Ciba-Geigy Corporation

Georges Haas

Alberto Rossi

Pier G Ferrini

Knut A Jaeggi

Alex Sele

Martin Ruegg

Roland Jaques

Erwin F Jenny

Friedrich Karrer

Saleem Farooq

Alfred Sallmann

Andreas Von Sprecher

Atso Ilvespaa

Oswald Schier

The invention relates to novel thiopyrones, especially novel benzothiopyranones of the general formula ##STR1## in which R.sub.1 represents hydrogen or an aliphatic radical, n represents 0, 1 or 2, Ph represents substituted or unsubstituted 1,2-phenylene and A represents a group of the formula --NH--CO--R in which R represents carboxy or esterified carboxy, and to their salts, processes for the manufacture of compounds of the formula (I) and their salts, pharmaceutical preparations containing such compounds and to the use of compounds of the formula (I) and their salts as the active ingredients of medicaments and/or for the manufacture of pharmaceutical preparations. The compounds of the formula (I) and their salts have anti-allergic properties.

Anti-allergic 3-(carboxycarbonyl)amino benzothiopyran-4-one derivatives,

Substituted benzophenones of the formula ##STR1## in which Ph represents unsubstituted or substituted phenyl and R represents free, esterified or amidated carboxy, have anti-inflammatory and/or analgesic properties and can be used as active ingredients in medicaments. They are manufactured, for example, as follows: a compound or a mixture of compounds of the formula ##STR2## in which X.sub.1 and X.sub.2 together represent a group of the formula --C(.dbd.O)--O that is bonded via the carbonyl group to the radical Ph and X.sub.3 represents hydrogen, or one of the radicals X.sub.1 and X.sub.3 represents a group of the formula --C(.dbd.O)--Z, the other represents hydrogen and X.sub.2 represents a group R'O-- in which R' represents hydrogen or a hydroxy-protecting group, is subjected to acid treatment and the primary product is decomposed solvolytically.

Benzophenones

Substituted anthranilamides of the formula ##STR1## in which R.sub.1 is hydrogen or an aliphatic, cycloaliphatic or cycloaliphatic-aliphatic hydrocarbon radical, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, R.sub.3 is hydrogen or an aliphatic or substituted or unsubstituted araliphatic or heteroaryl-aliphatic hydrocarbon radical and alk and alk' are identical or different lower alkylene radicals which separate the nitrogen atoms by 2 or 3 carbon atoms, and salts thereof, possess analgesic, anti-inflammatory and anti-allergic properties and may be used as active ingredients of analgesic, anti-inflammatory and anti-allergic pharmaceuticals. They are prepared, for example, by reacting an acid of the formula ##STR2## or a reactive functional derivative thereof, with an amine of the formula ##STR3## or a reactive derivative or salt thereof.

Substituted anthranilamides and pharmaceutical preparations containing

3,4-Dihydro-2H-1,2-benzothiazine 1,1-dioxides of the formula ##STR1## wherein Ph represents a substituted or unsubstituted 1,2-phenylene radical, R represents a substituted or unsubstituted benzopyrone radical, and R.sub.1 represents hydrogen or a substituted or unsubstituted hydrocarbon radical of aliphatic character, and their salts, possess antiinflammatory properties and are useful as medicaments.

N,N-Di and N,N,N-tri(hydroxy-lower alkyl) ammonium salts of substituted

New 4,7-phenanthroline derivatives of the formula (I) ##STR1## in which Ch represents an optionally substituted 5,6-quinolinylene radical of which the 6-position is joined to the --N(R.sub.E)-- group, and

Novel 4,7-phenanthroline derivatives and pharmaceutical compositions

The present invention relates to novel benzopyrane derivatives, especially 3-oxaloamino-4-oxo-4H-1-benzopyrane derivatives of the formula I ##STR1## in which Ph is substituted or unsubstituted 1,2-phenylene, R is free, esterified or amidated carboxyl and R.sub.1 is hydrogen or a substituted or substituted hydrocarbon radical, in the free from or in the form of a salt, exhibit antiallergic activities and are accordingly useful as active ingredients of antiallergic pharmaceutical preparations.

Process for the preparation of novel benzopyrane derivatives

Compounds of the general formula I ##STR1## wherein one of the two radicals R.sub.1 and R.sub.2 denotes the acyl radical of a carboxylic acid of aromatic character and the other denotes hydrogen or optionally esterified or etherified hydroxyl, R.sub.3 denotes hydrogen, alkyl or hydroxyalkyl, R.sub.4 denotes optionally esterified or amidized carboxyl, m denotes 1 or 2 and n denotes 0 or 1, in the free form or in the form of their salts are useful as antiphlogistics, mild analgesics, antipyretics and as anti-rheumatic agents.

Benzoyl indane carboxamides as antiphlogistics

The present invention relates to novel benzopyrane derivatives, especially 3-oxaloamino-4-oxo-4H-1-benzopyrane derivatives of the formula I ##STR1## in which Ph is substituted or unsubstituted 1,2-phenylene, R is free, esterified or amidated carboxyl and R.sub.1 is hydrogen or a substituted or substituted hydrocarbon radical, in the free form or in the form of a salt, exhibit antiallergic activities and are accordingly useful as active ingredients of antiallergic pharmaceutical preparations.

Azathianaphthalenes

New 4-(phenyl)-piperidine compounds of the general formula I ##STR1## in which R.sub.1 represents hydrogen or lower alkyl, Ph represents a p-phenylene group optionally substituted by lower alkyl, lower alkoxy, nitro and/or halogen, and R.sub.2 represents lower alkyl, and pharmaceutically acceptable acid addition salts thereof are useful as antidepressant agents.

New phenylazacycloalkanes

The invention relates to novel etherified cycloalkanols of the formula ##STR1## wherein X.sub.1 represents oxygen, sulphur or methylene, X.sub.2 represents oxygen or sulphur, A represents an unsubstituted or substituted phenyl radical and n is an integer from 1 to 10 inclusive, and processes for the production thereof. These compounds, especially 2-(4-phenoxyphenoxy)-cyclo-pentan-1-ol, effect a lowering of the lipid content in the blood serum. They are also intermediates for the production of insecticidal cyclopropanecarboxylic acid esters.

Etherified cycloalkanols

New pyridine compounds of the general formula I ##STR1## wherein R denotes an optionally substituted cycloaliphatic hydrocarbon radical, Ph denotes an ortho-phenylene radical or especially a para-phenylene radical, A denotes a lower alkylene radical or a direct bond, X denotes an optionally functionally modified oxo group and Py denotes a pyridine radical, are useful as fibrinolytics, thrombolytics, antiphlogistics and as mild analgesics.

Cyclo aliphatic-phenylene-carbonyl-pyridines

Certain pyridyl methanones and pharmaceutical compositions containing

Compounds of the general formula I ##STR1## wherein one of the two radicals R.sub.1 and R.sub.2 denotes the acyl radical of a carboxylic acid of aromatic character and the other denotes hydrogen or optionally esterified or etherified hydroxyl, R.sub.3 denotes hydrogen, alkyl or hydroxyalkyl, R.sub.4 denotes optionally esterified or amidised carboxyl, m denotes 1 or 2 and n denotes 0 or 1, in the free form or in the form of their salts are useful as antiphlogistics, mild analgesics, antipyretics and as anti-rheumatic agents.

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Oberwil, Switzerland

Georges Haas