Linomide

Linomide
Clinical data
ATC code	L03AX02 (WHO) ;
Pharmacokinetic data
Elimination half-life	26-42 hours
Identifiers
	IUPAC name 4-hydroxy-N,1-dimethyl-2-oxo-N-; phenyl-1,2-dihydroquinoline-3-carboxamide;
CAS Number	84088-42-6 ;
PubChem CID	55197;
ChemSpider	10619239 ;
UNII	372T2944C0;
CompTox Dashboard (EPA)	DTXSID4045680 ;
ECHA InfoCard	100.163.758
Chemical and physical data
Formula	C18H16N2O3
Molar mass	308.337 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O;
	InChI InChI=1S/C18H16N2O3/c1-19(12-8-4-3-5-9-12)17(22)15-16(21)13-10-6-7-11-14(13)20(2)18(15)23/h3-11,21H,1-2H3 ; Key:SGOOQMRIPALTEL-UHFFFAOYSA-N ;
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Roquinimex (Linomide) is a quinoline derivative immunostimulant which increases NK cell activity and macrophage cytotoxicity. It also inhibits angiogenesis and reduces the secretion of TNF alpha.

Roquinimex has been investigated as a treatment for some cancers (including as adjuvant therapy after bone marrow transplantation in acute leukemia) and autoimmune diseases, such as multiple sclerosis and recent-onset type I diabetes. Several trials have been terminated due to serious cardiovascular toxicity.

Synthesis

Ethyl 2-(methylamino)benzoate is condensed with ethyl malonate. Amine-ester interchange of that compound with N-methylaniline results in formation of the amide roquinimex.

References

^ E. Eriksoo et al., EP 59698 ; eidem, U.S. patent 4,738,971 (1982, 1988 both to AB Leo).

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[1] E. Eriksoo et al., EP 59698 ; eidem, U.S. patent 4,738,971 (1982, 1988 both to AB Leo).

[1]