Ciba-Geigy Corporation

Ciba-Geigy Ag

Angelo Storni

Hans Zweifel

Daniel Bellus

Walter Schilling

Hans Blattner

Armin Zust

Roland Heckendorn

Raymond Bernasconi

Max Wilhelm

Karl Schenker

Erich Schmid

Dieter Beck

Gunther Dorhofer

Jacques Gosteli

Alex Meisels

Georg V Sprecher

Serge F Bischoff

The present invention relates to a new laevorotatory basic derivative of 9,10-ethanoanthracene, namely R-(-)-.alpha.-[(methylamino)methyl]-9,10-ethanoanthracene-9(10H)-ethanol of the formula I ##STR1## and the acid addition salts thereof, to pharmaceutical compositions containing these new substances and to a method for treating dysphoric conditions, psychovegetative or psychosomatic disorders.

Pharmaceutical use of laevorotatory basic derivative of

Benzamides of the formula ##STR1## in which R.sub.1 and R.sub.2, independently of one another, each represents lower alkyl, R.sub.3 represents lower alkoxy, C.sub.3 -C.sub.5 -alkenyloxy, C.sub.3 -C.sub.7 -cycloalkoxy or C.sub.3 -C.sub.7 -cycloalkyl-lower alkoxy, R.sub.4 represents halogen and R.sub.5 represents cyano, and their salts can be used, for example, as pharmaceutical agents and can be manufactured in a manner known per se.

Benzamides and their salts

Azatetracyclic compounds of the formula ##STR1## wherein the various substituents are defined hereinbelow. The novel compounds can be used as tranquillizing, antipsychotic and excitation-inhibiting compounds for the treatment of states of agitation. Specific embodiments are 3-methyl-2,3,4,5-tetrahydro-1H-dibenzo[2,3:6,7]thiepino[4,5-d]azepine and 3-methyl-2,3,4,5-tetrahydro-1H-dibenzo[2,3:6,7]oxepino[4,5-d]azepine.

Treating states of agitation with azatetracyclic compounds

Compounds of the class of 2,2'-azines of 2,4-thiazolidinediones which are substituted in at least one of the 3-positions by allyl, 1-methylallyl, 2-methylallyl or 2-propynyl and in at least one of the 5-positions by hydroxy, and may further contain methyl groups in the remaining 3-position and in the 5-positions, and the corresponding tautomeric 1-[[4-oxo-2-thiazolidinylidene]amino]-5-hydroxy-2-thiohydantoins and 5,5'-dihydroxy-2,2'-dithio-1,1'-bihydantoins have valuable pharmacological properties. In particular, they inhibit the growth of tumours, while their toxicity is low in comparison with their tumour-inhibiting effectiveness. A specific embodiment is the 2,2'-azine of 3-(2-methylallyl)-5-methyl-2,4-thiazolidinedione and of 3-methyl-5-hydroxy-2,4-thiazolidinedione.

Derivatives of 2,4-thiazolidinedione

Compounds of the formula ##STR1## in which one of the symbols R.sub.1 and R.sub.2 represents an alkyl radical that has 3 or 4 carbon atoms and is unsaturated in the 2,3-position, and the other represents such a radical or lower alkyl, R.sub.3 and R.sub.4 each represents, independently of the other, hydrogen or methyl, and A represents a radical of the formula ##STR2## in which Z.sub.1, or each of Z.sub.2 and Z.sub.3 independently of the other, represents hydrogen or lower alkyl, or Z.sub.2 and Z.sub.3 together represent lower alkylene, each of R.sub.5 and R.sub.6, independently of the other, represents hydrogen, lower alkyl, halogenated lower alkyl, or lower alkenyl or R.sub.5 and R.sub.6 together represent lower alkylene that is optionally interrupted by oxygen, sulphur or by optionally substituted nitrogen, and X represents OR.sub.7 or NR.sub.8 R.sub.9 in which R.sub.7 represents hydrogen or lower alkyl and each of R.sub.8 and R.sub.9, independently of the other, represents hydrogen, lower alkyl, halogenated lower alkyl, or lower alkenyl or R.sub.8 and R.sub.9 together represent lower alkylene that is optionally interrupted by oxygen, sulphur or by optionally substituted nitrogen, or R.sub.6 together with R.sub.7 or R.sub.8 represents a lower alkylene group Alk, and salts of such compounds in which Z.sub.1, or Z.sub.3 and optionally also Z.sub.2, or R.sub.7 represent(s) hydrogen, exhibit tumor-inhibiting activities.

Substituted thiazolidinyl esters of mineral acids

The invention relates especially to pharmaceutical preparations containing N-(piperidinyl-alkyl)-carboxamides of the general formula ##STR1## in which R represents hydroxy, hydroxy etherified by an aliphatic alcohol, or halogen,

Carboxamides

Azatetracyclic carbonitriles of the formula ##STR1## in which R represents hydrogen, lower alkyl, cycloalkyl-lower alkyl having up to 10 carbon atoms, lower alkenyl, lower alkynyl or free, etherified or esterified hydroxy-lower alkyl, and acid addition salts thereof, processes for their manufacture, pharmaceutical compositions that contain such compounds and their use. They are distinguished especially by their central nervous system-depressant, agitation-inhibitory (amphetamine-antagonistic) action. They can therefore be used as tranquillizing, anti-psychotic, agitation-inhibitory compounds for the treatment of agitated states having various causes.

Azatetracyclic carbonitriles

Compounds of the formula ##STR1## in which one of the symbols R.sub.1 and R.sub.2 represents an alkyl radical that has 3 or 4 carbon atoms and is unsaturated in the 2,3-position, and the other represents such a radical or lower alkyl, R.sub.3 and R.sub.4 each represents, independently of the other, hydrogen or methyl, and A represents a radical of the formula ##STR2## in which Z.sub.1, or each of Z.sub.2 and Z.sub.3 independently of the other, represents hydrogen or lower alkyl, or Z.sub.2 and Z.sub.3 together represent lower alkylene, and salts of such compounds in which Z.sub.1, or Z.sub.3 and optionally also Z.sub.2, represent(s) hydrogen, exhibit tumor-inhibiting activities.

Anhydrides of formula V ##STR1## where A' is --CH.sub.2 CH.sub.2 --, and R and R.sub.1 independently of one another are hydrogen, halogen, alkyl having 1 to 4 carbon atoms or methoxy are valuable intermediates for the preparation of tricyclic imidyl derivatives. These imidyl derivatives form photocrosslinkable polymers useful for making printing plates and photoresists.

6,7-Dihydro-5H-benzocycloheptene-8,9-dicarboxylic acid anhydrides

Anhydrides of formula V ##STR1## where A' is --OCH.sub.2 -- with the oxygen atom bonded to the aromatic ring and R and R.sub.1 independently of one another are hydrogen, halogen, alkyl having 1 to 4 carbon atoms or methoxy are valuable intermediates for the preparation of tricyclic imidyl derivatives. These imidyl derivatives form photocrosslinkable polymers useful for making printing plates and photoresists.

2,3-Dihydro-1-benzoxepine-4,5-dicarboxylic acid anhydrides

Novel tricyclic imidyl derivatives, for example those of the formula ##STR1## �n=1 or 2, Y=a bridge member and X=a functional group! are described. The novel tricyclic imidyl derivatives are suitable for the preparation of photocrosslinkable polymers by incorporation into existing polymer chains or by building up the polymer chain from tricyclic imidyl derivatives, according to the definition, with suitable functional groups X by polymerization or polycondensation. The photocrosslinkable polymers obtained by this means can be used, for example, to produce printing plates for the offset printing process and especially as photoresists.

Tricyclic imidyl derivatives

Novel tricyclic imidyl derivatives, for example those of the formula ##STR1## [n=1 or 2, Y=a bridge member and X=a functional group] are described. The novel tricyclic imidyl derivatives are suitable for the preparation of photocrosslinkable polymers by incorporation into existing polymer chains or by building up the polymer chain from tricyclic imidyl derivatives, according to the definition, with suitable functional groups X by polymerization or polycondensation. The photocrosslinkable polymers obtained by this means can be used, for example, to produce printing plates for the offset printing process and especially as photoresists.

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Rheinfelden, Switzerland

Angelo Storni