Syntex (u.s.a.) Inc.

Roche Palo Alto LLC

Alexander Victor Muehldorf

Counde O'Yang

Francisco Javier Lopez-Tapia

Robin D Clark

Thomas Weitao Sun

Alam Jahangir

Bruce Andrew Kowalczyk

Keith Roger Bley

Dennis Mitsugu Yasuda

Paul Francis Keitz

Richard Leo Cournoyer

Lee Edwin Lowrie, Jr

Daniel Lee Severance

Owen W Gooding

Counde O-Yang

Rekha P Bansal

This invention relates to compounds which are generally IP receptor antagonists and which are represented by Formula I: wherein:

Carboxylic acid derivatives as IP antagonists

This invention relates to IP receptor antagonists selected from the group of compounds represented by Formula I: where: and other substituents as defined in the specification, and their pharmaceutically acceptable salts or crystal forms thereof; and pharmaceutical compositions containing them; and methods for their use as therapeutic agents.

2-(substituted-phenyl)amino-imidazoline derivatives

Aryl carboxylic acid and aryl tetrazole derivatives as IP receptor modulators

This invention relates to IP receptor antagonists selected from the group of compounds represented by Formula I:

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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Sunnyvale, CA, United States of America

Alexander Victor Muehldorf