Ciba-Geigy Corporation

Andreas Beck

Robert W Lang

Andreas Von Sprecher

Alfred Sallmann

Paul Wenk

Werner Breitenstein

Konrad Oertle

Marc Gerspacher

Ivan Ernest

Alan J Main

Bruno Schaub

Compounds of formula I ##STR1## wherein R.sub.1 -R.sub.5, X, Ar and Y are as defined in the description, have valuable pharmaceutical properties and are especially effective as leukotriene antagonists. They are prepared in a manner known per se.

Quinoline compound

Substituted alkanophenones of general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is phenyl that is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterified or amidated carboxy, or is lower alkyl that is unsubstituted, substituted by fluoro and chloro or substituted by free esterified or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties and can be used as anti-allergic active ingredients in medicaments.

Alkanophenones useful for treating allergies

Substituted alkanophenones of the general formula ##STR1## in which R.sub.1 is unsubstituted or fluorinated lower alkyl, R.sub.2 is hydrogen, or unsubstituted or fluorinated lower alkyl or lower alkenyl, X is lower alkylene, oxy, thio or a direct bond, alk is lower alkylene, n is 1 or 2, R.sub.3 is a 5-membered heteroaryl radical that contains 1N, O or S atom as hetero atom and is unsubstituted or is substituted by unsubstituted or fluorinated lower alkyl, by etherified or esterified hydroxy, by unsubstituted or lower alkylated amino and/or by free, esterfied or amidated carboxy, R.sub.4 is free, esterified or amidated carboxy or 5-tetrazolyl, and R.sub.5 is hydrogen or lower alkyl, have leucotriene-antagonistic properties can e used as antiallergic active ingredients in medicaments.

4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.

Novel fluorinated resorcinol ethers and their use as anti-allergics and

Novel 4-acylresorcinol ethers of the formula ##STR1## in which R.sub.1 represents lower alkyl, R.sub.2 represents lower alkyl, lower alkenyl or lower alkynyl, R.sub.3 represents hydrogen, lower alkoxy, trifluoromethyl or halogen, alk represents an alkylene radical, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 that is other than a group of the formula --NH--C(.dbd.0)--R.sub.8 is a radical R.sub.9 and a radical R.sub.7 that is other than a group of the formula --NH--C(.dbd.0)--R.sub.8 is a radical R.sub.10, R.sub.6 represents hydrogen, lower alkyl, halogen, trifluoromethyl, optionally esterified or amidated carboxy, cyano or lower alkanoyl, R.sub.8 represents optionally esterified or amidated carboxy, or 5-tetrazolyl, R.sub.9 represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and R.sub.10 represents hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or optionally esterified or amidated carboxy, and their salts have LTD.sub.4 -antagonistic and PLA.sub.2 -phospholipase-inhibiting properties. They can be manufactured according to methods known per se.

Novel resorcinol ethers and anti-inflammatory and anti-allergic use

4-Acylresorcinol esthers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties. They are prepared, for example, by reacting compounds of the formulae ##STR2## in which one of the radicals X.sub.5 and X.sub.6 is hydroxyl which is free or in salt form and the other is an alkoxy radical substituted by reactive esterified hydroxy or epoxy. The invention also relates to intermediates of the formula ##STR3## in which R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen and R.sub.11 is hydrogen or a group of the formula R.sub.1 --C(--O)--, in which R.sub.1 is lower alkyl, and their salts.

Oxaloamino substituted fluorinated resorcinol ethers and anti-allergic

Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: a is an integer of from 1 to 7,

.alpha.-Hydroxy thioethers

Novel 4-acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, alk is a hydroxyalkylene radical which can be interrupted by oxygen and R.sub.2 is 5-tetrazolyl, it being possible for the ring A to be additionally substituted by a lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy and/or halogen and for the ring B to be additionally substituted by lower alkyl, lower alkanoyl, lower alkoxy, lower alkoxycarbonyl, carboxyl, cyano, carbamyl, halogen and/or trifluoromethyl, and salts thereof have antiallergic properties and can be used as active compounds for medicaments. They are prepared by methods known as per se.

N-(substituted phenyl) tetrazol-5-yl carboxamides and anti-allergic use

Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,

Aromatic thioethers

4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties. They are prepared, for example, by reacting compounds of the formulae ##STR2## in which one of the radicals X.sub.5 and X.sub.6 is hydroxyl which is free or in salt form and the other is an alkoxy radical substituted by reactive esterified hydroxyl or epoxy. The invention also relates to intermediates of the formula ##STR3## in which R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen and R.sub.11 is hydrogen or a group of the formula R.sub.1 --O(.dbd.O)--, in which R.sub.1 is lower alkyl, and their salts.

Novel fluorinated resorcinol ethers

Novel asymmetric thioethers of the formula ##STR1## in which R.sup.1 represents a C.sub.1-3 -alkyl radical or a C.sub.1-3 -hydroxyalkyl radical of which the hydroxy group may be in esterified form,

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Freiburg, Germany

Andreas Beck