IP Library Granted Patent US 7,662,771
Granted Patent B2
US 7,662,771 · App. 10/566,342 · Granted Feb 16, 2010

Compounds, methods and formulations for the oral delivery of a glucagon-like peptide (GLP)-1 compound or a melanocortin-4 receptor (MC4) agonist peptide

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Quick Facts
Patent No.
US 7,662,771
App. No.
10/566,342
Granted
Feb 16, 2010
Kind
B2
Abstract

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.

Claims (29)

1. A compound of

wherein: R 1 is selected from OH or NH 2 and is at the ortho-position relative to heterocycle X;

R 2 is selected from OCH 3 and H and is at the para-position relative to heterocycle X;

R 3 is H;

X a is a 5 membered aromatic heterocycle that is optionally substituted with C 1 -C 4 alkyl; wherein said heterocycle contains at least two or three heteroatoms selected from N, S and O wherein at least one heteroatom must be N and wherein said heterocycle may not be 1,3,4-oxadiazole; and

n is 2, 3, 4, 5, 6, or 7;

or a pharmaceutical salt thereof.

2. A compound which is:

or a pharmaceutical salt thereof.

3. A compound which is:

or a pharmaceutical salt thereof.

4. A compound which is:

or a pharmaceutical salt thereof.

5. A compound which is:

or a pharmaceutical salt thereof.

6. A compound which is:

or a pharmaceutical salt thereof.

7. A pharmaceutical composition comprising:

a) the compound of claim 1 or a pharmaceutical salt thereof; and

b) a GLP-1 compound.

8. The composition of claim 7 , wherein the GLP-1 compound is Val 8 -Glu 22 -GLP-1 (7-37)OH.

9. A pharmaceutical composition comprising:

a) the compound of claim 1 or a pharmaceutical salt thereof; and

b) an MC4 agonist peptide.

10. The composition of claim 9 wherein the MC4 agonist 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 .

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2022
From: NOVO NORDISK NORTH AMERICA OPERATIONS A/S
To: NOVO NORDISK A/S
Reel/Frame 060352/0663 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2021
From: EMISPHERE TECHNOLOGIES, INC.
To: NOVO NORDISK NORTH AMERICA OPERATIONS A/S
Reel/Frame 056750/0169 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2007
From: ELI LILLY AND COMPANY
To: EMISPHERE TECHNOLOGIES, INC.
Reel/Frame 019900/0952 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2006
From: HERR, ROBERT JASON; VALLURI, MURALIKRISHNA
To: ALBANY MOLECULAR RESEARCH, INC.
Reel/Frame 017530/0242 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2006
From: JUNGHEIM, LOUIS NICKOLAUS; MCGILL III, JOHN MCNEIL; THRASHER, KENNETH JEFF; ALBANY MOLECULAR RESEARCH, INC.
To: ELI LILLY AND COMPANY
Reel/Frame 017530/0255 →