	US 11,884,748 B2
	Oral peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory bowel diseases
Ashok Bhandari, Pleasanton, CA (US); Gregory Thomas Bourne, Brisbane (AU); Xiaoli Cheng, Mountain View, CA (US); Brian Troy Frederick, Ben Lomand, CA (US); Jie Zhang, Salisbury (AU); Dinesh V. Patel, Fremont, CA (US); and David Liu, San Francisco, CA (US)
Assigned to Protagonist Therapeutics, Inc., Newark, CA (US)
Filed by Protagonist Therapeutics, Inc., Newark, CA (US)
Filed on Jan. 28, 2021, as Appl. No. 17/161,370.
Application 15/442,229 is a division of application No. 14/800,627, filed on Jul. 15, 2015, granted, now 9,624,268, issued on Apr. 18, 2017.
Application 17/161,370 is a continuation of application No. 16/217,864, filed on Dec. 12, 2018, granted, now 10,941,183.
Application 16/217,864 is a continuation of application No. 15/442,229, filed on Feb. 24, 2017, granted, now 10,196,424, issued on Feb. 5, 2019.
Claims priority of provisional application 62/119,685, filed on Feb. 23, 2015.
Claims priority of provisional application 62/119,688, filed on Feb. 23, 2015.
Claims priority of provisional application 62/025,899, filed on Jul. 17, 2014.
Prior Publication US 2021/0363185 A1, Nov. 25, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07K 7/08 (2006.01); C07K 7/02 (2006.01); C07K 7/50 (2006.01); C07K 7/64 (2006.01); C07K 14/54 (2006.01); A61K 38/00 (2006.01)

CPC C07K 7/08 (2013.01) [C07K 7/02 (2013.01); C07K 7/50 (2013.01); C07K 7/64 (2013.01); C07K 14/54 (2013.01); A61K 38/00 (2013.01); G01N 2800/065 (2013.01)]

21 Claims

1. 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.