Acid-labile anchor groups for the synthesis of peptide amides by a solid-phase method

US5124478A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Gerhard Breipohl · Scheinfeld, DE
• Jochen Knolle · Kriftel, DE
• Werner Stuber · Lahntal, DE

Key dates

• Filing date: Dec 20, 1988
• Grant date: Jun 23, 1992
• Expiry date: Dec 20, 2008

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to new compounds of the formula ##STR1## in which R.sup.1 denotes (C.sub.1 -C.sub.8)-alkyl, R.sup.2 denotes an amino acid residue which is protected with a urethane protective group which can be eliminated with weak acid or base, or denotes an amino protective group which can be eliminated with weak acid or base, R.sup.3 denotes hydrogen or (C.sub.1 -C.sub.4)-alkyl, and Y.sup.1 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy or --O--(CH.sub.2).sub.n --COOH (with n=1 to 6), with one of these radicals being --O--(CH.sub.2).sub.n --COOH, or Y.sup.1, Y.sup.2 and Y.sup.5 -Y.sup.9 denote identical or different radicals hydrogen, (C.sub.1 -C.sub.4)-alkyl or (C.sub.1 -C.sub.4)-alkoxy, Y.sup.3 denotes hydrogen or (C.sub.1 -C.sub.8)-alkoxy and Y.sup.4 denotes --(CH.sub.2).sub.n --COOH or --NH--CO--(CH.sub.2).sub.n --COOH (with n=1 to 6). Processes for the preparation thereof and the synthesis of peptide amides by a solid-phase method using these new compounds (spacers) are described.