US 12,351,652 B2
Hemagglutinin-binding peptide
Keiichi Masuya, Kawasaki (JP); and Masaki Ohuchi, Kawasaki (JP)
Assigned to PeptiDream Inc., Kanagawa (JP)
Appl. No. 17/432,072
Filed by PeptiDream Inc., Kawasaki (JP)
PCT Filed Feb. 17, 2020, PCT No. PCT/JP2020/006146
§ 371(c)(1), (2) Date Aug. 18, 2021,
PCT Pub. No. WO2020/171028, PCT Pub. Date Aug. 27, 2020.
Claims priority of application No. 2019-026185 (JP), filed on Feb. 18, 2019.
Prior Publication US 2024/0228544 A1, Jul. 11, 2024
Int. Cl. C07K 7/64 (2006.01); A61K 38/00 (2006.01); A61P 31/16 (2006.01); G01N 33/569 (2006.01)
CPC C07K 7/64 (2013.01) [A61P 31/16 (2018.01); G01N 33/56983 (2013.01); A61K 38/00 (2013.01); G01N 2333/11 (2013.01); G01N 2469/10 (2013.01)] 12 Claims
 
1. A hemagglutinin-binding peptide, a pharmaceutically acceptable salt thereof, or a solvate thereof, wherein the hemagglutinin-binding peptide is:
(1) a polypeptide consisting of an amino acid sequence represented by SEQ ID NO: 1 or 2:
(SEQ ID NO: 1)
  Trp-Thr-MeGly-Asp-MePhe-MePhe-Ala-MeAla-His-Tyr-
 
 
 Thr-Val-hydPro-Ala-Cys,
 
 and
 
(SEQ ID NO: 2)
 
 Trp-Thr-MeGly-Asp-MePhe-MePhe-Ala-MeAla-His-Tyr-
 
 
 Thr-Val-hydPro-Ala-Cys-Lys;
(2) a polypeptide consisting of an amino acid sequence in which, in the SEQ ID NO: 1 or 2, the N-terminal Trp is chloroacetyl-Trp;
(3) a polypeptide consisting of an amino acid sequence in which, in the SEQ ID NO: 1, the N-terminal Trp is chloroacetyl-Trp and the C-terminal Cys has been modified as represented by Formula (I) via an amide bond;
(4) a polypeptide consisting of a sequence in which, in the SEQ ID NO: 2, the N-terminal Trp is chloroacetyl-Trp and the C-terminal Lys has been substituted with a modified lysine derivative represented by Formula (II);
(5) a polypeptide consisting of an amino acid sequence in which, in the SEQ ID NO: 1, the C-terminal Cys has been modified as represented by Formula (I) via an amide bond;
(6) a polypeptide consisting of a sequence comprising a lysine derivative represented by Formula (II) in which, in the SEQ ID NO: 2, a side chain of Lys has been modified with an acyl group; or
(7) a peptide having an amino acid sequence in which, in the amino acid sequence in any of (1) to (6) above, one or two amino acids have been added or substituted to the C-terminal Cys in the SEQ ID NO: 1 or to the C-terminal Lys in the SEQ ID NO: 2 (however a sequence in which, in the SEQ ID NO: 1, the C-terminal Cys has been deleted, and a sequence in which, in the SEQ ID NO: 2, the C-terminal Lys has been deleted, are excluded)

OG Complex Work Unit Chemistry
(In Formula (I), * denotes a linking moiety to a carbonyl group of the C-terminal Cys, and A1 denotes a C8-C12 alkyl group)

OG Complex Work Unit Chemistry
(In Formula (II), * denotes a linking moiety to a carbonyl group of the C-terminal Cys, and A1 denotes a C8-C12 alkyl group).