Compounds, methods and formulations for the oral delivery of a glucagon-like peptide (GLP-1) compound or a melanocortin-4 receptor (MC4) agonist peptide
View Patent ↗The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.
1. A compound of formula (I), or a pharmaceutically acceptable salt thereof:
wherein
R 1 is NH 2 ;
R 2 is H;
R 3 is H;
n is 2, 3, 4 or 5; and
X is
where the phenyl substituent is attached at carbon atom number 4 and the alkanoic acid chain is attached at carbon atom number 2.
2. The compound according to claim 1 , selected from
and pharmaceutically acceptable salts thereof.
3. A compound according to claim 2 , which is:
or a pharmaceutical salt thereof.
4. A compound according to claim 2 , which is:
or a pharmaceutical salt thereof.
5. A compound according to claim 2 , which is:
or a pharmaceutical salt thereof.
6. A compound according to claim 2 , which is:
or a pharmaceutical salt thereof.
7. A pharmaceutical composition comprising:
a) a compound according to claim 1 , or a pharmaceutical salt thereof; and
b) a GLP-1 compound.
8. The pharmaceutical composition according to claim 7 , wherein the GLP-1 compound is a GLP-1 derivative.
9. The pharmaceutical composition according to claim 7 , wherein the GLP-1 compound is a GLP-1 analog.
10. The composition according claim 7 , wherein the GLP-1 compound is Val 8 -Glu 22 -GLP-1(7-37)OH.
11. A pharmaceutical composition comprising:
a) a compound of claim 1 or a pharmaceutical salt thereof; and
b) an MC4 agonist peptide.
12. The composition of claim 11 , wherein the MC4 agonist peptide is selected from the group consisting of:
Ac-Arg-cyclo[Cys-Glu-His-D-Phe-Arg-Trp-Cys]-NH 2 ;
Ac-cyclo[hCys-His-D-Phe-Arg-Trp-Cys]-NH 2 ;
Ac-cyclo [hCys-His-D-Phe-Arg-Trp-penicillamine]-NH 2 ; and
N-cyclohexanecarbonyl-cyclo[hCys-His-D-Phe-Arg-Trp-penicillamine]-NH 2 .