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. It 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

Used in Anticancer Applications:
Tasquinimod is used as an anti-cancer agent for inhibiting HDAC4 signaling, which affects cancer cell survival and makes it a promising compound in the fight against cancer.
Used in Prostate Cancer Treatment:
Tasquinimod is used as a supplement to radiation or chemotherapy for enhancing the treatment outcomes in animal models of prostate cancer.
Used in Inhibiting Tumor Angiogenesis:
Tasquinimod is used as an antiangiogenic agent to inhibit the formation of new blood vessels that supply nutrients to the tumor, thereby limiting its growth and spread.
Used in Autoimmune Disease Treatment:
Tasquinimod is used as an immunomodulatory agent for its potential applications in treating autoimmune diseases, although further research is needed to fully understand its effectiveness in this area.

Upstream product

• 1897-52-5 2,6 difluorobenzonitrile 
• 1332581-19-7 2-methoxy-6-(methylamino)benzonitrile 
• 254964-68-6 6-methoxy-N-methyl-anthranilic acid 
• 1354639-61-4 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester 
• 22864-65-9 N-methyl-4-(trifluoromethyl)aniline 
• 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 
• 248282-13-5 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxylic acid ethyl ester 

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.