Merck Patent Gesellschaft

Merck Patent Gmbh

Merck Patent Gesellschaft MIT Beschrankter Haftung

Tioga Pharmaceuticals, Inc.

Bernd Helfert

Andreas Bathe

Steffen Neuenfeld

Heike Kniel

Matthias Bartels

Susanne Rudolph

Henning Böttcher

Henning Bottcher

Kurt Schuster

Rudolf Gottschlich

Christoph Saal

Henning Boettcher

Karl-August Ackermann

Henning B&ouml;ttcher

Ingeborg Stein

Ralf Knierieme

Steffen Emmert

Jens Budak

Ronald Keiner

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 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 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 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.

Process for the preparation of 5-(1-piperazinyl)benzofuran-2-carboxamide in which, as intermediate step, 5-bromosalicylaldehyde or one of its derivatives is reacted in a transition metal-catalysed amination with R -piperazine, in which R is as defined in claim

Method for producing 5-(1-piperazinyl)-benzofuran-2-carboxamide by transition metal-catalyzed amination

Benzofurane derivatives of formula (I), wherein R and R&prime; have the meanings given in claim no. ( ), and salts thereof are suitable for use as intermediate products in the synthesis of medicaments.

Benzofurane derivatives

The invention relates to a novel process for the alternative preparation of N-methyl-N-&lsqb;(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)ethyl&rsqb;-2,2-diphenylacetamide or N-methyl-N-&lsqb;(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidin-1-yl)ethyl&rsqb;-2,2-diphenylacetamide, and the novel compounds N-methyl-N-&lsqb;(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)ethane&rsqb; and N-methyl-N&lsqb;(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidin-1-yl) ethane&rsqb;, which are prepared as intermediates.

Method for producing enantiomer-free N-methyl-N-&lsqb;(1S)-1-phenyl-2-((3S)-3-hydroxypyrolidine-1-yl)ethyl&rsqb;-2,2-diphenylacetamide

Benzofurans of the formula I ##STR1## and their salts in which R.sup.1, R.sup.2 and X have the meanings indicated in claim 1, are suitable as intermediates in the synthesis of medicaments and show effects on the central nervous system.

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Ober-Ramstadt, Germany

Bernd Helfert