5-chloro-4-hydroxy-1-methyl-2-oxo-n-phenyl-1,2-dihydroquinoline-3-carboxamide, salts and uses thereof

Patent metadata

Field	Value
Publication number	US-2016279121-A1
Application number	US-201615180727-A
Country	US
Kind code	A1
Filing date	Jun 13, 2016
Priority date	Jul 9, 2010
Publication date	Sep 29, 2016
Grant date	—

Abstract

The subject invention provides 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, its salts and uses.

First claim

1 . A composition comprising a compound having the structure:

in an amount from more than 3 ppm to less than 90 wt %, based on the total weight of the composition, and a carrier.

2 . A pharmaceutical composition comprising a mixture of:
a) laquinimod or a pharmaceutically acceptable salt thereof; b) at least one pharmaceutically acceptable carrier; and c) a compound having the structure:

present in an amount less than 0.1% based on the combined weight of the compound and laquinimod.

3 . The pharmaceutical composition of claim 2 , wherein the compound is present in an amount less than 3 ppm based on the combined weight of the compound and laquinimod.

4 . The pharmaceutical composition of claim 3 , wherein the compound is present in an amount less than 2 ppm based on the combined weight of the compound and laquinimod.

5 . The pharmaceutical composition of claim 2 in the form of a tablet.

6 . A process for preparing the pharmaceutical composition of claim 2 , comprising:
a) obtaining a batch of laquinimod or a pharmaceutically acceptable salt thereof; b) determining by apparatus the total amount of 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide present in the batch of laquinimod or a pharmaceutically acceptable salt thereof; and c) preparing the pharmaceutical composition using the batch only if the batch is determined to have less than 0.10% by weight of 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide.

7 . (canceled)

8 . (canceled)

9 . (canceled)

10 . (canceled)

11 . A process for preparing 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, comprising:
a) reacting 5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester and aniline under suitable conditions; and b) obtaining 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide from the reaction.

12 . The process of claim 11 , wherein the reacting step is performed in a mixture of heptane and octane.

Assignees

• Teva Pharma

Inventors

• Fristedt Ulf Tomas

Classifications

• A61P25/00

  Drugs for disorders of the nervous system · CPC title

• A61K31/47 Primary

  Quinolines; Isoquinolines · CPC title

• A61K31/4704 Primary

  2-Quinolinones, e.g. carbostyril · CPC title

• C07D215/56

  with oxygen atoms in position 4 · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title