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Glucagon like peptide 1 (glp-1) fusion peptide coupled cyclic peptide tyrosine tyrosine conjugates and uses thereof

A technology of GLP-1 and glucagon, applied in the field of cyclic peptide tyrosine-tyrosine conjugates, which can solve the problems of impracticality and short half-life

Pending Publication Date: 2020-11-27
JANSSEN PHARMA NV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

GLP-1 is characterized by a short half-life, which makes the use of GLP-1 as a potential therapeutic impractical

Method used

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  • Glucagon like peptide 1 (glp-1) fusion peptide coupled cyclic peptide tyrosine tyrosine conjugates and uses thereof
  • Glucagon like peptide 1 (glp-1) fusion peptide coupled cyclic peptide tyrosine tyrosine conjugates and uses thereof
  • Glucagon like peptide 1 (glp-1) fusion peptide coupled cyclic peptide tyrosine tyrosine conjugates and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0357] Embodiment 1 is a conjugate comprising a glucagon-like peptide (GLP-1 ) fusion peptide coupled to a cyclic PYY peptide, wherein the GLP-1 fusion peptide comprises GLP-1 peptide, a first linker peptide, a hinge-Fc region peptide and a second linker peptide, wherein said first linker peptide is optionally absent.

Embodiment approach 2

[0358] Embodiment 2 is the conjugate according to embodiment 1, wherein the cyclic PYY peptide is represented by Formula I or a derivative or pharmaceutically acceptable salt thereof:

[0359]

[0360] in

[0361] p is 0 or 1;

[0362] m is 0, 1, 2, 3, 4 or 5;

[0363] n is 1, 2, 3 or 4;

[0364] q is 0 or 1; the precondition is only if Z 30 When not present, q is 1;

[0365] BRIDGE to -Ph-CH 2 -S-, -triazolyl-, -NHC(O)CH 2 S-, -SCH 2 C(O)NH-,

[0366] -(OCH 2 CH 2 ) 2 NHC(O)CH 2 S, -NHC(O)- or -CH 2 S-;

[0367] Z 4 is K, A, E, S or R;

[0368] Z 7 be A or K;

[0369] Z 9 is G or K;

[0370] Z 11 is D or K;

[0371] Z 22 be A or K;

[0372] Z 23 is S or K;

[0373] Z 26 be A or H;

[0374] Z 30 is L, W or absent,

[0375] The precondition is that only when q is 1, Z 30 does not exist;

[0376] Z 34 for

[0377] Z 35 for

[0378] Wherein said derivative is a compound of formula I modified by one or more methods selected from amidation,...

Embodiment approach 3

[0379] Embodiment 3 is the conjugate according to embodiment 2, wherein the cyclic PYY peptide is represented by Formula I or a derivative or pharmaceutically acceptable salt thereof, wherein:

[0380] p is 0 or 1;

[0381] m is 0, 1, 2, 3, 4 or 5;

[0382] n is 1, 2, 3 or 4;

[0383] q is 0 or 1; the precondition is only if Z 30 When not present, q is 1;

[0384] BRIDGE to -Ph-CH 2 -S-, -triazolyl-, -NHC(O)CH 2 S-, -SCH 2 C(O)NH 2 -,

[0385] -(OCH 2 CH 2 ) 2 NHC(O)CH 2 S, -NHC(O)- or -CH 2 S-;

[0386] Z 4 is K, A, E, S or R;

[0387] Z 7 is A or K, wherein the amino side chain of K is optionally substituted by

[0388] wherein i is an integer from 0 to 24, and X=Br, I or Cl,

[0389] -C(O)CH 2 Br, -C(O)CH 2 I or -C(O)CH 2 Cl;

[0390] Z 9 is G or K, wherein the amino side chain of K is optionally substituted by

[0391] wherein i is an integer from 0 to 24, and X=Br, I or Cl,

[0392] -C(O)CH 2 Br, -C(O)CH 2 I or -C(O)CH 2 Cl;

[0393] Z 11...

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Abstract

The present invention comprises conjugates comprising a glucagon-like peptide 1 (GLP-1) fusion peptide coupled to a cyclic PYY peptide. The invention also relates to pharmaceutical compositions and methods for use thereof. The novel conjugates are useful for preventing, treating or ameliorating diseases and disorders disclosed herein.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to PCT Application PCT / US2018 / 029284, filed April 25, 2018, and US Provisional Application 62 / 662,313, filed April 25, 2018. The entirety of each publication is incorporated herein by reference. technical field [0003] The present invention generally relates to novel glucagon-like peptide 1 (GLP-1) fusion peptide coupled cyclic peptide tyrosine-tyrosine (PYY) conjugates, which are neuropeptide Y2 receptors and GLP-1 Modulators of receptors. The invention also relates to pharmaceutical compositions and methods of their use. The novel GLP-1 fusion peptide-coupled cyclic PYY conjugate can be used to prevent, treat or improve diseases and disorders such as obesity, type 2 diabetes, metabolic syndrome, insulin resistance and dyslipidemia. [0004] Reference Sequence Listing Submitted Electronically [0005] This application contains a Sequence Listing submitted electronically via EFS-W...

Claims

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Application Information

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IPC IPC(8): C07K14/605A61K47/26C07K14/575C07K19/00A61K38/26
CPCC07K14/57545C07K14/605C07K16/00C07K2317/52C07K2317/53C07K2319/30A61K9/0019A61K47/55A61K47/64A61K38/00A61P3/04A61P3/10A61P3/06
Inventor Y-M·张R·卡马乔M·A·凯斯E·池S·埃德维塔尔W·爱德华兹L·诺基M·J·沃尔R·张S·郑
Owner JANSSEN PHARMA NV
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