Process for preparing (5S)-{[2-(4-carboxyphenyl)ethyl] |2-(2-{|3-chloro-4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)ethyl]aminol-5,6,7,8-tetrahydroquinoline-2-carboxylic acid and its crystalline forms for use as pharmaceutically active compound

US12202805B2 · kind B2 · utility

Assignees

• BAYER HEALTHCARE LLC · DE
• Bayer Pharma Aktiengesellschaft · DE

Inventors

• Britta Olenik · Bottrop, DE
• Birgit Keil · Düsseldorf, DE
• Bernd RÖSLER · Wuppertal, DE
• Peter Fey · Wuppertal, DE
• Heiko Schirmer · Solingen, DE
• Guido Becker · Krefeld, DE
• Julian EGGER · Remscheid, DE
• Clemens BOTHE · Leverkusen, DE
• Helene FABER · Dormagen, DE

Key dates

• Filing date: Nov 10, 2023
• Grant date: Jan 21, 2025
• Expiry date: Nov 10, 2043

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P11/08
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention relates to a novel and improved process for preparing (5S)-{[2-(4-carboxyphenyl)ethyl][2-(2-{[3-chloro-4′-(trifluo-romethyl)biphenyl-4-yl]methoxy}phenyl)ethyl]amino}-5,6,7,8-tetrahydroquinoline-2-carboxylic acid of the formula (I) and to novel crystalline forms of it, which is i.a. the pseudopolymorphic form monohydrate I (I-M-I) or the pseudopolymorphic form monohydrate II (I-M-II), furthermore the present invention relates to a novel and selective crystallization process for preparation of the pseudopolymorphic form monohydrate I (I-M-I) or the pseudopolymorphic form monohydrate II (I-M-II), preferably monohydrate I of formula (I-M-I) and to pharmaceutical compositions comprising monohydrate I of formula (I-M-I) and to its use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of pulmonary and cardiopulmonary and cardiovascular diseases.