-azetidinylethyl-1-phenyl-2-imidazolidinones

Compounds of the following formula ##STR1## wherein R is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.-butyl; R.sub.1 is hydrogen, methyl, ethyl or phenyl; R.sub.2 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.-butyl; R.sub.3 is hydrogen, methoxy, trifluoromethyl, chloro, bromo or fluoro; and R.sub.4 is methyl. The new compounds are useful as CNS depressants, anticonvulsants, anti-inflammatories and inhibitors of the enzymes which promote the synthesis of prostaglandins.

Pharmacologically active pyrrolodiazepines

Imidazolidinone derivatives of the formula ##STR1## where R, R.sub.1, R.sub.2 and R.sub.3 independently are hydrogen or lower alkyl, X represents one or two substituents selected from the group lower alkyl, halo, lower alkoxy, trifluoromethyl, and their pharmaceutically-acceptable acid salts. The compounds are prepared essentially by the method described by Wright in J. Med. Chem. 9, 852 (1966). The compounds have high depressant activity on the central nervous system.

2-Imidazolidione derivatives

Pharmacologically active diphenylmethane derivatives of formula (I) ##SPC1## wherein: R is halo, nitro or lower alkoxy; R.sub.1 is hydrogen, halo, nitro, lower alkyl or lower alkoxy; R.sub.2 is hydrogen, lower acyl, carbamyl or substituted carbamyl; X is an --OR.sub.3 or --NHR.sub.4 group wherein R.sub.3 is hydrogen, lower alkyl, phenyl, substituted phenyl, phenyl-lower alkyl, acyl, carbamyl or substituted carbamyl; R.sub.4 is hydrogen, lower alkyl or lower acyl; and x and y are integers from zero to two, provided that the sum of x and y is at least one. The compounds are prepared by hydrogenation of an o-benzoylbenzoic acid of formula (II) to the corresponding diol of formula (III) according to the following scheme: ##SPC2## Wherein R, R.sub.1, x and y have the same meaning given above and Z is O or H.sub.2. As hydrogenating agents, a hydride or mixed metal hydrides are used. The diols of formula (III) may be subsequently coverted to other inventive compounds of formula (I) by simple chemical operations. The compounds have CNS depressant activity.

5-Chloro-2-hydroxymethyl benzhydrol

New reserpine-like compounds of the general formula ##SPC1## Wherein R is a member of the class consisting of hydrogen, lower alkyl, lower alkenyl and acyl; R.sub.1 is selected from hydrogen and lower alkyl, and R.sub.2 is hydrogen or lower alkyl. The new reserpine-like compounds are useful anti-hypertensive agents.

Reserpine derivatives

5,6,7,7A-Tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3-(2H)-diones of the formula ##SPC1## In which R is phenyl, substituted phenyl or cyclohexyl, X is oxygen or sulfur and R.sub.1 is hydroxy, lower alkoxy, di-lower alkylamino-lower alkoxy, an --NR.sub.2 R.sub.3 radical wherein R.sub.2 and R.sub.3 each independently represents hydrogen, lower alkyl, hydroxy-lower alkyl, phenyl, substituted phenyl, benzyl or together with the adjacent nitrogen atom represent a pyrrolidino, a piperidino, a morpholino or a piperazino radical. The compounds of the invention are useful as C.N.S. depressants and in particular as tranquilizing and anxiolytic agents.

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Milan, Italy

Luigi Fontanella