Method for producing cereulide and derivative thereof, intermediate for production of cereulide, and cereulide derivative

Patent metadata

Field	Value
Publication number	US-9422341-B2
Application number	US-201314377748-A
Country	US
Kind code	B2
Filing date	Feb 7, 2013
Priority date	Feb 8, 2012
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The purpose of the present invention is to provide a novel method for producing cereulide and a derivative thereof; an intermediate for cereulide; and a novel cereulide derivative. A novel didepsipeptide, a novel tetradepsipeptide, a novel octadepsipeptide and a novel dodecadepsipeptide are prepared. A linear precursor of cereulide or a derivative thereof, which is composed of any one of the novel depsipeptides, is cyclized by forming an intramolecular amide bond.

First claim

The invention claimed is:

1. A cereulide derivative represented by the following formula:

wherein R represents (CH 2 ) 2 COOH or (CH 2 ) 2 CONH(CH 2 ) 5 COOH.

2. A precursor of a cereulide derivative, selected from the group consisting of the following formulae:

wherein Y represents OH or NH(CH 2 ) 5 COOH.

3. A method for producing a cereulide derivative represented by:

wherein X represents (CH 2 ) 2 COOH or (CH 2 ) 2 CONH(CH 2 ) 5 COOH, comprising combining a precursor of a cereulide derivative as defined in claim 2 and a condensing agent in a solvent to perform a cyclization reaction by formation of an intramolecular amide bond of the precursor of a cereulide derivative as defined in claim 2 ;
wherein the Y group of the cereulide derivative precursor comprises a protecting group; and
wherein the method further comprises the step of removing the protecting group after the cyclization reaction.

Assignees

• Stella Pharma Corp
• Univ Osaka Prefect Public Corp

Inventors

• Kirihata Mitsunori
• Uehara Kohki

Classifications

• C07D273/00

  Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 · CPC title

• C07C229/08

  the nitrogen atom of the amino group being further bound to hydrogen atoms · CPC title

• C07K11/02 Primary

  cyclic, e.g. valinomycins {; Derivatives thereof} · CPC title

• C07C229/24

  having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid · CPC title

• C07C237/12

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups (peptides C07K) · CPC title