Preparation of cabergoline

Details Preparation of cabergoline Preparation of cabergoline

2007-03-06

2007-03-06

Aulakh, Charanjit S. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S067000

Reexamination Certificate

active

11060991

ABSTRACT:
The present invention discloses a method for preparing cabergoline form I by combining cabergoline and a solvent comprising ethylbenzene to form a solvate and obtaining form I from the solvate. Also disclosed in a method for preparing cabergoline form I by combining cabergoline and a first solvent to form a solution and additionally including a second solvent to the solution, followed by crystallization to form cabergoline form I. Further disclosed is a solvate form of cabergoline comprising cabergoline and ethylbenzene and, optionally, n-heptane.

REFERENCES:
patent: 3920664 (1975-11-01), Clemens et al.
patent: 4180582 (1979-12-01), Kornfeld et al.
patent: 4202979 (1980-05-01), Kornfeld et al.
patent: 4229451 (1980-10-01), Fehr et al.
patent: 4246265 (1981-01-01), Kornfeld et al.
patent: 4526892 (1985-07-01), Salvati et al.
patent: 4675404 (1987-06-01), Bernardi et al.
patent: 4782152 (1988-11-01), Misner
patent: 5382669 (1995-01-01), Candiani et al.
patent: 6395901 (2002-05-01), Mangia et al.
patent: 535235 (1973-03-01), None
patent: 535236 (1973-03-01), None
patent: 144634 (1972-07-01), None
patent: 287176 (1999-04-01), None
patent: 2479829 (1981-10-01), None
patent: 1451724 (1976-10-01), None
patent: 1499420 (1978-02-01), None
patent: 2014140 (1979-08-01), None
patent: 2103603 (1983-02-01), None
patent: 0409785-3 (2004-06-01), None
patent: WO 01/70740 (2001-09-01), None
patent: WO 01/72746 (2001-10-01), None
patent: WO 01/72747 (2001-10-01), None
patent: WO 03/78392 (2003-09-01), None
patent: WO 03/78433 (2003-09-01), None
patent: WO 04/101510 (2004-11-01), None
I. Candiani, W. Cabri, F. Zarini, A. Bedeschi and S. Penco, Synlett, The Ligand Effect in Copper (I)—Catalyzed Chemoselective Amide . . . , (1995), 605-606.
Sabatino, Sanseverino and Tonani, X-Ray Crystal Structure and Conformation Analysis of [Cabergoline] . . . , Il Farmaco, 50(3), (1995), 175-178.
E. Brambilla, E. di Salle, G. Briatico, S. Mantegani and A. Temperilli, Synthesis and Nidation Inhibitory Activity . . . , New Eur. J. Med. Chem., 24, (1989), 421-426.
S. Montegani, E. Brambilla and A. Ermoli, Synthesis of Tritium and Carbon-14 labeled N . . . , J. Labelled Compd. Radiopharm., vol. 29, No. 5., 519-533, (1991).
S. Ohno, Y. Adachi, M. Koumori, K. Mizukoshi, M. Nagasaka, K. Ichihara and El Kato, Synthesis and Structure . . . , Chem. Pharm. Bull., 42(7), vol. 42, No. 7, (1994), 1463-1473.
R. Battaglia, M. Strolin Benedetti, S. Mantegani, M.G. Castelli, G. Castelli, G. Cocchiara and P. Dostert, Disposition . . . , Xenobiotica, vol. 23, No. 12, (1993), 1377-1389.
J. Benes, A. Cerny, V. Miller and S. Kudrnac, Epimerization of Esters of Stereoisomeric . . . , Coll. Czech. Chem. Commun., vol. 48, (1983), 1333-1340.
A. Stoll and A. Hofman, Die Dihydroderivate der rechtsdrehenden . . . , Helv. Chim. Acta, vol. 29, Fasc. 3, (1946), 635-653.
P.S. Stadler, Eine einfache Veresterungsmethode im Eintopf-Verfahren, Helv. Chim. Acta, vol. 61, Fasc. 5, (1978), 1675-1681.
T. Fehr, P. Stadler and A. Hofman, Demethylierung des Lysergsauregerustes, Helv. Chim. Acta, vol. 53, Fasc. 8, (1970), 2197-2201.
J. Krepelka, A. Cerny, R. Kotva and M. Semonsky, Some 6-Alkyl Derivatives of D-8-Cyanomethyl . . . , Coll. Czech. Chem. Commun., vol. 42, (1977), 1209-1215.
W.A. Jacobs and L.C. Craig, Isomeric Dihydrolysergic Acids and the Structure of Lysergic Acid, J. Biol. Chem., (1936), 227-239.
A. Cerney and M. Semonsky, Mutterkornalkaloide, Pharmazie, vol. 26(12), (1971), 740-741.
E.C. Kornfeld, E. J. Fornefeld, G. B. Kline, M. J. Mann, R. G. Jones and R. B. Woodward, The Total Synthesis of Lysergic Acid, J. Am. Chem. Soc., (1956), 3087-3114.
C.Z. Zhang, J.H. Yang, and J. Zhou, Zhongguo Yi Xue Ke Xue Yuan Xue Bao, vol. 6, No. 1, (1984), 70-72.
A. Kleeman, J. Engel, B. Kutscher, D. Reichert, Georg Thieme Verlag, Pharmaceutical Substances, 4th ed., 312-313, 2001.
C. Dollery and Churchill Livingstone, Therapeutic Drugs, 2nd ed., (1999), C1-C4.
K. Parfitt, The Pharmaceutical Press, Martindale, 32nd ed., (1999), 1135-1136.
M.D. Gottwald, J.L. Bainbridge, G.A. Dowling, M.J. Aminoff and B.K. Alldredge, Ann. Pharmacother., vol. 31, (1997), 1205-1217.
L.R. Wiseman and F. Fitton, Cabergoline—A Review of its Efficacy in the Treatment of Parkinson's Disease, CNS Drugs, vol. 12(6) (1999), 485-497.
K. Ichikawa and M. Kojima, Nippon Yakurigaku Zasshi, vol. 117, (2001), 395-400.
The Merck Index, 13th ed., (2001), 270.
V. Gotor, Non-Conventional Hydrolase Chemistry: Amide and Carbamate Bond Formation Catalyzed by Lipases, Bioorg. Med. Chem., vol. 7, (1999), 2189-2197.
A.M. Crider, R. Grubb, K.A. Bachmann and A.K. Rawat, Convenient Synthesis of 6-nor-9,10-dihydrolysergic Acid Methyl Ester, J. Pharm. Sci., vol. 70, No. 12, (1981), 1319-1321.
R.A. Olofson and J. Martz, A New Reagent for the Selective, High Yield N-Dealkylation of Tertiary Amines . . . , J. Org. Chem., vol. 49, (1984), 2081-2082.
R.A. Olofson and D.E. Abbott, Tests of a Piperidino Mask for the Protection of Functionalized Carbon Sites in Multistep Syntheses, J. Org. Chem., vol. 49, (1984), 2795-2799.
C. Allievi and P. Dostert, Quantitative Determination of Cabergoline in Human Plasma . . . , Rapid Commun. Mass Spectrom., vol. 12, (1998), 33-39.
V. Prelog, B.C. McKusick, J.R. Merchant, S. Julia and M. Wilhelm, Helv. Chim. Acta., vol. 39, (1956), 498-504.
J.R. Vaughan, Acylalkylcarbonates as Acylating Agents for the Synthesis of Peptides, J. Am. Chem. Soc., vol. 73, (1951), 3547.
E.R.H. Walker, The Functional Group Selectivity of Complex Hydride Reducing Agents, Chem. Soc. Rev., vol. 5, (1976), 23-51.
M.J. Kornet, P.A. Thio amd S.I. Tan, The Borane Reduction of Amido Esters, J. Org. Chem., vol. 33, No. 9, (1968), 3637-3639.
J.M. Lalancette, A. Freche, J.R. Brindle and M. Laliberte, Reductions of Functional Groups with Sulfurated Borohydrides. Synthesis, (1972), 526-532.
G. Cainelli, L. Caglioti and W. Barberi, Farmaco, Ed. Sci., vol. 22, No. 6, (1967), 456-462.
R.C. Larock, Comprehensive Organic Transflormations, 2nd ed., Wiley VCH, (1999), 1940-1977.
J.M. Humphrey and A.R. Chamberlin, Chemical Synthesis of Natural Product Peptides . . . , Chem. Rev., vol. 97, (1997), 2243-2266.
L.A. Carpino, A. Elfaham and F. Albericio, Racemization Studies During Solid-Phase Peptide Synthesis . . . , Tetrahedron Letters, vol. 35 (1994), 2279-2282.
J.C. Spetzler, M. Meldal, J. Felding, P. Vedso and M. Begtrup, Novel Acylation Catalysts in Peptide Synthesis . . . , J. Chem. Soc., Perkin Trans. vol. 1, (1998), 1727-1731.
F.S. Gibson, M.S. Park and H. Rapoport, Bis[[4-(2,2-dimethyl-1,3-dioxolyl)]methyl]-carbodiimide (BDDC) . . . , J. Org. Chem., vol. 59, (1994), 7503-7507.
F.S. Gibson and H. Rapoport, Carboxy Terminus Coupling Using 1,1′-Carbonylbis (3-methylimidazolium triflate) (CBMIT) . . . , J. Org. Chem., vol. 60, (1995), 2615-2617.
M. Soledad de Castro and J.V. Sinisterra-Gago, Lipase-Catalyzed Synthesis of Chiral Amides . . . , Tetrahedron, vol. 54, (1998), 2877-2892.
V.M. Sanchez, F. Rebolledo and V. Gotor, Candida Antarctica Lipase-Catalyzed Doubly Enantioselective Aminolysis Reactions . . . , J. Org. Chem., vol. 64, (1999), 1464-1470.
V.M. Stepanov, Proteinases as Catalysts in Peptide Synthesis, Pure and Appl. Chem., vol. 68, No. 6, (1996), 1335-1339.
G. Marzoni, W. Garbrecht, P. Fludzinski, and M. Cohen, 6-Methylergoline-8-carboxylic Acid Esters . . . , J. Med. Chem., vol. 30, (1987) 1823-1826.

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