IP Library › Granted Patent US 12703731
Granted Patent B2
US 12703731 · App. 17/758,113 · Granted Aug 11, 2026

Long-acting GLP-1 compound

Inventors: Zhongru Gan (Beijing, CN); Wei Chen (Beijing, CN); Yining Zhang (Beijing, CN); Fangkai Xue (Beijing, CN); Lingyu Cai (Beijing, CN); Jianghong Niu (Beijing, CN); Bin Mu (Beijing, CN)
Assignee: Gan & Lee Pharmaceuticals Co., Ltd.
C07K14/605A61K38/28A61K47/02A61K47/10A61P3/04A61P3/10
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Quick Facts
Patent No.
US 12703731
App. No.
17/758,113
Filed
Jun 28, 2022
Granted
Aug 11, 2026
Kind
B2
Art Unit
1658
USPC
514/5.3
Abstract

A novel GLP-1 derivative, compared with GLP-1 derivatives such as liraglutide and semaglutide which are on the market, has comparable or better effect, potency or efficacy, longer or comparable duration of action in vivo or half-life in vivo, has better or comparable GLP-1 receptor binding affinity and has better or comparable DPP-IV stability.

Claims (30)

1 . A compound of formula (B):

or a pharmaceutically acceptable salt, amide or ester thereof,

wherein

G1 is a [Gly8, Arg34]GLP-1-(7-37) peptide of SEQ ID NO: 2;

[Acy-(L1) r -(L2) q ] is a substituent linked to the ε amino group of the Lys residue at position 26 of the [Gly8, Arg34]GLP-1-(7-37) peptide;

r is 1;

q is 1 or 2;

Acy is a fatty diacid comprising 20, 21 or 22 carbon atoms, wherein formally, a hydroxyl group has been removed from one of the carboxyl groups in the fatty diacid;

L1 is the amino acid residue of γGlu;

L2 is-HN-(CH 2 ) 2 -O-(CH 2 ) 2 -O-CH 2 -CO-;

Acy, L1 and L2 are linked by amide bonds; and

the C-terminus of L2 is linked to the ε amino group of the Lys residue at position 26 of the [Gly8, Arg34]GLP-1-(7-37) peptide.

2 . The compound according to claim 1 , wherein, Acy is HOOC-(CH 2 ) 18 -CO-, HOOC-(CH 2 ) 19 -CO-, or HOOC-(CH 2 ) 20 -CO-.

3 . The compound according to claim 2 , wherein, Acy is HOOC-(CH 2 ) 18 -CO-, or HOOC-(CH 2 ) 20 -CO-.

4 . The compound according to claim 3 , wherein the compound is selected from the group consisting of:

N-ε 26 -[2-(2-[2-(2-[2-(2-[4-(19-carboxynonadecanoylamino)-4 (S)-carboxybutanoylamino]ethoxy)ethoxy]acetylamino)ethoxy]ethoxy) acetyl][Gly8, Arg34]GLP-1-(7-37) peptide;

N-ε 26 -[2-(2-[2-(4-[19-carboxynonadecanoylamino]-4 (S)-carboxybutanoylamino)ethoxy]ethoxy) acetyl][Gly8, Arg34]GLP-1-(7-37) peptide; and

N-ε 26 -[2-(2-[2-(2-[2-(2-[4-(21-carboxyheneicosanoylamino)-4 (S)-carboxybutanoylamino]ethoxy)ethoxy]acetylamino)ethoxy]ethoxy) acetyl][Gly8, Arg34]GLP-1-(7-37) peptide.

5 . A pharmaceutical composition comprising the compound according to claim 1 , and a pharmaceutically acceptable excipient.

6 . A compound selected from the group consisting of:

N-ε 26 -[2-(2-[2-(4-[19-carboxynonadecanoylamino]-4 (S)-carboxybutanoylamino)ethoxy]ethoxy) acetyl][Gly8, Arg34]GLP-1-(7-37) peptide; and

N-ε 26 -[2-(2-[2-(2-[2-(2-[4-(21-carboxyheneicosanoylamino)-4 (S)-carboxybutanoylamino]ethoxy)ethoxy]acetylamino)ethoxy]ethoxy) acetyl][Gly8, Arg34]GLP-1-(7-37) peptide,

or a pharmaceutically acceptable salt, amide or ester thereof.

7 . A pharmaceutical composition comprising the compound according to claim 6 , and a pharmaceutically acceptable excipient.

8 . A compound having the structure:

wherein the amino acid sequence in the compound is that of SEQ ID NO: 2.

9 . A pharmaceutical composition comprising the compound according to claim 8 , and a pharmaceutically acceptable excipient.

10 . A compound having the structure:

wherein the amino acid sequence in the compound is that of SEQ ID NO: 2.

11 . A pharmaceutical composition comprising the compound according to claim 10 , and a pharmaceutically acceptable excipient.