39718-89-3

Alminoprofen is an arylpropionic acid analgesic/antiinflammatory agent indicated for the short term management of dental, traumatic and postpartum pain.

Labs. Dr. E. Bouchara (France)

Alminoprofen is a nonsteroidal antiinflammatory drugs (NSAID) of the phenylpropionic acid class. Alminoprofen maybe a useful therapeutic option in the management of immune dysfunction in rheumatoid ar thritis.

ChEBI: A substituted aniline that is ibuprofen in which the isobutyl group is replaced by a (2-methylprop-2-en-1-yl)amino group. A non-steroidal anti-inflammatory drug, it is used for treatment of inflammatory and rheumatic disorders.

Methyl 2-(p-aminophenyl)propionate:
Methyl 2-(p-nitrophenyl)acrylate (52 g) is hydrogenated in ethanol (500 ml) in the presence of 5% palladium-over-charcoal, while maintaining the temperature at +5°C. The theoretical amount of hydrogen is taken up within one hour. After separation of the catalyst and concentration to dryness, the resulting material gives methyl 2-(p-aminophenyl)proprionate which crystallizes: MP: = 40°-43°C.
Methyl 2-(p-methallylaminophenyl)propionate hydrochloride:
A mixture of methyl 2-(p-aminophenyl)propionate (44.75 g), methallyl chloride (34 g) and pyridine (30 ml) in isopropanol (400 ml) is boiled during 30 hours. The solvent is removed in vacuo and the residue is taken up into water and ether. After separation, the organic phase is washed repeatedly with water, after which it is dried and concentrated in vacuo. The resulting oil is fractionally distilled in vacuo (0.1 mm Hg; 5 g of oil essentially consisting of methyl 2-(p-aminophenyl)propionate are collected at 115°-120°C; 30 g of oil consisting of a mixture of mono- (80%) and disubstituted (20%) amines is collected at 128°-130°C. This oil is used to prepare the hydrochloride, which is recrystallized from ethyl acetate, to give white crystals (22.7 g) melting at 115°C. Saponification in the cold methanolic hydroxide gives the desired 2-(4- (methallylamino)phenyl)propionic acid (alminoprofen). MP: 120°C.

MINALFENE

Analgesic, Antiinflammatory