Novel peptide conjugates
AssigneeZealand Pharma A/S
InventorsBjarne Larsen, Jorgen Petersen, Daniel Kapusta, Kenneth Harlow
Life of this patent
Estimating the term…
Abstract
Disclosed are a variety of peptide conjugates represented by the following general formula: R1-Z-X-Z′-R2 including methods of making and using such conjugates. Also provided are antibodies that specifically bind the peptide conjugates. The present invention has a wide spectrum of important applications including use in the treatment of disorders impacted by nociceptin and related opioid-like peptides.
Claims35
A peptide conjugate of formula III
- R1—X-Z′-R2 (III)
- wherein X represents a hexapeptide of the formula II
- A1-A2-A3-A4-A5-A6 (II)
- wherein A1 represents Arg, Lys, His, or Asp, A2 represents Tyr, Trp, or Phe, A3 represents Tyr, Asn, Trp, or Phe, A4 represents Lys, Arg, or His, A5 represents Phe, Tyr, Trp, Leu, Val, or Ile, and A6 represents Arg, Lys, or His, wherein each amino acid residue in said hexapeptide may be in the L or D form;
- Z′ represents a charged peptide chain of from 4 to 20 amino acid residues having the D or L configuration;
- R1 represents H or an acyl group;
- R2 represents NR3R4 where each of R3 and R4 independently represents hydrogen, C(1-6)alkoxy, aryloxy, or a lower alkyl;
- or R2 represents OH;
- or
- a salt, hydrate, or solvate thereof, or an all-D form, a retro form, or a retro all-D form thereof.
5-10. (canceled)
A peptide conjugate selected from the group consisting of
- Compound 4 Ac-RYNRWKKKKK-NH2,
- Compound 8 Ac-RYYRWKKKK -NH2 (all D),
- Compound 9 Ac-KYYRWKKKK-NH2,
- Compound 10 Ac-RYYRIKKKKKKK-NH2,
- Compound 11 Ac-RYYRWKAKKKKK-NH2, and
- Compound 13 Ac-RYYRWKKKKC-NH2;
- a C-terminal free acid thereof, an esterified derivative thereof, or a pharmaceutically acceptable acid addition salt thereof.
(canceled)
A peptide conjugate X-Z′ selected from the group consisting of RYYRWKAK5, KYYRWK6, RYYRWKK6, RYYRWRK6, RYYRIKK6, and RYYRWK5, a pharmaceutically acceptable salt thereof, or a derivative thereof, wherein said derivative is an N-terminally acetylated, C-terminally amidated, or esterified derivative.
22-63. (canceled)
A biologically active substance comprising a positively charged peptide conjugate of formula III and a negatively charged counterion, wherein said counterion is a pharmaceutically acceptable anion.
Dependencies are inferred from the claim text.