84088-42-6

Basic information

• Product Name: Roquinimex
• Synonyms: N-PHENYLMETHYL-1,2-DIHYDRO-4-HYDROXYL-N,1-DIMETHYL-2-OXO-QUINOLINE-3-CARBOXAMIDE;ROQUINIMEX;LINOMIDE;LS-2616;1,2-DIHYDRO-4-HYDROXY-N,1-DIMETHYL-2-OXO-N-PHENYL-3-QUINOLINECARBOXAMIDE;1,2-DIHYDRO-4-HYDROXY-N,N-DIMETHYL-2-OXO-N-PHENYL-3-QUINOLINECARBOXAMIDE;4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide;1,2-Dihydro-4-hydroxy-1,N-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide
• CAS NO: 84088-42-6
• Molecular Formula: C₁₈H₁₆N₂O₃
• Molecular Weight: 308.33
• Product Categories: Antitumour
• Mol File: 84088-42-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 200-204°
• Boiling Point: 436.187 °C at 760 mmHg
• Flash Point: 217.598 °C
• Appearance: /solid
• Density: 1.357g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: 2-8°C
• Solubility: DMSO: 11 mg/mL
• Merck: 14,8259
• CAS DataBase Reference: Roquinimex(CAS DataBase Reference)
• NIST Chemistry Reference: Roquinimex(84088-42-6)
• EPA Substance Registry System: Roquinimex(84088-42-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 84088-42-6(Hazardous Substances Data)

Usage

Description

Roquinimex is an immunomodulator with diverse biological activities, characterized by its ability to increase myocardial MHC class II-expressing cells, alter the ratio of cytotoxic to helper T cells, and enhance survival while decreasing necrotic lesion area in a mouse model of myocarditis. It also induces IFN-γ production, reduces TNF-α and IL-1β production, prevents proteinuria, ameliorates nephritis, decreases colonic myeloperoxidase activity, reduces mucosal damage, and diminishes tumor weight and blood flow in various mouse models.

Uses

Used in Pharmaceutical Industry:
Roquinimex is used as a biological response modifier and immunomodulator for its diverse biological activities and potential therapeutic effects in various conditions.
Used in Oncology:
Roquinimex is used as an immunomodulator with antitumor properties, inhibiting T-cell apoptosis in vivo and angiogenesis in rats, which can contribute to the development of cancer treatment strategies.
Used in Autoimmune Diseases:
Roquinimex is used to prevent the development of proteinuria and ameliorate nephritis in a mouse model of chronic graft versus host disease (GVHD), indicating its potential use in treating autoimmune conditions.
Used in Gastroenterology:
Roquinimex is used to decrease colonic myeloperoxidase (MPO) activity and mucosal damage in a mouse model of colitis induced by dextran sulfate (DSS), suggesting its potential application in treating inflammatory bowel diseases.
Used in Cardiovascular Medicine:
Roquinimex is used to increase the number of myocardial MHC class II-expressing cells and the ratio of cytotoxic to helper T cells, as well as enhance survival and decrease necrotic lesion area in a mouse model of murine coxsackievirus B3-induced myocarditis, indicating its potential use in treating cardiovascular conditions.

Biological Activity

Immunomodulator with stimulatory and antitumor properties. Inhibits in vivo apoptosis of T-cells and inhibits angiogenesis in rats in vivo .

InChI:InChI=1/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

Upstream product

• 10328-92-4 N-Methylisatoic anhydride 
• 84088-88-0 methyl 3-(N-methyl-N-phenylamino)-3-oxopropanoate 
• 57513-54-9 ethyl 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 
• 100-61-8 N-methylaniline 
• 118-48-9 isatoic anhydride 
• 118-92-3 anthranilic acid 
• 57931-81-4 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid 
• 84088-50-6 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester 

Downstream Products

• 330817-62-4 N-(4-fluorophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide 

Relevant articles and documents

Using DOE to achieve reliable drug administration: A case study

Design of experiments (DOE), a statistical tool, and mathematical modeling techniques are established and proven methodologies for process and product improvements in the pharmaceutical industry. This contribution presents a case study where an unsatisfac

Preparation method of roquinimex

A preparation method of roquinimex comprises the following steps: carrying out a reflux reaction on 1, 2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-methyl formate shown as a formula II, N-methylaniline shown as a formula III and a catalyst calcium chloride in a solvent, removing methanol generated by reaction and trace water in the system by adopting an A-type molecular sieve pervaporation inorganic membrane, ending the reaction, filtering a reaction solution at 60-70 DEG C after the reaction is finished, cooling and crystallizing a filtrate, and carrying out filtering and drying to obtain the N-methyl-N-phenyl-1, 2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-formamide (roquinimex) shown in a formula I. The yield reaches 98.5%, and the product content reaches 99.7% (liquid spectrum external standard). The preparation method has the advantages of simple process, no need of distillation, high product purity and yield and the like.

Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders: Structure-Activity Relationship

Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).