Linomide
- L03AX02 (WHO)
- 4-hydroxy-N,1-dimethyl-2-oxo-N-
phenyl-1,2-dihydroquinoline-3-carboxamide
- 84088-42-6 Y
- 54676478
- DB11366
- 10619239 N
- 372T2944C0
- D05756
- CHEBI:92056
- ChEMBL11672
- DTXSID4045680
- Interactive image
- CN1C2=CC=CC=C2C(=C(C1=O)C(=O)N(C)C3=CC=CC=C3)O
- 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 N
- Key:SGOOQMRIPALTEL-UHFFFAOYSA-N N
Linomide (Roquinimex) is a quinoline derivative immunostimulant which increases NK cell activity and macrophage cytotoxicity. It also inhibits angiogenesis and reduces the secretion of TNF alpha.
Linomide 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[1][2] and recent-onset type I diabetes.[3] 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 linomide.
References
- ^ Weilbach EX, Hartung HP (August 1996). "[Immune modulation in multiple sclerosis: linomide]". Der Nervenarzt (in German). 67 (8): 701–5. doi:10.1007/s001150050044. PMID 8805117. S2CID 31845910.
- ^ Hedlund G, Link H, Zhu J, Xiao BG (June 2001). "Effects of Linomide on immune cells and cytokines inhibit autoimmune pathologies of the central and peripheral nervous system". International Immunopharmacology. 1 (6): 1123–30. doi:10.1016/s1567-5769(01)00041-8. PMID 11407306.
- ^ Gross DJ, Weiss L, Reibstein I, Hedlund G, Dahlén E, Rapoport MJ, Slavin S (June 2001). "The immunomodulator Linomide: role in treatment and prevention of autoimmune diabetes mellitus". International Immunopharmacology. 1 (6): 1131–9. doi:10.1016/s1567-5769(01)00042-x. PMID 11407307.
- ^ EP 59698, Eriksoo, Edgar; Sandberg, Eva Britt-Marie & Stalhandsk, Lars Johan Torbjörn, "Heterocyclic carboxamides, compositions containing such compounds, processes for their preparation and methods of treatment therewith", published 1982-09-08, assigned to AB Leo ; E. Eriksoo et al., U.S. patent 4,738,971 (1988 to AB Leo).
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