Cyclic peptidomimetic compounds as immunomodulators

Patent metadata

Field	Value
Publication number	US-10106581-B2
Application number	US-201615332805-A
Country	US
Kind code	B2
Filing date	Oct 24, 2016
Priority date	Sep 6, 2013
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

Methods of making a compound according to the following scheme:

wherein:
R 1 is a side chain of an amino acid residue selected from Ala, Ser, Thr and Leu; R 2 is a side chain of an amino acid residue selected from Asp, Glu, Gln and Asn; [Aaa] is an amino acid residue selected from Ser, Asp, Ala, Ile, Phe, Trp, Lys, Glu and Thr; R 3 is hydrogen or alkyl; Each of R 4 and R 4 ′ independently is hydrogen or alkyl; Both R a and R a ′ are hydrogen; or together are an oxo(═O) group; Both R b and R b ′ are hydrogen; or together are an oxo (═O) group; L is

X is CH 2 , O or S;
R 5 is hydrogen or alkyl;
m is an integer from 1 to 3; and
n is an integer from 2 to 20.

First claim

What is claimed is:

1. A method of making a compound according to the following scheme:

wherein:
R 1 is a side chain of an amino acid residue selected from Ala, Ser, Thr and Leu;
R 2 is a side chain of an amino acid residue selected from Asp, Glu, Gln and Asn;
[Aaa] is an amino acid residue selected from Ser, Asp, Ala, Ile, Phe, Trp, Lys, Glu and Thr;
R 3 is hydrogen or alkyl;
each of R 4 and R 4 ′ independently is hydrogen or alkyl;
both R a and R a ′ are hydrogen; or together are an oxo(═O) group;
both R b and R b ′ are hydrogen; or together are an oxo (═O) group;
L is

X is CH 2 , O or S;
R 5 is hydrogen or alkyl;
m is an integer from 1 to 3; and
n is an integer from 2 to 20.

2. The method of claim 1 , wherein [Aaa] is an amino acid residue selected from Ser or Thr.

3. The method of claim 1 , wherein R 1 is the side chain of the amino acid residue Ser or Thr.

4. The method of claim 1 , wherein the base is diisopropylethylamine.

5. The method of claim 1 , wherein the solvent is tetrahydrofuran.

6. The method of claim 1 , wherein the peptide coupling agent is benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBOP).

Assignees

• Sasikumar Pottayil Govindan Nair
• Ramachandra Muralidhara
• Naremaddepalli Seetharamaiah Setty Sudarshan
• Aurigene Discovery Tech Ltd

Inventors

• Sasikumar Pottayil Govindan Nair
• Ramachandra Muralidhara
• Naremaddepalli Seetharamaiah Setty Sudarshan

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• A61P35/02

  specific for leukemia · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A61P31/12

  Antivirals · CPC title

• A61P37/02

  Immunomodulators · CPC title