C - Chemistry – Metallurgy – 07 – B
Patent
C - Chemistry, Metallurgy
07
B
167/260, 260/468
C07B 57/00 (2006.01) A61K 31/195 (2006.01)
Patent
CA 1251220
TITLE OF INVENTION Threo-adrenalinecarboxylic acid, and the production and uses thereof. ABSTRACT OF THE DISCLOSURE DL- or L-Threo-3-(3,4-dihydroxyphenyl)-N-methyl-serine which may also be termed as DL- or L-threo-adrenalinecarboxylic acid are now provided, which are new compounds useful for therapeutic treatment of Parkinson's disease and mental depression disease. DL-Adrenalinecarboxylic acid may be produced by a new process comprising reacting glycine with O-protected 3,4-dihydroxybenzaldehyde, hydrolyzing the resultant reaction product under acidic conditions to form O-protected DL-3-(3,4-dihydroxyphenyl)serine, isolating the O-protected DL-3-(3,4-dihydroxyphenyl)serine into the threo isomer and the erythro isomer by recrystallization from a suitable organic solvent, introducing an unsubstituted or substituted benzyl group into the 2-amino group of the resulting O-protected DL-threo-3-(3,4-dihydroxyphenyl)serine, then N-methylating the resulting O-protected DL-threo-3- -(3,4-dihydroxyphenyl)-N-benzylserine, and removing the O-protecting groups as well as the unsubstituted or sub- stituted benzyl group at the 2-methylamino group of the N-methylation product. L-Adrenalinecarboxylic acid may be produced by a new process comprising introducing a p-methoxybenzyloxycarbonyl group into the 2-amino group of the O-protected DL-threo-3- (3,4-dihydroxyphenyl)serine obtained as an intermediate product, optically resolving the resultant O-protected DL- threo-3-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl- -serine by reacting the latter with an optically active amine and recrystallizing the resultant amine salt products from a suitable organic solvent, removing the p-methoxy- benzyloxycarbonyl group from the resultant O-protected L-threo-(3,4-dihydroxyphenyl)-N-p-methoxybenzyloxycarbonyl -serine, reacting the resultant O-protected L-threo-(3,4- -dihydroxyphenyl)serine with dimethyl sulfate in dry acetone to form an O-protected L- or D-threo-(3,4-dihydroxyphenyl)- -N-methylserine methyl ester, saponifying this methyl ester and then removing the O-protecting groups from the saponifi- cation product.
434966
Iwadare Shuichi
Matsumoto Ikuo
Morishima Hajime
Nagatsu Toshiharu
Narabayashi Hirotaro
Macrae & Co.
Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
LandOfFree
Threo-adrenalinecarboxylic acid, and the production and uses... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Threo-adrenalinecarboxylic acid, and the production and uses..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Threo-adrenalinecarboxylic acid, and the production and uses... will most certainly appreciate the feedback.
Profile ID: LFCA-PAI-O-1212104