Method for producing lacosamide and intermediate thereof

Patent metadata

Field	Value
Publication number	US-11623943-B2
Application number	US-202117196167-A
Country	US
Kind code	B2
Filing date	Mar 9, 2021
Priority date	Nov 13, 2015
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

The present invention provides a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Adopting a particular isomerization-crystallization condition makes it possible to a method of industrially and safely producing lacosamide high in diastereomeric excess at a high yield and a low cost. Additionally, an intermediate efficacious for producing lacosamide is provided.

First claim

What is claimed is:

1. A crystal of a salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-acetylamino acid, wherein
the N-acetylamino acid is N-acetyl-D-Leucine; and
the salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-acetylamino acid

has a powder X-ray diffraction measuring pattern using a CuKα ray exhibiting peaks at diffraction angles (2θ±0.2°)=6.3°, 15.8°, 18.1°, 23.4° and 25.2°.

2. A crystal of a salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-acetylamino acid, wherein
the N-acetylamino acid is N-acetyl-D-Valine; and
the salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-acetylamino acid

has a powder X-ray diffraction measuring pattern using a CuKα ray exhibiting peaks at diffraction angles (2θ±0.2°)=7°, 14.8°, 18.7°, 21.9° and 24.6°.

3. A crystal of a salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-formylamino acid, wherein
the N-formylamino acid is N-formyl-L-Leucine; and
the salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-formylamino acid

has a powder X-ray diffraction measuring pattern using a CuKα ray exhibiting peaks at diffraction angles (2θ±0.2°)=4.9°, 9.4°, 12.4°, 18.7°, 24.9° and 26.9°.

4. A crystal of a salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-formylamino acid, wherein
the N-formylamino acid is N-formyl-L-Alanine; and
the salt of R-configuration of
N-benzyl-2-amino-3-methoxypropionamide and
N-formylamino acid

has a powder X-ray diffraction measuring pattern using a CuKα ray exhibiting peaks at diffraction angles (2θ±0.2°)=9.9°, 12°, 17.8°, 19.8°, 22.4°, 24° and 25.3°.

Assignees

• Api Corp

Inventors

• Nagahama Masaki

Classifications

• C07B57/00

  Separation of optically-active compounds · CPC title

• A61K31/165

  having aromatic rings, e.g. colchicine, atenolol, progabide · CPC title

• A61P25/08

  Antiepileptics; Anticonvulsants · CPC title

• C07C231/20

  by separation of optical isomers · CPC title

• C07C231/02 Primary

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title