Floctafenine

Floctafenine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	N02BG04 (WHO) ;
Legal status
Legal status	CA: ℞-only;
Identifiers
	IUPAC name 2,3-Dihydroxypropyl 2-{[8-(trifluoromethyl)-4-quinolinyl]amino}benzoate;
CAS Number	23779-99-9;
PubChem CID	3360;
DrugBank	DB08976 ;
ChemSpider	3243;
UNII	O04HVX6A9Q;
CompTox Dashboard (EPA)	DTXSID8057695 ;
ECHA InfoCard	100.041.696
Chemical and physical data
Formula	C20H17F3N2O4
Molar mass	406.361 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c1cccc2c(ccnc12)Nc3ccccc3C(=O)OCC(O)CO;
	InChI InChI=1S/C20H17F3N2O4/c21-20(22,23)15-6-3-5-13-17(8-9-24-18(13)15)25-16-7-2-1-4-14(16)19(28)29-11-12(27)10-26/h1-9,12,26-27H,10-11H2,(H,24,25); Key:APQPGQGAWABJLN-UHFFFAOYSA-N;

Floctafenine is a nonsteroidal anti-inflammatory drug (NSAID).

Synthesis

Floctafenine can be synthesized beginning with the conversion of ortho-trifluoromethyl aniline (1) to a quinolol.^[2]^[3]^[4] The compound is then condensed with ethoxy methylene malonic diethyl ester (EMME) and cyclized thermally (2). That intermediate is then saponified; the resulting acid is decarboxylated and finally converted to the 4-chloroquinoline (3) by reaction with phosphorus oxychloride. The displacement of chlorine with methyl anthranilate (4) then affords the coupled intermediate (5). An ester interchange of that product with glycerol leads to the glyceryl ester, floctafenine (6).

Flocatfenine synthesis

References

^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
^ DE 1815467A1, Allais, André & Meier, Jean, "Neue Chinolidinderivate und Verfahren zu ihrer Herstellung [Novel quinolidine derivatives and processes for their preparation]", published 1969-07-24, assigned to Roussel-Uclaf
^ U.S. patent 3,644,368 Roussel Uclaf
^ Mouzin G, Cousse H, Autin JM (1980). "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis. 1980: 54–55. doi:10.1055/s-1980-28923. S2CID 97164628.

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[1] "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.

[2] DE 1815467A1, Allais, André & Meier, Jean, "Neue Chinolidinderivate und Verfahren zu ihrer Herstellung [Novel quinolidine derivatives and processes for their preparation]", published 1969-07-24, assigned to Roussel-Uclaf

[3] U.S. patent 3,644,368 Roussel Uclaf

[4] Mouzin G, Cousse H, Autin JM (1980). "A New, Convenient Synthesis of Glafenine and Floctafenine". Synthesis. 1980: 54–55. doi:10.1055/s-1980-28923. S2CID 97164628.

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