US20180072689 1,2,4-oxadiazole derivatives as immunomodulators

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United States of America

Application Number 15713671

Application Date 24.09.2017

Publication Number 20180072689

Publication Date 15.03.2018

Grant Number 10173989

Grant Date 08.01.2019

Publication Kind B2

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Applicants Pottayil Govindan Nair Sasikumar
Aurigene Discovery Technologies Limited
Muralidhara Ramachandra
Seetharamaiah Setty Sudarshan Naremaddepalli

Inventors Pottayil Govindan Nair Sasikumar
Muralidhara Ramachandra
Seetharamaiah Setty Sudarshan Naremaddepalli

Agents Benjamin Aaron Adler

Priority Data 4011/CHE/2013 06.09.2013 IN

Title

(EN) 1,2,4-oxadiazole derivatives as immunomodulators

Abstract

(EN)

The present invention relates to synthetic methods for 1,2,4-oxadiazole compounds. The general synthetic scheme is:

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R₁represents −CH₂O^tBu or −CH(CH₃)O^tBu, R₃represents −CH₂C(O)NHCPh₃, −CH₂CH₂C(O)NHCPh₃, −CH₂C(O)O^tBu, or −CH₂CH₂C(O)O^tBu, and Aaa is an amino acid residue selected from Thr and Ser; wherein the C-terminus thereof is esterified, and wherein the hydroxy moiety of the side chain of Thr or Ser is substituted with tbutyl; the base is triethylamine; and the solvent is tetrahydrofuran.

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
D	HETEROCYCLIC COMPOUNDS
271	Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
02	not condensed with other rings
06	1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

C	CHEMISTRY; METALLURGY
07	ORGANIC CHEMISTRY
D	HETEROCYCLIC COMPOUNDS
273	Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/-C07D271/183
08	having two nitrogen atoms and more than one oxygen atom

A	HUMAN NECESSITIES
61	MEDICAL OR VETERINARY SCIENCE; HYGIENE
K	PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31	Medicinal preparations containing organic active ingredients
33	Heterocyclic compounds
395	having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
41	having five-membered rings with two or more ring hetero atoms, at least one of which is nitrogen, e.g. tetrazole
4245	Oxadiazoles

A	HUMAN NECESSITIES
61	MEDICAL OR VETERINARY SCIENCE; HYGIENE
K	PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
45	Medicinal preparations containing active ingredients not provided for in groups A61K31/-A61K41/132
06	Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca

A	HUMAN NECESSITIES
61	MEDICAL OR VETERINARY SCIENCE; HYGIENE
K	PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31	Medicinal preparations containing organic active ingredients
33	Heterocyclic compounds
395	having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins

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1. US20180072689 - 1,2,4-oxadiazole derivatives as immunomodulators