US 12,269,902 B2
Peptide compounds and peptide conjugates for the treatment of cancer through receptor-mediated chemotherapy
Richard Béliveau, Montreal (CA); Borhane Annabi, Brossard (CA); Michel Demeule, Beaconsfield (CA); Alain Larocque, St-Laurent (CA); Jean-Christophe Currie, Repentigny (CA); and Cyndia Charfi, La Prairie (CA)
Assigned to Transfert Plus, S.E.C., Quebec (CA)
Filed by TRANSFERT PLUS, S.E.C., Montreal (CA)
Filed on Aug. 30, 2023, as Appl. No. 18/240,295.
Application 18/240,295 is a continuation of application No. 17/239,544, filed on Apr. 23, 2021, granted, now 11,780,882.
Application 17/239,544 is a continuation of application No. 15/778,626, granted, now 11,034,727, issued on May 26, 2021, previously published as PCT/CA2016/051379, filed on Nov. 24, 2016.
Claims priority of provisional application 62/259,178, filed on Nov. 24, 2015.
Prior Publication US 2024/0199695 A1, Jun. 20, 2024
This patent is subject to a terminal disclaimer.
Int. Cl. C07K 7/08 (2006.01); A61K 31/337 (2006.01); A61K 38/00 (2006.01); A61K 47/64 (2017.01); A61P 35/00 (2006.01); C07K 1/06 (2006.01); C07K 14/00 (2006.01)
CPC C07K 7/08 (2013.01) [A61K 31/337 (2013.01); A61K 47/64 (2017.08); A61P 35/00 (2018.01); C07K 1/061 (2013.01); C07K 14/001 (2013.01); A61K 38/00 (2013.01)] 20 Claims
 
1. A conjugate compound having the formula of A-(B)n,
wherein:
n is 1, 2, 3 or 4;
A is a peptide compound; and
B is a therapeutic agent, wherein B is connected to A, (i) at a free amine of said peptide compound, (ii) at an N-terminal position of said peptide compound, (iii) at a free-SH of said peptide compound, (iv) at a free carboxyl of said peptide compound, or (v) any combination of (i) to (iv);
the peptide compound is a compound chosen from compounds of formula (I), formula (II), formula (III), formula (IV), formula (V), formula (VI), formula (VII), formula (VIII), formula (IX), formula (X), formula (XI), formula (XII) and formula (XIII), and if chosen from compounds of formulas (V) through (XIII) the peptide compound has at least 80% sequence identity to those compounds:
X1X2X3X4X5GVX6AKAGVX7NX8FKSESY (SEQ ID NO: 1)
(I)
 
 
(X9)nGVX10AKAGVX11NX12FKSESY (SEQ ID NO: 2)
(II)
 
 
YKX13LRRX14APRWDX15PLRDPALRX16X17L (SEQ ID NO: 3)
(III)
 
 
YKX18LRR(X19)nPLRDPALRX20X21L (SEQ ID NO: 4)
(IV)
 
 
IKLSGGVQAKAGVINMDKSESM (SEQ ID NO: 5)
(V)
 
 
IKLSGGVQAKAGVINMFKSESY (SEQ ID NO: 6)
(VI)
 
 
IKLSGGVQAKAGVINMFKSESYK (SEQ ID NO: 7)
(VII)
 
 
GVQAKAGVINMFKSESY (SEQ ID NO: 8)
(VIII)
 
 
GVRAKAGVRNMFKSESY (SEQ ID NO: 9)
(IX)
 
 
GVRAKAGVRN(Nle)FKSESY (SEQ ID NO: 10)
(X)
 
 
YKSLRRKAPRWDAPLRDPALRQLL (SEQ ID NO: 11)
(XI)
 
 
YKSLRRKAPRWDAYLRDPALRQLL (SEQ ID NO: 12)
(XII)
 
 
YKSLRRKAPRWDAYLRDPALRPLL (SEQ ID NO: 13)
(XIII)
 
wherein
X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12, X13, X14, X15, X18 and X19 are independently chosen from any amino acid;
X16, X17, X20 and X21 are independently chosen from Q, P, Y, I and L;
m is 0, 1, 2, 3, 4 or 5;
when X9 is present more than once, each of said X9 is independently chosen from any amino acid;
when X19 is present more than once, each of said X19 is independently chosen from any amino acid;
wherein a cysteine residue is added to said peptide compound at an N- and/or C-terminal end;
wherein at least one protecting group and/or at least one labelling agent is optionally connected to said peptide compound at an N- and/or C-terminal end; and
wherein B is connected to A via a linker.