Roquinimex

Roquinimex

Systematic (IUPAC) name
4-hydroxy-N,1-dimethyl-2-oxo-N- phenyl-1,2-dihydroquinoline-3-carboxamide
Pharmacokinetic data
Biological half-life	26-42 hours
Identifiers
CAS Number	84088-42-6
ATC code	L03AX02 (WHO)
PubChem	CID 55197
ChemSpider	10619239
UNII	372T2944C0
Chemical data
Formula	C18H16N2O3
Molar mass	308.331 g/mol
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

Roquinimex synthesis:^[1]

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

References

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