Amino acids and peptides having a modified tyrosine residue, their preparation and their application as medicaments

US5190921A · kind A · utility

Assignee

• Institut National de la Sante et de la Recherche Medicale (INSERM) · FR

Inventors

• Bernard Roques · Paris, FR
• Isabelle Marseigne · Val-de-Reuil, FR
• Bruno Charpentier · Biot, FR

Key dates

• Filing date: Jan 24, 1992
• Grant date: Mar 2, 1993
• Expiry date: Jan 24, 2012

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61K38/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

These compounds are represented by formula (I), in which each of R.sub.1 R.sub.2 =H, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, or aromatic; (when R.sub.1 =H, R.sub.2 can be an amine function-protecting radical, amino acid residue or peptide fragment; R.sub.1 and R.sub.2 being capable of forming, with N, a 5-7 component ring); A=carbonyl or methylene; W=hydroxy, phenoxy, C.sub.1 -C.sub.8 alkoxy; phenoxy(C.sub.1 -C.sub.8 alkyl), amino, (C.sub.1 -C.sub.8 alkyl)amino, di(C.sub.1 -C.sub.8 alkyl)amino, (when A=carbonyl, W=amino acid residue or peptide fragment); Y=--OSO.sub.2 OR.sub.3 (II), --OPO(OR.sub.3).sub.2 (III), --(CH.sub.2 (.sub.m --SO.sub.2 OR.sub.3 (IV) or --(CH.sub.2).sub.m --PO(OR.sub.3).sub.2 (V) [R.sub.3 =H, C.sub.1 -C.sub.8 alkyl; m=1 to 4]; Z=cyclohexane, pyridyl or phenyl; n=0 to 4; on the condition that when Y=(II) or (III), -A-W is other than a sequence composed of natural amino acids. They have antipsychotic properties, an effect facilitating the memorization processes, analgesic properties; they are useful as anorexia-producing agents, and they have stimulatory effects on intestinal motility. ##STR1##