Cyclic peptides multimers targeting alpha-4-beta-7 integrin

Patent metadata

Field	Value
Publication number	US-11111273-B2
Application number	US-201716348103-A
Country	US
Kind code	B2
Filing date	Nov 10, 2017
Priority date	Nov 11, 2016
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

There is described herein, multimers comprising a plurality of compounds covalently linked together, the compounds independently being of formula (I).

First claim

The invention claimed is:

1. A homodimer of two moieties covalently linked together by an amide bond to a diphenic acid residue, the moieties both being of formula (I):

wherein
R 1 is H;
R 2 is H;
R 3 is CH 3 ;
R 4 is H;
R 5 is an amide of the formula —C(O)NR**R***, wherein R** is H and R*** is tert-butyl;
R 6 along with R 7 together form the pyrrolidine ring of Pro;
R 8 is H;
n is 1;
wherein Z is an amino terminus of an amino acid; —C═O— adjacent L is the carboxy terminus of an amino acid; and L along with Z and —C═O— is a peptide having the following formula:
X y —X z —X 1 —X 2 —X 3

wherein
X y is 3-aminomethyl-4-[4-(1-piperazinyl)-phenyl]-benzoic acid, in which the piperazinyl amine nitrogen at the 4-position of the piperazinyl ring is covalently bound via the amide bond to the diphenic acid residue to form the homodimer;
X z is absent;
X 1 is Leucine;
X 2 is Asp; and
X 3 is Thr;

or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition comprising the homodimer of claim 1 along with a pharmaceutically acceptable carrier.

3. The pharmaceutical composition of claim 2 , formulated for oral delivery, topical delivery or parenteral delivery.

Assignees

• Zealand Pharma As

Inventors

• Morshed Mohammed Monzur
• Chakka Sai Kumar
• Hickey Jennifer L
• Vazquez Manuel Perez
• Roughton Andrew
• Kafal Adam Paul
• Patel Narendrakumar B

Classifications

• A61P37/06 Primary

  Immunosuppressants, e.g. drugs for graft rejection · CPC title

• Y02A50/30

  Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change · CPC title

• A61K38/00

  Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00) · CPC title

• A61P1/00

  Drugs for disorders of the alimentary tract or the digestive system · CPC title

• C07K7/52 Primary

  with only normal peptide links in the ring · CPC title