Preparation of active peptides
AssigneeBASF SE
InventorsWilhelm Amberg, Harald Bernard, Ernst Buschmann, Andreas Haupt, Bernd Janssen, Ulrich Karl, Andreas Kling, Stefan Muller, Kurt Ritter, Thomas Zierke
Life of this patent
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Abstract
A process for preparing pentapeptides of the formula I ##STR1## where A and R.sup.1 -R.sup.3 have the stated meanings, comprises assembling the pentapeptide stepwise starting from a prolinamide of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and eliminating the group --NR.sup.1 R.sup.2 by hydrolysis where appropriate the peptide obtained in this way.
Claims9
A process for preparing a pentapeptide of the formula I ##STR17## where A is OH or NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1-7 -alkyl, phenyl which is unsubstituted or carries up to three substituents selected from the group of alkyl, CF.sub.3, nitro and halogen, or benzyl which is unsubstituted or carries up to three substituents selected from the group of alkyl, CF.sub.3, nitro and halogen,
- R.sup.3 is ethyl, isopropyl, isobutyl, tert-butyl or 1-methylpropyl,
- R.sup.4 is ethyl, isopropyl, isobutyl, tert-butyl or 1-methylpropyl, and
- R.sup.5 is ethyl, isopropyl, isobutyl, tert-butyl or 1-methylpropyl, wherein said process comprises
- (a) converting a prolinamide of the formula II ##STR18## into the dipeptide of the formula III ##STR19## (b) converting the dipeptide of the formula III into the tripeptide of the formula IV ##STR20## (c) converting the tripeptide of the formula IV into the tetrapeptide of the formula V ##STR21## and (d) converting the tetrapeptide of the formula V into the pentapeptide of the formula I wherein A is NR.sup.1 R.sup.2, and, if required,
- (e) hydrolyzing the resulting pentapeptide I with propyl endopeptidase (PEP) to give the pentapeptidecarboxylic acid VI ##STR22##
An intermediate having the formula IV or the formula V, ##STR23## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1-7 -alkyl, phenyl which is unsubstituted or carries up to three substituents selected from the group of alkyl, CF.sub.3, nitro and halogen, or benzyl which is unsubstituted or carries up to three substituents selected from the group of alkyl, CF.sub.3, nitro and halogen,
- R.sup.3 is ethyl, isopropyl, isobutyl, tert-butyl or 1-methylpropyl.
- R.sup.4 is ethyl, isopropyl, isobutyl, tert-butyl or 1-methylpropyl.
Dependencies are inferred from the claim text.