Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Reexamination Certificate
2011-08-09
2011-08-09
Anderson, Rebecca (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
Reexamination Certificate
active
07994315
ABSTRACT:
Production method of an optically active morpholine compound represented by the formula 10, or a compound represented by the formula 55, which includes the following steps:orwherein each symbol is as defined in the specification. An optically active 2-aryl-substituted morpholine compound and 3-oxo-3-(pyrimidin-4-yl)propionate, which are important as starting materials for synthesizing 2-(2-arylmorpholin-4-yl)-1-methyl-1H-[4,4′]bipyrimidinyl-6-one having a tau protein kinase 1 inhibitory activity and useful as a therapeutic drug for Alzheimer's disease and the like, can be produced in a high yield by an industrially advantageous method.
REFERENCES:
patent: 4104386 (1978-08-01), Barreau et al.
patent: 4105790 (1978-08-01), Hughes
patent: 4603019 (1986-07-01), Lafon
patent: 6130243 (2000-10-01), Takahashi et al.
patent: 6515023 (2003-02-01), Barrow et al.
patent: 2005/0187388 (2005-08-01), Cebula et al.
patent: 1 211 126 (1986-09-01), None
patent: 0 007 206 (1983-02-01), None
patent: 1 525 298 (1968-04-01), None
patent: 2 285 886 (1976-04-01), None
patent: 52-105181 (1977-09-01), None
patent: 60-152450 (1985-08-01), None
patent: 63-192744 (1988-08-01), None
patent: 03-200751 (1991-09-01), None
patent: 722481 (1980-03-01), None
patent: 837324 (1981-06-01), None
patent: 965351 (1982-10-01), None
patent: 83/29891 (1983-09-01), None
patent: 93/10074 (1993-05-01), None
patent: 95/02407 (1995-01-01), None
patent: 96/35685 (1996-11-01), None
patent: 02/48090 (2002-06-01), None
patent: 02/094770 (2002-11-01), None
patent: 03/027080 (2003-04-01), None
patent: 2004/043443 (2004-05-01), None
patent: 2004/052372 (2004-06-01), None
patent: WO 2004/052372 (2004-06-01), None
patent: 2004/085408 (2004-10-01), None
patent: 2005/061468 (2005-07-01), None
patent: 2006/036015 (2006-04-01), None
Database CAS Online and CASREACT on STN, Chem. Abstr., accession No. 1995: 72184, Yordanova et al., Dokladi na Bulgarskata Akademiya na Naukite (1993), 46(3), 63-5, abstract.
J. Y. L. Chung et al., “Enantioselective Nitrile Anion Cyclization to Substituted Pyrrolidines. A Highly Efficient Synthesis of (3S,4R)-N-tert-Butyl-4-Arylpyrrolidine-3-Carboxylic Acid,” J. Org. Chem., vol. 70, pp. 3592-3601 (2005).
M. Sawamura et al., “The Asymmetric Aldol Reaction of Tosylmethyl Isocyanide and Aldehydes Catalyzed by Chiral Silver(I) Complexes,” J. Org. Chem., vol. 55, No. 24, pp. 5935-5936 (1990).
V. I. Kuliskii et al. “Radioprotective effect of hydroxyphenylethanolamines phenolic hydroxyl esters,” published in Radiatsionnaya Biologiya, Radioekologiya, 38(1), pp. 55-61 (1998).
S. Sohda et al., “New Bronchodilators. Synthesis and Bronchodilating Activity of Some 3-(Alkoxymethyl)-α-(N-substituted aminomethyl)-4-hydroxybenzyl Alcohols,” J. Med. Chem., vol. 22, No. 3, pp. 279-286 (1979).
Chemical Abstract of M. I. Dorokhova et al., “Conversion of the configuration of optically active 1-(m-nitropheny1)-2-(methylamino)ethanols,” published in Khimiko-Farmatsevticheskii Zhurnal, vol. 8, No. 4, pp. 14-16 (1974).
B. Hu et al., “2,4-Thiazolidinediones as Potent and Selective Human β3Agonists,” Bioorganic & Medicinal Chemistry Letters, vol. 11, pp. 757-760 (2001).
R. L. Dow et al., “Potent and selective, sulfamide-based human β3-adrenergic receptor agonists,” Bioorganic & Medicinal Chemistry Letters, vol. 14, pp. 3235-3240 (2004).
M. A. Ashwell et al., “4-Aminopiperidine Ureas as Potent Selective Agonists of the Human β3-adrenergic receptor,” Bioorganic & Medicinal Chemistry Letters, vol. 11, pp. 3123-3127 (2001).
PD Avramova et al., “Synthesis, toxicological and pharmacological assessment of esters of carbonic and carbamic acids with 2-aryl-4-hydroxyethylmorpholines,” Eur. J. Med. Chem., vol. 31, pp. 909-914 (1996).
K. Yordanova et al., “Eine neue Methode zur Darstellung von 2,4-disubstituierten Morpholinen,” Chem. Ber., vol. 115, pp. 2635-2642 (1982).
K. Yordanova et al., “Synthese von 3,4-Dialkyl-2-phenylmorpholinen,” Arch. Pharm. (Weinheim), vol. 323, pp. 41-42 (1990).
R. Perrone et al., “Oxygen Isosteric Derivatives of 3-(3-Hydroxyphenyl)-N-n-propylpiperidine,” J. Med. Chem., vol. 35, pp. 3045-3049 (1992).
D. T. Greenwood et al., “2-Aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines, a New Class of Antidepressants,” J. Med. Chem., vol. 18, No. 6, pp. 573-577 (1975).
T. Kojima et al., “Synthesis of (±)-2-[Inden-7-yloxy]methyl]morpholine Hydrochloride (YM-08054, Indeloxazine Hydrochloride) and Its Derivatives with Potential Cerebral-Activating and Antidepressive Properties,” Chem. Pharm Bull., vol. 33, No. 9, pp. 3766-3774 (1985).
R. Houssin et al., “Synthesis and Configurational Study of 2-Arylmorpholines,” Heterocycles, vol. 34, No. 7, pp. 1343-1352 (1992).
R. Nieduzak et al., “Multigram Lipase-Catalyzed Enatioselective Acylation in the Synthesis of the Four Stereoisomers of a New Biologically Active α-Aryl-4-Piperidinemethanol Derivative,” Tetrahedron Asymmetry, vol. 2, No. 2, pp. 113-122 (1991).
P. Saravanan et al., “Synthesis of chiral non-racemic 1,2-diamines fromO-acetyl mandelic acid: application in enantioselective deprotonation of epxoides and diethylzinc addition to aldehydes,” Tetrahedron, vol. 58, pp. 4693-4706 (2002).
H. Nakatani, “Studies on Pharmaceutical Preparation of Orotic Acid. VII. Water Soluble Properties of Orotic Acid Salts.,” Yakugaku Zasshi, vol. 84, No. 11, pp. 1057-1061 (1964).
W. Klötzer et al., “Synthese von 5-deuterierter Orosäure und 5-deuterierten Orotsäurederivaten,” Scientia Pharmaceutica, vol. 51, pp. 374-378 (1983).
H. Gershon, “Pyrimidines. II. Chlorinated Pyrimidines Derived from Orotic Acid,” J. Org. Chem., vol. 27, pp. 3507-3510 (1962).
L. O. Ross et al., “Potential Anticancer Agents. XLIV. Some Derivatives of Uracil-5-and-6-carboxylic Acid,” J. Org. Chem., vol. 25, pp. 1950-1953 (1960).
W. Fürst et al., “Prodrug approach of orotic acid using an absorption model,” International Journal of Pharmaceutics, vol. 61, pp. 43-49 (1990).
H. Vanderhaeghe, “La Préparation de l'acide orotique et de quelques dérivés,” Bull. Soc. Chim. Belg., vol. 62, pp. 611-618 (1953).
J. J. Fox et al., “Spectrophotometric Studies of Nucleic Acid Derivatives and Related Compounds as a Function of pH,” Biochemica et Biophysica Acta., vol. 23, pp. 295-305 (1957).
M. Bachstez, “Über die Konstitution der Orotsäure.,” Chem. Ber., vol. 63, pp. 1000-1007 (1930).
M. Bachstez, “Über die Alkylderivate der Orotsäure.,” Chem. Ber., vol. 64, pp. 2683-2688 (1931).
Khimiya Seterotsiklicheskikh Soedinenii, No. 6, pp. 818-821 (1986).
G. D. Daves et al., “Primidines. II. Orotic Acid Analog,” J. Org. Chem., vol. 26, pp. 2755-2763 (1961).
J.-P. Gallemaers et al., “Synthesis and Conversion of 5-Amino-4-Pyrimidinecarboxylic Acids into 4-Hydroxypyrumidines via Their Diazonium Salts,” Tetrahedron Lett., No. 9, pp. 693-694 (1976).
G. A. Archer et al., “Quinazolines and 1,4-Benzodiazepines. 82. 5-Pyrimidyl- and 5-Pyrazinylbenzodiazepines,” J. Med. Chem., vol. 20, No. 10, pp. 1312-1317 (1977).
J. L. Wong et al., “The Synthesis of Pyrrolo[1,2-c]pyrimidine (6-Azapyrrocoline),” J. Org. Chem., vol. 30, pp. 2398-2402 (1965).
J. F. W. Mcomie et al., “Pyrimidines. Part VI. 5-Bromopyrimidine.,” J. Chem. Soc., pp. 3129-3131 (1953).
Khimiya Seterotsiklicheskikh Soedinenii, No. 4, pp. 530-535 (1981).
English translation of S. A. Stekhova et al., “Tautomerism of Azine Derivatives. 4. * Keto-Enol Tautomerism of β-Keto Esters of the Azine Series,” Khimiya Seterotsiklicheskikh Soedinenii, No. 6, pp. 822-826 (1980).
A. M. Kawamoto et al., “Enantioselective synthesis of β-hydroxy amines and az
Iwamura Hiroshi
Okuyama Masahiro
Uehara Fumiaki
Watanabe Kazutoshi
Anderson Rebecca
Greenblum & Bernstein P.L.C.
Mitsubishi Tanabe Pharma Corporation
Sanofi-Aventis
LandOfFree
Intermediate compound for synthesizing pharmaceutical agent... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Intermediate compound for synthesizing pharmaceutical agent..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intermediate compound for synthesizing pharmaceutical agent... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2741601