US 11,884,748 B2Granted

Oral peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory bowel diseases

AssigneeProtagonist Therapeutics, Inc.

InventorsAshok Bhandari, Gregory Thomas Bourne, Xiaoli Cheng, Brian Troy Frederick, Jie Zhang, Dinesh V. Patel, David Liu

Life of this patent

Estimating the term…

Abstract

Peptide inhibitors of the interleukin-23 receptor, and related compositions and methods of using these peptide inhibitors to treat or prevent a variety of diseases and disorders, including inflammatory bowel disease, are disclosed.

Claims21

Dependent claims

A pharmaceutical composition comprising a peptide inhibitor of an interleukin-23 receptor, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, excipient, or diluent,

wherein the peptide inhibitor of an interleukin-23 receptor is selected from the group consisting of:
(SEQ ID NO:
702)
Ac-[Abta]-QTWQC-[Phe(4-OMe)]-[2-Nal]-[α-Me-Lys]-
ENG-NH2;
(SEQ ID NO:
704)
Ac-[Abta]-QTWQCY-[2-Nal]-[α-Me-Lys]-ENG-NH2;
(SEQ ID NO:
782)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]-W-
[α-Me-Lys]-ENG-NH2;
(SEQ ID NO:
861)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-[Lys(isovaleric acid)]-NG-NH2;
(SEQ ID NO:
877)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]
AiN-QNG-NH2;
(SEQ ID NO:
880)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[AibMLys(Ac)]-NA-NH2;
(SEQ ID NO:
900)
Ac-[Abu]-QTWQC-[Phe[4-(2-(acetyl-aminoethoxy)]]-
[2-Nal]-[α-Me-Lys(Ac)]-[Lys(Ac)]-NG-NH2;
(SEQ ID NO:
911)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENQ-NH2;
(SEQ ID NO:
912)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
915)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-MeVal]-[Lys(Ac)]-NG-NH2;
(SEQ ID NO:
954)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Leu]-[Cit]-NN-NH2;
(SEQ ID NO:
970)
Ac-[(D)Phe]-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
972)
Ac-T-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
976)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[acbc]-ENN-NH2;
(SEQ ID NO:
980)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
984)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[alphα-methyl-L-Leucine]-QN-[betaAla]-NH2;
(SEQ ID NO:
992)
Ac-(D)Phe-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
993)
Ac-[(D)Arg]-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
1043)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[acpc]-ENN-NH2;
or
(SEQ ID NO:
1047)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]
achc]-ENN-NH2;
wherein the peptide inhibitor is cyclized via a thioether bond between Abu and C.

82 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/161,370Filed 28 Jan 2021 · continuation
Priority: 17 Jul 2014
Published: US 2021/0363185 A125 Nov 2021
Granted: 30 Jan 2024
Term ends: Not estimatedThe source records don’t support an estimate.

Classification26 codes

A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
C07K 7/08
Linear peptides containing only normal peptide links: having 12 to 20 amino acids
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…

Family

Application62/025,899Us provisional application · filed 17 Jul 2014
Application62/119,685Us provisional application · filed 23 Feb 2015
Application62/119,688Us provisional application · filed 23 Feb 2015
Application14/800,627Parent of this division · filed 15 Jul 2015
Application15/442,229Parent of this continuation · filed 24 Feb 2017
US 9,624,268 B2Parent of this division · filed 18 Apr 2017
Application16/217,864Parent of this continuation · filed 12 Dec 2018
US 10,196,424 B2Parent of this continuation · filed 5 Feb 2019
US 2021/0363185 A1Pre-grant publication · published 25 Nov 2021
US 10,941,183 B2Parent of this continuation
Application15/442,229Parent of this division
US 2016/0145306 A1Published application
US 2018/0022778 A1Published application
US 2019/0337983 A1Published application
US 11,884,748 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Citations

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Abstract

wherein the peptide inhibitor of an interleukin-23 receptor is selected from the group consisting of:
(SEQ ID NO:
702)
Ac-[Abta]-QTWQC-[Phe(4-OMe)]-[2-Nal]-[α-Me-Lys]-
ENG-NH2;
(SEQ ID NO:
704)
Ac-[Abta]-QTWQCY-[2-Nal]-[α-Me-Lys]-ENG-NH2;
(SEQ ID NO:
782)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]-W-
[α-Me-Lys]-ENG-NH2;
(SEQ ID NO:
861)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-[Lys(isovaleric acid)]-NG-NH2;
(SEQ ID NO:
877)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]
AiN-QNG-NH2;
(SEQ ID NO:
880)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[AibMLys(Ac)]-NA-NH2;
(SEQ ID NO:
900)
Ac-[Abu]-QTWQC-[Phe[4-(2-(acetyl-aminoethoxy)]]-
[2-Nal]-[α-Me-Lys(Ac)]-[Lys(Ac)]-NG-NH2;
(SEQ ID NO:
911)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENQ-NH2;
(SEQ ID NO:
912)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
915)
Ac-[Abta]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-MeVal]-[Lys(Ac)]-NG-NH2;
(SEQ ID NO:
954)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Leu]-[Cit]-NN-NH2;
(SEQ ID NO:
970)
Ac-[(D)Phe]-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
972)
Ac-T-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[α-Me-Lys]-ENN-NH2;
(SEQ ID NO:
976)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[acbc]-ENN-NH2;
(SEQ ID NO:
980)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
984)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[alphα-methyl-L-Leucine]-QN-[betaAla]-NH2;
(SEQ ID NO:
992)
Ac-(D)Phe-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
993)
Ac-[(D)Arg]-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-
[2-Nal]-[4-amino-4-carboxy-tetrahydropyran]-
ENN-NH2;
(SEQ ID NO:
1043)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]-
[acpc]-ENN-NH2;
or
(SEQ ID NO:
1047)
Ac-[Abu]-QTWQC-[Phe[4-(2-aminoethoxy)]]-[2-Nal]
achc]-ENN-NH2;
wherein the peptide inhibitor is cyclized via a thioether bond between Abu and C.

82 more elements

Facts

Application

17/161,370Filed 28 Jan 2021 · continuation

Priority

17 Jul 2014

Published

US 2021/0363185 A125 Nov 2021

Granted

30 Jan 2024

Term ends

Not estimatedThe source records don’t support an estimate.

Classification26 codes

A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
C07K 7/08
Linear peptides containing only normal peptide links: having 12 to 20 amino acids
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…

Family

Application62/025,899Us provisional application · filed 17 Jul 2014

Application62/119,685Us provisional application · filed 23 Feb 2015

Application62/119,688Us provisional application · filed 23 Feb 2015

Application14/800,627Parent of this division · filed 15 Jul 2015

Application15/442,229Parent of this continuation · filed 24 Feb 2017

US 9,624,268 B2Parent of this division · filed 18 Apr 2017

Application16/217,864Parent of this continuation · filed 12 Dec 2018

US 10,196,424 B2Parent of this continuation · filed 5 Feb 2019

US 2021/0363185 A1Pre-grant publication · published 25 Nov 2021

US 10,941,183 B2Parent of this continuation

Application15/442,229Parent of this division

US 2016/0145306 A1Published application

US 2018/0022778 A1Published application

US 2019/0337983 A1Published application

US 11,884,748 B2This patent

From the US filing history. Foreign family members aren’t listed.