254964-60-8

Basic information

• Product Name: tasquinimod
• Synonyms: tasquinimod;ABR-215050;3-QuinolinecarboxaMide, 1,2-dihydro-4-hydroxy-5-Methoxy-N,1-diMethyl-2-oxo-N-[4-(trifluoroMethyl)phenyl]-;4-Hydroxy-5-methoxy-N-methyl-1-methyl-2-oxo-N-(4-trifluoromethylphenyl)-1,2-dihydroquinoline-3-carboxamide;N-Methyl-N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxamide;4-Hydroxy-5-Methoxy-1-Methyl-2-oxo-1,2- dihydro-quinoline-3-carboxylic acid Methyl- (4-trifluoroMethyl-phenyl)-aMide;1,2-dihydro-4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-trifluoromethyl)phenyl]-3-quinolinecarboxamide;4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-c
• CAS NO: 254964-60-8
• Molecular Formula: C₂₀H₁₇F₃N₂O₄
• Molecular Weight: 406.3551896
• Product Categories: Angiogenesis inhibitor;S100 calcium binding protein A9 modulator;Inhibitors
• Mol File: 254964-60-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 501.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.427±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: insoluble in H2O; ≥20.32 mg/mL in DMSO; ≥4.75 mg/mL in EtOH with gentle warming and ultrasonic
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: tasquinimod(CAS DataBase Reference)
• NIST Chemistry Reference: tasquinimod(254964-60-8)
• EPA Substance Registry System: tasquinimod(254964-60-8)

Safety Data

• Hazardous Substances Data: 254964-60-8(Hazardous Substances Data)

Usage

Description

Tasquinimod is an orally-active quinoline-3-carboxamide derived from roquinimex, an immunomodulatory quinolone with applications in some cancers and autoimmune diseases. Tasquinimod inhibits tumor angiogenesis and supplements radiation or chemotherapy in animal models of prostate cancer. While its precise mechanism of action remains unclear, tasquinimod has been reported to alter signaling through S100A9, thrombospondin-1, HIF-1α, androgen receptor, VEGF, and HDAC3/4.

Uses

Tasquinimod is an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.

Upstream product

• 22864-65-9 N-methyl-4-(trifluoromethyl)aniline 
• 248282-13-5 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester 
• 1354639-61-4 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester 
• 1897-52-5 2,6 difluorobenzonitrile 
• 1332581-19-7 2-methoxy-6-(methylamino)benzonitrile 
• 254964-68-6 6-methoxy-N-methyl-anthranilic acid 
• 248282-18-0 1,2-Dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid 
• 91105-97-4 5-methoxy-1-methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 67765-42-8 5-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione 
• 53600-33-2 6-methoxyanthranilic acid 

Relevant articles and documents

METHOD FOR MANUFACTURING OF QUINOLINE-3-CARBOXAMIDES

A method for preparing a compound of formula (I) by reacting the appropriate alkyl ester and an aniline derivative, in a refluxing mixture containing an aliphatic solvent or a mixture of aliphatic solvents having a boiling point in the range of 68-191 °C; condensing vapors of the refluxing mixture; treating the condensed vapors with an alcohol scavenging agent or a mixture of alcohol scavenging agents; and returning the condensed vapors back to the reaction mixture.

QUINOLINE DERIVATIVES

The invention is related to compounds of general formula (I), wherein R is methyl, ethyl, n-propyl, iso-propyl, n-butyl or allyl; R' is methyl, methoxy, fluoro, chloro, bromo, trifluoromethyl, or OCHxFy, wherein x = O - 2, y = 1 - 3 with the proviso that x + y = 3; R'' is hydrogen, fluoro or chloro; with the proviso that R'' is fluoro or chloro only when R' is fluoro; R4 is hydrogen or pharmaceutically acceptable inorganic or organic cations; R5 is ethyl, n-propyl, iso-propyl, methoxy, ethoxy, chloro, bromo, trifluoromethyl, OCHxFy, or OCH2CHxFy wherein x = 0 - 2, y = 1 - 3 with the proviso that x + y = 3; R6 is hydrogen; or R5, and R6 taken together are methylenedioxy; and any tautomer thereof. The invention also relates to pharmaceutical compositions containing a compound of general formula (I) together with a pharmaceutically acceptable carrier. Included are also processes for the preparation of the compounds of formula (I), as well as methods for the treatment of mammals suffering from diseases resulting from autoimmunity and pathological inflammation by administering of a compound having formula (I) to said mammal.