Peptides derivatized with a-b-c-d- and their therapeutical use

a technology of peptides and derivatized peptides, applied in the field of therapeutic peptides, can solve the problems of a serious obstacle to the widespread use of clinically very promising compounds, fear of injection,

Inactive Publication Date: 2010-10-14
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the type 2 diabetes segment most patients are treated with oral hypoglycemic agents, and since GLP-1 compounds are expected to be an injectable pharmaceutical product these patients will be administered, the fear of injections may become a serious obstacle for the widespread use of the clinically very promising compounds.

Method used

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  • Peptides derivatized with a-b-c-d- and their therapeutical use
  • Peptides derivatized with a-b-c-d- and their therapeutical use
  • Peptides derivatized with a-b-c-d- and their therapeutical use

Examples

Experimental program
Comparison scheme
Effect test

example 1

N-ε37{2-[2-(2-{2-[2-((R)-3-carboxy-3-{[1-(19-carboxynonadecanoyl)piperidine-4-carbonyl]amino}propionylamino)ethoxy]ethoxy}acetylamino)ethoxy]ethoxy}acetyl [desaminoHis7,Glu22,Arg26,Arg34,Lys37]GLP-1(7-37)amide

[0722]

[0723]Preparation method: A

[0724]HPLC method B6

[0725]RT=35.49 min

[0726]LCMS: m / z=1096.2 (M+3H)3+

[0727]Calculated MW=4380.0

example 2

N-ε20-{2-[2-(2-{2-[2-((R)-3-carboxy-3-{[1-(19-carboxynonadecanoyl)piperidine-4-carbonyl]amino}propionylamino)ethoxy]ethoxy}acetylamino)ethoxy]ethoxy}acetyl [Aib2,Leu14,Lys20,Gln28,Ser(O-benzyl)39]exendin-4 (1-39)amide

[0728]

[0729]Preparation method: A

[0730]HPLC method B6:

[0731]RT=37.63 min

[0732]LCMS: m / z=1705.9 (M+3H)3+

[0733]Calculated MW=5113.9

example 3

N-ε26{2-[2-(2-{2-[2-((R)-3-carboxy-3-{[1-(19-carboxynonadecanoyl)piperidine-4-carbonyl]amino}propionylamino)ethoxy]ethoxy}acetylamino)ethoxy]ethoxy}acetyl [desaminoHis7,Arg34]GLP-1-(7-37)

[0734]

[0735]Preparation method: A

[0736]HPLC method B6:

[0737]RT=36.45 min

[0738]LCMS: m / z=1404.3 (M+3H)3+

[0739]Calculated MW=4209.8

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Abstract

The invention relates to protracted peptide derivatives such as Glucagon-Like Peptide-1 (GLP-1), exendin-4, and analogues thereof, as well as therapeutic uses thereof. The peptide derivative of the invention comprises a peptide wherein at least one amino acid residue is derivatized with A-B-C-, or A-B-C-D-. These compounds are useful in the treatment or prevention of diabetes type 2 and related diseases. The compounds are potent, have a low ratio of binding affinity to the GLP-1 receptor in the presence of high/low albumin concentrations, have long half-lives, and have a high affinity of binding to albumin, all of which is of potential relevance for the overall aim of achieving long-acting, stable and active GLP-1 derivatives with a potential for once weekly administration.

Description

FIELD OF THE INVENTION[0001]This invention relates to the field of therapeutic peptides, i.e. to new protracted peptides derivatized with A-B-C-D, and their therapeutical use. Examples of therapeutic peptides of particular relevance for the present invention are Glucagon-Like Peptide-1 (GLP-1) and exendin-4, as well as analogues thereof.BACKGROUND OF THE INVENTION[0002]A range of different approaches have been used for modifying the structure of therapeutical peptides such as GLP-1 and exendin-4 in order to provide a longer duration of action in vivo. For example, WO 2006 / 097538, WO 2006 / 097536, WO 2006 / 037810, WO2006005667, WO 2005 / 027978. WO 98 / 08871 and US 2001 / 0011071 describe various GLP-1 analogues and derivatives thereof.[0003]Many diabetes patients particularly in the type 2 diabetes segment are subject to so-called “needle-phobia”, i.e. a substantial fear of injecting themselves. In the type 2 diabetes segment most patients are treated with oral hypoglycemic agents, and sin...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K38/26C07K14/00A61P3/10A61P3/04A61P9/10
CPCA61K38/00A61K47/48169A61K47/48046A61K47/48061A61K47/48215C07K14/57563C07K14/605C07K14/001A61K38/16A61K38/22A61K38/26A61K47/48023C07K14/00C07K14/575A61K38/17A61K47/48A61K47/48007A61K47/48038A61K47/60A61K47/50A61K47/51A61K47/54A61K47/542A61K47/543A61K47/545A61K47/56A61P1/00A61P1/04A61P25/28A61P3/00A61P3/10A61P3/04A61P3/06A61P9/00A61P9/10A61P9/12
Inventor SPETZLER, JANESCHÄFFER, LAUGELAU, JESPERKRUSE, THOMASGARIBAY, PATRICK WILLIAMØSTERGAARD, SØRENREEDTZ-RUNGE, STEFFENTHØGERSEN, HENNING
Owner NOVO NORDISK AS
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