An improved process for the production of rivastigmine tartrate, a cholinesterase inhibitor

Letters in Organic Chemistry

Volumn 7, Issue 2, 2010, Pages 149-154

  Reddy, Vajrala Venkata ^a,b   Naga, Mandava Venkata ^a   Rao, Brahmeswara ^a   Ganesh, Varanasi ^a   Kumar, Adla Vijaya ^a   Praveen, Cherukupally ^a   Mukkanti, Khagga ^b   Reddy, Ganta Mahesh ^a   Reddy, Ganta Madhusudhan ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

A cholinesterase inhibitor; Alzheimer's disease; Improved process; Impurities; Rivastigmine tartrate

Indexed keywords

EID: 77951443924     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810790796246     Document Type: Article

References (20)

1. Bar-on, P.; Millard, C.B.; Harel, M.; Dvir, H.; Enz, A.; Sussman, J.L.; Silman, J. Kinetic and structural studies on the interaction of cholinesterases with the anti-alzheimer drug rivastigmine. Biochemistry, 2002, 41, 3555.
2. Pommier, F.; Frigola, R. Quantitative determination of rivastigmine and its major metabolite in human plasma by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry J. Chromatogr., 2003, B 784, 301.
3. Shukla, V.K.; Otten, N.; Coyle, D. Drug treatments for Alzheimer's disease. Tech. Rep., 2000, Vol. 11, pp. 1-64.
4. Braak, H.; Braak, E. Pathology of Alzheimer's disease: Calne, D. B. Ed., Neurodegenerative Diseases, Philadelphia, WB Sanders, 1994, pp. 565-613.
5. Hana, S.; Josef, H.; Stanislav, S. A method of production of (-)-(S)- 3-[1-(dimethylamino)ethyl]phenyl-N-ethyl-N-methylcarbamate. PCT Int. Appl. WO Patent 2004/037771, 2004.
6. Abhay, G.; Mangesh, M.; Sanjay, P.R. Process for the preparation of aminoalkyl phenylcarbamates. PCT Int. Appl. WO Patent 2005/061446, 2005.
7. Boeaio, A.A.; Pytkowicz, J.; Cote, A.; Charette, A.B. Asymmetric, catalytic synthesis of a-chiral amines using a novel bis(phosphine) monoxide chiral ligand. J. Am. Chem. Soc., 2003, 125, 14260.
8. Sakai, K.; Hashimoto, Y.; Kinbara, K.; Saigo, K.; Murakami, H.; Nohira, H. Optical resolution of 1-(3-methoxyphenyl)ethylamine with enantiomerically pure mandelic acid, and the crystal structure of less-soluble diastereomeric salt. Bull. Chem. Soc. Jpn., 1993, 66, 3414.
9. Ma, D.W.; Pan, Q.B.; Pan, S. Process for preparing (S)-N-ethyl-N- methyl-3-[1-dimethylamino)ethyl]phenylcarbamate and tartrate thereof. PCT Int. Appl. WO Patent 2007/025481, 2007.
10. Garrido, M.; Vicente, J.; Montserrat, A.; Miguel; Jorge, M.J. Method of obtaining phenyl carbamates. PCT Int. Appl. WO Patent 2007/014973, 2007.
11. Cha, K.H.; Lim, D.S.; Lee, H.W.; Lee, H.K.; Paeng, H.K.; Park, S.S. Synthetic method of phenylcarbamate derivative. PCT Int. Appl. WO Patent 2006/068386 A1, 2006.
12. Moreshwar, G.M.; Manikrao, B.B.; Bipinbha, S.V.; Rewaji, Z.U.; Ramanlal, M.S. An efficient method for preparation of [(S)-3-(1- dimethylamino)ethyl] phenyl-N-ethyl-N-methyl carbamate. PCT Int. Appl. WO Patent 2006/048720 A1, 2006.
13. Mandava, V.N.B; Vajrala, V.R.; Varanasi, G.; Adla, V.K.; Jambula, M.R.; Kanumathireddy, V.R. Preparation of revastigmine and its salts. U.S. Patent 2008/0255383 A1, 2008.
14. Leuckart reaction: (a) deBenneville, P.L.; Macartney, J.H. The behavior of aliphatic aldehydes in the Leuckart-Wallach reaction. J. Am. Chem. Soc., 1950, 72, 3073.
15. (b) Moore, M.L. The Leuckart reaction. Org. React., 1949, 5, 301. (Review)
16. This intermediate has been prepared recently by chemoenzymatic method but whole process involves flash chromatographic purifications to prepare rivastigmine. Mangas-Sanchez, J.; Rodriguez-Mata, M.; Busto, E.; Gotor-Fernandez, V.; Gotor, V., Chemoenzymatic synthesis of rivastigmine based on lipase- catalyzed processes. J. Org. Chem., 2009, 74, 5304.
17. Eschweiler-Clarke reaction: (a) Eschweiler, W. Eschweiler-Clarke reaction. Chem. Ber., 1905, 38, 880.
18. (b) Clarke, H.T.; Gillespie, H.B.; Weisshaus, S.Z. The action of formaldehyde on amines and aminoacids. J. Am. Chem. Soc., 1933, 55, 4571.
19. (a) Burba, J.V.; Murnaghan, M.F. Catechol-O-methyltransferase inhibition and potentiation of epinephrine responses by desmethyl papaverine. Biochem. Pharm., 1965, 14, 823.
20. Enz, A., Phenylcarbamates. G.B. Patent 2,203,040, 1987.