Gruppo Lepetit

Luigi Mariani

Giorgio Tarzia

Luigi Fontanella

1,7-Dihydro-pyrrolo[3,4-e][1,4]diazepin-2(3H)-one derivatives of the formula ##STR1## wherein R is (C.sub.1-4)alkyl, R.sub.1 stands for hydrogen, methyl, ethyl, phenyl, bromo, chloro or nitro, R.sub.2 is hydrogen or (C.sub.1-4)alkyl, R.sub.3 represents hydrogen, chloro, fluoro, bromo, trifluoromethyl and methoxy, and X is ##STR2## wherein n is zero or 1, or --NH--R.sub.4 wherein R.sub.4 represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, or phenyl group. The novel compounds are useful as anticonvulsant and anti-anxiety agents. Also encompassed by the present invention are the process for preparing the novel pyrrolodiazepines and the pharmaceutical compositions containing them.

1,7-Dihydro-pyrrolo[3,4-e][1,4]diazepin-2(3H)-one derivatives a process

1,7-Dihydro-pyrrolo[3,4-e][1,4]diazepin-2(1H)-ones of the formula ##STR1## wherein R is lower alkyl, R.sub.1 stands for hydrogen, methyl, ethyl or phenyl, R.sub.2 is hydrogen or lower alkyl and R.sub.3 is hydrogen, chloro, fluoro, bromo, trifluoromethyl or methoxy are described with anticonvulsant and anti-anxiety activity. Also described is the process for preparing the above compounds and pharmaceutical preparations containing them.

1,7-Dihydro-pyrrolo[3,4-e][1,4]diazepin-2(1H)-one derivatives

A new class of pyrrolo-diazepines with anticonvulsant and anti-anxiety activity of the general formula ##STR1## wherein R is (C.sub.1 -C.sub.4)alkyl, R.sub.1 is chloro, bromo or nitro, R.sub.2 is hydrogen or (C.sub.1 -C.sub.4)alkyl and R.sub.3 is hydrogen, chloro, bromo, fluoro, trifluoromethyl or methoxy. The new compounds are prepared starting from the corresponding compounds wherein R.sub.1 is hydrogen through halogenation or nitration. Pharmaceutical preparations containing the new compounds of formula I are also described.

Pyrrolo-diazepine derivatives and their pharmaceutical compositions

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

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.

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Milan, Italy

Luigi Mariani