Crystalline form of 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide methanesulfonate and pharmaceutical composition comprising same

Patent metadata

Field	Value
Publication number	US-9988372-B2
Application number	US-201415325521-A
Country	US
Kind code	B2
Filing date	Jul 18, 2014
Priority date	Jul 18, 2014
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The present invention relates to a novel crystalline form of 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide methanesulfonate and a pharmaceutical composition containing the same. The novel crystalline form of a compound according to the present invention exhibits excellent stability even in high-temperature and humidity environments, and thus can be favorably used to prevent or treat diseases, such as thrombosis, myocardial infarction, atherosclerosis, inflammation, stroke, angina pectoris, restenosis after angioplasty, and thromboembolism.

First claim

The invention claimed is:

1. An anhydrous crystalline 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide methanesulfonate, whose X-ray powder diffraction spectrum using Cu-Kα radiation comprises peaks at an angle of diffraction 2θ of 12.022, 15.721, 15.971, 18.125, 18.928, 19.979, 20.311, 20.726, 21.66, 22.805, 23.18, 23.985, 25.857, 27.25, 27.829, 28, 28.189 and 29.753.

2. The anhydrous crystalline 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide methanesulfonate of claim 1 , which shows a peak at 186±2° C. in a differential scanning calorimetry analysis.

3. A pharmaceutical composition comprising the anhydrous crystalline 5-chloro-N-({(5S)-2-oxo-3-[4-(5,6-dihydro-4H-[1,2,4]triazin-1-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide methanesulfonate according to claim 1 and a pharmaceutically acceptable carrier or excipient.

4. A method for treating a disease or symptom selected from the group consisting of thrombosis, myocardial infarction, arteriosclerosis, inflammation, stroke, angina pectoris, recurrent stricture after angioplasty, and thromboembolism in a subject in need thereof, said method comprising administering the pharmaceutical composition of claim 3 to the subject.

Assignees

• Green Cross Corp
• Legochem Biosciences Inc
• Legochem Biosciences Inc

Inventors

• Choi Soongyu
• Choi Jungsub
• Yoon So-Hyun
• Kim Yoo Hoon
• Kim Jae Yeon
• Lee Suk Ho
• Cho Young Lag
• Song Ho Young
• Lee Dae Yon
• Baek Sung Yoon
• Chae Sang Eun
• Park Tae Kyo
• Woo Sung Ho
• Kim Yong Zu

Classifications

• A61K31/53

  having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine (melarsoprol A61K31/555 {; with four nitrogen atoms A61K31/495}) · CPC title

• C07D253/065

  having three double bonds between ring members or between ring members and non-ring members · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C07D409/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D413/14 Primary

  containing three or more hetero rings · CPC title