Merck Patent Gmbh

Merck Patent Gesellschaft

Merck Patent Gesellschaft MIT Beschrankter Haftung

Tioga Pharmaceuticals, Inc.

Andreas Bathe

Bernd Helfert

Steffen Neuenfeld

Matthias Bartels

Susanne Rudolph

Heike Kniel

Henning Böttcher

Henning Bottcher

Wolfgang Hierse

Peer Kirsch

Elvira Montenegro

Nikolai (Mykola) Ignatyev

Henning Boettcher

Heinz Hermann Bokel

Steffen Emmert

Ralf Knieriemen

Thomas Keil

Martin Seidel

Kurt Schuster

Dieter Dorsch

Norbert Beier

Werner Mederski

Klaus-Otto Minck

Pierre Schelling

Rudolf Gottschlich

Ingeborg Lues

Christoph Saal

Mathias Osswald

Eckhard Claus

Karl-August Ackermann

Helene Crassier

Henning B&ouml;ttcher

Steffen Schellenberger

Ingeborg Stein

Ralf Knierieme

Christoph Mürmann

Thorsten Hartig

Herbert Tilly

Christoph Muermann

Ronald Keiner

Jens Budak

Uwe Eckert

Melanie Kleineidam

Jan Krause

Heinz Bokel

The invention relates to new crystalline modifications of the hydrochloride of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine, crystalline modification of the dihydrochloride of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine and amorphous 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride which are suitable in particular for the preparation of solid medicaments for the treatment or prevention of depressive disorders, anxiety disorders, bipolar disorders, mania, dementia, substance-related disorders, sexual dysfunctions, eating disorders, obesity, fibromyalgia, sleeping disorders, psychiatric disorders, cerebral infarct, tension, for the therapy of side-effects in the treatment of hypertension, cerebral disorders, chronic pain, acromegaly, hypogonadism, secondary amenorrhea, premenstrual syndrome and undesired puerperal lactation.

Polymorphic forms of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl) piperazine hydrochloride

The present invention relates to novel compounds containing fluorinated end groups, to the use thereof as surface-active substances, and to processes for the preparation of these compounds.

Fluorosurfactants

The invention relates to new crystalline modifications of the hydrochloride of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine, crystalline modification of the dihydrochloride of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine and amorphous 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride which are suitable in particular for the preparation of solid medicaments for the treatment or prevention of depressive disorders, anxiety disorders, bipolar disorders, mania, dementia, substance-related disorders, sexual dysfunctions, eating disorders, obesity, fibromyalgia, sleeping disorders, psychiatric disorders, cerebral infarct, tension, for the therapy of side-effects in the treatment of hypogonadism, secondary amenorrhea, premenstrual syndrome and undesired puerperal lactation.

Polymorphic forms of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine hydrochloride

Polymorphic forms of 1-'4-(5-cyanoindol-3-yl) butyl-4-(2-carbamoylbenzofuran-5-yl)piperazine hydrochloride

Polymorphic forms of 1-'4-(5-cyanoindol-3-yl)butyl-4-(2-carbamoylbenzofuran-5-yl)piperazine hydrochloride

Polymorphic forms of 1-'4-(5-cyanoindol-3-yl) butyl-4-(2-carbamoylbenzofuran-5-yl) piperazine hydrochloride

The present invention relates to fatty acid esters of polyols or sulfonated fatty acid esters or sulfonated fatty acid amides containing at least one group Y, where Y stands for CF&#x2014;(CH)&#x2014;O&#x2014;, SF&#x2014;, CF&#x2014;(CH)&#x2014;S&#x2014;, CFCFS&#x2014;, [CF&#x2014;(CH)]N&#x2014; or [CF&#x2014;(CH)]NH&#x2014;, where a stands for an integer selected from the range from 0 to 5, or formula (I), where Rf stands for CF&#x2014;(CH)&#x2014;, CF&#x2014;(CH)&#x2014;O&#x2014;, CF&#x2014;(CH)&#x2014;S&#x2014;, CFCF&#x2014;S&#x2014;, SF&#x2014;(CH)&#x2014; or [CF&#x2014;(CH)]N&#x2014;, [CF&#x2014;(CH)]NH&#x2014; or (CF)N&#x2014;(CH)&#x2014;, B stands for a single bond, O, NH, NR, CH, C(O)&#x2014;O, C(O), S, CH&#x2014;O, O&#x2014;C(O), N&#x2014;C(O), C(O)&#x2014;N, O&#x2014;C(O)&#x2014;N, N&#x2014;C(O)&#x2014;N, O&#x2014;SOor SO&#x2014;O, R stands for alkyl having 1 to 4 C atoms, b stands for 0 or 1 and c stands for 0 or 1, q stands for 0 or 1, where at least one radical from b and q stands for 1, and r stands for 0, 1, 2, 3, 4 or 5, to processes for the preparation of these compounds, and to uses of these surface-active compounds. 

The present invention relates to fatty acid alkanolamides or polyolamides containing at least one group Y, where Y stands for CF&#x2014;(CH)&#x2014;O&#x2014;, SF&#x2014;, CF&#x2014;(CH)&#x2014;S&#x2014;, CFCFS&#x2014;, [CF&#x2014;(CH)]N&#x2014; or [CF&#x2014;(CH)]NH&#x2014;, where a stands for an integer selected from the range from 0 to 5, or formula (I), where Rf stands for CF&#x2014;(CH)&#x2014;, CF&#x2014;(CH)&#x2014;O&#x2014;, CF&#x2014;(CH)&#x2014;S&#x2014;, CFCF&#x2014;S&#x2014;, SF&#x2014;(CH)&#x2014; or [CF&#x2014;(CH)]N&#x2014;, [CF&#x2014;(CH)]NH&#x2014; or (CF)N&#x2014;(CH)&#x2014;, B stands for a single bond, O, NH, NR, CH, C(O)&#x2014;O, C(O), S, CH&#x2014;O, O&#x2014;C(O), N&#x2014;C(O), C(O)&#x2014;N, O&#x2014;C(O)&#x2014;N, N&#x2014;C(O)&#x2014;N, O&#x2014;SOor SO&#x2014;O, R stands for alkyl having 1 to 4 C atoms, b stands for 0 or 1 and c stands for 0 or 1, q stands for 0 or 1, where at least one radical from b and q stands for 1, and r stands for 0, 1, 2, 3, 4 or 5, to processes for the preparation of these compounds, and to uses of these surface-active compounds.

The present invention relates to a hitherto unknown crystal form B of (3-cyano-1H-indol-7-yl)-[4-(4-fluorophenethyl)-piperazin-1-yl]methanone, hydrochloride, to a process for the preparation thereof, and to the use thereof for the preparation of a medicament.

Crystal form of (3-cyano-1H-Indo1-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone, hydrochloride

The invention relates to new crystalline modifications of the hydrochloride of 1-[4-(5-cyanoindol-3-yl) butyl]-4-(2-carbomyl-benzofuran-5-yl)-piperazine, crystaline modification of the dihydrochloride of 1-[4-(5-cyanoindol-3-yl) butyl]-4-(2-carbomyl-benzofuran-5-yl)-piperazine and amorphous 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride which are suitable in particular for the preparation of solid medicaments for the treatment or prevention of depressive disorders, anxiety disorders, bipolar disorders, mania, dementia, substance-related disorders, sexual dysfunctions, eating disorders, obesity, fibromyalgia, sleeping disorders, psychiatric disorders, cerebral infarct, tension, for the therapy of side-effects in the treatment of hypogonadism, secondary amenorrhea, premenstrual syndrome and undesired puerperal lactation.

Polymorphic forms of 1-'4-(5-cyanoindol-3-yl)butyl-4-(2-carbamoylbenzofuran-5-yl) piperazine hydrochloride

The invention relates to a process for the preparation of 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide and/or one of its physiologically acceptable salts, characterized in that a compound of the formula (I), in which L denotes Cl, Br, I, SOF, SOCF, SOCF, is reacted with 3-(4-piperazin-1-ylbuyl)indole-5-carbonitrile by transition-metal-catalyzed coupling by means of Pd complexes, and/or in that the 5-(4[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide formed is converted into one of its acid-addition salts by treatment with an acid, and to a second process, characterized in that a compound of the formula (II), as the base or HX salt (where X=Cl, BR), is reacted with 3-(4-oxobutyl)-1H-indole-5-carbonitrile by reductive amination, and/or in that 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide is converted into one of its acid-addition salts by treatment with an acid. 

Process for the preparation of 5-(4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl)benzofuran-2-carboxamide

The invention relates to a process for the preparation of 5-arylnicotinaldehydes by reduction of the corresponding 5-arylnicotinic acids by catalytic hydrogenation in the presence of carboxylic anhydrides in which the catalyst used is a palladium/ligand complex, characterized in that the molar ratio between palladium and ligand is from 1:5 to 1:15 in the case of monodentate ligands and from 1:2.5 to 1:7.5 in the case of bidentate ligands.

Method for producing 5-aryl nicotinaldehydes

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Darmstadt, Germany

Andreas Bathe