Boehringer Mannheim Gmbh

Roche Diagnostics Gmbh

Smith Kline & French Laboratories Limited

Epis S.a.

Ernst-Christian Witte

Karlheinz Stegmeier

Hans P Wolff

Egon Roesch

Max Thiel

Liesel Doerge

Gisbert Sponer

Kurt Stach

Johannes Pill

Hans-Peter Wolff

Rudi Weyer

Volker Hitzel

Robert A Slater

Ruth Heerdt

Manfred Hubner

Hans Kuhnle

Bernd Hagenbruch

Hansjorg Beckh

Hans-Frieder K&uuml;hnle

Robert John Ife

Wolfgang Schaumann

David G Cooper

Karl Dietmann

Kurt Stach, Deceased

Androniki Roesch

Jacob Bar-Tana

Harald Stork

Hans-Frieder Kuhnle

Peter Neubert

Hans-Frieder Kuehnle

Hans P Wolfe

Leisel Doerge

Karlheinz Stegmeir

Method for producing thiazolidinediones, and new thiazolidinediones

Improved process of compound of formula III

Sulfonamides of phenylalkylamines or phenoxyalkylamines processes for

The present invention provides sulphonamides of the general formula: ##STR1## wherein R.sup.1 and R.sup.2, which can be the same or different, are hydrogen or halogen atoms or C.sub.1 -C.sub.6 -alkyl, trifluoro-methyl, cyano, carboxyl, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl or N,N-dialkylaminocarbonyl radicals or, when R.sup.1 and R.sup.2 are alkyl radicals ortho to one another, R.sup.1 and R.sup.2 together with the carbon atoms to which they are attached, form a saturated or unsaturated C.sub.5-C.sub.7 -alkylene ring, R.sup.3 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical, a phenylalkyl or phenylalkenyl radical, the phenyl moiety of which can be substituted by halogen, alkyl or trifluoromethyl, C is a --(CH.sub.2).sub.m --radical, in which m is 0, 1, 2 or 3, or a branched C.sub.2 -C.sub.5 -alkylene radical, whereby a methylene radical --CH.sub.2 --of the group C can be replaced by an oxygen or sulphur atom or by a hydroxymethylene radical --CHOH--or carbonyl group --CO--, B is a 1,2-, 1,3-, 1,4-cyclohexylidene or 1,2- or 1,3-cyclopentylidene radical.

Sulphonamidocycloalkane compounds, pharmaceutical compositions

Carboxylic acid derivatives of the formula ##STR1## R.sub.1 is alkoxy, alkylthio, alkylsulphinyl, alkulsulphonyl, alkylamino, cycloalkyl, or cycloalkoxy or optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl or arylamino. R.sub.2 is optionally substituted aryl or, when B is alkylene also a hydrogen atom. A is a straight-chained or branched, saturated or unsaturated alkylene containing 3 to 10 carbon atoms which is optionally interrupted by a heteratom attached to a saturated carbon and has a chain length of at least 3 atoms. Y is S(O).sub.n group or oxygen, n being 0, 1 or 2. B is a valency bond or a straight-chained or branched, saturated or unsaturated alkylene containing 1 to 18 carbon atoms. Physiologically acceptable salts, esters and amides thereof are also included. The compounds are useful in the treatment of metabolic diseases.

Carboxylic acid derivatives, and pharmaceutical compositions containing

The present invention provides sulphonamides of the general formula: ##STR1## wherein R.sup.1 and R.sup.2, which can be the same or different, are hydrogen or halogen atoms or C.sub.1 -C.sub.6 -alkyl, trifluoro-methyl, cyano, carboxyl, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl or N,N-dialkylaminocarbonyl radicals or, when R.sup.1 and R.sup.2 are alkyl radicals ortho to one another, R.sup.1 and R.sup.2, together with the carbon atoms to which they are attached, form a saturated or unsaturated C.sub.5 -C.sub.7 -alkylene ring, R.sup.3 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical, a phenylalkyl or phenylalkenyl radical, the phenyl moiety of which can be substituted by halogen, alkyl or trifluoromethyl, C is a --(CH.sub.2).sub.m -- radical, in which m is 0, 1, 2 or 3, or a branched C.sub.2 -C.sub.5 alkylene radical, whereby a methylene radical --CH.sub.2 -- of the group C can be replaced by an oxygen or sulphur atom or by a hydroxymethylene radical --CHOH-- or carbonyl group --CO--, B is a 1,2-, 1,3-, 1,4-cyclohexylidene or 1,2- or 1,3-cyclopentylidene radical.

The present invention provides sulphonamides of the general formula: ##STR1## wherein R is a hydrogen or halogen arom, a cyano group or a C.sub.1 -C.sub.6 -alkyl or trifluoromethyl radical, n is 1, 2 or 3, m is 0 or 1 to 5, X is a valency bond, an oxygen atom, a carbonyl group or a --CHOH-- group, A is a valency bond or a carbonyl group and B is a valency bond or an --NH-- group; the physiologically acceptable salts thereof with inorganic and organic acids, as well as the optical isomers thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.

Sulphonamides containing a tetrazolyl radical

The invention relates to phenylsulphonamidolkanoic acids which have thromboxane A.sub.2 receptor antagonist activity.

Biologically active compounds

The present invention concerns compounds of the formula: ##STR1## where R.sub.1 is an alkyl or alkenyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3 to 7 carbon atoms, an aralkyl, aralkenyl or aryl radical in which the aryl radical or moiety can be substituted one or more times by halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.12 -dialkylamino, C.sub.1 -C.sub.6 -acylamino, C.sub.1 -C.sub.16 -acyl, C.sub.1 -C.sub.6 -alkylsulphenyl, -sulphinyl or -sulphonyl or by azido, R.sub.2 is hydrogen atom or a C.sub.1 -C.sub.6 -alkyl, aralkyl, aralkenyl or acyl radical, A and B are saturated or unsaturated alkylene chains containing up to 10 carbon atoms which can be substituted one or more times by C.sub.1 -C.sub.3 -alkyl radicals, the sum of carbon atoms in chains A and B being at least 4 and at most 11, Q is an oxygen or sulphur atom, a sulphonyl or sulphinyl group or an amino group --N(R.sub.2)--, R.sub.2 having the same meaning as above, and Y is a free carboxylic acid group or a carboxylic acid ester, carboxylic acid amide, hydroxymethyl or tetrazolyl radical; the pharmacologically acceptable salts thereof and the optically active and E-Z isomers thereof, as well as mixtures thereof. These compounds are useful as they have an antagonistic action towards thromboxane A.sub.2 as well as against prostaglandin endoperoxide. They inhibit the aggregation of blood platelets and prevent the constriction of the smooth musculature as well as bronchoconstriction.

Substituted sulphonamides, pharmaceuticals thereof and methods of using

The present invention provides sulphonylphenylalkylamines of the general formula: ##STR1## wherein R.sub.1 is an alkyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3-7 carbon atoms or an aralkyl, aralkenyl or aryl radical, the aryl moiety, in each case, being optionally substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.16 acyl or azide, R.sub.2 is a hydrogen atom, an alkyl radical containing up to 6 carbon atoms, an acyl radical or an aralkyl or aralkenyl radical, the aryl moiety, in each case, optionally being substituted one or more times by halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.1 -C.sub.12 dialkylamino, C.sub.1 -C.sub.6 acylamino, C.sub.1 -C.sub.16 acyl or azide, B is an unbranched or branched alkylene chain with a maximum of 4 carbon atoms and A an alkyl or alkenyl radical containing up to 6 carbon atoms, a C.sub.1 -C.sub.6 formylalkyl radical, a C.sub.1 -C.sub.6 hydroxy-alkyl group or a radical --D--R.sub.3, in which D is a ##STR2## and R.sub.3 is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl, a C.sub.1 -C.sub.5 hydroxyalkyl or a C.sub.1 -C.sub.5 alkylcarboxylic acid radical, as well as the pharmacologically acceptable salts thereof, the esters and amides thereof and the lactones of those compounds which contain a hydroxyl and a carboxyl group, with the exception of the compound benzene-sulphonic acid-(4-acetylphenethylamide). The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.

Sulphonylalkylamines, processes for the preparation thereof and

Carboxylic acid derivatives, processes for the preparation thereof, the

##STR1## .alpha., .omega.-dicarboxylic acids having the general formula (I') in which: R.sub.1 and R.sub.2, which may be different or the same, represent a lower alkyl group which can be substituted by hydroxy, lower alkoxy, halogen or phenyl, the phenyl being capable of substitution one or several times by hydroxy, lower alkoxy, lower alkyl or halogen; a lower alkenyl or alkinyl group; a C.sub.3 -C.sub.7 -cyclo-alkyl group or a phenyl group possibly substituted by hydroxy, halogen, lower alkyl or lower alkoxy, and X and Y, which may be different or the same, represent hydrogen, lower alkyl, lower alkoxy, hydroxy, cyano, halogen, carboxyl, lower alkoxycarbonyl or carbamoyl, and Q represents non-ramified, saturated or unsaturated alkyl chain with 8-14 C atoms, which can be substituted, interrupted by hetero-atoms, and form part of a cyclic system, as well as their carboxylic acid derivatives in vivo, provided that when Q represents an unramified, saturated alkyl chain with 8-14 C atoms, and R.sub.1 and R.sub.2 represent methyl and Y represents hydrogen, X may not represent hydrogen, ethoxy-carbonyl, bromine, cyano or methyl, and if R.sub.1 and R.sub.2 represent methyl and X and Y hydrogen, then Q may not represent any formula (II) group. Process for their preparation and medicines containing these compounds, which have an anti-diabetic action and lower the level of lipids.

.alpha., .omega.-dicarboxylic acids and medicaments which contain these

The present invention provides 2H-1-benzopyran-2-one derivatives of the general formula: ##STR1## wherein either R.sub.1 is a lower alkyl radical, optionally substituted by phenyl, which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen, and R.sub.2 is trifluoromethyl, cyano, hydroxymethyl, alkoxymethyl, acyloxymethyl, halogenomethyl, aminomethyl, mono- or dialkylaminomethyl, acyl, carboxyl, alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by lower alkyl; or R.sub.1 is trifluoromethyl, cyano, hydroxymethyl, alkoxymethyl, acyloxymethyl, halogenomethyl, aminomethyl, mono- or dialkylaminomethyl, acyl, carboxyl, alkoxycarbonyl or carbamoyl, which can be mono- or disubstituted by lower alkyl, and R.sub.2 is a lower alkyl radical, optionally substituted by phenyl, which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen, and R.sub.3 is a phenyl or benzyl radical which can be substituted by lower alkyl, lower alkoxy, hydroxyl or halogen; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these 2H-1-benzopyran-2-one derivatives and pharmaceutical compositions containing them.

2H-1-benzopyran-2-one derivatives, processes for the preparation thereof

The present invention is concerned with new carboxylic acid derivatives, with processes for the preparation thereof and with pharmaceutical compositions for lipid depression and thrombocyte aggregation, containing them, and to methods for treating infirmaties caused by excess lipids or thrombocyte aggregation. The new carboxylic acid derivatives according to the present invention are compounds of the general formula: ##STR1## wherein A is a valency bond or a lower alkylene chain, B is a valency bond or a saturated or unsaturated lower alkylene chain, R is hydrogen, an alkyl group which can be substituted by hydroxyl, carboxyl, sulphonic acid or optionally substituted phenoxy group, or R is an aralkyl radical, the aryl moiety of which can be substituted and the alkyl moiety of which is optionally unsaturated and can contain up to 4 carbon atoms, or R is a phenacyl radical, the phenyl moiety optionally substituted, or R is an acyl radical derived from aliphatic, araliphatic or aromatic carboxylic or sulphonic acid, or R is an aryl radical optionally substituted with the proviso that when A is a valency bond, R cannot be hydrogen, methyl, ethyl, hydroxyethyl, benzyl or phenyl, and the physiologically acceptable salts, esters and amides thereof.

Piperazine-substituted aryl and aralkyl carboxylic acids useful for

The invention provides sulphonamides of the formula ##STR1## wherein R is a hydrogen atom or a lower alkyl radical;

Sulphonamidophenylcarboxylic acid compounds and pharmaceutical

Growing community of inventors

Mannheim, Germany

Ernst-Christian Witte