Labelled peptide compounds

US6194386A · kind A · utility

Assignee

• MALLINCKRODT LLC · US

Inventors

• John Mertens · Brussels, BE
• Dirk Tourwe · Brussels, BE
• Marc André Ceusters · Diest, BE

Key dates

• Filing date: Jun 16, 1999
• Grant date: Feb 27, 2001
• Expiry date: Jun 16, 2019

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K2123/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The invention relates to a labelled peptide compound, wherein the peptide has a selective neurotensin receptor affinity and is represented by the general formula EQU R.sub.1 --(.sup.1 Pro).sub.n --.sup.2 Xaa--.sup.3 Xbb--.sup.4 Xcc--.sup.5 Xdd--.sup.6 Xee--.sup.7 Leu--OH(SEQ ID NO.2) (I) wherein: PA1 R.sub.1 is a (C.sub.1 -C.sub.3)alkanoyl group, an arylcarbonyl group, an aryl-(C.sub.1 -C.sub.3)alkanoyl group, or a chelating group attached by an amide bond or through a spacing group to the peptide molecule; PA1 Xaa and Xbb are each individually Arg or Lys; PA1 Xcc is an unsubstituted or substituted cyclic amino acid, preferably selected from Pro and Hyp; PA1 Xdd is Tyr, Trp or Phe; PA1 Xee is Leu, Ile or t.-butylalanine; and PA1 n is 0 or 1; and wherein said peptide is labelled with (a) a metal isotope, or (b) with a radioactive halogen isotope; on the understanding that: (i) if the label is a metal isotope, R.sub.1 represents a chelating group for chelating said isotope; and (ii) if the label is a radioactive halogen isotope, said halogen isotope is attached to .sup.4 Tyr in the 2-position of the phenyl ring, to .sup.4 Trp, or to the aryl group of substituent R.sub.1. The inventio…