Method for preparing (−)-cibenzoline succinate

Patent metadata

Field	Value
Publication number	US-12533343-B2
Application number	US-201917279674-A
Country	US
Kind code	B2
Filing date	Sep 20, 2019
Priority date	Sep 28, 2018
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

The present invention relates to a crystal form of (−)-Cibenzoline succinate. In addition, the present invention relates to a method for preparing (−)-cibenzoline succinate having a chiral purity of 99.9% or higher. Additionally, the present invention provides a method for preparing (−)-cibenzoline succinate and a crystal form thereof.

First claim

The invention claimed is:

1 . A crystalline form of (−)-Cibenzoline succinic acid salt of formula (IA)

wherein the crystalline form has an X-ray powder diffraction (XRPD) pattern comprising diffraction peaks at 11.2°, 14.1°, 17.3°, 22.10, 23.0°, and 24.3° (2θ±0.2°).

2 . The crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 1 , wherein the crystalline form has the XRPD pattern further comprising one or more diffraction peaks selected from the group consisting of 17.6°, 18.2°, 21.4°, and 26.4° (2θ±0.2°).

3 . A crystalline form of (−)-Cibenzoline succinic acid salt of formula (IA)

wherein the crystalline form has an XRPD pattern comprising diffraction peaks at 8.99°, 11.15°, 13.36°, 14.09°, 14.30°, 17.29°, 17.59°, 18.15°, 19.81°, 21.37°, 22.06°, 22.93°, 24.25°, 25.41°, 26.36°, 27.59°, and 29.50° (2θ).

4 . The crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 1 , wherein the crystalline form has a differential scanning calorimetry (DSC) endothermic peak at 187 to 193° C. at heating rate of 10° C./min.

5 . The crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 4 , wherein the crystalline form has a differential scanning calorimetry (DSC) endothermic peak at 190±1° C. at heating rate of 10° C./min.

6 . A pharmaceutical composition comprising the crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 1 as an active ingredient and a pharmaceutically acceptable carrier, diluent, or excipient.

7 . The composition of claim 6 , which is of the form of a capsule or a tablet for oral administration.

8 . A pharmaceutical composition comprising the crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 2 , as an active ingredient and a pharmaceutically acceptable carrier, diluent, or excipient.

9 . The composition of claim 8 , which is of the form of a capsule or a tablet for oral administration.

10 . A pharmaceutical composition comprising the crystalline form of (−)-Cibenzoline succinic acid salt as claimed in claim 3 as an active ingredient and a pharmaceutically acceptable carrier, diluent, or excipient.

11 . The composition of claim 10 , which is of the form of a capsule or a tablet for oral administration.

Assignees

• Celltrion Inc

Inventors

• Desi Reddy Srinivas Reddy
• Mathad Vijayavitthal Thippannachar
• Rane Dnyandev Ragho
• Patil Vikas Shivaji

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D233/10 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms · CPC title

• C07C55/10

  Succinic acid · CPC title

• A61P9/06

  Antiarrhythmics · CPC title

• A61K31/4164 Primary

  1,3-Diazoles · CPC title