Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-07-26
2011-07-26
Aulakh, Charanjit (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S045000
Reexamination Certificate
active
07985858
ABSTRACT:
The present invention is directed to the conversion of a 6-keto morphinan to a 6-alpha-hydroxy morphinan in the presence of a ruthenium, rhodium, or iridium asymmetric catalyst and a hydrogen source.
REFERENCES:
patent: 2772270 (1956-11-01), Weiss
patent: 4089855 (1978-05-01), Chatterjie et al.
patent: 4443605 (1984-04-01), Kotick et al.
patent: 4673679 (1987-06-01), Aungst et al.
patent: 4775759 (1988-10-01), Rice et al.
patent: 4795813 (1989-01-01), Schwartz
patent: 4912114 (1990-03-01), Revesz
patent: 5240933 (1993-08-01), Merz et al.
patent: 5336483 (1994-08-01), de Costa et al.
patent: 5668285 (1997-09-01), Rice et al.
patent: 5693820 (1997-12-01), Helmchen et al.
patent: 5756745 (1998-05-01), Kavka
patent: 6184381 (2001-02-01), Ikariya et al.
patent: 6509467 (2003-01-01), Blacker et al.
patent: 7045646 (2006-05-01), Tanis et al.
patent: 2006/0182692 (2006-08-01), Fishburn et al.
patent: 0 034 480 (1981-08-01), None
patent: 0 879 823 (1998-11-01), None
patent: WO 95/32973 (1995-12-01), None
patent: WO 98/05667 (1998-02-01), None
patent: WO 2005/100361 (2005-10-01), None
patent: WO 2006/008562 (2006-01-01), None
patent: WO 2006/035195 (2006-04-01), None
patent: WO 2006/052710 (2006-05-01), None
Van Gurp et al., “Synthesis of 7,8-Didehydro-3,4-Dimethoxy . . . ”, Bull. Soc. Chim. Belg., vol. 96
° Apr. 1987, p. 325-329.
Uwai et al., “Syntheses and receptor-binding studies of derivatives . . . ”, Bioorganic & Medicinal Chemistry, 12, 2004, p. 417-421, XP 002488979.
Malspeis et al., “Metabolic Reduction of Naltrexone I. Synthesis, Separation . . . ”, Res. Commun. Chem. Pathol. Pharmacol, 2(43), 1975.
Olsen et al., “Conjugate Addition Ligands of Opioid Antagonists . . . ”, J. Med. Chem., 1990, 33(2), p. 737-741.
Koolpe et al., “Opioid Agonists and Antagonists. 6-Desoxy-6-substituted . . . ”, J. Med. Chem., 1985, 28(7), p. 949-957.
Fuiji et al., “Ruthenium(II)-Caatalyzed Asymmetric Transfer . . . ”, J. Am. Chem. Soc., 1996, 118, p. 2521-2522.
Yamakawa et al., “The Methal-Ligand Bifunctional Catalysis: A Theoretical Study on . . . ”, J. Am. Chem. Soc., 2000, 122, p. 1466-1478.
Uematsu et al., “Asymmetric Transfer Hydrogenation of Imines”, J. Am. Chem. Soc., 1996, 118, p. 4916-4917.
Wu et al., “Asymmetric transfer hydrogenation of imines and iminiums . . . ”, Chem. Commun., 2006, p. 1766-1768.
Mao et al., “A Chiral Rhodium Complex for Rapid Asymmetric Transfer . . . ”, Organic Letters, 1999, vol. 1, No. 6, p. 841-843.
Uba et al., “Stereospecific Synthesis of Codeine . . . ”, Chem. Pharm. Bull., vol. 27, Issue 9, 1979, p. 2257-2258.
Leland et al., “Analgesic narcotic antagonists. 5. 7,7-Dimethyldihydrocodeinones . . . ”, J. Med. Chem.., 1981, 24, p. 717-721.
Burke et al., “Probes for narcotic Receptor Mediated Phenomena . . . ”, Heterocycles, vol. 23, No. 1, 1985, p. 99-110.
Sagara et al., “Specific Affinity Labeling of . . . ”, Bioorganic & Medicinal Chemistry Letters, vol. 5, No. 15, 1995, p. 1609-1614.
Gao et al., “Synthesis of 7-Arylmorphinans . . . ”, J. Med. Chem., 1998, 41, p. 3901-3098.
White et al., “Asymmetric Total Synthesis of (+)-Codeine via . . . ”, J. Org. Chem., 1999, 64, p. 7871-7884.
Fuiji et al., “The First Example of the Stereoselective Synthesis of . . . ”, Chem. Pharm. Bull., 52(6), 2004, p. 747-750.
Kalimin et al., “Palladium-Catalyzed 2-Phenylethenylation of Codeine . . . ”, Helevetica Chimca Acta, vol. 89, 2006, p. 861-869.
Chatterjie et al., “Reduction of 6-Ketones of the Morphine Series . . . ”, J. Org. Chem., vol. 41, No. 22, 1976, p. 3624-3625.
Brine et al., “Formamidinesulfinic Acid Reduction of Dihydrocodeinone Derivatives”, J. Org. Chem., vol. 43, No. 8, 1978, p. 15551557.
De Costa et al., “Probes for Narcotic Receptor Mediated Phenomena . . . ”, J. Med. Chem., 19972, 35, p. 2826-2835.
Olieman et al., “Conversion of (−)-dihydrocodeinone into . . . ”, Laboratory of Organic chemistry Technische Hogeschool Delft, Julianalaan 136, Delft, The Netherlands, Mar. 15, 1976.
White et al., “Asymmetric Synthesis of (+)-Morphine . . . ”, J. Org. Chem., 1997, 62, p. 5250-5251.
Borch et al., “The cyanohydridoborate Anion as a Selective Reducing Agent”, Journal of the American Chemical Society, 93:12, Jun. 16, 1971, p. 2897-2904.
Abdel-Magid et al., “Reductive Animation of Aldehydes and Ketones . . . ”, Tetrahedron Letters, vol. 31, No. 39, 1990, p. 5395-5598.
Gribble et al., “Reactions of Sodium Borohydride in Acidic Media . . . ”, Communications, Aug. 1987, p. 709-711.
Campbell et al., “The Preparation of Unsymmetrical Secondary Aliphatic Amines”, Jan. 1944, vol. 66, p. 82-84.
Hashiguchi et al., “Asymmetric Transfer Hydrogenation of Aromatic ketones Catalyzed by chiral Ruthenium(II) Complexes”, J. Am. Chem. Soc., vol. 177, No. 28, 1995, p. 7562-7563.
Palmer et al., “Asymmetric transfer hydrogenation of C=O and C=N bonds”, Tetrahedron: Asymmetry 10, 1999, p. 2045-2061, XP 004174087.
Schellenberg, “The Synthesis of Secondary and Tertiary Amines by Borohydride Reduction”, Nov. 1963, p. 3259-3261.
Spadoni et al., “2-[N-Acylamino(C1—C3)alkyl]indoles as MT1. . . ”, J. Med. Chem., 1998, 41, p. 3624-3634.
Ohno et al., “Solid-Phase synthesis of 6-Sulfionylamino Morphinan Libraries”, Synlett, 2002, No. 1, p. 93-96.
Lazar et al., “A Selective Removal of Benzyl Protecting Groups in Arylphosphate Esters with Bromotrimethylsilane”, Synthetic Communications, 22(6), 1992, p. 923-931.
Butora et al., “Chemoenzymatic Synthesis of the Morphine Skeleton via Radical . . . ”, Tetrahedron Letters, vol. 37, No. 45, 1996, p. 8155-8158.
Watanabe et al., “Novel Synthesis of the Ortho Ester Derivative of 4,5-Epoxymorphinan”, Organic Letters, vol. 8, No. 3, 2006, p. 523-526.
Nagase et al., “The Facility of Formation of a Δ6Bond in Dihydromorphinone and Related Opiates”, J. Org. Chem., 1989, 54, p. 4120-4125.
“A New Reagent for the Selective, High-Yield N-Dealkylation of Teritary Amines: Improved Syntheses of Naltrexone and Nalbuphine”, J. Org. Chem.., 1984, 49, p. 2081-2082.
Gorlitzer et al., “Diepoxy-bis-(iminoethano)-dinaphth[2,1-b:1′,2′-i]acridine2,3+)”, Arch. Pharm. (Weinheim) 325, 1992, p. 637-641.
Lau et al., “Evolutiion of a Series of Non-Quinoline Leukotriene D4Receptor Antagonist . . . ” , Bioorganic & Medicinal chemistry Letters, vol. 5, No. 15, 1995, p. 1615-1620.
Schmidhammer, “134. Synthesis and Biological ion of 14-Alkoxymorphinans Part 4) Opioid Agonists and Partial Opioid Agonists in a Series of . . . ” , Helevitca Chimca Acta, vol. 72, 1989, p. 1233-1239.
Bognar et al., Izvestiya po Khimiya, 1975, 81(1), p. 203-215.
Noyori et al., “Asymmetric Catalysts by Architechtural and Functional Molecular . . . ”, Agew. Chem.. Int., Ed. 2001, 40, p. 40-73.
Borch et al., “A New Method for the Methylation of Amines”, J. Org. Chem., vol. 36, No. 10, 1972, pp. 1673-1674.
Olofson et al., “A New Reagent for the Selective, High-Yield N-Dealkylation of Tertiary Amines: Improved Syntheses of Naltrexone and Nalbuphine”, Journal of Organic Chemistry, 49, 1984, pp. 2081-2082, XP 000615842.
Iijima et al., “Studies in the (+)-Morphinan Series. 5. Synthesis and Biological Properties of (+)-Naloxone”, Journal of Medicinal chemistry, 1978, 21(4), pp. 398-400, XP 002428747.
Gates et al., “Some Potent Morphine Antagonists Possessing High Analgesic Activity”, Journal of Medicinal Chemistry, 7(2), 1964, pp. 127-131, XP 009097368.
March, “Advanced Organic Chemistry”, 1985, pp. 800-802, XP 002571909.
Ullrich et al., “
Cantrell Gary L.
Grote Christopher W.
Jiang Tao
Moser Frank W.
Thomasson Catherine E.
Aulakh Charanjit
Mallinckrodt Inc.
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