Syntex (u.s.a.) Inc.

Biotage Ab

Owen W Gooding

Keith Adrian Walker

David Bruce Repke

Jeffrey W Labadie

Roger L Whiting

Sukanta Bhattacharyya

Alexander Victor Muehldorf

Counde O-Yang

Sunil Rana

Rekha P Bansal

Philip Jay Teitelbaum

Gregory Ricardo Martinez

A modified solid-support for use as a supported reagent for use in reduction reactions, including reductive amination comprising a solid-support having an tetrasubstituted ammonium cation species ionically bonded to a borohydride anion species extending therefrom having the general formula: wherein

Compositions for reductive aminations utilizing supported tricarboxyborohydride reagents and methods of using the same

The present invention relates to novel benzocycloalkylazolethione compounds which are dopamine .beta.-hydroxylase inhibitors in which the benzocycloalkyl portion of the compound is selected from indanyl, 1,2,3,4-tetrahydronaphthalenyl and 6,7,8,9-tetrahydro-5H-benzocycloheptenyl (in which the benzo is optionally substituted with one to three substituents) and the azolethione portion of the compound is selected from 2-thioxo-2,3-dihydro-1H-imidazol-3-yl, 5-thioxo-4,5-dihydro-1H-�1,2,4!triazol-4-yl and 5-thioxo-4,5-dihydro-1H-�1,2,4!triazol-1-yl (each optionally substituted with one to three substituents); and the prodrugs, pharmaceutically acceptable salts, individual isomers and mixtures of isomers and the methods of using and preparing such benzocycloalkylazolethione compounds.

Benzocycloalkylazolethione derivatives and processes for preparing the

The present invention relates to a process for preparing a 5-(N-substituted)aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thio ne (wherein the N-substituent is selected from formyl, aminocarbonyl, (C.sub.1-4)alkylcarbonyl or trifluoro (C.sub.1-4)alkylcarbonyl), which process comprises reacting a benzocycloalkylamine with thiocyanic acid and dihydroxyacetone to give a corresponding 5-hydroxymethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thione and then reacting the 5-hydroxymethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thione with a compound of the formula H.sub.2 NC(0)R.sup.2 in which R.sup.2 is hydrogen, amino, (C.sub.1-4)alkyl or trifluoro(C.sub.1-4)alkyl or with an ammonium salt of the formula NH.sub.4.sup.+ - OC(0)R.sup.3 in which R.sup.3 is hydrogen, (C.sub.1-4)alkyl or trifluoro(C.sub.1-4)alkyl. The present invention also relates to a process for preparing 5-aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thiones, which process comprises preparing a 5-(N-substituted)aminomethyl-1-benzocycloalkyl-1,3-dihydroimidazole-2-thio ne (wherein the N-substituent is selected from formyl, (C.sub.1-4)alkylcarbonyl or trifluoro(C.sub.1-4)alkylcarbonyl) by the process described above and then hydrolyzing with acid.

Process for making 1-benzocycloalkyl-1,3-dihydroimidazole-2-thione

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Los Gatos, CA, United States of America

Owen W Gooding