Method of producing proton pump inhibitor compound having optical activity

Patent metadata

Field	Value
Publication number	US-10589262-B2
Application number	US-201916381879-A
Country	US
Kind code	B2
Filing date	Apr 11, 2019
Priority date	Dec 26, 2014
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

A highly pure optically active proton pump inhibitor compound can be produced safely and inexpensively in a high yield and enantioselectivity by a method of producing an optically active sulfoxide of Formula 2 or a salt thereof, comprising oxidizing a sulfide of Formula 1 or a salt thereof with hydrogen peroxide using an iron salt in the presence of a chiral ligand of Formula 3; wherein A is CH or N; R 1 is hydrogen atom, an alkyl optionally substituted by halogen(s), or an alkoxy optionally substituted by halogen(s); one to three R 2 may exist, and each of R 2 is independently an alkyl, a dialkylamino, or an alkoxy optionally substituted by halogen(s) or alkoxy(s); each of R 3 is independently hydrogen atom, a halogen, cyano or the like; R 4 is a tertiary alkyl; and * and ** represent respectively R configuration or S configuration.

First claim

The invention claimed is:

1. An iron complex coordinated with a chiral ligand of Formula 4:

wherein ** represents R configuration or S configuration.

2. A combination comprising the iron complex of claim 1 and an optionally substituted benzoic acid or a salt thereof.

Assignees

• Univ Tokyo
• Towa Pharmaceutical Co Ltd

Inventors

• Nakamura Eiichi
• Ilies Laurean
• Oderaotoshi Yoji
• Izumi Takuhiro
• Nishiguchi Shigenobu

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• C07B53/00

  Asymmetric syntheses · CPC title

• B01J23/745

  Iron · CPC title

• C07F15/025

  without a metal-carbon linkage · CPC title

• A61P1/04

  for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants · CPC title