Method of production of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S304000, C564S305000

Reexamination Certificate

active

07544840

ABSTRACT:
The compound of formula (III), optionally its alkaline salt, is reacted with a compound of formula VII, wherein X is a leaving group, resulting in (S)-rivastigmine of formula II, which is then optionally converted into (S)-rivastigmine hydrogentartrade of formula I.

REFERENCES:
patent: 5602176 (1997-02-01), Enz
Grazyna Ciszewska, Heidi Pfefferkoru, Y.S.Tang, Lawrence Jones, Richard Tarapata and Ustun B. Sunay Synthesis of Tritium, Deuterium, a . . . an Investigational Drug for the treatment of Alzheimer's Disease: Journal of Labelled Compounds and Radiopharmaceuticals, vol. 39, No. 8, pp. 651-668.
Joseph McL. MacDonald and Edgar Stedman The Resolution of alpha-m-hydroxyphenylethyl-methylamine and the preparation of d- and I-miotine (methylurethanes of d- and I-alpha-m-hydroxphenyl-ethyldimethylamine), J. Chem. Soc. pp. 2513-2519.
Bhattacharyya S., “Reductive Alkylations of Dimethylamine Using Titanium (IV) Isopropoxide and Sodium Borohydride; An Efficient, Safe and Convenient Method for the Synthesis of N,N-Dimethylated Tertiary Amines”, J. Org. Chem., 1995, 60, 4928-4929.
Chen, Chung-Pin et al. “A General Enantioselective Synthesis of alpha-Arylethylamines”, Tetrahedron Letters, vol. 32, No. 49, pp. 7175-7178, XP009025296 1991.
Ciszewska, Grazyna et al. “Synthesis of Tritium, Deuterium, and Carbon-14 Labeled (S)-N-Ethyl-N-methyl-3-[1-(dimethylamino)ethyl]carbamic acid, phenyl ester, (L)-2,3-dihydroxbutanedioic acid salt (SDZ ENA 713 hta), an Investigational Drug for the Treatment of Alzheimer's Disease”, Journal of Labelled Compounds and Radiopharmaceuticals, vol. 39, No. 8, pp. 651-668, XP002269029 1997.
MacDonald, Joseph McL. et al. “The Resolution of alpha-m-Hydroxyphenylethyl-methylamine and the Preparation of d-and I-Miotine (Methylurethanes of d- and I-alpha-m-Hydroxphenyl-ethyldimethylamine)”, J. Chem. Soc, pp. 2513-2519, XP009034872 1932.

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