10252. Laquinimod

Nomenclature

CAS number: 248281-84-7
5-Chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide; N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxamide; ABR-215062.
C19H17ClN2O3; mol wt 356.80.
C 63.96%, H 4.80%, Cl 9.94%, N 7.85%, O 13.45%.

Description and references

Immunomodulator. Prepn: A. Bjrk et al., WO 9955678; eidem, US 6077851 (1999, 2000 both to Active Biotech AB). Large scale synthesis: K. Jansson et al., J. Org. Chem. 71, 1658 (2006) DOI PubMed; J. Wennerberg et al., Org. Process Res. Dev. 11, 674 (2007) DOI. Structure activity studies: S. Jnsson et al., J. Med. Chem. 47, 2075 (2004) DOI PubMed. Determn in plasma by HPLC: K. Edman et al., J. Chromatogr. B 785, 311 (2003) DOI PubMed; by LC/MS/MS: C. J. Sennbro et al., Rapid Commun. Mass Spectrom. 20, 3313 (2006) DOI PubMed. Role of cytochrome P450 3A4 in metabolism: H. Tuvesson et al., Drug Metab. Dispos. 33, 866 (2005) DOI PubMed. Clinical evaluation in relapsing multiple sclerosis (MS): C. Polman et al., Neurology 64, 987 (2005) PubMed.

Chemical structure

Properties

White to off-white crystals from n-heptane, mp 201° (dec). pKa 4.2.

Derivative

Sodium salt.

Nomenclature

CAS number: 248282-07-7
C19H17ClN2NaO3; mol wt 379.79.
C 60.09%, H 4.51%, Cl 9.33%, N 7.38%, Na 6.05%, O 12.64%.

Properties

White, non-hygroscopic crystals from ethanol.

Therapeutic Category

Immunomodulator; in treatment of multiple sclerosis.

Keywords

Immunomodulator