Ciba-geigy Corporation

Other

Roland Heckendorn

Hans Allgeier

Rene Meier

Christof Angst

Andre Gagneux

Guido Bold

Angelo Storni

Rudolf Duthaler

John G Dingwall

Armin Zust

Antonio Togni

Erich Schmid

Derek E Brundish

Daniel Wallach

Gunther Dorhofer

Graham E Fagg

Yves Auberson

Nicholas David Cosford

Michel Biollaz

Fabrizio Gasparini

Edwin Carl Johnson

Rainer Kuhn

G&ouml;n&uuml;l Veli&ccedil;elebi

Mark Andrew Varney

Pyridine derivatives

Substituted 2-aminoalk-3-enoic acid derivative of formula I ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon radical that is substituted by hydroxy, and R.sub.2 is free or esterified carboxy, and their salts exhibit NMDA-antagonistic properties and are useful as active ingredients of anticonvulsive medicaments.

4-substituted 2-aminoalk-3-enoic

Substituted 2-aminoalk-3-enoic acid derivative of formula I ##STR1## wherein R.sub.1 is an aliphatic hydrocarbon radical that is substituted by optionally acylated or aliphatically or araliphatically etherified hydroxy, by halogen, by optionally acylated and/or aliphatically substituted amino or by an aza-, diaza-, azoxa- or oxa-cycloaliphatic radical, or is an oxacycloaliphatic hydrocarbon radical bonded via a carbon atom, or is an optionally aliphatically N-substituted or N-acylated azacycloaliphatic hydrocarbon radical, and R.sub.2 is free or esterified carboxy, and their salts exhibit NMDA-antagonistic properties and are useful as active ingredients of anticonvulsive medicaments.

4-substituted 2-aminoalk-3-enoic acids

The invention relates to unsaturated amino acids of the formula I ##STR1## in which R.sup.1 represents hydroxy or etherified hydroxy, R.sup.2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R.sup.4 represents hydrogen, alkyl or aryl, R.sup.5 represents hydrogen or alkyl, R.sup.6 represents carboxy or esterified or amidated carboxy, R.sup.7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted .alpha.,.omega.-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.

Unsaturated amino acids

The invention relates to novel polycyclic polyazaheterocycles having psychopharmacological properties, especially antidepressive and anxiolytic activity, corresponding to the formula I ##STR1## in which R.sub.1 and R.sub.2 each represents, independently of the other, hydrogen, lower alkyl or hydroxy-lower alkyl, or together represent lower alkylene or ethyleneoxyethylene, ethyleneazaethylene or N-lower alkyl- or N-(2-hydroxy-lower alkyl)-ethyleneazaethylene, R.sub.3 represents hydrogen or a lower aliphatic hydrocarbon radical or a saturated lower cycloaliphatic hydrocarbon radical or unsubstituted or substituted phenyl, R.sub.4 and R.sub.5 represent hydrogen or lower alkyl, and Ar represents an unsubstituted or substituted benzo or pyrido radical, and to acid addition salts of compounds of the general formula I, especially the pharmaceutically acceptable acid addition salts of compounds of the general formula I, to pharmaceutical preparations containing these novel substances and to a method of treating conditions of depression or anxiety by administering them.

Tricyclic polyazaheterocycles for treating depression or anxiety

The present invention relates to new triazole derivatives of the formula ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, optionally esterified or etherified hydroxymethyl, formyl, optionally functionally modified carboxy, or optionally mono- or disubstituted aminomethyl, R.sub.2 represents lower alkyl, and R.sub.3 represents hydrogen or lower alkyl, whereby R.sub.2 and R.sub.3 as lower alkyl can be bound directly, or in .beta.- or .gamma.-position also by way of oxygen, sulphur or the imino radical or a lower alkylimino radical, and the rings A and B independently of each other can be unsubstituted or substituted, and to their addition salts with inorganic and organic acids, in particular the pharmaceutically acceptable acid addition salts. These new compounds possess valuable pharmacological properties. In particular they have an anticonvulsive activity and are useful for the treatment of epilepsy and of conditions of tension and of agitation. Specific embodiments are the 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(morpholinomethyl)-1H-1,2,4-triaz ole-3-carboxamide and the N,N-dimethyl-1-[2-(o-fluorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-met hyl]-1H-1,2,4-triazole-3-carboxamide.

Triazole derivatives

The present invention relates to new triazole derivatives of the formula ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, optionally esterified or etherified hydroxymethyl, formyl, optionally functionally modified carboxy, or optionally mono- or disubstituted aminomethyl,

Compounds of the class of 6-phenyl-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxamides, their 5-oxides and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties and are active ingredients for therapeutic compositions. In particular, these new compounds have an anti-convulsive and anti-aggressive action and inhibit somatic reflexes. Specific embodiments are N,N-dimethyl-6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-c arboxamide, 6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carb oxamide, N,N-dimethyl-6-(o-fluorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodia zepine-2-carboxamide and N,N-dimethyl-6-(o-chlorophenyl)-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodia zepine-2-carboxamide.

Triazolyl benzophenones

The invention relates to new heterocyclic S-imino-S-oxides of the formula I ##STR1## in which one of the symbols X.sub.1 and X.sub.2 denotes a direct bond and the other denotes the vinylene group --CH=CH-- or the epithio radical --S--, Y.sub.1 and Y.sub.2 conjointly denote an additional bond or one of the symbols denotes hydrogen and the other denotes hydrogen or, conjointly with the symbol R.sub.1 or R.sub.2, which is present on the same carbon atom, denotes the oxo radical, one of the symbols R.sub.1 and R.sub.2 denotes hydrogen or lower alkyl and the other denotes hydrogen or lower alkyl or, conjointly with the symbol Y.sub.1 or Y.sub.2, which is present on the same carbon atom, denotes the oxo radical, or, if Y.sub.1 and Y.sub.2 conjointly denote an additional bond, also denotes lower alkoxy, and R.sub.3 and R.sub.4 independently of one another denote hydrogen, halogen up to atomic number 35, lower alkyl, lower alkoxy or trifluoromethyl and R.sub.5 denotes hydrogen or lower alkyl, and to their acid addition salts in particular the pharmaceutically with inorganic and organic acceptable acid addition salts. These new compounds possess valuable pharmacological properties. In particular they have an anticonvulsive activity and are useful for the treatment of epilepsy and of states of tension and states of agitation.

Heterocyclic S-imino-S-oxides

Diazepine derivatives

The invention relates to new aminoacyl compounds of the formula I, ##SPC1##

Aminoacyl compounds

Compounds of the class of 6-phenyl-4H-v-triazolo[1,5-a][1,4] benzodiazepines, which in the 3-position are unsubstituted or substituted, particularly by a carbamoyl group or a substituted carbamoyl group, their 5-oxides and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties and are active ingredients for therapeutic compositions. In particular, these new compounds have an anticonvulsive and anti-aggressive action. Specific embodiments are N,N-dimethyl-6-phenyl-8-chloro-4H-v-triazolo [1,5-a][1,4]benzodiazepine-3-carboxamide and N,N-dimethyl-6-(o-fluorophenyl)-8-chloro-4H-v-triazolo [1,5-a][1,4]benzodiazepine-3-carboxamide.

Growing community of inventors

Arlesheim, Switzerland

Roland Heckendorn