Peptides and peptide derivatives as well as pharmaceutical compositions containing the same

• US 7,799,758 B2
• Filed: 02/23/2007
• Issued: 09/21/2010
• Est. Priority Date: 02/23/2006
• Status: Expired due to Fees

• Current Assignee: Fibrex Medical Research & Development GmbH
• Original Assignee: Ikaria Development Subsidiary Two LLC (Mallinckrodt plc)
• Inventors: Henning, Rainer, Reingruber, Sonja, Petzelbauer, Peter
• Primary Examiner(s): Ha; Julie
• Application Number:
  US11/678,535
• Publication Number:
  US 20080039388A1
• Time in Patent Office: 1,306 Days
• Field of Search: None
• US Class Current: 514/1.6
• CPC Class Codes: A61K 38/00 Medicinal preparations containing peptides peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: C07K 14/75 Fibrinogen
• CPC Class Codes: Y02A 50/30 Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

Therapeutic compositions can include modified peptides which are derived from the chain of the Bbeta(15-42)-fibrin fragment and wherein one or several of the amino acids of the sequence have been substituted by genetically encoded or not genetically encoded amino acids or peptidomimetics. They may exist as free peptides or as C-terminal derivative and/or being linked to a polyethylene glycol (PEG)-polymer, and have anti-inflammatory and/or endothelium stabilizing effects. Esters or amides may for instance be taken into consideration as C-terminal derivatives. Processes for production of the peptides and derivatives thereof are also described.

Claims

1. A peptide of Formula (II),

H₂N-GHRPLDKKREEAPSLRPAPPPISGGGYR-X₁₇ 

 

(II) (SEQ ID NO;

     67),

wherein;

X₁₇ denotes a residue C(NR₂R₃)-(S-succinimido)-(PEG_5-60K), the succinimido residue being linked to the sulfur atom of the cysteine residue via C-atom 3, and R₂ and R₃ being identical or different and being hydrogen or (C₁-C₁₀)-alkyl, as well as a physiologically acceptable salt thereof.

4. A pharmaceutical drug composition, containing the peptide according to any of claims 1 to 3.

2. A peptide of Formula (III),

H₂N-GHRPLDKKREEAPSLRPAPPPIS-X₁₉-X₂₀-X₂₁-YR-X₁₇ 

 

(III) (SEQ ID NO;

     10),

wherein two of the residues X₁₉, X₂₀ and X₂₁ each are a glycine residue and the remaining one is a residue C-(S-succinimido)-(PEG_5-40K), the succinimido residue being linked to the sulfur atom of the cysteine residue via C-atom 3, and wherein X₁₇ denotes NR₂R₃, R₂ and R₃ being identical or different and being hydrogen or (C₁-C₁₀)-alkyl, as well as a physiologically acceptable salt thereof.

3. A peptide of Formula (III),

H₂N-GHRPLDKKREEAPSLRPAPPPIS-X₁₉-X₂₀-X₂₁-YR-X₁₇ 

 

(III) (SEQ ID NO;

     11),

wherein two of the residues X₁₉, X₂₀ and X₂₁ each are a glycine residue and the remaining one is a residue K-(PEG_5-40K), the PEG-residue being linked via the nitrogen atom in the side chain of the lysine residue, and wherein X₁₇ denotes NR₂R₃, R₂ and R₃ being identical or different and being hydrogen or (C₁-C₁₀)-alkyl, as well as a physiologically acceptable salt thereof.