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US 2008/0306242 A1Published application
Intermediates for lhrh antagonist synthesis, process for the production, and process for lhrh antagonist production
AssigneePolypeptide Laboratories A/S
InventorsJon H. Rasmussen, Palle H. Rasmussen, Wolfgang O. Wachs, Stefan Hansen, Jens Fomsgaard
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Abstract
The peptides Ac-D-2Nal-D-4ClPhe-D-3Pal-OH and Boc-D-2Nal-D-4ClPhe-D-3Pal-OH are intermediates useful in the synthesis of LHRH analogs by coupling with suitable heptapeptides, in particular with the heptapeptides P1-Ser(P2)-MMeTry(P3)-D-Lys(Nic)-Leu-Lys(iPr,P4)-Pro-D-AlaNH2 and P1-Ser(P2)-NMeTry(P3)-D-Asn-Leu-Lys(iPr,P4)-Pro-D-AlaNH2.
Claims16
A process for preparing a tripeptide, including a salt thereof, of the formula (I)
- Ac-D-2Nal-D-4ClPhe-D-3Pal-OH (I)
- or
- Boc-D-2Nal-D-4ClPhe-D-3Pal-OH (IX),
- comprising the following consecutive steps for the preparation of (I):
- (a) Reacting Boc-D-4ClPhe-OH with HONSu to form Boc-D-4ClPhe-OSu (VII);
- (b) Reacting Boc-D-4ClPhe-OSu (VII) with H-D-3Pal-OH to form Boc-D-4ClPhe-D-3Pal-OH (VIII);
- (c) Reacting Boc-D-4ClPhe-D-3Pal-OH (VIII) with Boc-D-2Nal-OSu prepared by reacting Boc-D-2Nal-OH with HONSu to form Boc-D-2Nal-D-4ClPhe-D-3Pal-OH (IX);
- (d) Reacting Boc-D-2Nal-D-4ClPhe-D-3Pal-OH (IX) with acetic acid to form Ac-D-2Nal-4ClPhe-D-3Pal-OH (I);
- or the consecutive steps (a) through (c) for the preparation of (IX).
6 more elements
Dependencies are inferred from the claim text.