alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate

Chemical properties

White solid

Originator

Dusodril,Roland,W. Germany,1968

The Uses of alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate

antineoplastic

What are the applications of Application

Nafronyl oxalate salt is exhibits properties of a vasodilator

Manufacturing Process

30 grams (0.106 mol) of β-(1-naphthyl)-β'-tetrahydrofuryl isobutyric acid are heated under reflux for 8 1/2 hours in 230 cc of isopropanol with 14 grams (0.103 mol) of β-chloroethyl-N-diethylamine. After evaporation of the isopropanol in vacuo, the syrupy residue is treated with a solution of K2CO3. Extraction with ether is carried out after drying over Na2SO4.
Distillation of the extract yields 28.5 grams of a very viscous yellow liquid with a BP0.95-1.09millibar = 198° to 202°C. The yield is 70.5% (theoretical quantity = 40.5 grams).1.3 grams (0.0103 mol) of dihydrated oxalic acid are dissolved while being made tepid in 8 cc of acetone. The cooled solution has added thereto 4 grams (0.0104 mol) of N-diethylaminoethyl-β-(1-naphthyl)-β'- tetrahydrofuryl isobutyrate, obtained according to the process described above and dissolved in 10 cc of acetone. The solution is brought to boiling point for 15 minutes. After cooling to ambient temperature, it is placed in a refrigerator. Crystallization occurs after 2 hours, the crystals which have formed are separated by centrifuging, and after washing in hexane and drying in vacuo 3.5 grams of white crystals are obtained. After being recrystallized three times, in alcohol and then in a mixture of alcohol and ethyl acetate, the product is analytically pure and has a MP = 110° to 111°C (heating stage).

brand name

Praxilene (Lipha, S.A., France).

Therapeutic Function

Vasodilator

Clinical Use

Vasodilator:
Peripheral and cerebral vascular disease

Metabolism

Metabolised by plasma pseudo-cholinesterases to 3 active metabolites.