Fedrilate

Fedrilate is a centrally acting cough suppressant. It was patented as a mucolytic by UCB in 1971, but was never brought to market in the US.[1] In the Netherlands, it has been marketed as Tussefan and in combination with guaifenesin as Tussefan expectorans.[2]

Fedrilate
Clinical data
Trade namesTussefan
ATC code
Identifiers
IUPAC name
  • 4-morpholin-4-ylbutan-2-yl 4-phenyloxane-4-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard100.041.390
Chemical and physical data
FormulaC20H29NO4
Molar mass347.455 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OC(CCN1CCOCC1)C)C3(c2ccccc2)CCOCC3
InChI
  • InChI=1S/C20H29NO4/c1-17(7-10-21-11-15-24-16-12-21)25-19(22)20(8-13-23-14-9-20)18-5-3-2-4-6-18/h2-6,17H,7-16H2,1H3 Y
  • Key:RDEOYUSTRWNWLX-UHFFFAOYSA-N Y
  (verify)

Synthesis
Patents:[3][4] Starting acid:[5]

Sodamide alkylation between benzyl cyanide (1) and bis(chloroethyl)ether [111-44-4] (2) gives 4-phenyloxane-4-carbonitrile [1202-81-9] (3). Hydrolysis of the nitrile gives 4-phenyloxane-4-carboxylic acid [182491-21-0] (4). Treatment with thionyl chloride gives the corresponding acid chloride (5). Ester formation with 4-(morpholin-4-yl)butan-2-ol [858440-45-6] (6) gives Fedrilate proper (7).

References
  1. US patent 3567835, Henri Morren, "Mucolytic salts, compositions and process for treating mucus", issued March 2, 1971
  2. Kok J, Oosterveld WJ, Sibilo SR (1979). Pharmacotherapeutisch Vademecum (in Dutch). Bussum: Romen. ISBN 90-228-8006-0.
  3. DE1518403 idem Morren Henri, GB 1060005 (1967 to UCB SA).
  4. Henri Morren, U.S. Patent 3,422,102 (1969 to UCB SA).
  5. Eisleb, O. (6 August 1941). "Neue Synthesen mittels Natriumamids". Berichte der deutschen chemischen Gesellschaft (A and B Series). 74 (8): 1433–1450. doi:10.1002/cber.19410740814.



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